Most of them are not.

They’re actually frustrated. They’re working hard. The job got harder. That’s not war¹. Hard work is a constant; an existential threat is a variable. That’s just the job.

Being frustrated and calling it wartime does not make it wartime. And it definitely does not give you license to yell at people, fire randomly, or run the company on pure anxiety.

Done right though, it can give you the ability to actually share exactly what you need to happen and what your expectations are.²

Here’s what the post actually said: peacetime is when your company has an advantage and the market is growing. Wartime is when you face an existential threat. One bullet. Must hit the target.

The reality is that most companies today do face real challenges and do need to change how they run.

While there are often more things than just this, you can start here.

If you are a frustrated or unsatisfied CEO, you can borrow this and channel your energy productively.

To do so, three things need to be true.

Name the enemy.

Not a feeling. Not “we need to be better.” A real, specific, external threat. A competitor eating your market. A metric that determines whether you survive. A window that’s closing.

You cannot rally a team around a vague sense of urgency. The enemy has to be concrete. Name it. Say it out loud. Make sure everyone knows what they’re fighting.

Earn the intensity.

Wartime CEOs push harder. They’re less tolerant. They get into details they’d normally delegate. All appropriate.

But your team needs to understand why. Not a speech about hustle. Not a rallying cry. A real explanation: what’s the threat, why does it matter right now, and what does winning look like.

I’ve seen founders deliver the intensity without the context. The team feels it. They just don’t know what to do with it. So they get nervous. They second-guess. They wait to see what the CEO is going to blow up next instead of doing their best work.

That’s the opposite of what you need.

Say the thing. We are behind on revenue and the fundraise window closes in 90 days. We are losing deals to one competitor and I need everyone focused on why. Be specific about the threat. Be specific about the goal. Then turn them loose.

Fill the backpack.

You can set an unrealistic bar. That’s fine. You can and should expect the best from your team. But then you have to support the people while they do it. You need to create the conditions for them to succeed³. Pay them right. Give them equity. Remove the obstacles. Point them in the right direction.

Demanding results without creating the conditions to deliver them is not wartime leadership. It’s just bad management.

Most founders I work with know something needs to change before they can name exactly what. That frustration is useful. It’s telling you something.

But the work is to turn it into a strategy, not a personality.

Name the enemy. Explain the stakes. Support the team. That’s wartime.

The job got hard. That's not a surprise. It was always going to get hard. The question is whether you're going to lead through it or just react to it. Wartime CEOs do the former. They name what's true, set a bar, and build the conditions for their team to clear it. That's the whole job.

If this resonated, forward it to a founder who needs to hear it. Or just reply and tell me what's actually going on in your business right now. I read every response.

As it often does with me, the presentation comes down to Clarity, Focus, and Urgency.

When my CEOs tell me that “the team is struggling” or that “new hires aren’t ramping fast enough” or “everyone treats this like it’s just a job, not a mission,” I always ask them if their teams have total clarity — crisp, undeniable understanding of what they need to do.

The gap is rarely a people problem. It’s most often a communication problem. The founder knows, eats, sleeps, breathes the mission in their bones. They just rarely write it down in a way the team could run on.

And if they haven’t created one yet, I encourage them to write a Manifesto.

Jerry Maguire stayed up until one in the morning and wrote “The Things We Think and Do Not Say.” He printed110 copies and put one in every mailbox¹. Reed Hastings wrote 127 slides in 2009. Sheryl Sandberg called it the most important document ever to come out of the Valley. Writing down what you actually believe has consequences. Good ones.

The last company I built was Castiron, it was kind of like Etsy for homemade food. I wrote the manifesto before I had a single employee. There are no rules for what needs to be in here, but I included the following sections:

1. Welcome Letter — personal, written from me, to everyone on the team.

2. Our “Why” — in this case, in service of our artisans²

3. Company Values — don’t skip these.

4. “Wouldn’t it Be Great If?” — my take on optimism and thinking big

5. How We Work — Our operating principles, decision making frameworks, and norms.

You can see the entire version here.

Take as much as you want.³ But you should 100% create a manifesto and get your team aligned.

Feel free to take what you like. Share back what you create; I’d love to see it.

You're sitting on a Zoom call after a board meeting. Camera off. Everyone else has dropped. You told them you had it under control. You weren't sure you did.

You knew it. They probably suspected it. And yet you performed confidence, fielded questions, nodded at suggestions, and closed your laptop alone.

That's not weakness. That's the job.

But it accumulates.

The loneliness doesn't get talked about much. When it does, it gets dressed up as "the weight of leadership." Real. But not quite it.

What actually happens is structural. The role puts you in a position where full honesty with anyone becomes complicated.

You can't show fear to your team. They need to believe in the direction. Doubt travels fast. So you hold it. You walk into the all-hands with energy you manufactured in the ten minutes before.

You can't show uncertainty to your board. They need to believe you have it under control. The moment they start wondering if you do, you've got a different problem on top of all your existing ones. So you project confidence. You lead with the plan.

You can't let anyone see that you don't have all the answers. You're supposed to be the one who knows. The team needs to believe in the person at the top. So even when you're not sure, you project certainty. You give direction. You close the conversation. Because the alternative - admitting out loud that you don't know - feels like pulling a thread that unravels everything.

Being the final decision-maker, the keeper of information for every constituency, creates a specific kind of alone. Most people around you don't experience it. They can defer. They can escalate. They can build consensus. You can't. The stop sign is you.

Most CEOs solve this wrong.

They push through. They perform control so long the performance starts to feel like the truth. White-knuckle it through the hard quarter, the re-org, the thing they can't tell anyone about yet.

This works. Until it doesn't.

The failure mode isn't dramatic. It's slow. You stop being curious. You start being reactive. You're always responding to the room instead of leading it. You get good at looking like you have it handled.

Isolated. And performing like you're not.

What actually helps is simple. One person. Someone you can be completely honest with. No agenda. No equity. No reporting relationship.

A peer who's been in the seat. A spouse who can hold it. A mentor. A coach. Someone.

Not a network. One actual human who hears the real version. The scared version. The one who doesn't know what to do.

The structural problem doesn't go away. The board still needs the performance. The team still needs the confidence. But if there's one place you can set it down, even for an hour, it becomes manageable.

If you're reading this at 11pm after a hard board meeting. The conversation you're dreading tomorrow.

You're not broken. That's the truth of the job.

If you're in it right now, reach out. mark@markjosephson.net

Mark Josephson coaches founders and CEOs of high-growth companies. If this landed, subscribe or forward it to someone who needs it.

My friend Michele Setzer is a people and organizational effectiveness executive who has spent her career inside companies from three-person startups to global enterprises. She just published the first in a five-part series on building culture intentionally. Her framing is direct:

That gap is where culture actually lives. Not in your values doc. Not in an offsite. In the gap.

Culture is how people behave when you’re not in the room. What they say about working here to their friends and family about their job. Whether someone speaks up when something feels wrong, or stays quiet because experience has taught them it’s not safe. How people get rewarded, and for what. Whether your best people grow with you or peace out after a rough patch.

All of that is yours to define. Specifically. On purpose. Or someone else defines it for you.

Some folks think they can solve this with an HR hire… when they’re ready to do one. This isn’t an HR problem. It’s probably the most important leadership decision you make, and most founders aren’t treating it like a decision at all.

Michele draws a useful distinction: intentional culture versus over-engineered culture. Not culture by committee. A practical architecture your team can actually operate from. Defined behaviors. Operating principles. How people work together when things get hard.

Take a look at your last few weeks. Did anyone say something uncomfortable in a meeting? Do decisions made in the room stay made, or get relegated in the hallway? Have your best people stopped bringing you hard problems?

If the answers aren’t great, that’s drift. Drift is correctable. But only if you decide to correct it, on purpose, with specificity.

You’ll know you have a great culture when your team is bringing their friends into the company or when they show up energized to solve problems during a hard time. You’ll know you have a great culture when one of your leaders fires someone for violating your values, even when they’re a top performer. You’ll know you have a great culture when you can sit back in a meeting and the team is driving the business, just like you always wanted.

Culture is a leadership output. Not a byproduct.

Get cracking.

Start with part one here: Intentionally Build The Culture You Need And It Will Change Everything and follow Michele for the rest of the series.

Here’s the template I use with my clients. Copy it. Adapt it. Make it yours.

But first, understand what this actually is.

The Friday Update is not a status report. It’s not a newsletter. It’s leadership. Every week you grab the wheel, show the company where you’re going, and drive. You’re telling a story, honestly, consistently, urgently, about what matters and why. It’s a gift of time for you to think critically about the business and communicate the most important things to your team. Done right, over time, it becomes the single most powerful communication tool you have.

Start with a real opening

One or two sentences. Your voice. How the week actually felt.

One of my clients opened last week’s update with: “I spent the weekend going deep on Claude Code and realized we need to get everyone in this company on board with this revolution, fast.” That’s not a corporate communication. That’s a CEO thinking out loud. His team read every word.

Another opened with the story of sitting next to a prospect on a four-hour flight and what she learned that she hadn’t known before, about how they were perceived, what the market actually wanted, where the competition was moving. She shared it raw. Her team felt like they were on that flight with her.

Another walked into one of his biggest customer’s offices for an onsite and realized midway through the day they were off track and at serious risk of losing the business. He wrote about it that Friday, what he saw, what it meant, what they were going to do about it. Uncomfortable to write. Unforgettable to read.

And one CEO, every now and then, opens with his actual life. His son’s 18th birthday¹. What it made him think about. How it connects to what he’s building. Those are the ones people forward.

I’ve even tried opening with a Bruce Springsteen lyric to sum up the week.² The point is to show up as a human. Don’t skip it. Don’t sanitize it. That’s the whole game.

The structure

1. Honest overview

Two or three paragraphs on what actually happened. Not spin. What you won, what you lost, what surprised you, what you learned.

This is also where you keep steering, every single week. The same themes, the same priorities, the same direction, said differently, connected to what just happened. You are not going to say something once and have it land. The best CEOs I work with repeat the same three or four strategic priorities consistently, woven into the story of that week. That repetition is how strategy becomes culture. That consistency is what makes people feel like there are hands on the wheel.

2. Priorities, what mattered, what’s next

Two things only.

What were the most important things this week, and did we do them?

What are the most important things next week?

Be specific. “Closing the Q1 pipeline gap” is a priority. “Growth” is not. “Shipping the new onboarding flow by Thursday” is a priority. “Product” is not.

This section should feel consistent week over week. Your team should be able to predict roughly what’s here because you’ve been clear and repetitive about what matters. When they can, you’ve won. That means clarity has reached the whole organization.

End of quarter approaching? This section gets urgent. Not just a list, a rally. “We have three weeks to hit the number. Here is exactly what we need. Let’s go.” Say it every week until you’re there.

Big release coming? You’re talking about it before it ships, the week it ships, and after it ships. Before: why it matters. During: this is the moment, execute. After: what happened, what we learned, who made it happen.

3. KPIs

Show the numbers. Weekly actuals toward monthly goals. Every week, same format. Table with current week numbers, progress to goal for month. Share them when they’re good. Share them when they’re bad. Share them.

Don’t editorialize. Just show them. Let the team see what you see. When things move, everyone feels it together. When they don’t, no one is surprised on the last day of the month.

4. Wins, and the people behind them

Specific people. Specific things. Not “the team did great.”

“Sarah closed Acme after six months of work.” “David found the bug at 11pm and had a fix live by midnight.” “Priya’s deck got us the intro we’d been trying to get for a year.”

Here’s the move most CEOs miss: connect the shoutout to your company values. If a value is “customer obsession,” say so. “This is what customer obsession looks like in practice.” If a value is “ownership,” name it. This is how values stop being words on a wall and start being real. Your team learns what good looks like, in context, every week.

5. Customer or market signal

Bring in a voice from outside. A quote from a customer call. Something a prospect said. What you saw on that onsite. What the competitor just shipped. What you heard on the plane.

Your team is heads-down executing. You’re out there. Share what you’re seeing. It keeps everyone connected to the reason the work matters and oriented to the world outside the building, where the real game is being played.

6. One thing worth reading

One link. Something you actually read or listened to that week. Two sentences on why it matters right now. Not a roundup. One thing.

7. A question for your team

One genuine question. Not rhetorical.

“Where are we moving too slow right now?” “What are we not hearing from customers that we should be?” “Where do you need more from me?”

Invite direct replies. And the next week, close the loop: here’s what I heard, here’s what I’m doing with it. Skip that last step and the answers dry up within a month.

The template

Subject: Company Update, [Date]

[Opening: your real voice. What happened to you this week. How it felt. What it made you think about.]

OVERVIEW [2-3 paragraphs: honest account of the week, wins, losses, surprises, lessons, and woven through it, the same strategic themes you come back to every single week]

PRIORITIES This week: [2-3 specific things, did we do them?] Next week: [2-3 specific things that matter most] [End of quarter / big release: make this a rally, not a list]

KPIS [Metric]: [actual] / [monthly goal] [Metric]: [actual] / [monthly goal] [Metric]: [actual] / [monthly goal]

WINS [Name] -- [specific thing they did] -- [company value it reflects] [Name] -- [specific thing they did] -- [company value it reflects]

CUSTOMER / MARKET [One real thing you heard or saw from outside the building]

WORTH READING [Link] -- [Two sentences: what it is, why it matters right now]

QUESTION FOR YOU [One genuine question, invite direct replies] [Close the loop on last week’s question]

How to run it well

Send it every Friday. No exceptions. Your team starts to count on it. Miss one and you’ve broken something that takes weeks to rebuild.

Keep it short. 400-600 words. If it runs long, cut the overview in half.

Write it yourself. The whole value is that it sounds like you. Don’t delegate the draft.

Crowdsource the inputs. Ask your EA or a direct report to send you by Thursday noon: three shoutout nominations, KPI actuals, one customer quote. You take those raw materials and write. Thirty minutes, not ninety.

Repeat yourself. This feels unnatural. Do it anyway. The same priorities, the same values, the same direction, said differently each week, connected to what just happened. That repetition is what creates alignment. That’s how you get a whole company pointed the same way.

Bring in guest authors. When you’re traveling, offsite, or want to give someone a platform, hand the update to a VP, a team lead, a voice your company doesn’t always hear from. Done occasionally, it signals trust and builds leadership. Done well, it’s often the update people remember longest. Set the template and the standard. The format stays consistent even when the author changes.

Let it evolve. The format is a starting point. Add a section that fits, drop one that doesn’t. Your update at year two should look different from week one. That’s fine. Cadence matters more than format.

Here are some other resources that might be helpful:

The CEO Weekly Note, Visible.vc (https://visible.vc/blog/ceo-weekly-note-update-template/) -- Scott Dorsey ran his Friday Note at ExactTarget for five and a half years without missing a single week, through 2,000+ employees. His words: it was one of the defining factors of their culture as they scaled.³

Visible Update Templates (https://visible.vc/templates/) -- A full library of templates. The “Weekly Wins” and “CEO Weekly Note” under Leadership are the most relevant starting points.

The Weekly CEO Update, Friday.app (https://friday.app/p/weekly-ceo-update) -- Good breakdown of each section with real examples. Key insight: if it’s full of numbers the CEO cares about and nothing the front-line needs, expect mediocre results. Always ask what’s in it for the reader.

Gokul Rajaram’s framework (https://laurenadellecoaching.medium.com/the-weekly-ceo-update-a-great-way-to-increase-your-teams-performance-404ce0cde62c) -- Gokul ran product at DoorDash, Square, Facebook, and Google. His thinking on connecting KPIs to the human story of the week is the best I’ve read on making numbers land with a team.

The Friday Update is one of the highest-leverage habits a CEO can build. It forces clarity once a week. It keeps your team aligned without meetings. It creates a living record of your company’s year, in your voice, in real time.

More than that: it’s how you lead. Consistently. Authentically. With your hands on the wheel, steering through all the stuff, week after week after week.

Start this Friday. Don’t overthink the format.

Just write.

The original post on why this habit matters: Why You Should Send Friday Updates

Their business could be growing nicely. They’re beating plan. Things are “working.”

But there is a gnawing feeling deep inside them that they are no longer on track or that everything has changed and they haven’t.

Every investor is feeling this too. What were once investable benchmarks for your next fundraise have changed. There will only be so many PE roll-up exit opportunities for your business.

Something needs to change.

If this resonates, consider doing a Radical Rethink of your business.

Start with asking yourself and your team:

1. What would you do if you were starting this business today?

Not tweaking what you have. Starting over. Same market, same insight, but no legacy code, no inherited processes, no sunk costs. Total blank slate. What do you actually build and how do you build it?

Would your team be the same size? Would pricing be different? Would you burn the boats?

2. If a pure AI-Native YC company launched today to compete with you, what would they be doing?

They’re not constrained by what you’ve already built. They have no installed base to protect. They’re using AI from day one. What does their version of your product look like, and how much time would you have before your customers notice?

3. What hard truth are you ignoring?

Every CEO I work with knows. There’s something they’re not saying out loud. About their product. Their team. Their competitive position. AI just made that thing more urgent, and maybe a Radical Rethink gives you the moment to change it.

4. Have you made any changes to your business because of AI?

Not “we’re exploring it” or “we have a working group.” Actual changes. To how you operate, what you build, who you hire, what you stop doing. What percent of your code is written by AI? How are you using AI to source and qualify your leads? Is AI accelerating your customer onboarding? These are table stakes today. If your team isn’t proactively driving this, you’re way behind.

5. Have you personally built anything with AI?

Not ChatGPT for emails. Built something. Automated something. Changed your own behavior. Because if you haven’t felt it yourself, you don’t actually know what you’re asking your team to do. I’ve written about that here.

6. How much runway do you have?

Once you get real clarity on the above, it’s time to think about how quickly you can get there. As one CEO said to me “I know what company I want to have in three months. Why not start today?!”

If you’re considering a Radical Rethink, please reach out, I’d love to help.

You got this.

LFG.

If this post helped you — or made you think of someone — please forward it. And let me know what resonated or missed. I read every reply.

What started as a plan to rebuild my website from scratch became a deep dive and many many hours of exploring, building, rebuilding, learning, and complete and total amazement at what is possible now.

I want to share with you what I found.

What I Actually Built

Inspired by my friend Chad’s new site, I wanted to get off my crappy templated website at Squarespace.¹ I wanted to have more control and to make sure I was optimizing for SEO and AEO.

New Website: You can see for yourself, it’s fine. After a full year of coaching, I needed to redo my messaging, and think through how to not just vomit everything onto the page. It was cool to have Claude as my thought partner, strategist, PM, designer, engineer, and more. (See below on Build a Team!)

Second Brain OS: I’ve had this dream of a fully automated Chief of Staff who knows everything about my business, my clients, my hopes, my dreams. This wonder-app runs 24/7/365 and helps me be better at my job and deliver better results, etc. etc. I tend to dream really big and then get hard doses of reality when I try to make them real.

Take a look at what I was able to build². Like, seriously, this is mind-blowing. I replaced Google Sheets, Calendar, HubSpot, and more.

The Key Unlocks

This is not meant to be an exhaustive report, nor a “how to,³” but there are a few key things that I learned, that might be helpful

1. CEO skills are still relevant: Like any other thing you’re used to building, it starts with “why” — all of these models are good at doing exactly what you tell it to do, but you still need start with a vision or a problem to solve. You need clarity and focus on the problem to solve before you get to the next step:

2. Build a team! As I started to work on my website for example, I spun up chats in my “Website Rebuild” project, and gave each chat specific expectations for the discussion I wanted to have. For example:

   1. Product Manager:

      “You are a world-class product manager. You went to Harvard undergrad, UChicago MBA, two years at McKinsey, and five years at Google. You know how to get to the root of the product needs and are world-class at delivering plans, products, and outcomes that drive significant business results. Ask me 50 questions, one at a time, to clarify and understand what problem I am trying to solve. I have a tendency to be too optimistic and overbuild. I am ok doing an MVP and iterating from there, but I will ALWAYS have more ideas. I will be having chats with your teammates (see below) and will bring back all of their findings. Your task will be to help me turn this into a successful project.”

   2. UI / UX Product Designer

      “You are a world-class product designer, skilled in best practices for UX and UI. You have built award winning websites that understand and prioritize the most important items for our ICP. You ask me as many questions as you need, one at a time, to truly understand my asks and don’t say yes just to make me feel good.”

   3. Security Twins⁴

      “You are the world’s most dangerous and successful cyber criminal. There is no system you can’t hack into. You will stop at nothing to get access to my sensitive data in my new app. Review the entire repo and plan and tell me exactly how you would do it. Be exhaustive. Leave no stone unturned. Tell me every secret, trick, and potential vulnerability. Trust NO ONE.”

      and

      “You are the world’s best security engineer, with 25+ years of successful experience safeguarding and protecting the most sensitive data and systems ever created. You will be given the plans from the most dangerous cybercriminals in the world. Your job is to make sure we never get hacked nor leak any information at all. Take the criminals’ plans and lock our shit down hard-core. Trust NO ONE.”

      You get the point. Build the team. Be an expert at what you do, not what you don’t. Set clear expectations and lead.

3. Claude + Terminal: I never thought I would work in Terminal.⁵ The unlock for me was when I realized that I could work with Claude as my PM and Terminal as my engineer. What that means, is that, just like in real companies, I work with product to understand what to build and why and then we communicate that to the engineering team in Terminal. I talk to Claude and Claude literally gives me the prompts to paste into Terminal⁶. My stack is pretty advanced and it’s practically idiot-proof, I think.

   

4. Talk to Claude (Claude + Wispr Flow): This one is nuts. If you’re not using speech to text, you’re wasting time. Unlike humans, Claude loves to hear EVERYTHING I have to say and rather than spend a bunch of time trying to craft every word, I simply press the fn key and say whatever I have on my mind in a stream of consciousness and let Claude figure it out. Spoiler alert: it does. If you’re interested in trying Wispr Flow, here’s my link. We both win.

The Holy Shit Moment

Product managers. Designers. Engineers. Sprint planning. Roadmaps. Backlogs. Dependencies.

Every single idea had to go through six people and three meetings before anything happened.

That’s gone now.

I have an idea at 9am. It’s live by 9:30am. With actual code. In production. Live.

I’m not saying expertise doesn’t matter. I rebuilt components 50 times and there is SO MUCH that I do not know.

But the gap between idea and execution has collapsed.

And most CEOs have no idea this just happened.

What This Means for You

If you run a company, you need to understand what just changed.

TAM creation: This literally explodes TAM for builders and investors. I think we may be drastically underestimating how much new stuff is going to get built. The barrier is gone. And, it’s only going to get better from here.

Rapid iteration: Ideas you killed because they were “too small” or “not worth engineering time” are suddenly viable. You can test products, build tools, validate markets without burning eng cycles.

The aperture just widened dramatically.

Team dynamics: You’re about to learn what your product and eng teams actually do. Not in a threatening way. In a clarifying way.

I broke so much stuff and did things in the wrong order so many times. I understand before how the sausage is made in a way I never did before. Working with my Claude team, I got a greater appreciation for what excellence looks like on a team and the folks I’ve worked with who exemplified this. Knowing how, what, and what order, and doing it right the first time does indeed save time in the long run.

Velocity: This isn’t about replacing your team. It’s about understanding what is possible. If I, a dorky, non-technical, CEO turned Coach, can elevate my skills so dramatically, imagine what your team of experts could do. Anthropic has said that the code written for Claude itself is 100% generated by Claude Code.

You Have to Try It

I don’t care if you build a website or a dashboard or a tool you’ll never use.

You need to get your hands on this.

Not because every CEO should learn to code. Because every CEO needs to feel what just became possible.

The muscle you’ll build isn’t technical. It’s strategic.

You’ll start seeing opportunities you couldn’t see before. Markets that suddenly make sense. Products that suddenly seem buildable. Constraints that suddenly aren’t constraints.

This isn’t a how-to post. I’m not going to walk you through setting up GitHub or writing your first function. I’d just ask Claude.

I’m telling you: the world just changed, and if you don’t feel it yourself, you won’t know what’s coming.

I rebuilt my entire practice infrastructure in the equivalent of a few days. By myself. While coaching full-time.

Not because I’m technical. Because the barrier is gone.

So go build something. Anything. Just start.

You’ll know within an hour if this matters.

Trust me, it does.

If this post made you think, forward it to a CEO who needs to try Claude Code this week.

But when I asked “what’s the plan for 2026?” there was a pause.

One started telling me about out-of-office policies. Another walked me through their Q1 hiring plan. A third gave me a detailed rundown of a customer negotiation.

All good stuff. All tactics. None of it was the plan.

Strategy isn’t a nice-to-have. It’s the foundation. It’s how you make decisions. It’s how your team knows what matters. Without it, you can’t build a plan. Without a plan, no budget. Without a budget, no KPIs. Without KPIs, no goals. Without goals, no accountability. No clarity.

But there’s a ton of confusion between tactics and strategy. Between what you’re doing and where you’re going. Between the dance floor and the balcony.

The Balcony vs. The Dance Floor

When you’re on the dance floor, everything feels like a mosh pit. You’re bumping into people, trying not to get knocked over, can’t see the whole room. Just trying to survive the next song.

The balcony is different. From up there, you see the whole thing. Your job as CEO is to get up there regularly and figure out how to turn the mosh pit into a conga line.

When you’re scaling fast, it’s easy to live on the dance floor. You know the tactics cold. You can name every problem. But ask yourself to go up a level, to articulate where the company is in its arc, what this year needs to be about, what success looks like in December, and you struggle.

Not because you don’t know. Because most founders were never shown where to start.

That’s what this post is about. Not the whole plan. Just zero to one.

The Strategy Is Already In Your Head

Most founders can articulate their strategy if forced to say it out loud. The problem isn’t that they don’t know. It’s that they haven’t stopped long enough to name it.

On one of those calls, I kept pushing. “Go up a level to the balcony.” “Push back from the keyboard.” “Where are we in the arc of this company?”

Fifteen minutes in, the founder said something he’d never said that cleanly before: “We need to lock down market share and maintain technological leadership.”

Boom! That’s the strategy. It was in there the whole time.

A Few Questions That Help

If you’re in January¹ without a clear plan, try these:

Where are you in the arc? Every company has a journey. Build it, nail it, scale it. Where are you? One sentence.

What was last year’s theme? What’s this year’s? This founder was “finding product/market fit” last year. This year is “building the GTM engine.” Finish this sentence: “This is the year of _______.”

What are the 2-4 pillars? Not fifteen priorities. The strategic pillars everything else hangs on. Usually something about product, something about market, something about the company itself.

If you’re celebrating on December 31st, what happened? Get specific. What are you high-fiving about? What needs to be true for this year to be a success? This forces you out of vague aspirations into concrete outcomes.

Some people grind anyway because they’re built that way. Others drift. You end up with a bimodal team: half killing themselves, half coasting. Everyone’s frustrated because nobody knows what winning looks like.

Clarity creates focus. Focus creates urgency. Urgency creates results.²

It starts with going up to the balcony and deciding what the conga line looks like.

You already know your strategy. You just have to say it out loud.

Some are business related that I send to clients. Some are ignored in the family chat. Some are proud dad posts¹. Others are funny because they hit a little close to home.

Since you, my loyal readers, are in my life, I’m going to share one with you below.

I have not met Sim Wason², but her video hit my feed³ and she unpacks a term that founders hear all the time — “traction,” as in “we’d like to see more traction” or “what kind of traction are you seeing?”

Founders are always looking for “product/market fit” and “traction” and sometimes it’s hard to put your finger on it and, all too often, we lie to ourselves that we have it by focusing on the wrong metrics or just say “we know it when we see it.”

Sim does a great job breaking this down into something more useful. She is clear that:

But, you ask, what is evidence?

Sim outlines five rungs on what she calls “The Evidence Ladder” and you can’t skip any of them.

1. Usage — are real users actually touching without you pushing them?

2. Repeat Behavior — do they come back on their own or only when you remind?

3. Pain Relief — does your product replace something painful, slow, or expensive?

4. Willingness to Pay — not interest or compliments - real money, real time and real commitment.

5. The Pull — referrals, expansion, or users asking for more before you’re ready.

I found this really helpful. I hope you do too. Please let me know.

Sim is here on Substack with and she is running a twelve day startup series on her TikTok. It is worth a follow.

That’s what one of his direct reports told me. The CEO thought he was being clear. His team heard chaos.

This is the part about clarity that nobody talks about: it’s not just what you say. It’s what they hear.

I spend a lot of time with CEOs on my management Holy Trinity: Clarity, Focus, Urgency. Most founders get that they need to be clear. But they think clarity is one-way: am I saying the right things clearly enough?

Wrong.

Clarity is a two-way street. You transmit. They receive. Either side can fail. And when one does, everything breaks.

The Problem

Leaders think they’re crystal clear. They’ve thought about something for weeks. They’ve internalized the strategy. They know exactly what needs to happen. They are clear on what THEY want, but then they say it once in a meeting or in a 2am Slack message, and assume everyone got it.

Teams think they’re sending clear signals. They’re frustrated. They’re overworked. They don’t understand the direction or the why behind it. But instead of saying it directly, they do what one team did: “Let’s just appease him, then go back to what we know how to do.”

Both sides think they’re communicating. Neither side is connecting.

The hard truth: if your team isn’t doing what you need them to do, you haven’t been clear enough.

Even if you think you have.

Your Side: Are You Actually Clear?

Test yourself: Can anyone on your team explain your top priority in one sentence? Can they tell you who owns it? Can they tell you what success looks like?

If not, you weren’t clear.

Some common failures I see:

The 3am vomit of text. You’re thinking through something at midnight. You send seventeen messages. Your team wakes up to chaos and no idea what you actually want them to do. Clarity isn’t volume. It’s signal.

The Surprise Spotlight. Complete darkness, then blinding light. You ignore something for weeks, then suddenly demand everything. Your team can’t tell what matters because your attention is random.

The closed-door decision. You have big conversations with customers or investors, then don’t loop in your team. They could add value. They could make better decisions. But you’ve left them in the dark, so they’re guessing.

Before you speak, ask: What does this person need from me to be successful?

Not what do I need to say. What do they need to hear, understand, and act on.

That’s the difference between talking and communicating.

Their Side: Are They Actually Hearing You?

Here’s the uncomfortable part: you can be perfectly clear, and they still won’t get it.

Why?

They’re not listening. One team kept saying “okay” in meetings, then doing exactly what they wanted. They heard him fine. They just didn’t agree, and instead of saying so, they quietly resisted.

They’re filtering. We all hear what we want to hear. We process information through our own goals, fears, and biases. You say “move faster.” They hear “panic and do stuff!”

They don’t have your context. You’ve been thinking about this for months. You understand the market, the competition, the board pressure. They don’t. So when you say “this is urgent,” they don’t understand why, and that breaks execution.

What you do about it:

Check for understanding. Don’t ask “does that make sense?” That’s permission to lie. Ask “what are you going to do?” Make them play it back. If they can’t, you weren’t clear.

Create space for disagreement. If your team is just appeasing you, you don’t have a communication problem. You have a trust problem.

Address resistance directly. When you sense someone isn’t on board, when they’re saying yes but doing no—name it. “I get the sense you don’t actually agree with this. Let’s talk about it.” Most resistance comes from not feeling heard.

Why This Matters

Without clarity, you can’t have focus. Nobody knows what to focus on.

Without clarity, you can’t have urgency. People don’t understand why it matters.

Without clarity, you can’t have accountability. Success isn’t defined.

Every other leadership problem stems from this one.

The companies that win aren’t the ones with the smartest people or the best product. They’re the ones where everyone knows what matters, who owns what, and what success looks like.

That only happens when clarity flows both ways.

To be clear, your job as CEO is to communicate with total clarity and to make sure your team understands you crystal clearly. Period. Do you have any questions about this or what my expectations are?¹

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If this resonated, forward it to a founder who needs it. And if you’ve got examples of clarity breaking down (or working beautifully), reply and tell me. I read every one.

The one that hits your chest before it hits your brain. You read it once, twice, three times, and each time the temperature goes up. You can feel your jaw clench. You can feel your fingers wanting to type something fast and sharp just to get that energy out.

I’ve got a client in the middle of a heated negotiation with their board right now. They’re going through a sale process and everyone is fighting for every dollar. One particularly sharp (obnoxious?) and pointed email came through and my client’s reaction was pure anger and a desire to snap right back.

The disagreement and intense negotiations aren’t the hard part. This is the big leagues. It’s part of the job. The hard part is what happens inside your body the moment you feel accused or cornered. Your pulse jumps. Your breath shortens. You feel misunderstood, or disrespected, or just plain done with the whole thing. And everything in you wants to react. That urge feels righteous. It feels like strength.

But it isn’t strength. It’s your lizard brain taking over.

The lizard brain sees threat, not context. Attack, not information. It is fast, dumb, and loud. Useful if a bear jumps out of the woods. Terrible when you’re negotiating with people who control your company’s future.

There’s research that backs this up. When you’re under stress, the part of your brain you actually need goes offline. Stress floods the prefrontal cortex and shuts down the place where judgment and planning live. Your thinking brain goes dark. Your survival brain runs the show.

That’s why the first draft of that angry reply always feels so good. And why sending it always feels so stupid an hour later.

Reacting feels like motion. Responding feels like leadership. There’s a reason for that.

I’ve seen this over and over with clients and in my own days as well. A hard challenge about strategy. A note from a board member that comes in hot. The moment the spike hits, the instinct is always the same. React. Fix it. Push back. Make it go away. Do something now.

But reacting almost never gets you the outcome you want.

Waiting, thinking, processing, and then responding isn’t soft. It’s controlled and strategic. It’s often the difference between a good CEO and a great CEO.

We used to preach the 24 hour rule. Sleep on it. Let the chemicals flush out. But that was 10 years ago. Today everything moves too fast. Waiting a whole day feels like ignoring the issue. So maybe it’s the 24 minute rule now. Long enough for your heart rate to drop, for your lizard brain to quiet down so your actual brain can come back online.

If you’re following along, you know there’s research behind this too. James Gross at Stanford has spent years studying cognitive reappraisal. Pausing long enough to reframe a situation reduces emotional reactivity and leads to better decisions. Viktor Frankl talked about the space between stimulus and response. That space is your actual power. And most CEOs blow right past it.

So what I coach my clients to do is simple. Put down the phone. Walk away from the keyboard. Breathe. Call your coach and vent! Acknowledge the feeling and give yourself time to let it wash through you. Then think. You’ll often find more information and clarity in the aftermath of the reaction.

Here’s the real point. You get hit all day. Investors. Employees. Markets. Board members who wake up with ideas. Every input feels like a demand for speed. But nobody pays you to be fast and wrong. They pay you to stay calm when everyone else is losing the script. They pay you to be right (and fast). They pay you to respond, not react.

Your reaction lasts ten seconds. A bad reaction can last ten weeks or longer.

All too often, the answer is muddled. “We all do” or “It’s a joint marketing and sales call.”

If it’s everyone, it’s no one.¹

When there is not a clear way your company makes decisions, you are at risk for bad stuff.

I regularly see teams who are stuck on this simple but really hard question: who decides?

They have talent, momentum, and money, but every decision feels slow, painful, and fraught. Nobody wants to step on toes. Everyone wants to be heard. They mistake endless discussion for alignment.

This is one of the hardest transitions any leadership group has to make: moving from everyone decides everything to one person decides something.

The Problem

Some founders think consensus is a superpower. I don’t.

I see consensus building in start-ups as a band-aid for other problems.

Consensus feels good because it keeps the peace. Everyone gets a say, everyone feels safe. But it’s a trap. It slows you down, solves to the middle (or less), and stifles the superpowers that made your team great in the first place.

No great company was ever built on consensus.²

Here’s how I see it:

• Consensus kills speed. When every call requires total agreement, the company moves at the pace of its slowest conversation.

• No clarity, no accountability. When ownership is vague, outcomes are vague. Decisions get revisited, undone, or forgotten. Everyone’s involved, but no one is responsible.

• Fear of authority. Founders often start equal, so naming authority feels taboo. They avoid saying who owns what, which can breed resentment and stall progress.

That mix of consensus, confusion, and fear burns time, drains trust, and kills urgency.

The Foundation

To fix decision-making, you don’t start with process or frameworks. You have to start with what’s underneath it all: trust, authority, and clarity.

Trust means believing that the person who owns a decision will act in good faith, seek input, and make the best call for the company, not for themselves. If you don’t trust your co-founders or your team, there’s a bigger issue here.³

Authority means giving someone real power to make and own a decision. Not pretend power. Not “you decide but I’ll second-guess.” Real authority.

Clarity means everyone knows who decides, what input is expected, and when the decision will be made. No mystery. No shadow vetoes.

Those three are the foundation for how decisions get made. Everything else sits on top.

So, once you’re good there, now what?

The Model

Once you have trust, authority, and clarity, you can operate on a simple model⁴ I use with teams:

• Responsible. Every decision has one owner. This is paramount, IMO. Always and only one person. Clear and defined. That person is responsible for gathering input from all the relevant parties, makes the call, and owns the result.

• Accountable. The owner is measured on the outcome, not on how many people agreed with them. Accountability brings reality into the system. We celebrate their success and support them when they miss.⁵

• Input. Others contribute context and expertise, not votes. Input is required, consensus is not.

If you’re not the owner, you have two options: “agree and commit” or “disagree and commit.” Anything else sucks, is weak, and should be rooted out.

When every important decision has one responsible person, clear accountability, and thoughtful input, companies move faster and feel lighter.

Why Speed and Accountability Matter

Speed is not about recklessness. It’s about momentum.

Every delay has a cost. When decisions linger, people wait. Energy drains. The best ideas fade under the weight of more meetings and more opinions.

The fastest teams aren’t the ones who make perfect decisions. They’re the ones who make decisions, learn quickly, and adjust. Speed gives you more turns of the wheel. More experiments. More learning.

Speed is a strategy. It’s a competitive advantage. It signals confidence and earns trust. You can fix a bad decision. You can’t fix a slow culture.

And accountability is what keeps it all honest. When people know they’re accountable, they show up differently. They prepare. They think. They own results, good or bad. Accountability builds trust and maturity. It replaces fear with pride.

Every company I’ve ever led or coached got better the moment we stopped trying to get everyone to agree to everything.

So, in your next meeting, ask two questions:

1. Who owns this decision?

2. From whom do they need to get input?

If the answer to either one isn’t obvious, make it so. That’s your job as CEO.

I love me a daily stand-up. Ten, maybe fifteen minutes, tops. Same time every day. Everyone on the exec team…or everyone in the company if really early stage.

Cameras on. Standing up.

You go around the horn:

What did you do yesterday?

What are you doing today?

Any blockers?

That’s it. Fast, clear, focused. Nobody pontificating, nobody checking email. It’s called a stand-up for a reason.

Here’s why I love it.

It builds clarity, focus, and urgency. Every single day. You’d be shocked how much drifts when you don’t have that daily rhythm.

It keeps people connected. Especially remote teams. You can feel the energy, the accountability, the small moments of connection that keep teams human.

It gives me eyes on everyone. You can see who’s up, who’s dragging, who’s quietly struggling. You can’t manage what you don’t see.

It reinforces culture. My teams always found ways to make it fun. A quick dad joke. A team mascot in the Zoom window. Something small, but real.

It also gives you a spot to put deliverable dates — “can you get that done by stand-up tomorrow” or an easy way to catch-up with someone on something timely — “Leah, can you stay on for a minute?”

Most people push back at first. “Every day? What are we going to talk about?” Then two weeks in, they get it. The momentum. The alignment. The pulse.

We tried Slack bots. Async updates. Shared docs. None of them work as well as just looking each other in the eye and saying, “Here’s what I’m doing. Here’s what I need.”

Sometimes we’d make Monday’s longer and go over our goals for the week or extend Friday to review our progress towards, goals. You get it, make it your own.

But do it. If you’re the CEO, run one. Don’t delegate it. Don’t let it bloat. Start on time, end on time, and keep it sharp.

It’s not about status updates. It’s about rhythm, connection, and accountability.

Start your day with that, and everything else runs smoother.

If you’re running daily stand-ups (or thinking about it), I’d love to hear how it’s going. I read every reply.

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My answer was always the same: “Does my team know exactly what we need to do? Are we all on the exact same page?”

We’ve all been in the meeting where the heads all nod or shared the Slack post and received all the 👍 responses. We think we’ve done our job, but in reality, you get drift, that slow slide that happens after a meeting when everyone nods, leaves the room, and goes off with slightly different interpretations of what we just agreed to.

Everything starts with clarity.

Clarity about what you want.

Clarity about what the company is doing.

Clarity about where you’re going and what success looks like when you get there.

It sounds obvious, but it’s rare.

Most leaders think they’re being clear when they’re really being clever. Or vague. Or rushed. They think people understand when they nod or add a 👍.

Clarity means I know exactly what’s expected of me.

Clarity means I know what success looks like.

Clarity means there’s zero doubt about what matters most.

In detail. What, how much, by when.

Your team wants to win and it is a gift to share that with them.

It’s big and small. Strategic and personal. Between you and your board. Between a manager and their team. Between two people in a one-on-one.

Clarity removes doubt.

Clarity removes waste.

That’s the enemy. Drift kills alignment, kills momentum, kills trust.

So let me be clear¹: your team can’t read your mind. Be specific. Be explicit. Be clear.

How can you expect success if you aren’t clear on what success means?

How can you expect your team to deliver if you don’t tell them what winning looks like?

How can you expect to get what you want if you’ve never said what you want²?

It’s not fair to hold people accountable to a mystery.

Clarity isn’t just what you have as a CEO, it’s what you create.

You’re the clarity engine. You set it. You repeat it. You check for it.

Every person on your team should know, without hesitation, what success looks like and how they contribute to it.

Your job is to remove all doubt.

No fog. No FUD. No guessing.

Clarity. Clarity. Clarity.

Do you have clarity and are you sharing it with everyone?

I’d love to know.

Next up, Focus, and how lacking it kills companies.

In Mark’s Hierarchy of Fuck-Ups, it’s a Level 4¹. I’ve screwed up plenty and plenty bigger than that. Being in customer-centric companies means having to address mistakes, missteps, and outright errors often. It often feels like the end of the world. It rarely is, but it still sucks.

For high achievers, the feeling of failure on anything big or small really can sting. Worse is when we let down someone important to us. The loss of trust, perceived or real is the real killer.

So, if you’ve fucked up, here’s my simple framework for getting out of it and moving forward.

1. Own it fully and fast.

“I made a mistake. This is on me.” No excuses, no context, no soft landings. Just own it. Admitting the error and getting in front of it can immediately disarm and lower the heat. Ideally you get to them before they find the error.

2. Align on what actually went wrong.

Their definition might be different than yours. Say what you think happened in one sentence and ask, “Is that your view as well?” You need to both make sure that you understand what went wrong and that you understand the implications for them². This shows that you’re not just reacting to the error, but that you truly “get it.”

3. Mitigate immediately.

Don’t dwell on the mistake, act. Be specific about what you are doing or have done to address and fix it. Show that you’ve not only owned and understood the problem, but done all the things you can do to solve it. Energy belongs on the repair, not the remorse.

4. Rebuild trust through consistency.

If you’ve lost trust, the only way to get it back is to deliver on your promises going forward. Say what you’re going to do and do it. And repeat over and over again.

I can’t stress this enough — don’t dwell on the drama.

Communicate clearly and don’t assume they know you’re doing it. Over-communicate and deliver small wins until the balance resets.

High-intensity environments amplify small misses, so treat them like big ones. Stay steady, accountable, and forward-looking. The only way through is fast ownership, clear alignment, and visible follow-through.

###

I’ve lived here for years and that sign has not changed once. Not once in at least three years.

Every time I drive by, I imagine the person dragging it out. Not giving it a second thought. Not thinking if it is still the best sign they can use. Just going through the motions. Do they even have acai bowls anymore? Have they added anything new to the menu in the last 3 years? Are their acai bowls really special? Do they even think about what they put on that sign?

And then I realized: I’ve been that person. In meetings. After nearly seven years running Bitly. With my team. With my board. Walking in, saying the same things, going through the motions, not actually leaning in and trying to do my best work.

That’s one of the traps of leadership. Not failure. Apathy. The slow slide into lethargy, where you’re technically “open” but not really alive. Where you’re showing up, but nobody, including you, feels any energy.

I’ve coached enough CEOs to see this pattern over and over. It’s not burnout. It’s autopilot. And autopilot is dangerous, because it feels harmless in the moment. But it compounds. Your team notices. The culture shifts. Meetings get duller. Decisions get softer. You wake up one day and realize you’ve been dragging the same damn acai bowls sign out for months.

What’s helped me avoid this is creating rituals like my Friday Updates and Sunday To Do Lists. The Friday Updates weren’t just a status report but a tool to drive focus and urgency for me and the company. It reminded everyone, including me, what mattered most right now.

My Sunday To-Do List served a similar purpose. It forced me to think ahead, to be clear with myself about priorities, and to walk into Monday ready to lead instead of react.

Preparation has been another anchor. Before a meeting, I don’t just skim the deck on the way in. I ask myself: what do I want people to walk out knowing, deciding, or feeling? I even try to do a little mentalizing. That one minute of intention changes everything.

That’s the difference between dragging the sign out front and actually running the store. One is autopilot. The other is leadership. Your team doesn’t need you to be perfect; they need you to be awake. To show up with clarity, focus, and urgency. Because if you keep putting the same sign out every day, sooner or later nobody even bothers to look.

If this post helped you, or made you think of someone, please consider forwarding it to them. And let me know what resonated or missed. I read every reply.

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Remember that Clarity, Focus, and Urgency are the core pillars of being a great CEO.

Clarity comes from the Friday Update.

Focus comes from forcing yourself to pick only a few non-negotiable “big rocks.”

Urgency is founder mode, you already have it, but this system points it at the right things.

Your Friday Update is your balcony time. It’s when you reflect on the most strategic issues and opportunities in the business. The biggest wins, the biggest blockers, the patterns you see. It’s one of my favorite tools for what it does for me, my team, and my board.

Now that you’ve done that, let’s turn it into a To Do List and a plan for the following week. I found that Sunday mornings, before everyone in the house was up and it got busy was the best time for me.

First, I start with a brain dump. Every thought, every task, every worry. Just get it out. No editing, no prioritizing. Just clear the mental clutter. I have tried every app and tool to keep track of my action items, but keep coming back to pen and paper¹.

I will keep a messy running list all week and then I take that messy list and sort it into four buckets:

• Now: This Week Must Do

  The big rocks. Three to five things that absolutely must get done this week. Dated, measurable, non-negotiable. You have probably talked about these already in your Friday Update.

• Next: Direction and Delegation

  Work that matters but shouldn’t live on my plate. Define the problem, set a goal, assign one clear owner. Again, if they are important, you’ve mentioned them as priorities for next week in your Update.

• Later: Not Due This Week

  Strategic projects that matter and need to be worked on this week, but aren’t due. Capture them so they don’t distract you.

• Always: Leadership and BAU

  This is a list of things that I want to keep top of mind and do every day or week. Things like my Friday Update or finding ways for positive reinforcement, bringing urgency, and setting tone.

The way out isn’t a longer to-do list. That just multiplies the overwhelm. The way out is to empty your head, then organize what’s in front of you so you can see what actually matters.

How do you organize your to-do list?

I keep noticing a pattern with some of the best performing CEOs I work with. The words people use to describe them are almost always the same: relentless, 24/7, hungry, unreasonable. They want more, faster, now.

They don’t operate with a traditional hierarchy. They live in the weeds, with a massive context window that takes in every detail about the business, the customer, the numbers. Speed is their killer feature. They accelerate at every single opportunity.

They make unreasonable asks of their teams, things that feel impossible in the moment but somehow get delivered. The people who thrive around them are stretched, pushed, and often transformed. Not everyone lasts forever, but the right ones show up for the right chapter.

I don’t think this is something they learned. It’s how they’ve always been wired. Founder mode is their default operating system, not something they switch on at work.

At the same time, we’re watching AI shrink, reorder, and accelerate the jobs of every part of their companies — developers, marketers, product managers, finance, sales, etc. Every part of the organization is being rewired. of Writer.com recently wrote about this shift in a piece on The Orchestration Graph. His argument is that execution is quickly becoming free, but supervision is expensive. The real job of the firm, and its leaders, is moving from doing the work to orchestrating how the work gets done across people, agents, and systems.

That makes me wonder if what used to look like micromanagement, this relentless appetite for detail, speed, and unreasonable asks, might actually be the right operating system for the AI era. A CEO with a near-infinite context window isn’t just driving their team, they’re supervising a hybrid network of humans and machines. Think of a product manager who used to need a team of five, now running a swarm of agents that prioritize bugs, draft specs, and run simulations. The leverage is huge, but the oversight is everything.

If execution is abundant, maybe the scarce resource is orchestration. And maybe these CEOs are showing us what that looks like. Or maybe it’s just a faster way to burn through people and systems.

Here’s where I say, “I’m not sure of the right answer yet, but it is something I’ve been thinking a lot about.”

What are your thoughts?

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Friday updates also built trust, which was just as important. I cared deeply about being aligned with my team, up and down. If we were all on the same page, we were far more likely to win. By showing up consistently, sharing both the good and the bad, and hitting send every week, I was training my team and investors to expect candor and accountability. No one ever had to wonder what was happening or be surprised by news. That consistency closed the gap between me and my stakeholders. I never wanted an investor to say, “I had no idea” or “That’s the first I’m hearing of this.”

The most effective updates are authentic and in your voice. Don’t copy someone else’s format, make it yours. For me, the structure looked like this:

• Intro note: This is where I stepped into the balcony. I used it to share the big problems I was thinking about, the things that went wrong, or the strategic questions that kept me up at night. I was honest about what mattered most to the business and I wrote it in my own words. My team got these too, so it doubled as an alignment tool.

• Customer story: A win, a loss, or a learning. Our first value was “customers first,” and I wanted to reinforce that every week by starting here.

• KPIs: I kept it tight, usually 4–6 top-level metrics. Sales and pipeline, conversion rates and new logos if we were PLG or self-serve, core product usage, churn, and maybe one or two others depending on our stage. The point wasn’t to overwhelm with data, it was to show the levers we looked at every day and week. If a number was crooked — off weirdly in one way or another, I’d add color. Why did it move? Was it unexpected or on purpose? Anticipate the questions any reasonable person would ask.

• Operational updates: Product launches, upcoming events, or the top priorities for the company. These are the things that we’re working on and those that wehave planned for the next week. Only the things that truly mattered.

• Team wins: I made sure to call out team achievements by name. This turned the update into a recognition tool, not just a status report. It showed investors and the company that we were building a bench of leaders, not just chasing numbers. CEOs build winning teams, and these notes were a way to show how we were doing it.

• Ask for help: This was critical. Every update included a way people could lean in, whether introductions, key hires, or connections to target customers and partners. Your team and investors want to help, give them the chance.

This rhythm didn’t just keep investors in the loop, it made my exec team sharper week to week.

One pro tip: I tracked who was reading them. I used Bitly links (thank you, Bitly) so I could see who clicked through. If I sent the update to 20 people and only 10 clicked, I knew where engagement stood. Yes, I tracked who read them, of course I did. It helped me learn what was working and what wasn’t, and how I could get better.

And always share the bad news, not just the wins. Too many CEOs only send updates when things are going well, and that’s a red flag. The best CEOs communicate consistently, especially when things are hard. Investors tell me all the time, especially in 360s, that their favorite CEOs are the ones who communicate regularly, openly, and ask for more.

One trick that helped me stick with it: I blocked off Fridays from 2pm on. I kept an open draft email all week where I’d throw notes and ideas. By the time Friday rolled around, the update usually took about 20 minutes to pull together. But I always gave myself the time to push back from the day-to-day and look at the business from the balcony. And honestly, no good meetings happen after 2 on a Friday anyway.

This simple weekly ritual delivered outsized returns. It kept everyone aligned, gave me control of the narrative, and reinforced a culture of transparency and accountability. It’s good governance, it’s good hygiene, and it’s good leadership.

If you’re a founder or CEO and you don’t have a consistent update rhythm, start with Fridays. Put it on your calendar. Make it yours. And stick with it.

For inspiration, Visible.vc has a strong library of update templates: https://visible.vc/templates/

Thanks for reading. I write How to CEO as a collection of practical, real-world guides for first-time and early-stage CEOs. If this was useful, please share it with another founder who might benefit. You can subscribe for future posts here: blog.markjosephson.net.

And, if you’d like, I’m happy to read your first draft of your first update. Share with me as a Google Doc at mark <at> markjosephson.net.

###

It doesn’t have to be like that.

You can say the hard thing early and clearly, and still walk out with trust intact. You just need a plan. Here’s a four-part approach I share with clients who need to have the RealTalk™ conversation but don’t know how. I didn’t invent it, and I may be misremembering where I saw it, but I know this: it works.

1. Say up front: this is going to be a hard conversation

No drama. Just name it.

“Hey, I want to have a hard conversation with you.”

That line does a lot. It shows respect. It gives the other person a second to brace. And it sets the tone: this is a direct conversation, not a surprise attack.

2. Preview what we’re going to talk about

“There are three things I want to cover: A, B, and C.”

You’re laying down a map. It gives focus and structure, which helps when emotions run high. Even if the topics are hard, they’re not hidden. You’re showing up prepared, and that helps the other person do the same.

For example, “I’m frustrated that we haven’t hit our goals and you haven’t made meaningful progress in the past few quarters.” And, “I hate that I have to be the one to hold everyone accountable when I see that as your role.” And, “this needs to change or we can’t continue this way.”

3. Say how you want to walk away

“My goal is that we leave this aligned and moving forward.”

Or: “We may not agree on everything, but we’ll know what’s next.” Or: “Even if it’s tough, I want to come out of this with clarity and respect.”

This resets the temperature. You’re not picking a fight. You’re being honest about where you’re trying to land. That helps people stay engaged instead of getting defensive.

4. Ask for agreement

“Is that okay with you?”

This might be the most important part. When someone says yes, even quietly, the whole dynamic shifts. You’re not doing something to them. You’re having the conversation with them.

More often than not, they have been waiting for you to have this conversation. They’re smart and they know you’re not aligned.

This structure doesn’t make the conversation easy. But it makes it better. Cleaner. More productive. It’s helped leaders fire people the right way, give feedback that actually lands, and work through tension without losing the relationship.

It lines up with what the authors of Difficult Conversations talk about: clarity up front builds safety. And it mirrors ideas from Crucial Conversations, that the way you open a conversation shapes everything that follows.

Give this a try and let me know if works.

I write for CEOs and leaders who want to get better at the hard parts. If this helped, share it with someone who’s got a hard conversation coming up. Or #leadership #howtoceo #coaching #startups #management and tell me how you’ve handled these moments.

It’s an easy, thoughtful read, structured around the Techstars Mentor Manifesto. Brad defines terms clearly, shares real-world examples, and gives readers a practical, human framework for mentorship that works over the long haul of one’s career.

“Give First means being willing to put energy into a relationship or a system without defining the transactional parameters. However, it’s not altruism. You can and should expect to get something back. But you don’t know when, from whom, in what form, or over what time frame.”

Give First isn’t about paying it forward in some vague, feel-good way. It’s not martyrdom. It’s not manipulation. To me it’s a way of living and working that is both strategic and generous. It works, and it feels right. And if you do it consistently, people are more likely to want to work with you, help you, and root for you.

I didn’t have a name for it at the time, but I’ve tried to operate this way for years. After I left Bitly, I started what I called a Gratitude Tour. I reached out to people I had worked with and admired along the Bitly journey, not to pitch them, but to thank them, to reconnect, and to offer help. No agenda. Just “how can I help?”

During that Gratitude Tour I reconnected with Brad. After a bunch of conversations, Brad offered me a job one Friday. He rescinded it on Monday (for all the right reasons)! And then on Tuesday, he introduced me to Scott Dorsey and the High Alpha team and told them they should start a company with me. We did start that company together. Castiron. A year later, Brad and Foundry invested. This was Give First in the wild.

That same Gratitude Tour also led to my first coaching client, someone I’m still working with today. No pitch. No ask. Just showing up, listening, and offering help, until she asked me if I could be her coach. Giving first came back tenfold.

And Brad lives this. I’ve worked with him and can attest that this is how he operates. Early on, he told me I could call him anytime about anything. And whenever I did, he would call me right back or reply almost immediately. No games. No filters. Just presence and generosity.

Reach out before you need something. Offer help without a pitch. Don’t make the first call an ask. That’s not altruism. It’s just good way of showing up and building your own personal brand. This kind of behavior builds trust. That builds reputation.

You can and should expect to get something back. That’s what makes this different from altruism. But you don’t get to set the terms. You don’t know when it will come back to you, who it will come from, what it will look like, or how long it will take. It might be an introduction you never asked for, a door that opens months later, or a reputation that quietly builds until one day it matters. The return isn’t guaranteed, but it’s real. And it almost always shows up. Just not on your schedule.

That’s why I say give, give, give. Not just because it feels good. Not just because it reflects the kind of human I want to be. It does. But because it works. It’s good business. And the world needs more of it.

That’s also why I started my podcast, Critical Moments. I wanted to give people space to tell their stories, he real ones, not the polished versions. Everyone has a moment that changed them. I wanted to give those moments the airtime they deserve.

Brad’s voice in this book is exactly what I’ve always appreciated about him. He’s real. No airs. No need to flex, even when he’s the smartest or most experienced person in the room. He speaks clearly, directly, and focuses on giving the best advice he can. That’s the spirit of Give First. And it’s why this book matters.

If this resonated, I write more posts like this each week for founders and CEOs trying to build something real without losing themselves along the way.

→ Subscribe here:

→ Or send me a note and let’s talk:

→ And check out the podcast: Critical Moments.

###

For a long time, triple-triple-double-double was the blueprint. Grow at that rate and you were on track. But that model feels slow now. If you’re not on a breakout trajectory, you’re at risk. You’re at risk of being out-raised, outpaced, out-hired, and out-built.

I was talking to an investor the other day about one of their companies. It’s doubling at real scale. And he said, “Unfortunately, that’s not going to be good enough.” Inside the business, that feels like progress. Outside, it might not even register.

That’s part of why we sold Castiron. The business was kinda sorta doubling. But in a venture context, that wasn’t going to cut it. We were not going to hit venture scale. The bar had moved.

I’m not saying this is good. I’m saying it’s real. The pace is brutal. The war for talent is more competitive and more expensive. Everything feels compressed. And if you’re a CEO who has taken venture, this is the game you’re in. Whether or not you like the rules.

You are at real risk of not making it if you’re not going for it. All in. That’s different from being deliberate. That’s different from carefully nailing each step. The speed is noticeably different now. And the margin for pacing yourself has collapsed.

What I’m seeing again and again: you can’t just build for where you are. You have to behave like the company you want to be in 12 months. That means hiring, resourcing, and operating at a different level before it feels comfortable. Whatever your goals are for next year, you can’t wait to start acting like that company. You need the team, systems, and motion in place now.

That might mean hiring the VP you’re not “ready” for. And yes, that can backfire. Sometimes hiring too early creates misalignment, burn, or confusion. But if you’ve chosen this game, you might not have the luxury of waiting. You’re on the clock. You don’t get to pace yourself. You have to build the company the market expects you to be. That’s the trade.

You still need repeatability. You still need precision. But you also need speed. Bigger bets, shorter cycles, faster learning. Hire ahead. Build ahead. Move.

History doesn’t quite repeat itself, but it is rhyming right now with other booms we’ve seen. So, I expect to see some normalization over time, so yhis isn’t advice. It’s just what I’m seeing. I don’t love it and it can be very stressful and hard to do, but, if you’re in the game, this is what the game looks like right now.

#startups #leadership #clarity #venturebacked #founders

They call it the First Ten / Last Ten approach.

It comes from a post by Stewart Butterfield about how Slack built product, and Nick explained how they’ve turned it into a ritual that helps their team move faster and work smarter. Here’s the idea:

The First Ten is the first 10 percent of the work. This is where you slow down to go fast. You talk strategy. Goals. Why now. What problem are we solving? Who’s it for? What does success look like? Who’s working on it, and what do they need to get it done? This is when CEOs should be involved. Not reviewing a doc after weeks of progress, but helping shape the intent while the team is still open and adaptable.

Then comes the Middle 80 percent. That’s where the team runs. They build, test, collaborate, and adjust. This is the execution phase. The CEO shouldn’t be in the way. You’re not adding value by popping in with random opinions. You build trust and speed by letting the team work.

Then you come back in for The Last Ten. That final 10 percent before launch. This is where you zoom in and get sharp. You check quality. You challenge assumptions. You look at copy, design, UX, and logic. You ask the hard questions. And most importantly, you do it early enough that changes can actually be made. Not the night before launch. Not when everything’s locked.

I learned this one the hard way. I used to give feedback too late, when teams were already stressed and proud of their work. That never went well. But when I got involved earlier, when we still had time to make the work better, everyone won. The team felt supported. The product got sharper. And I felt like I was doing my job really well.

This framework gives you that rhythm. Start with clarity. End with accountability. Let the team own the middle.

Kudos to Nick and the HelpScout team for sharing it.

###

Clarity always comes first. Because without it, nothing works. You can’t focus on the right things. You can’t move with urgency. You’re likely wasting time.

And the killer is that lack of clarity usually doesn’t look like chaos. It looks like busy people doing good work. Until you realize they’re doing the wrong work. Or rowing in slightly different directions. Or waiting for a signal that never comes.

I see it all the time between CEOs and their teams.

A CEO thinks the plan is obvious, but hasn’t said it out loud in weeks. The team fills the silence with assumptions.

A product leader thinks they’re executing on vision, but they’re chasing metrics that no longer matter.

A CFO is trying to preserve runway, while the CEO is pushing to hire fast.

No one’s wrong. They’re just not clear. And no one wants to say it.

That’s where this simple tool comes in.

One of my clients showed me an alignment exercise they use with their team. It’s only four questions, but it cuts through the fog every time. Turns out, it’s rooted in something leadership experts have been studying for decades: boundary spanning.

The formal definition comes from Michael Tushman, who described boundary spanners as people who connect internal teams to external networks and ideas. His work focused on innovation systems, but the same concept applies inside organizations too. Especially when trust is shaky or communication is cloudy. You need people who can bridge across roles, functions, and perspectives to make progress happen.

“Boundary spanning refers to individuals within an innovation system who have, or adopt, the role of linking the organization’s internal networks with external sources of information.”

—Tushman, M.L., Administrative Science Quarterly, 1977

That’s the theory. Here’s what it looks like in practice.

You sit down with someone you work closely with—your co-founder, your head of product, your board chair—and you each answer these four questions:

1. What I need from you

2. What I think you need from me

3. What I expect of you

4. What I think you expect of me

That’s it. You each share. You talk it out. You check for mismatches, surprises, and blind spots. And then you recalibrate.

This isn’t a performance review. It’s not feedback. It’s not therapy. It’s alignment. It’s RealTalk™.

And it works.

The version I learned might not have an official name, but it lines up with other structured tools like the ICBD exercise from Jurriaan Kamer. That one asks people to clarify intentions, concerns, boundaries, and dreams. It’s designed to surface hidden assumptions and get teams on the same page before they hit a wall. This version uses different language, but gets to the same result: clarity, faster.

If you’re a CEO or a leader, this kind of clarity is your job. Alignment isn’t a vibe. It’s a conversation. And most of the time, the thing that’s blocking progress isn’t a strategy problem. It’s a “we never said it out loud” problem.

So say it out loud.

Ask the questions.

And don’t wait until things break.

Twelve-hour workdays. Slack pings. Inbox anxiety. Watching the sunset through the window instead of walking into it. It was a beautiful setting, but the life didn’t feel like hers.

That’s the thing about burnout. It doesn’t always show up as collapse. Sometimes it shows up as clarity. And if you listen to it, like Clara did, you might actually discover something that changes your life.

Clara left her job without a plan. She gave herself three months. She wandered through Spain. She learned Spanish. She went through a breakup. She read fiction again. She ate too many solo tapas. And somewhere in the space she created, a new idea emerged.

She didn’t intend to build a company. She just wanted to extend her trip.

But three successful placements later, she realized she was onto something. Ask a Chief of Staff was born, not from a spreadsheet or pitch deck, but from lived experience, curiosity, and agency.

That’s the part that stuck with me most: Clara gave herself permission. She paused. She wandered. She listened. And what came back to her, again and again, was what she actually cared about.

There’s a lot we can learn from that.

The next time you feel stuck, or burnt out, or like the life you’re living doesn’t quite match the one you imagined—ask yourself the questions Clara asked.

Wouldn’t it be great if…?

Then follow the answer.

You might be closer than you think.

I love feedback, so please leave a comment or send me a message:

And, if you think someone would like this post, please share.

###

Especially for first-time or CEOs earlier in their careers, there’s this pressure to show up a certain way. Confident. Polished. Driven. Certain. Like you’re in full control at all times. It makes sense. There’s a lot on the line, and people are looking to you for answers. But I’m not sure that kind of performance really works. Not for long.

It’s exhausting. It creates distance. And in some ways, it makes it harder to actually lead.

I’ve been a CEO three times. It wasn’t until the third time that I truly started showing up as myself. I stopped pretending to have all the answers. I said the hard things. I admitted what I didn’t know. I tried to build a team and systems that made space for the stuff I wasn’t great at.

It didn’t always feel natural. But over time, it felt like the only way to keep going.

In my coaching work, I try to help people lead from that place. I don’t believe in fixing anyone. Most CEOs don’t need fixing. They need space to see who they are, and permission to lead like that. I’ve seen it work. I’ve felt it myself. And when it clicks, it can be powerful.

Being authentic doesn’t mean over-sharing. It doesn’t mean being emotional all the time. It means telling the truth. About what’s happening. About what’s hard. About what’s not working. About what’s real.

It can sound like:

• I don’t know the answer. What do you think?

• We’re stuck here, and I’d love your input.

• This is harder than I expected.

• I’m worried about how this is landing.

• I need help.

Saying these things can feel risky. Like you’ll lose credibility. Like people will think you’re not up for the job. But in my experience, the opposite is usually true. People already sense the truth. What builds trust is being the one willing to say it out loud.

I don’t always get this right. I still catch myself defaulting to the act or “how I’m supposed to show up.” But I spot it faster now. And I know what it feels like when I’m leading as me.

If you want to try this, start small.

Find one moment this week where you feel that instinct to perform. Where you feel yourself gearing up to sound confident or certain or “in control.” Instead, pause. Take a breath. Don’t react right away.

Ask yourself: What am I really thinking? What do I actually want to say?

Start by saying that.

Not the version that sounds polished or strategic. Just the true part.

It might feel uncomfortable. It might feel like a risk. But it might also feel like relief.

If this landed with you, I’d love to hear what’s resonating. Hit reply or drop a comment. And if you know a CEO who needs to read this, feel free to pass it on.

##

I was trying to find some threads and meaning to turn this into a blog post about learnings for CEOs, but frankly, I am just really proud and thankful that I had this opportunity to help him tell his story.

Many in the audience knew NWA was, but not That DOC wrote many of their early lyrics, co-founded Death Row Records, mentored Snoop Dogg and Eminem, and saw his own debut album No One Can Do It Better climb to number one on the R&B/Hip-Hop chart in 1989. In 2022, he was even awarded a Grammy Lifetime Achievement Award.

As he ascended to the top of the game, a tragic car crash resulted in a crushed larynx and stole the voice that had just made him famous. When I asked him to tell us about the accident that changed everything, he paused and the auditorium went silent.

Today he pours his energy and superpowers into DOC Cares and the forthcoming Dreams Experience Academy (DEA) in South Dallas. The program gives teenagers practical paths into media, technology, and entertainment—options he never saw at fifteen. He has partnered with my friend (and podcast guest) Chris Gannett and Gannett Partners to build and grow these great programs.

A new chapter is also taking shape. DOC is using artificial-intelligence tools to recreate his voice for a new album, and his life story film, which premiered at Tribeca, is expected to reach a wide audience in 2026.

I left the stage grateful. Grateful to give a legend the space to speak. Grateful to hear a story that moves from rise, through loss, into purposeful rebuilding. Mostly grateful for the reminder that the work we are meant to do can arrive through circumstances we would never choose.

Thanks for reading. If this story resonates, let me know where you are finding your own voice right now.

###

This weekend we celebrated our eldest son’s college graduation. It was a major milestone and his mom and I are beyond proud of him. We had a great “memory weekend” full of family, fun, and great food. I’m still riding high.

Now I’m back at my desk, coffee in hand, inbox glaring.

I’ve got so much this week that I am excited about: client work, the next podcast interview, a boot camp outline, my next webinar (with a cool partner!) and all of this is in the context of wanting to be present and enjoy the summer and time with my family.

Now it’s time to get organized. I start with my Big List. Five minutes, pen on paper, everything that’s rattling around gets a line. No judging, no sorting, just a total brain dump. I then prioritize them and get to work. Usually I do this on Sunday, but we were traveling yesterday. The list is long, but getting it out of my head and onto paper feels like a win.

I’ve tied Apple Reminders, ToDoist, Google Tasks, and other tools (miss you Evernote) anas well but always come back to some combination of Apple Notes and pen and paper. I wonder if Granola will evolve or get swallowed by ChatGPT, but that’s another blog post.

What do you use to organize and track your to-dos?

I love to try new things, so please share!

And, of course, have a great week.

When I’m asked to make a connection or intro, I always use the Double Opt In method — that means, I never (rarely) blind intro without the recipient explicitly saying, “yes, I am interested in meeting this person.”

In order to do that, I ask the requester to send me forwardable note. Not a pitch, but an honest request with the context and reason for the ask. I will add color to the note (i.e. “I’ve know Jen for 20 years and vouch for her” or “I don’t know Tim well, but the product looks interesting”) and ask specifically “are you interested in me making this connection.”

Here’s a great example of a forwardable note when looking for a job.

It includes the context, why the ask is relevant, and in this case, a request to meet hiring manager, it includes a resume and LinkedIn profile.

If this was an ask to meet an investor, it would include the rationale for the ask, why the specific product or business is relevant to the investor’s thesis, and any relevant materials (pitch, docsend link, etc…). For example:

I hope this helps make all of your connection dreams come true.

If this is helpful to you, please share, sign-up, or comment below!

✌️🔥

We’re learning how to speak clearly to AI so we get our desired result, but we don’t use the same clear and direct communication with our team?

WTF?

So, I’m trying something new. I’ll put together some slides and walk through what we can learn from a good AI prompt and how to lead with more clarity, specificity and precision to get better results.

Please join me!

Thanks and please share with anyone you think would like this.

✌️🔥

M

Hiring a CFO is different from every other exec role, and it should be. This is the one part of the business where there’s zero room for gray. Zero room for half-truths, improv, or “we’ll fix it later.”

Finance has to be bulletproof. The numbers have to be right. The books have to be closed. The story has to hold up to investors, auditors, the board, and you.

“A great CFO doesn’t just report the numbers, they understand what’s behind them and help you make the hard calls because of them.”

There’s no room for creativity here. No innovation points. You want a CFO who tells you the truth, every time, with no spin. You want transparency, accuracy, and maturity. And you want someone who sees their job as keeping the company safe and helping it grow.

The One Axis That Matters Most

Controller-Strong vs. FP&A-Strong

Most CFOs come up through one of two paths: Accounting and Controller, or Financial Planning and Analysis (FP&A).

• A Controller-strong CFO knows the numbers cold. Payroll, compliance, cash flow, audit, taxes, board-ready reporting, they don’t miss. You can hand them to any board member, investor, or auditor, and know they’ll have the answer.

• An FP&A-strong CFO is a strategic thinker. They model scenarios, analyze risk, and help you see around corners. They’re your partner in planning growth, managing burn, funding investments, and preparing for acquisitions, yours or theirs.

You need both. But know which one they default to, and which one your company can’t afford to be weak in.

And One Non-Negotiable Expectation

A CFO must be your truth-teller and your steady hand.

This isn’t optional. The best CFOs tell the CEO the truth, always. But they know when and where to do it.

• With you: brutally honest. Private, clear, no spin.

• With the team: calm, confident, protective of the company’s stability.

This is about trust and maturity, not background.

The 5 Questions That Reveal Who They Really Are

1. “Walk me through your experience running finance and accounting. How do you make sure the numbers are bulletproof?”

• How do you ensure accuracy in reporting, compliance, payroll, and cash flow?

• Show me: what does a finance team you’ve led look like, how many people, what roles, what systems?

2. “What are your go-to benchmarks and operating ratios? How do you evaluate the health of a company financially and operationally?”

• Sales and Marketing vs. Engineering spend?

• CAC to LTV?

• Sales comp, quota attainment?

• How do you know when the business is performing, or not?

3. “Tell me about a time you helped a company raise money or prepared for an acquisition. How did you support the CEO and the process?”

• What was your role in fundraising or M&A?

• How do you think about capital strategy, debt, equity, dilution?

4. “If I talked to your last CEO, how would they describe your relationship? How did you disagree, and how did you support them publicly?”

• When did you have to deliver hard truths privately?

• How did you manage alignment with them, and confidence with the team?

5. “Let’s talk about our business. What do you want to know, and what would you look at first?”

• What would you ask me about our financials?

• What would you want to understand about our business model?

• What jumps out to you as key risks or levers?

Closing Set (Always):

1. What’s your long-term ambition?

2. What’s your superpower—what do people rely on you for?

3. What’s something you’re not great at, or still working on?

4. If I talked to your last manager, what would they say your biggest growth area is?

CFO Interview Scorecard

Want a version you can actually use in interviews?

Grab the CFO Interview Scorecard here

Make a copy and take it into your next CFO interview.

Final Gut Check:

Do I trust this person with every number in the business, and am I hiring a partner or a scorekeeper? Do I want them at the table helping shape the future, or just keeping the books straight?

“You don’t want someone who just tracks your business. You want someone who helps build it.”

The CEO Move

Decide if you want a partner, or just someone to keep score. Then hire accordingly.

The biggest mistake CEOs make is hiring a CFO for what they think they need, when they haven’t been honest about what they actually want. You can hire someone to give you the truth, help shape strategy, and challenge your thinking. Or you can hire someone to keep the books tight and the reports clean. Both matter. But you can’t confuse them.

And don’t forget, the kind of business you’re running changes everything. A CFO who knows SaaS might not know marketplaces. A PLG business isn’t the same as sales-led enterprise. Hire someone who knows how to manage and grow this kind of company, not just any company.

Not because they’re lazy. Not because they don’t care. But because you’re not being clear enough.

That’s the hard truth I share with nearly every CEO I coach. You think you’re being clear—but your team is guessing. And when people have to guess, things go sideways. Fast.

Recently, I started using a new frame to explain this: prompt engineering. The same concept you use with AI—be specific, give examples, define the output—is exactly what your team needs from you. (P.S. I’m running a free live webinar on this — details at the bottom.)

Think about it:

When we prompt our AI tools, we’re learning to be more precise.

What’s the goal? What’s the format? What specific results do I want? What do I want it to sound like?

And when we don’t get the right answer, we fix the prompt—not the AI.

That’s how it works with humans, too.

You say, “We need to grow faster.”

They hear, “Panic and go do stuff.”

You say, “This isn’t good enough.”

They hear, “I have no idea what success looks like.”

You say, “Take ownership.”

They hear, “I’m on my own, I hope this is right.”

Reframe the problem.

It’s not them. It’s your prompt.

Try this instead:

• Instead of “We need to grow faster”

  Try “I want to grow revenue by 30% in the next 90 days. Let’s generate and prioritize 10 experiments by Friday.”

• Instead of “This isn’t good enough”

  Try “The goal was a one-page summary that highlights the trade-offs. Let’s look at how we missed that.”

• Instead of “Take ownership”

  Try “This is yours to lead. That means making the plan, getting the right people involved, and driving daily activity, and updating me weekly.”

Clear input = better output.

AI or human, it’s the same idea.

I’m putting together a free workshop on this—real prompts, real feedback, real-time coaching. Comment below, message me, or register here if you want to attend.

You can read:

• How to Write a Job Description for a Senior Exec

• How to Interview a Product Leader

• How to Interview a CTO

This one is about zooming out, seeing your company clearly, and focusing on what actually matters right now.

Most startups don’t fail from lack of effort. They fail from working hard on the wrong thing.

This framework that I learned from one of my clients —Build It. Nail It. Scale It.—exists to fix that.

It helps you get out of the weeds and ask the only question that matters:

What’s the single most important thing right now?

Not what’s on fire. Not what’s politically important. Not what’s exciting. The one thing that actually moves the business forward. From the balcony, there’s always a clearest next step. This framework helps you find it.

The best CEOs I coach—especially the ones who’ve done it before—know how to stop, push back from the table, and say, “Let’s get clear.” Not just to themselves, but to their boards, their teams, and their investors. That clarity builds momentum. That clarity is what this is about.

Let’s break it down.

Build It

You’re not building a company yet. You’re building a product and a feedback loop.

You know you’re still in Build It when:

• You don’t have customers using the product

• You haven’t collected any real feedback

• You can’t point to actual traction—just potential

This is the phase for “founder mode.” You do whatever it takes to get something into market and into someone’s hands. You text friends. You walk dogs. You hand-deliver the cookies. You get signal.

And yet—this is where a lot of teams stall without knowing it. They overbuild. Overthink. Obsess over long-term tech choices or org charts. I had a head of engineering once burn a month picking the “right” platform for future extensibility—before we had a single user.

That’s not strategy. That’s fear.

You’re not playing chess. You’re playing checkers. Move fast, learn something, get in the game.

Until you have something in market and someone paying attention, nothing else matters.

Nail It

You’ve seen sparks. Now you need to figure out what’s actually working—and why. You’re testing price points. Channels. Messaging. ICPs. You’re listening closely. Adjusting. Watching patterns emerge.

Think of your company like a fire:

• Build It is where you collect sparks.

• Nail It is where you learn how to make fire.

• Scale It is when you build a team to keep it burning—without you feeding it constantly.

Nail It is where most startups die.

Not because they don’t try hard enough, but because they believe they’ve nailed it before they have. These happy ears are deadly.

They confuse early wins for repeatability. They close a few deals. Get some positive feedback. Hire three reps before they’ve really nailed it. Spend $100K on ads without knowing CAC. It feels like traction—but it’s noise.

Traction ≠ repeatability.

Repeatability means: we do this, and this happens. It’s boring. Reliable. Unsexy. Profitable—or on the way.

You know you’re ready to move on when growth is bottlenecked by capacity—not chaos.

More budget = more customers. More SDRs = more pipeline. More reps = more Closed Won. You’re not guessing. You’re executing.

Scale It

Now you’re building the company. Hiring managers. Tracking metrics. Delegating. Replacing “heroics” with systems.

But scaling doesn’t mean coasting. It means everything gets harder.

The team gets bigger. Communication breaks. Customers expect more. You stop being the doer. You become the coach.

This is where founders get caught clinging to old ways of working. Or holding onto people who were great in the chaos but can’t grow with the company. Or losing touch with the customer signal because layers have formed and feedback gets filtered.

And the biggest trap? Thinking you’re ready to scale just because you raised money.

You’re not.

Fuel doesn’t help if the engine isn’t running.

From the Balcony: What Phase Are You In?

Build It

Top Priority: Get something into market and start learning

You’re Ready to Move On When:

You have an MVP in market, real user feedback, and sparks of traction—someone’s using it, paying for it, or telling a friend.

Example Behavior:

CEO is doing sales calls. PM is shipping fast. You’re begging friends to try it. One customer says, “This is exactly what I needed.”

Nail It

Top Priority: Find a repeatable, predictable, projectable go-to-market motion

You’re Ready to Move On When:

You can acquire and serve customers reliably—and growth is gated by spend or team, not uncertainty.

Example Behavior:

You A/B price points. You test channels. You hire a rep—and they close without shadowing the founder. You know which customers to say no to.

Scale It

Top Priority: Build the machine and expand capacity

You’re Ready to Move On When:

Your core playbook works. Now it’s about hiring, systems, and keeping it from breaking as you grow.

Example Behavior:

You add reps—and they hit quota. Ops dashboards go from “vibes” to accurate. The CEO isn’t the only one who can close. Team is focused and executing.

So where are you, really?

Not based on funding round. Not based on vibes. Based on truth.

This framework isn’t cute. It’s brutal. It calls the bluff.

It says: stop skipping the hard part.

Because every startup wants to scale.

But only the ones who build it and nail it actually earn the right.

I hope this can help you find some clarity.

Your feedback is welcome!

##

But that’s the top-down view.

This post is about the bottom-up. The work underneath. The part most people avoid. The part that actually builds the business.

Because once you know what you’re trying to drive, you need a clear, detailed map of how it actually works—and how you’re going to make it happen.

After we sold Bitly to Spectrum Equity, one of the first things we did together was build a detailed operating plan. Not a quick forecast. Not a board-ready deck. We built the entire machine in Google Sheets—line by line, cell by cell, lever by lever.

This wasn’t diligence. It was post-sale planning. A new phase. A new world.

And it was exhausting.

We didn’t just model revenue—we modeled everything that led to it.

• Monthly sales rep productivity by cohort and ramp time

• Marketing channel performance

• Acquisition, retention, expansion, and churn assumptions by segment

• Cash burn forecasts layered against hiring plans

• and every other possible lever.

I was coming from the VC world, where speed was everything. We forecasted because we had to. We managed based on instinct, team velocity, and gut. I didn’t love the idea of getting this deep in the spreadsheet, so far out and at such excruciating detail. I honestly thought it might be a waste of time.

And I said it out loud: “This model is going to be wrong on day one.”

The partner I was working with nodded and said:

“Of course it will be. But when it is, we’ll know where to look.”

That was the unlock.

We weren’t trying to be right. We were building a way to run the business.

Not just to see where we missed—but to map the plan in excruciating detail.

Every step of the funnel.

Every user flow.

Every lever that mattered.

We built the model to answer hard questions before the business asked them.

To stop taking things for granted.

To make thoughtful assumptions about what we believed would happen—and what needed to happen to hit the plan.

Here’s what needs to happen.

Here’s how we’re going to make it happen.

Here’s where the leverage lives.

Doing that work upfront—painful as it was—de-risked execution. It forced alignment. It surfaced trade-offs. And it created a shared truth we could manage against.

It wasn’t fun. But it was one of the most useful things we did as a team. Now I better appreciate and have come to revel in that detail. Doing the real work.

The Work: A CEO Framework for Building a Real Operating Model

When I help a CEO build a model, we don’t start with a template. We start with a blank sheet.

I sit in front of an empty Google Sheet and walk through the revenue journey, end to end. Not at a high level—at the level of how the business actually works.

What happens first?

Where do leads come from?

What’s the next step?

What are the possible outcomes?

What happens after that?

One client and I recently built theirs from scratch, starting with:

• How does a prospect become a lead?

• When does that lead become a Marketing Qualified Lead (MQL), a Sales Qualified Lead (SQL), a Sales Qualified Opportunity (SQO) and then Closed Won.

• Then what happens post-sale? Onboarding, implementation, renewal, expansion?

We broke it down by channel. One path for inbound. One for outbound. One for self-serve. Each one has different steps, different drop-off points, different levers.

We didn’t guess. We wrote it all down. Line by line. Until we had a model that reflected the real business—not just the board version.

That’s the work. And it’s the CEO’s job.

Not because the CEO is the one who owns every input. But because the CEO needs to understand the whole system. Where it starts. Where it breaks. Where the leverage is.

This isn’t finance work. This is leadership work.

The best CEOs I know don’t hide from the detail. They live in it when they have to. They know you don’t get leverage by staying vague. You get it by doing the work.

And when the model is built right, it becomes the most powerful tool you have—not because it’s perfect, but because it’s useful.

You don’t build a model to be right.

You build it to be ready.

👉 Build the Model. Do the Work. Know the Business.

At AOL Local, I was running revenue for what felt like an incredibly complex machine. Hundreds of sellers. Local teams. Inside sales. Regional overlays. National partnerships. Dozens of products. I was deep in the chaos of it all—spinning out about some issue—when my Head of Sales, Jim Lipuma¹, stopped me mid-moment.

“Mark,” he said, “it’s a simple business.

• How many sellers do we have?

• How many deals do they close each week?

• What’s the average deal size?

That’s it.”

He wasn’t ignoring the complexity. He was building a bridge through it.

Because the truth is, every business has a simple math equation at the top. If you can’t write it down in a few lines, you’re probably too deep in the weeds.

Jim’s point wasn’t that the business was easy. It wasn’t. Hiring the right sellers? Hard. Keeping them? Hard. Helping them close? Really hard. But once you define the math, you know where to look. You’ve got a calm starting place. And when something’s off, you don’t panic—you zoom in.

Not enough deals getting done? Look at pipeline, close rates, pricing pressure, messaging, enablement.

Seller headcount too low? Look at recruiting, retention, comp structure, manager coverage.

Average deal size down? Look at discounting, packaging, competition, customer segmentation.

The math is simple. The drivers underneath it are not.

But that’s the point.

When you’re a CEO, it’s easy to get overwhelmed by the hundred dials you could be turning. You’ve got dashboards, updates, metrics, meetings—and everything feels important. The simple math gives you a way to start. It tells you which parts of the machine are working and which parts need your attention.

Start with your simple math. Are we Red, Yellow, or Green? If one number turns yellow, now you know where to look underneath.

I’m not saying this replaces the deeper model. You’ll need that too. (In fact, the next post is about exactly that—how we built a post-acquisition operating model for Bitly that broke everything down to the cell-level. Stay tuned.)

But this post isn’t about living in the model.

It’s about starting from the top.

It’s about building a bridge from calm clarity to informed action.

You don’t have to solve the whole machine at once.

You just have to find the math.

I remember the first time I interviewed a CTO. I brought in one of the partners from our lead investor—someone with a strong technical background—to help. At one point, he turned to the candidate and asked: “Imagine you’re standing on Earth. Spaceships to Mars leave every hour. Each trip takes X hours, and they return after a fixed turnaround. How many ships will you pass on your trip to Mars?”

It was one of those analytical brain-twisters meant to test how someone thinks. I gave it about ten seconds of thought before realizing: I WANT to solve it, but I’m not the best person to solve it. My job isn’t to solve that problem. My job is to hire someone who can. That was a real unlock for me. I didn’t need to pretend to be technical. I needed to be clear about what the company needed and find someone who could deliver it.

Most first-time CEOs don’t know how to interview a CTO. I didn’t either. I’ve now hired multiple technology leaders, some who helped us build real momentum, and one who lasted 30 days. This post is a distillation of what I’ve learned the hard way about evaluating technical partners.

If you’re a non-technical founder, it can feel intimidating. You’re supposed to know what great technical leadership looks like, but you can’t read their code or architect a system. So what do you do? Too often, CEOs just cede the whole conversation. They assume the CTO knows best and focus the interview on culture fit or vision alignment. That’s a mistake.

You’re hiring someone who will shape the future of your product, your company, and your team. You can’t afford to just hope you got it right. You have to ask better questions.

Here are mine. And before we get into the interview questions, here’s what else I’ve learned to look for:

First, I want to know if they can actually code—and if they still will. Are they jumping into problems on a Sunday at 3am when the system is down? Or do they need someone else to handle that? I’m not asking them to pull all-nighters every week, but I need to know they can go from strategy to keyboard when it counts.

Second, the tech itself matters—a lot. The best tech often wins. And when it comes time to raise money, sell, or even just explain your business to a strategic partner, the first thing they’ll ask is: is the tech real? Is it differentiated? Is it defensible? You can’t fake this. So I want a CTO who’s proud of what we’re building and holds the quality bar high.

And finally, I want to know what they’re curious about. What’s the last thing they built, even for fun? What’s the last thing they learned? You can’t teach curiosity, and I want someone who brings it with them.

1. Can they ship?

I once hired a CTO who couldn’t get us from zero to 0.1. We spent weeks debating platforms and tooling choices instead of putting product in front of users. That person was gone in 30 days. I learned that early-stage CTOs can’t just be smart—they have to be scrappy and pragmatic. Hands on. Committed to velocity over elegance.

So I ask:

“Tell me about a time you had a hard deadline for a product launch. What trade-offs did you make to hit it? What did you cut, what did you keep, and how did you make those calls?”

Then I listen for ownership, urgency, and realism.

2. Do they have range?

Early on, you probably don’t have a full EPD org. You might not even have a PM. I need to know my CTO can go end-to-end—front end, back end, infrastructure, cloud, and mobile. They don’t need to be an expert in all of it, but they have to know enough to build and enough to decide what not to build.

So I ask:

“When you’re building a new product—say in [insert your space]—how do you choose your stack? Walk me through your process: front end, back end, infra, mobile. What trade-offs do you consider, and how do your past experiences shape those decisions?”

And: "How do you think about balancing short-term speed with long-term scale? When have you had to make architecture decisions that supported a fast MVP now but wouldn't block future growth later?"

3. Do they understand the customer and the business?

I’m not looking for someone who just wants to write code. I’m looking for someone who wants to solve real problems. That means caring about customers, understanding competitors, and being able to work through ambiguity.

Some engineers want a finished spec. Others want to help shape the roadmap. Run from the ones who just want to be a cog — give me a spec and we’ll deliver types. You’ll be frustrted that they dont care about the business. They need to understand the customer, the market, and what the company is trying to achieve. I’m not looking for someone who just executes. I’m looking for someone who solves problems that matter.

So I ask:

“How do you get to know the customer and market when you join a new company? Do you prefer a clear spec, or do you want to help define the problem? How do you connect your team to the business goals?”

4. Can they recruit and retain talent?

The best CTOs are magnets for talent. They’ve worked with great people before, and they can bring them with them. I want to know who they’d call and if those people would actually pick up the phone.

So I ask:

“Who are the 3 to 5 people you’d try to bring with you if you took this job? Have you worked with them before—and would they join you?”

I also want to know how they build teams:

“What’s your approach to recruiting, especially when you can’t pay top of market? How do you sell the opportunity?”

5. Can they communicate?

Your CTO needs to talk to product, marketing, sales, and the board. They need to communicate trade-offs clearly, reset expectations when needed, and help the company make decisions.

So I ask:

“How do you keep non-technical stakeholders in the loop without slowing your team down?”

And:

“Tell me about a strong partnership you’ve had with a sales or marketing leader. What made it work—or not work?”

6. Who are they, really?

Every interview ends the same way. I ask the same four questions, no matter the role:

1. What’s your long-term career ambition?

2. What’s your superpower?

3. What’s something you’re not great at?

4. What would your last manager or CEO say about you in a formal review—especially constructive feedback?

You learn more in those answers than in any whiteboard exercise.

CEO Move:

Don’t outsource this. Just because you’re not technical doesn’t mean you don’t get to have an opinion. Stay in the room. Ask good questions. Know what your company needs—right now—and find someone who can deliver it. You don’t need to be an engineer. You need to be a CEO.

When your tech is great, everything gets easier. Fundraising. Hiring. Selling. You can feel it. So can everyone else.

Hiring a Head of Product is one of the most confusing interviews a CEO will ever lead—especially the first time. The resumes all look the same. The titles are all over the place. And worse: you’re often not even sure what kind of product leader you need. Are you looking for someone to build the vision? Ship what’s already on the roadmap? Or clean up a messy team dynamic?

Product leaders don’t work in a vacuum. The great ones show up ready to engage with your strategy, your customers, and your team—before the first roadmap is even written.

There are three key axes that define how a product leader works—and you need to know where your candidate lands on each one before you make the hire.

Builder vs. Refiner

Not everyone can build from scratch. Not everyone wants to. And that’s fine—as long as you know which one you need right now.

Builders are zero-to-one thinkers. They see opportunity in ambiguity, ask “why not,” and are energized by figuring it out. You want a builder when you don’t yet have product-market fit, are entering a new space, or need to define something from the ground up.

Refiners make what’s already there better. They tighten processes, ship cleaner product, and focus on efficiency, clarity, and iteration. You want a refiner when the direction is clear and the focus is delivery, scaling, or optimization.

The mistake: hiring a refiner when you need a visionary—or vice versa. You don’t want someone perfecting a product that isn’t working yet.

Operator vs. Innovator

This is bigger than “product vs. project.” It’s about whether your product leader is just managing throughput—or driving new thinking.

Operators keep the system working. They build teams, run rituals, track metrics, and bring predictability to delivery. They’re often excellent in complex orgs where coordination and clarity are essential.

Innovators challenge assumptions. They work upstream. They partner with you on what to build and why—not just when and how. They see around corners and take smart risks.

The mistake: mistaking an innovator’s ambiguity for disorganization—or expecting an operator to create a strategy from scratch.

Business Strategist vs. Product Craftsman

This one’s subtle—and where I’ve seen the some CEOs screw it up.

Craftsmen love great product. They obsess over flows, friction, polish, delight. And that’s good. But the best ones tie that work directly to business outcomes—retention, expansion, differentiation.

Strategists start with the business problem. They ask: what do our customers need to succeed—and how does that success power our success? They talk to Sales. They know how the company makes money. They understand that “delight” without conversion or retention is just aesthetic.

The mistake: hiring someone who builds beautiful things that don’t move the needle. Or worse, things that make your customers happy—but don’t keep them paying.

You don’t need someone who’s perfect across all three axes. You need someone whose default mode matches where your company actually is. And the only way to figure that out is to ask better questions.

The 5 Questions That Reveal Who They Really Are

1. “What questions do you have for me about our business?”

I’m looking for the questions you’d ask as if you were already the Head of Product here. What are you curious about? What have you already observed or assumed about our strategy, our customers, our challenges?

You’re not just making polite conversation. You’re testing for curiosity, preparation, and thinking. Did they form hypotheses before showing up? Or are they waiting to be spoon-fed information?

Red flag: “I didn’t want to make assumptions.” That sounds humble—but it’s usually a cover for weak prep or weak instincts.

2. “Tell me about a product you built or led. Walk me through the business problem, the strategy, the challenges, the wins, the losses, and the results.”

Be specific. What were the trade-offs? What do you wish you’d done differently? What results did it drive?

You’re listening for real-world experience, not just good storytelling. Do they own the hard parts? Can they talk about metrics, impact, and regret with equal clarity?

Red flag: All features, no outcomes.

3. “Tell me about a product you admire—ideally close to our space. What do you think makes it great? What does it teach you about strategy, trade-offs, or execution?”

What’s one thing that product gets right that we could apply here?

This reveals pattern recognition, curiosity, and whether they’re learning from the world around them. You’re looking for someone who dissects greatness—not just uses it.

Red flag: “I just love the design.” Cool, but… so what?

4. “Tell me about a time you drove a product forward through cross-functional work. What relationships made it successful—or not? What did you learn?”

Walk me through the actual situation—who was involved, where was the tension, how did you move it forward?

Great product leaders don’t live inside product. They live between product, engineering, sales, marketing, and customers. You’re looking for someone who knows how to get the messy stuff done—without hiding behind process.

Red flag: “I just kept everyone on the same page.” That’s not a story. That’s a sentence.

5. “Let’s talk about you for a minute…”

Ask these four to get the full picture:

a. What’s your long-term ambition?

b. What’s your superpower—what do people rely on you for?

c. What’s something you’re still working on—or not great at?

d. If I spoke to your last manager, what would they say your biggest growth area is?

You want to understand how they’re wired, how they grow, and whether they’re reflective enough to be coached and trusted at the highest level.

Red flag: “I care too much” or “I work too hard.” Nope. Be real.

Final Gut Check:

Would I trust this person to own the product, the team, and the learning—right next to me every day?

The CEO Move

Hire the product leader you want next to you every day, solving the same problem you care about most.

Not someone who’s just great at product. Someone who’s great at building this product, this way, with you. If you’re not aligned on what the company is here to do, it won’t matter how good they are.

“The hardest thing isn’t finding someone great—it’s finding someone great who wants to solve your problem.”

🚧 This is (maybe) the first post in a new series I’m exploring: How To Be a CEO. 🚧

I’m thinking about building a library of tactical, real-world guides for CEOs—based on what I’ve learned as a 3x CEO and coach. No fluff. No generic advice. Just practical tools, hard-won lessons, and real examples.

Starting with hiring and managing senior execs. If this is helpful—or if there’s something you want me to cover—let me know.

I read every reply.

—

One of the most common mistakes I see CEOs make is treating job descriptions like a box to check. They copy and paste from a website, slap a few bullets on top, and wonder why they’re not attracting the right candidates. Especially at the senior level, this is a big miss.

I’ve been there and I get it. By the time you’re hiring an exec, you’re usually already underwater. You’ve been shouldering the function yourself, or you’ve outgrown your current team, or someone just left and you’re scrambling. You’re under pressure. Time matters. You want to move fast.

I spoke with Rohan Vaidya, Head of Talent at Writer (formerly at Ramp, Teachers Pay Teachers, and Facebook) about this. He's worked with CEOs and hiring managers through amazing fast growth and pivots, and here's what he said that stuck with me:

“Most exec job descriptions fall into two traps: too vague or too bloated. The best ones are sharply focused on outcomes, not activity.”

This is exactly right.

Writing a job description isn’t just about outlining a role. It’s a strategic act of leadership. It’s your chance to get clear about what the business truly needs next. It’s your first signal to candidates about how you operate. It’s your shot to attract someone great—not just someone available.

A good job description is thoughtful, specific, and rooted in the truth. It defines expectations. It tells a compelling story. And it sets the tone for everything that comes next—how you hire, how you onboard, and how you manage.

Let’s break it down.

Describe the Company Like It Matters

Most JDs treat the company description like an afterthought. But for senior hires, who you are and why you exist are part of the job. They’re signing up for your mission and your way of working—not just your comp package.

So be clear. Be specific. Be human.

What to include:

• What you do (in plain English—ditch the jargon)

• Why it matters (what change you’re trying to make in the world)

• Where you’re at (stage, momentum, growth, size, funding)

• How you work (values, culture, leadership tone)

This is your moment to set the tone. Candidates don’t just want to know what the company does—they want to know how it feels.

Examples:

Castiron is a software platform built for independent food artisans. We help small food businesses thrive by giving them the tools they need to sell online, manage orders, and grow sustainably. We’re a small, mission-driven team that cares deeply about entrepreneurship, economic inclusion, and real human connection. We just raised our Series Seed and are growing quickly—but thoughtfully.

We’re a post-Series B SaaS company helping enterprise teams convert more site traffic through smarter personalization. Our platform combines experimentation, machine learning, and customer behavior tracking. We’re 60 people, remote-first, and intensely focused on outcomes over optics. Our culture is high-trust, low-ego, and dead serious about learning fast.

Share Your Values—Clearly and Specifically

Every company should have values. They’re not just internal slogans—they’re a signal to candidates about how people are expected to work, behave, and lead.

Senior execs aren’t just responsible for driving results. They shape the culture. They model the behavior. They become the “how we do things here.” So if you don’t tell them what that is, you’re leaving a massive gap—and risking a costly misfire.

Include the values you actually use—not the ones you wish you had. Keep it simple, specific, and real.

Examples of values that work in job descriptions:

Customers First, Always — We build with the people who use our product in mind. We solve real problems, not theoretical ones and always choose what is best for our customers.

Win as a Team — We don’t do heroics. We collaborate, share wins, and support each other when things get hard.

Go the Extra Mile — We take pride in the quality of our work. We sweat the details, deliver on time, and always push for better.

Clarity Over Consensus — We make decisions, move fast, and own outcomes. We listen, but we don’t stall.

No Surprises — We communicate early and often. We say the hard things, directly and respectfully.

You don’t need a paragraph for each one. But you do need to show candidates what matters to your team—because you’ll be holding them to it.

Sell the Opportunity

The JD isn’t just an internal doc—it’s a sales sheet. You’re selling the role, the team, the mission, and the chance to do something meaningful.

What makes this opportunity special? What kind of impact could this person have? What’s the personal upside—career-defining impact, wealth creation, purpose?

Here’s what that can look like in different contexts:

Bitly was about global scale, data, and influence. We told candidates:

“You’ll help make sense of one of the largest real-time data sets in the world—we deal in billions and billions—and shape how the internet moves.”

Castiron was about purpose and impact. We said:

“You’ll be building tools that help small food entrepreneurs—most of them women and people of color—run real businesses on their own terms. We’re trying to help them put food on their tables and to live the lives they want.”

Early-stage B2B SaaS might be about shaping the business from the ground up:

“This is a 0→1 opportunity. You’ll define the motion, build the team, and create the infrastructure for scale. What you design now will become the foundation of this company.”

Later-stage growth companies might highlight complexity, career inflection, and upside:

“We’re Series C, growing fast, and looking for someone who’s ready for a seat at the exec table. You’ll work directly with the CEO and board, lead a team of 15+, and have real equity in the outcome.”

Great execs don’t want a job. They want a mission. Show them why this one matters.

Start with the Problems

Once you’ve set the stage, now you tell them the truth about the real work ahead.

Senior execs don’t get hired to “run a function.” They’re hired to own big, complex business problems—ideally, problems you as the CEO no longer want to be solving yourself.

Ask yourself:

What are the 2–3 meaty business problems this person will be responsible for solving?

Examples:

– Our churn rate is too high and we don’t have visibility into why and we need a clear product roadmap to drive engagement and growth.

– We’ve never had a marketing engine—growth is all outbound.

– Our finance function can close the books, but can’t forecast and is not a partner in helping us grow the business.

What does success look like in this role?

Examples:

– Product is consistently shipping product that drives our business. Always on time and always with an impact.

– The GTM team has a predictable pipeline generation, forecasting, and closing model we can trust.

– We present financial plans to the board that actually hold up.

What would I expect them to teach me?

Examples:

– How to think about CAC and LTV in a multi-channel business.

– What makes a world-class product review process.

– How to build a comp plan that actually motivates sales.

This is how you move from “we need a VP of Product” to “we need someone who can solve this.”

Define Expectations, Not Just Responsibilities

Most job descriptions rely on vague verbs: lead, manage, own. Be more specific.

Instead of this:

– “Lead marketing strategy and execution.”

Say this:

– “Own end-to-end funnel performance, from awareness through retention.”

– “Accountable for:

• A 20% increase in qualified pipeline within 3 months

• A content strategy that drives at least 25% of inbound

• Building a 5-person team without ballooning CAC”

Clear expectations create alignment, attract better candidates, and make onboarding easier.

Be Real About Requirements

Yes, experience matters—but only if it’s tied to what the business needs now.

Sometimes you need someone who’s seen the movie before. Other times, you want fresh thinking. But don’t hide behind phrases like “10+ years in a high-growth environment.”

Instead, say:

– “Has built and led a 10+ person product org.”

– “Has owned board-level communication and investor updates.”

– “Has successfully scaled from $5M to $25M ARR.”

This is about miles on the road—not just titles on a resume.

Make It Beautiful and Thoughtful

The JD is your first signal of how you lead. If it’s vague, messy, or uninspired, that’s what your company will feel like.

Put in the effort. Tell a compelling story. Set the tone for how you work and what you expect. You’ll attract people who resonate with that—and save everyone a lot of time.

Pro-Tip.

This one comes from Rohan:

“Collaborate with the senior exec you’ve identified. Sometimes the JD you start with needs to be tailored as you get to the hire, and getting input and alignment is key to driving towards success.”

###

“We need to improve sales.”

“I want to communicate more clearly.”

“We should improve morale.”

They sound fine. But they’re not real goals. They’re vague intentions. Hopes, really. Which means they’re hard to rally around, hard to measure, and even harder to achieve.

My son Henry, wrote something recently that nailed it. It was part of a college advice post he shared, and this line jumped out:

“Set goals you can fail at. If a goal isn’t falsifiable, it isn’t actionable.”

That’s it. That’s the test. If you can’t fail, you haven’t really committed. You’ve just said something that sounds good. And when a goal is that soft, no one knows what success looks like — including you.

I’ve always liked SMART goals. I know, they sound like they came out of a corporate handbook, but they’ve stuck around for a reason. Specific, measurable, achievable, relevant, time-bound. It’s not complicated. It’s just clear. And that clarity forces decisions. That’s what real goals do.

“Get better at writing” is not a goal.

“Publish two blog posts a week for a month” is.

You either did it or you didn’t. That’s the power of a falsifiable goal — it holds you to something. And if you miss? Great. Now you’ve got a data point. You can adjust. You can try again.

Same thing at the company level.

“We need to improve culture” doesn’t mean anything.

But “Hold ten RealTalk™ check-ins with team leads this month and summarize what we hear” — now we’re getting somewhere.

“Ship better product” is vague.

“Release the new onboarding flow by May 1 and increase conversion by 10%” is concrete.

“We should publish more content” — maybe, but what does that mean?

“Ship one customer story per week for the next four weeks, each with a call-to-action and a click-through rate above our baseline” — now we’re talking.

The more specific and falsifiable your goals are, the more useful they become. Because now you’re accountable. Your team’s aligned. You know what to do, how to measure it, and whether you got there. If you missed it, you can have an honest conversation. If you hit it, you can celebrate.

And no, not everything has to be this crisp. Vision can be soft. Strategy can be fluid. But execution? Execution needs edges. Otherwise, you’re just wandering and calling it progress.

So next time you set a goal — for yourself or your team — ask the question my number one son, Henry posed:

Can I fail at this?

If the answer’s no, keep going. You’re not done yet.

Here’s the original post from Henry that inspired this.

Hat tip and #prouddad to H.

##

The business is doing okay. Not broken. Not failing.

But… you know it’s not going to take you where you need to go.

Growth has slowed. Competitors are catching up. The strategy that used to work doesn’t hit like it used to.

And you know—deep down—something major needs to change.

But here’s the problem: you’re not running a prototype. You’re running a business.

You’ve got real customers, real revenue, a real team.

You’ve got investors. You’ve got a board. You’ve got a team of people who rely on you.

You have a responsibility to protect what you’ve built.

You don’t get to burn it down because you had a feeling.

And yet… sometimes you know.

You just do.

The levers feel dull. The story doesn’t land like it used to.

The market’s moving.

And the question starts to whisper:

That’s what Nick Francis, CEO of Help Scout, found himself facing.

A thriving company. Loyal customers. A strong product.

But over time, the foundation—the business model itself—started to feel misaligned.

The per-seat pricing model they’d used for over a decade was limiting growth, clashing with their values, and drifting out of sync with how customers actually work.

And then the world changed.

The AI wave hit customer support head-on. Tech budgets shrank.

Customers started trimming seats. Competitors leaned into bots and deflection.

Help Scout—a company built on people-first support and customer delight—was caught in the middle.

Nick knew it was time.

But knowing isn’t enough. Especially when you’re talking about a decision that could upend everything.

So he did the work.

Over 14 months, Nick and his team:

• Modeled the new pricing structure across thousands of existing accounts

• Simulated historical data to understand how usage-based billing would’ve performed

• Pressure-tested different value metrics (they landed on unique contacts per month instead of seats or tickets)

• Designed rules like a rolling 3-month average to smooth billing volatility

• Piloted the model quietly on live sales and renewal calls

• A/B tested freemium pricing against paid trials

• Built a full go-to-market plan around the new pricing

• Partnered with Andy Raskin to craft a strategic narrative that could carry the weight of the change

• Re-trained the sales team, one call at a time

And they didn’t do it in a vacuum.

Nick brought the board along—slowly, methodically.

He listened to consultants. He heard their warnings.

Then he chose to ignore them.

Because he wasn’t making a hunch-driven bet.

He was acting on something he’d known for years—but had finally done the work to prove.

And that’s the real lesson here.

Being bold doesn’t mean being impulsive.

Being deliberate doesn’t mean playing it safe.

It means taking the time to understand what’s true—and then having the guts to act on it.

Most CEOs want to hedge.

To experiment quietly.

To optimize what they have instead of risking what might be.

And sometimes that works.

But other times, the only real move is to go all in.

Burn the boats.

Not because you’re fearless.

But because you’ve done the work

If you’re in the middle of your own “not broken, but not quite right” moment, I highly recommend listening to the full conversation with Nick on my podcast Critical Moments. It’s one of the clearest, most honest examples I’ve seen of a CEO making the hard call—and doing it the right way.

🎧 Listen here: https://mbj.im/nick-francis-pod

💬 Let me know what you think—or share your own “bet the company” story.

And if you’re enjoying these posts, you can follow Critical Moments wherever you get your podcasts. Every episode is a story of a real leader, at a real inflection point, making the calls that shaped everything.

Also, please let me know your thoughts. I am hungry for feedback!

We cover the actual work:

How to hire execs. How to manage them. How to build and run a company function by function—Product, Sales, Finance, Engineering, HR. How to set expectations, review performance, run a board meeting, inspect a pipeline, align a roadmap with GTM, or have the compensation conversation you’ve been avoiding.

Every post is grounded in real experience, and every one is written to help you move faster, with more clarity.

Already live:

• How to Write a Job Description for a Senior Exec

• How to Interview a Product Leader

More are coming soon. If there’s something specific you want covered—or something you’ve been struggling with—reach out and tell me. I’m building this to be the resource I wish I had every time I sat in that chair.

✌️🔥

I’m not sure that’s totally true, but I do know this—there’s a constant struggle to find balance. To be a great parent and a great partner and still deliver at the highest levels. To stay ambitious, stay available, and stay human.

Being a CEO only makes that harder. We often believe we have to be the hardest-working, most committed person in the company. That everything else should take a back seat. That anything less is weakness.

But when our identity becomes inseparable from our job, we lose something important.

Chris Gannett reminded me of that. Back in 2011, he was the Chief Marketing Officer of Core Media Group, the parent company of American Idol and other major global entertainment properties. It was high-stakes, high-gloss, high-pressure work.

On October 19th of that year, he was in Los Angeles at a media dinner with Idol talent and production partners. But it was also his twin sons’ first birthday. He wasn’t home. He was 2,500 miles away.

He told himself they wouldn’t remember. That he didn’t have a choice. That this was the cost of success.

One of the Idols offered to sign headshots for his sons. She wrote a birthday message to each of them. Chris still keeps those photos on his shelf today. Not as memorabilia. As a reminder.

Not of the moment itself, but of what that moment revealed.

He didn’t make a huge change the next day. Most of us don’t. But over time, more moments stacked up—including the loss of his father and the collapse of a business during COVID—and eventually, he started listening harder. To his kids. To his wife. To himself.

And he acted.

Chris and his family relocated to Dallas to be closer to extended family. He left behind a coast-based career track and started commuting to New York weekly, trying to bridge the gap. But it still wasn’t enough. When his son told him he felt like his dad lived in New York and just visited on weekends, something clicked.

So he changed the business he was in. He bought into a local experiential marketing firm. When COVID decimated that company’s business model, he pivoted again—this time not just professionally, but personally. He listened instead of solved. He grieved instead of just moving on. He got quiet enough to ask: What do I actually want now?

That led to something new.

Chris left the business. He got certified as an executive coach. He didn’t just reinvent his job—he re-centered his identity around values that had once taken a back seat.

This episode of the podcast isn’t about dramatic life overhauls. It’s about noticing the quiet moments that tell us something’s not working—and having the guts to do something about it, even if it takes years.

Your career doesn’t have to cost you your identity.

You’re allowed to want something else.

You’re allowed to write a different story.

Chris did. You can too.

🎧 We talk about all of this—and a lot more—on this week’s episode of Critical Moments. It’s one of the most honest conversations I’ve had. I hope you’ll give it a listen: http://mbj.im/pod

If you’ve ever felt torn between who you are and what your job demands, this one’s for you.

And if you’re in a moment like that right now—feeling the tension, sensing the drift—don’t ignore it. Talk to someone. Reassess. You don’t have to make a big leap today, but you owe yourself a clear look at what matters most.

Hit reply if this hit something for you. Or forward it to someone who’s been carrying too much for too long. Sometimes hearing someone else name it is the first step toward change.

We get stuck when we don’t know what’s next, or when the future feels too big, too vague, too out of our control. Whether it’s work, family, health, money—uncertainty can creep in and eat up your energy before you’ve even taken a step. Sitting in front of that big unknown can be very scary and overwhelming.

What helps?

A plan.

Not the perfect plan. Not the guaranteed-to-work plan. Just a plan. Something to run. A playbook. A starting point.

For me, I’m building a new business from zero—a coaching practice and a new career. That’s a lot of unknowns. And it’d be easy to spin out. But I’ve got a plan. I’m treating it like a SaaS business. I have revenue goals and to achieve them, I need leads, I need qualified opportunities, I need to know my ICP, etc... So I’m borrowing from what I’ve done before—sales, marketing, positioning, pricing—and applying it here.

Is it going to work? I have no idea. But I’m not stuck wondering. I’m working the plan.

The plan gives me direction. It helps me measure progress. And most importantly, it gives the anxiety less room to breathe.

This isn’t a post about what your plan should be. It’s about having one.

You can always adjust. But you can’t adjust something that doesn’t exist.

If you’re in the “sort of” or “not yet” camp—what’s holding you back? Hit reply or leave a comment. I read every one.

I’d love to hear from you.

The integration is done.

Nick Gould found himself there. After building a respected UX firm, selling it, then selling again, he had done everything “right.” But what followed wasn’t relief. It was disorientation.

I’ve seen this before in my career and now in coaching—especially with founders. When the work ends, the identity you’ve wrapped around it starts to unravel. And what you’re left with isn’t clarity. It’s space.

Here’s the truth:

We’re not taught how to just be in that space.

We’re taught to achieve. To climb. To move forward.

But when the old path ends, the next one doesn’t appear on command.

Three things Nick’s story reminded me:

1. Titles are a trap.

You’re not your role. But it’s easy to forget that when the work has defined you for decades. Letting go of a title isn’t just about a job—it’s about releasing old versions of yourself.

2. The in-between is where the growth happens.

Transitions aren’t clean. They’re messy, emotional, and disorienting. But if you can sit in the discomfort and do the inner work, the clarity that emerges will be stronger and more authentic than any resume refresh.

3. Your next chapter probably won’t look like your last.

Trying to recreate your old success in a new wrapper rarely works. Reinvention means going deeper—figuring out what truly drives you now, and building from there.

Nick didn’t just find a new job.

He found a new way of working. A new kind of leadership.

One rooted in purpose, presence, and truth.

After months of deep reflection, he stepped into a product leadership role at 2U, a high-growth edtech company. It wasn’t a carbon copy of his past—it was a pivot that honored the parts of his experience that mattered most. His curiosity about what makes a product truly work. His desire to build. His ability to navigate complexity and lead with clarity.

But what really made the difference wasn’t his resume. It was how he showed up.

Nick brought with him the sensibilities of a founder—accountability, urgency, adaptability—but paired it with something quieter and more powerful: executive presence. The ability to walk into a room, listen, and instill confidence. Not with noise, but with calm. Not with ego, but with conviction.

And over time, that way of being—rooted in service, reflection, and intentionality—became the foundation of his coaching work.

Today, Nick helps other leaders navigate their own critical moments. Not by giving them a playbook, but by helping them write their own. He’s proof that your next chapter doesn’t have to look like your last to be meaningful. It just has to be real.

Listen to our conversation here: https://mbj.im/pod and wherever you get your podcasts.

Anne Lamott, in her book Bird by Bird, coined the phrase “shitty first draft.” She describes it as the rough, messy, and completely unfiltered version of your work—the kind no one ever sees. It’s where you get your thoughts down without worrying about how polished they sound. Because the truth is, the real work comes later.

The magic of the shitty first draft is that it frees you from perfectionism. You’re not trying to impress anyone. You’re just getting the ideas out. And once they’re out, your brain can keep working on them in the background. I’ve found that stepping away—even for a few hours or overnight—can lead to those sudden flashes of insight when you least expect them. The next time you sit down, it’s not a blank page anymore. It’s something you can shape.

This isn’t just for writing. I’ve noticed the same thing happens when I do crossword puzzles. I’ll stare at a clue, convinced I’ll never get it. Then I walk away, and later, while I’m doing something totally unrelated, the answer pops into my head. It’s like my brain was still working on it in the background without me realizing it. The same thing happens with writing.

When I have a big presentation or a challenging piece of writing to do, I try to start at least a week in advance. I’ll bang out a shitty first draft, knowing it’s not even close to good. Then I revisit it a couple of times a day, tweaking and refining. After a couple of days, something shifts. Suddenly, I see things I didn’t see before. I find better words, clearer ideas, sharper points. The version I end up with is so much better than if I had tried to get it all right the first time.

The trick is trusting the process. Your brain is an incredible problem-solving machine, and sometimes it just needs space to do its thing. Letting that first draft sit for a bit can be like giving your brain an assignment and telling it to check back later with the answer.

So, the next time you’re staring at the blinking cursor, give yourself permission to write something terrible. No one has to see it. You can clean it up later. Let your brain do its thing, and trust that each pass will get you closer to something you’re proud of.

And hey, this post? Shitty first draft. Probably second or third, too. But it’s out there now.

“I knew it.”

They knew the person they hired wasn’t right, even in the interview.

They knew that a top employee was halfway out the door.

They knew the customer wasn’t going to renew, no matter what the Customer Success team said.

But they didn’t trust themselves.

They second-guessed.

They deferred to the group.

They didn’t want to come in “too hot” and get feedback about “too much micromanaging”

And then it played out exactly the way they feared.

Here’s the thing: that spidey sense? That gut feeling? It’s not magic.

It’s real. It’s earned. And it’s almost always right.

You’ve likey been in more meetings, seen more hiring cycles, watched more customer journeys. You’ve had the hard conversations, the good exits, the disastrous ones. You’ve heard every excuse and reason. You’ve been burned. You’ve been surprised. You’ve seen the patterns—and your brain has stored all of it.

That’s what gut instinct is.

Not some mystical sixth sense. It’s pattern recognition.

It’s a fast, subconscious sorting of all the data you’ve picked up over time—too complex or subtle to always articulate, but real nonetheless.

There’s academic backing for this, too. Nobel Prize winner Daniel Kahneman, in Thinking, Fast and Slow, breaks down the two systems of thinking:

• System 1 is fast, intuitive, emotional.

• System 2 is slower, deliberate, logical.

We tend to elevate System 2—because it feels more rigorous. But when you’re experienced, System 1 becomes incredibly powerful. That fast gut check is often the result of hundreds of System 2 decisions baked into instinct.

Gary Klein, a cognitive psychologist who studied how firefighters and ER doctors make split-second decisions, calls it recognition-primed decision making. The most experienced people make the best calls in high-stakes moments—not because they stop and run the numbers, but because they’ve seen this before.

Your gut is not to be ignored. It’s not infallible, but it’s not woo-woo either.

It’s a competitive advantage.

Yes, you should ask questions.

Yes, you should listen to your team.

Yes, you should stay open to being wrong.

But don’t gaslight yourself.

When your spidey sense tingles, lean in. Name it. Pressure-test it. Talk about it. Don’t bury it because it makes other people uncomfortable.

That instinct may be the exact thing that saves you from the next bad hire, customer loss, or team departure.

You’ve earned your gut.

It’s time to trust it.

###

P.S. If it made you think, feel, or nod your head—please share it with someone else who’d get value from it.

And if you’ve got thoughts or a story of your own, I’d love to hear it. Just hit reply.

And they’re not wrong—real urgency is critical to winning.

Founders and CEOs often have a real sense of urgency because they see the vision so clearly. They know what’s at stake, they feel the weight of responsibility, and they understand the cost of inaction. Their urgency isn’t about panic—it’s about clarity.

But here’s where it falls apart:

• Complacency = “Things are fine.” No real drive for change.

• False urgency = Panic, chaos, and reaction. It looks like urgency—meetings, Slack messages, late nights—but it’s just noise.

• Real urgency = Clarity, focus, and momentum. Moving fast in the right direction, for the right reasons.

This is where things get tricky. When a CEO tries to push urgency onto a team, it often feels like pressure and fear instead of clarity and opportunity.

A CEO sees the market shifting and needs the team to act fast. They tell everyone, “We’re running out of time! We have to move NOW!” Suddenly, teams are scrambling, stress levels spike, and people start covering their asses instead of executing.

This isn’t urgency. It’s false urgency. The team isn’t focused on winning—they’re just trying not to lose.

If you’re a CEO or leader trying to build urgency, ask yourself:

1. Are you leading with clarity or just demanding faster activity?

2. Does your team see the opportunity, or just feel the pressure?

3. Are they running toward something exciting, or running away from failure?

Urgency isn’t about scaring people into action or demanding more. It’s about helping them see what you see. It’s about making the mission so clear and compelling that people feel personally responsible for making it happen.

Because the truth is, people don’t move fast because they’re scared. They move fast because they believe.

###

It’s easy to assume that once you’ve communicated the mission, vision, values, and strategy at a kick-off event, everyone’s on the same page and that part of your job is done.

I still remember things Scott Kurnit, the founder of About.com, drilled into us more than 20 years ago. One in particular stands out: the inverted pyramid of audiences we prioritized. (“Guides, Advertisers, Investors, Team”) I heard him say it over and over, in different ways, in different contexts. And because of that, I never forgot it. Repetition doesn’t just help people remember—it makes it impossible for them to forget.

As a CEO, what kept me up at night wasn’t competition, market shifts, or the latest crisis. It was wondering if the team really knew what we needed to do. I always (mostly) felt great after big events. We spent time planning the message and delivered it clearly. Everyone was on centerline — the exact same page.

Then we leave the meeting and inertia starts pulling people off that centerline. It’s not that people don’t care or aren’t listening—it’s just that gravity and the reality of day-to-day lives pulls you apart.

If you’re not constantly bringing your team back to the center, they’ll naturally start pulling in different directions and you are at risk of missing your plan.

So, how do you keep everyone focused and aligned without sounding like a broken record?

• Be consistent, not robotic. Say the same thing in different ways. Use stories, data, examples, and metaphors.

• Vary the delivery. All-hands meetings, one-on-ones, Slack, emails, town halls—hit every channel.

• Tie everything back to the mission. Decisions, priorities, wins, failures—connect them all to the bigger picture.

• Don’t assume understanding. Ask people to repeat back what they heard. You’ll be surprised by the gaps.

Constant repetition isn’t a sign of failure. It’s actually how people learn. The Economist recently wrote about this same problem at work. Leaders often feel like they're repeating themselves too much, but they're probably not doing it enough. (Read more here)

Saying something once isn’t communication. It’s a memo. Saying it a hundred times—that’s leadership.

And I guarantee you that even when you feel you’ve nailed this you’ll get surprised by someone who swears that it’s news to them. 🤷‍♂️

###

Once I have my three main points, everything else gets easier—I can riff, expand, contract, whatever the situation calls for.

When I was pitching Castiron, my three points were:

1. The world of work is changing

2. Independent food sellers have probelms we can now solve

3. My career has led directly to this moment

Once I had those three, I added three under each of those:

1. The world of work is changing

   1. Multi-hypenate careers (nurse AND yoga teacher, accountant AND baker)

   2. >50% of workforce works for themselves

   3. >1,000,000 independent food sellers exist

2. The independent food sellers have addressable problems

   1. No system of record

   2. No scalable distribution

   3. No “co workers”

3. My career has led directly to this moment

   1. Community and network effects at About.com

   2. Hyperlocal commerce and moentization at Outside.in and Aol/Patch

   3. SaaS and PLG at Bitly

But, when I started my coaching business, I did it backward. I had pages of notes, a long-winded pitch, way too much going on. Forget about all the copy on my website. Then I forced myself to find my three. And now? Everything’s clearer. My message is tighter. I don’t have to think about it—I just know.

Now, when I’m asked “Why Mark?” for a coach, here are my 3:

1. I care deeply for my clients.

Like, really care. My clients’ success matters to me on a deep, personal level. I have their backs so fucking hard. This is a super power of mine, and something I need to keep an eye on. If you mess with my family, my friends, or my clients, I respond strongly.

2. I’ve had their job.

I know what it’s like. The stress, the pressure, the highs, the lows, the nonsense. Sometimes my calls are at 8 AM on a Sunday. 🤷 There is unlikely to be something we talk about that I haven’t seen before. Real empathy.

3. I have an opinion.

If you want someone who only asks questions and never takes a stance, that’s not me. I’ll listen, but I’ll also tell you what I think—based on real experience.

Once I had these three locked in, everything else got easier.

If you’re struggling to explain something—your pitch, your leadership philosophy, whatever—try getting it down to three. It forces clarity. And once you have them, you’ll never feel lost in your own message again.

What are your three?

###

Everyone in my family, is, though — both my parents, my brother, and my sister-in-law.

I have learned so much from them.

Recently, my sister-in-law taught me about Mentalization.

It might sound a bit academic, but it’s simply the ability to understand and interpret the thoughts, feelings, and intentions of others.

Some people are natural mentalizers—you know them. They’re the ones who listen deeply, focus on you when you’re talking, and ask the kinds of questions that make you feel truly heard and understood.

These are the people who make you feel like the only person in the room, even in a crowded meeting. They’re present, engaged, and their questions aren’t just for show—they’re designed to deeply understand where you’re coming from. They create an environment that feels supportive and constructive, even when the conversation is tough.

My mother was one of these gifted mentalizers. She had an uncanny ability to tune into the emotional currents of a conversation, to understand what was being said—and what wasn’t. She made people feel seen and valued, and it’s something I’ve tried to emulate in my own life.

For me, mentalization is about imagining putting myself in the shoes of the person I’m meeting with. I ask myself: What are they thinking? What do they need? What might they be trying to accomplish? When I force myself to take the time to consider these questions, it helps me understand the other person better, which in turn helps me guide the conversation toward a better outcome.

Mentalization allows you to build trust. When people feel understood, they’re more likely to trust you. Trust is the foundation of any successful team or company. It also enhances communication. By understanding the needs and motivations of others, you can communicate more effectively. Your messages are more likely to resonate and be well-received.

It fosters collaboration. When you’re able to see things from another person’s perspective, it’s easier to find common ground and work together toward a shared goal. And it helps navigate conflict. In times of disagreement, mentalization can help you de-escalate tension and find solutions that respect everyone’s needs.

While some people are naturally good at mentalization, it’s a skill that can be developed. Here are a few ways to cultivate it in your daily leadership practice:

• Listen more than you speak. Make a conscious effort to actively listen when others are talking. Pay attention not just to their words, but to their tone, body language, and what might be going on beneath the surface.

• Ask open-ended questions. Instead of asking yes or no questions, try to ask questions that encourage the other person to share more about their thoughts and feelings. For example, “What’s your take on this?” or “How do you feel about that?”

• Reflect on conversations. After meetings or interactions, take a moment to reflect on what was said. Consider the other person’s perspective and think about how you could respond in a way that acknowledges their needs and concerns.

• Put yourself in their shoes. This might sound cliché, but it’s powerful. Literally imagine yourself in the other person’s situation. What would you want or need if you were in their position?

The next time you’re in a meeting or a conversation, try practicing mentalization. Consider what the other person is thinking, what they need, and what they’re trying to achieve. You might be surprised at how much more effective your interactions become.

For more on the concept of mentalization, you can read this article on Wikipedia.

###

First, it was awesome to be at HBS. I loved EVERY minute of it. It makes me think about teaching some in this next chapter.

Second, watching the students work through these tough conversations was a reminder that these aren’t just theoretical exercises—co-founder negotiations set the tone for relationships that can last a decade or more. The way you negotiate now determines how you’ll work together when things get hard. And they will get hard.

At the end of the exercise, I asked each class:

“Raise your hand if you feel like you won your negotiation.”

A few hands went up.

“Now raise your hand if you feel like you lost.”

A few more hands.

But here’s the real question: If one of you “wins,” what does that mean for those that lost…. and for the overall value of your company?

A few learnings:

1. Winning ≠ Building

Too many people approach these conversations like a competition—trying to “win” at their co-founder’s expense. But negotiations between co-founders aren’t about one person coming out ahead. They’re about creating enterprise value together. If you act like an asshole now, or if your co-founder treats you like one, it won’t be a one-time thing. It will show up again and again in your working relationship. Trust me.

2. Equity ≠ Control

During the exercise, I watched teams fight for every last point of equity, thinking it would give them more authority. The truth? Equity and operational control are two different things. Shares are rarely voted except during major moments— like company sales and fundraises. Day-to-day, control lies with the CEO. And if you fight for equity at the expense of your co-founder, you might end up with a big slice of nothing. 51% of zero is still zero.

3. Clear Decision-Making Authority is Everything

One of my mentors used to walk into meetings and ask, “Who’s in charge here?” If the answer wasn’t obvious, that was a problem. Consensus might feel good, but it kills startups. Someone has to have the final say. Forget about “co-CEOs”—they almost never work. If there’s no clear decision-making structure, small disagreements turn into massive roadblocks.

So, the way you negotiate with a co-founder is the way you’ll work together. If you don’t trust each other now, you won’t trust each other when the stakes are real. If you fight over scraps today, you won’t build something worth fighting for tomorrow. And if you can’t agree on who’s in charge, your company won’t make it.

Co-founder relationships can last 10 years or more. The choices you make in these early conversations don’t just shape the deal—you’ll be living with them for a long time. Choose wisely.

Would love to hear from founders—how did your early negotiations shape your partnership?

###

You justify it to yourself: “They should know better.” “Maybe it’ll get better on its own.” “I’ll deal with it later when the timing is better.”

Spoiler alert: it never gets better on its own, and the timing is never perfect.

The truth is, by avoiding these conversations, you’re doing more damage than you think. Not just to your team or your company, but to yourself.

I once heard a great line from a client’s 360 review:

This hit me hard because it’s true. When you hold back, people know. They feel it. Your body language gives you away. Your tone changes. You’re not as present or engaged. It is obvious.

Even if you think you’re sparing someone’s feelings or maintaining harmony, you’re creating an undercurrent of tension and mistrust. Your team starts to sense that something’s off. They might not know what, but they feel it. And it impacts them.

Why do so many CEOs and leaders avoid these hard conversations? It’s usually because they don’t want to be the bad guy. They don’t want to deal with the discomfort. They’re worried about damaging relationships or hurting someone’s feelings.

Or they think they’re making a trade-off for other short-term priorities. “I just need them to close the quarter and THEN I’ll give them this rough feedback.”

But here’s the kicker: by avoiding it, you’re doing all of those things anyway—just slowly and quietly.

I’ve seen this play out time and again, which is why I always come back to RealTalk™. It’s about being direct, candid, and honest. It’s about getting to the point without dancing around the issue. And yes, it can be uncomfortable. But it’s also liberating.

Having the hard conversation not only clears the air but builds trust. It shows your team that you respect them enough to be honest. It sets clear expectations and paves the way for growth.

As Mike Vrabel of the New England Patriots said, “great players want to be told the truth.” This resonates because it’s about respect. If you truly care about someone’s growth and success, you owe them honesty—even when it’s uncomfortable. Especially then.

I get it. It’s hard. But the longer you wait, the worse it gets. The stakes get higher, the issues get bigger, and the tension grows thicker.

So rip off the band-aid. Have the conversation. Say what needs to be said. And then listen. Really listen.

Because there’s a lot of content in the unsaid—but there doesn’t have to be.

###

"I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel."

Maya Angelou

I was reminded of this quote recently.

There is someone in my life and career who has been incredibly important to me. Instrumental in so many ways. And I fucked up an important interaction with them.

At the time, I thought I was handling it well. I remember it as a complicated and delicate conversation. But looking back, I was focused and in my head more on delivering a message—on saying what I thought needed to be said—rather than truly understanding how it would land. My approach, my words, my delivery—they didn’t work. It hurt them. And as a result, it hurt our relationship.

After a couple of years and a pretty rough conversation, we eventually cleared the air. But in doing so, they reminded me of something I should have already known:

In business, we talk about strategy, execution, numbers, and results. We analyze data, we refine messaging, we optimize performance. But we don’t talk nearly enough about how we make people feel. And yet, that’s what sticks. That’s what defines relationships, reputations, and impact.

This experience reminded me that I only have one brand, and that brand is how I show up for people. And more than anything, I want people to feel better after interacting with me.

This isn’t just about mentalization—about seeing things from another’s perspective. It’s bigger than that. It’s about intention. About awareness. About ensuring that even in difficult conversations, even in moments of challenge, people walk away feeling respected, valued, and understood.

Because long after the words fade and the specifics of a moment blur, what remains is the feeling you left behind. And that’s what truly matters.

###

I talked with Kara Weber about this on my podcast Critical Moments, and her story is a perfect example of how the worst moments can set you up for something even better—if you’re willing to stay open to change.

Kara and I met almost 30 years ago when she was helping build Tripod, one of the first online communities and website builders. This was before anyone really knew what a personal website was, and long before social media made it easy to put yourself online. She was one of the people shaping the early internet, and I was… well, trying to keep up. We’ve stayed friends ever since, watching each other’s careers take shape in ways neither of us could have predicted back then.

Fast forward a couple of decades, and Kara was stepping into her first President role at Brud, a high-flying, venture-backed startup. (Lil Miquela, anyone?!) It was one of those companies that had everything—big-name investors, a celebrity-infused business model, and a shot at being the next big thing in media. It had all the buzzwords—AI, virtual influencers, storytelling 2.0. It was ambitious and had the potential to be massive.

And then March 2020 hit.

The world shut down overnight. The strategy she’d spent months building? Gone. Revenue? Stalled. The business model? No longer viable. She had 60 employees looking to her for leadership, a board expecting her to navigate the chaos, and a family to take care of in the middle of a global crisis.

No roadmap. No playbook. No certainty.

It would’ve been easy to panic. Most people would have. But Kara had been here before.

Years earlier, as a freshman at Williams College, she walked onto campus fully expecting to play soccer. It had been her identity for years—she was a captain, a top scorer, the kind of player who lived and breathed the sport. Then she got injured and cut from the team. Just like that, everything she thought she was—gone. It was a gut punch. But instead of sulking or giving up sports altogether, she did something unexpected.

She went to a party, met a guy, and in the middle of small talk, he asked, Do you know how to skate?

Turns out, she did. And a few months later, she wasn’t just playing a new sport—she was leading it. She became the first varsity captain of the women’s ice hockey team at Williams.

That experience—the moment when your identity gets ripped away, and you have to decide what now?—turned out to be exactly what she needed when the pandemic flipped her world upside down.

At first, she did what every leader in that moment did: tried to stabilize the team, reassure employees, keep the business alive. But the reality set in quickly—there was no way forward on the path they had been on. Every deal was either paused or canceled. The vision of building out a media empire around virtual influencers and real world experiences was suddenly impossible.

Instead of fighting to hold onto a plan that no longer made sense, Kara did something few leaders are willing to do.

She let go.

She threw out every assumption about what the business was supposed to be and started listening—really listening—to her team. They were younger, creative, and looking at the world differently. They challenged old-school ideas about content, media, and audience engagement. They weren’t just building for fans—they were building with them.

And that’s when everything changed.

Instead of trying to survive with a broken business model, they flipped the script. They leaned into blockchain, NFTs, and decentralized ownership. Instead of treating fans as passive consumers, they turned them into active participants. They weren’t just building a company; they were rethinking what ownership and engagement could look like in media.

It was a huge risk. It felt too early, too radical, too uncertain.

But it worked.

A year and a half after that March 2020 punch to the gut, Kara and her team sold Brud to Dapper Labs, one of the biggest players in the space. What could have been the end of the road turned into a successful exit, driven by a willingness to rethink everything.

The thing about leadership is that we like to believe it’s about having the answers. In reality, it’s often about knowing when to let go of the answers you thought you had.

Kara didn’t force a failing plan to work. She let go, listened, adapted. That’s what great leaders do.

Her story is a reminder that the best opportunities don’t always come when you’re ready. They don’t arrive on a neat timeline or fit within the plan you had for yourself. Sometimes, they show up disguised as failures, gut punches, and moments that feel like everything is falling apart.

The trick is knowing that these aren’t the moments to back down. They’re the moments to step up, skate onto the ice, and build something new.

Listen to Kara’s full story on Critical Moments on Spotify, Apple, Amazon, or wherever you listen to your podcasts. And, seriously, if you listen on platforms other than these three, let me know.

###

Vrabel said,

Let’s stop there. Clear, clean, concise, and direct. That’s the gold standard.

As a CEO, your team looks to you for guidance, and if your message is muddled, so is their focus. Think about your last all-hands meeting—did your team walk away knowing exactly what you expect? Or did they leave with more questions than answers?

He continues,

This is powerful. Being honest doesn’t mean being harsh. It means being direct, even when it’s uncomfortable. But the other half of that equation is listening—really listening. Not formulating your rebuttal while they’re talking, but trying to understand their perspective. As a leader, your job isn’t just to talk; it’s to get the best from your team.

Vrabel also lays down a boundary:

Then comes the part that really hit home for me:

This is a truth bomb for any CEO. You’re going to have team members who just want to clock in and out, and that’s fine—not everyone will be a superstar. But your best people? They crave feedback. They want to know how to get better. They seek the truth, even when it’s tough to hear.

“Every great player that I’ve been able to coach in the past six years has always come and said, ‘What do I need to do to be better? What do I need to do to be great?’ You tell them, and then they seek the truth, and then their job is to then handle the truth.”

As a CEO, your responsibility is to have as many of these conversations as possible. It’s not just about delivering hard truths—it’s about helping your team handle them, grow from them, and ultimately, excel because of them.

Vrabel’s words are a reminder: honesty and clear communication aren’t just nice-to-haves. They’re non-negotiables for building a strong team and a successful company. RealTalk™ isn’t always easy, but it’s always worth it.

###

That’s not just rock and roll—it’s leadership.

As a CEO, you have to hold two completely contradictory ideas in your head at all times. Ironclad confidence and relentless doubt. Full-speed execution and patient strategy. Optimism that fuels growth and paranoia that keeps you from driving off a cliff. It’s exhausting, but it’s the job. And if you can do it without losing your mind, it will make you stronger.

You have to believe in yourself, your team, and your strategy—but also question everything. Move fast but take the long view. Develop thick skin but stay open to feedback. Project unwavering confidence but be willing to admit when you're wrong. The best leaders don’t resolve these contradictions; they live with them, they balance them, and they use them to their advantage.

If you lean too far into confidence, you become arrogant and stop listening. If doubt takes over, you freeze. Scale too quickly, and you burn out. Move too slowly, and you get left behind. Think too short-term, and you’ll never build something great. Think only about the long-term, and you’ll never make it there.

The key is to embrace the tension. Be flexible in your thinking, get comfortable with discomfort, and surround yourself with people who will challenge you. That’s how you stay sharp. That’s how you make better decisions. That’s how you lead.

Springsteen ended his speech with: "Stay hard, stay hungry, stay alive. And when you walk onstage tonight to bring the noise, treat it like it’s all we have. And then remember, it’s only rock and roll." That’s a damn good mantra for CEOs, too. Show up every day ready to fight, learn, and push forward. Hold tight to your vision, but never stop questioning it. Hold tight to your dreams, but be ready to adjust.

Walk into the office like it’s your stage—because it’s all we have. Or, as Bruce put it best:

That’s the game. That’s the job. And if you can master that balance, you’ll be unstoppable.

And then, remember: it’s only business.

Not for food, but for data, for information, for some signal about the business.

Like a bear waking from a long slumber, I’d go looking for food. And, I would always find problems. That led to me “coming in hot” to the team and forcing them to react to my fire drill.

CEOs are wired to find problems. It’s what we do. We (think we can) solve anything ourselves. And, almost always, when we come in hot, we cause disruption, distraction, and nonsense. And we have no time for any of that!

This cycle taught me a lot of lessons, but as a rule, CEOs are wired to see what needs fixing, not what's working. We’re looking to confirm our fears, and that leads to fire drills, stressed teams, and poor performance. My teams didn’t like it when I did this, and neither did I. Now, as a coach for CEOs, I see this pattern frequently.

The CEO’s Data Diet

To ensure you're leading effectively and not just reacting, you need to build a healthy data diet¹. This diet should provide you with the right information at the right time, so you can make informed decisions and stay ahead of issues. And it will help you be a better leader too. You’ll be more present and able to support and lead your team, rather than catching them in gotcha moments.

Here’s an overview of what I’ve used successfully. If there is interest, I’ll flesh out each of these in future posts.

1. Daily Dashboard

Every business has a heartbeat. A rhythm that defines how things are going. IMO, it’s a great practice for the CEO at almost every stage, to have their finger on the pulse of the daily heartbeat.

“Did we have a good day yesterday?”

“Are we set up to have a good day today?”

“Did our Tuesday behave like a normal Tuesday?”

A daily dashboard is a quick, high-level overview of key performance indicators (KPIs) and metrics that are critical to your business. It should be easy to read and provide a snapshot of the company's health. Starting your day by reviewing the dashboard helps you get a sense of how things are going and how you may need to spend your time today.

2. Weekly Updates from Direct Reports

I advise all of my clients to set up this practice of sending or receiving weekly updates. At a minimum, they should be a few bullets. I’ve had success with “3 & 3” – three most important things from the previous week and the three most important things for next week.

If there are KPIs you’re tracking, this is a good place for your directs to keep you updated. It’s also a great place to share anything important. Perhaps the only thing worse than a hungry CEO is a surprised one.

3. Weekly Review with Leadership Team

A weekly review with your leadership team is a collaborative meeting to discuss the week’s progress, address any issues, and align on priorities for the coming week. During these meetings, each leader shares their team’s achievements and challenges, discusses cross-departmental issues, and reviews the progress of ongoing projects and strategic goals. This helps foster collaboration, address issues early, and ensure everyone is working towards the same objectives.

4. Monthly Data Pack

A monthly data pack is a comprehensive report that provides a deeper dive into the company’s performance. It includes detailed metrics, analysis, and insights. The data pack should cover financial, operational, customer, team and any competitive analyses. These should include, for example, every Closed Won deal, every churned customer, seller performance, etc. It’s comprehensive. Using this data, you can inform strategic decisions, evaluate the effectiveness of current strategies, and communicate with stakeholders.

5. Quarterly Board Reviews

Quarterly board reviews are formal presentations to your board of directors, providing a comprehensive overview of the company’s performance and strategic direction. These reviews should include an executive summary, detailed financial results, operational highlights, progress on strategic initiatives, risk management, and future outlook. There is lots of content about how to do great board decks, and I’ll likely create some too, but for starters, you want to have as little daylight between you and your board.

Building a healthy data diet for your CEO is essential for effective leadership. By ensuring you have the right information at the right time, you can lead with confidence, make informed decisions, and create a positive, productive environment for your team.

I’d love to hear from your thoughts. Fire away!

Then, an hour into the job, you get an email that changes everything.

That’s what happened to Aziz Hasan, the former CEO of Kickstarter. On his first day, as the announcement of his leadership went live, a second email followed—Kickstarter employees were unionizing.

No heads-up. No preparation. Just a full-blown leadership test dropped in his lap.

Aziz’s reaction? He didn’t react.

Most CEOs feel the pressure to take immediate action, to make a bold statement, to show authority. But sometimes, acting quickly means acting quickly to listen.

Instead of rushing to take a stance, Aziz took two months to learn. He studied the legal frameworks, listened to employees, and got outside perspectives. He didn’t go in with an anti-union stance or a pro-union stance—he went in with a desire to understand what was best for the company and the employees.

This is a lesson for every CEO: You don’t always need to have the answer immediately.

The world tells leaders to be decisive. To be firm. To have an opinion and stick to it. But that kind of leadership, especially in moments of crisis, can backfire. Aziz took the opposite approach—he led by being present, by listening, and by understanding before acting.

And that’s something every CEO should take to heart.

In this episode of Critical Moments, we break down what it really takes to step into a leadership crisis and come out stronger.

🎧 Listen here.

For Dave Morgan, the founder of pioneering Internet companies Real Media, TACODA, and Simulmedia, that moment came in his car, somewhere between New York and Pennsylvania. He had just met with Brad Burnham, a VC and one of the few people at the time who truly understood what the internet was going to become. Brad told him:

“No one wants to back an entrepreneur who isn’t all in.”

That was it. No hedge. No side hustle. You either commit, or you don’t.

The next morning, Dave walked into his boss’s office and quit his job. No funding. No business plan. Just a belief that he had to go all in.

If that sounds reckless, it’s because it was. But it’s also how some of the biggest successes happen. When you give yourself no way out, you force yourself to make it work.

This isn’t about quitting your job on a whim. It’s about deciding—really deciding—to commit. Too many CEOs try to keep one foot on the dock while the boat is leaving. It doesn’t work.

Think about your own company:

• Are you all in?

• Are you making the hard calls, or waiting for someone else to decide for you?

• Are you moving forward, or playing defense?

Founders love to talk about grit. But grit isn’t about working long hours—it’s about commitment. It’s about burning the boats so the only way forward is forward.

Dave’s story is a masterclass in taking big swings, trusting yourself, and making decisions that actually move the needle.

I highly recommend listening to this one. 🎧 Listen here.

My friend, Michelle Benfer, wasn’t looking for a job. She had the job—leading revenue for Bill, a billion-dollar public company with 500+ people on her team. But when a recruiter called about an operating partner role at Francisco Partners, in private equity, she wasn’t sure.

“Was it too soon? Had I earned it? Was I really ready to leave behind leading big teams and running a business at scale?”

In the latest episode of Critical Moments, Michelle shares the real story of how she navigated this huge decision, leaned on mentors for guidance, and ultimately took the leap.

After a lot of reflection (and a phone call with a lifelong friend), she made the leap.

There’s a lot to learn from Michelle’s experience:

1. Big Moves Rarely Feel Like Perfect Timing

When you’ve worked your whole career to reach a certain goal, it’s hard to imagine stepping away from it. But sometimes, staying put is the bigger risk. Michelle wasn’t sure if she was “ready,” but she recognized the opportunity for what it was—rare, exciting, and aligned with her long-term vision.

Lesson: If you wait until you feel 100% ready, you may miss the best opportunities.

2. Seek Input, Not Just Confirmation

Michelle didn’t make the decision alone. She reached out to mentors, former bosses, and peers—people who knew her well but had different perspectives. Some told her to go for it. Others thought she should stay put. That contrast helped her weigh her own priorities.

Lesson: Surround yourself with smart people who’ll challenge your thinking, not just validate it.

3. Follow Intellectual Curiosity, Not Just the Money

Michelle loved leading big teams. In her new role, she has zero direct reports. That shift felt uncomfortable, but it also meant she could focus on something she’d always been drawn to—analyzing businesses at a high level. She wasn’t making the move for a paycheck; she was making it for long-term growth.

Lesson: Compensation matters, but career fulfillment comes from challenge and curiosity.

4. Trust the People Who Believe in You

Michelle’s final push came from a trusted friend who told her, “You’ve delivered on every goal you’ve set—why wouldn’t you do it again?” That outside belief helped her see what she was capable of.

Lesson: Sometimes, others can see your potential before you can. Listen to them.

Take the Call

If a recruiter called you today about an unexpected opportunity, would you take the call? Michelle did—and it led to a game-changing career move. The best opportunities don’t always come when you expect them. The key is recognizing them when they do.

Be sure to listen to this episode of Critical Moments on Spotify, Apple, Amazon, or wherever you listen to this stuff.

I would love to hear from you. Have you ever made a career move that felt risky but turned out to be the right choice? Drop a comment below.

Take my friend Claudia Reuter, for example. In 2010, she was in the thick of it: building her first startup with her husband, School Chapters, while raising two young kids. She was making real progress—a contract with a major association, customers, revenue—and finally landed a term sheet from an investor. It felt like everything was falling into place.

Then came the email: “A very vexing issue.” The investment was suddenly at risk. With no childcare and a house full of chaos, Claudia took the call from her son’s closet, surrounded by toys, while trying to keep it together. In the moment, it felt like a disaster. Looking back, it was just another hurdle on the way to success. The round eventually came together; the company grew, and it was acquired. But that moment taught her something essential: resilience.

In our recent podcast episode of Critical Moments, Claudia opens up about this defining moment and how it shaped her outlook on entrepreneurship. She shares the emotional toll of managing uncertainty, the importance of staying focused, and why resilience is the cornerstone of success. You can listen to the full conversation, “A Very Vexing Issue,” on Spotify, Apple or wherever you get your podcasts.

Claudia went on to do great things and achieve significant success in her career. Her journey is inspiring. Among other things, she was Managing Director at Techstars in Boston, where she mentored dozens of startups, helping founders navigate the same challenges she once faced. Today, Claudia leads the Roberts Innovation Fund at Yale Ventures, supporting groundbreaking projects from the Yale School of Engineering and Applied Science. She’s also the host of the podcast The 43 Percent, where she shines a light on the untold stories of women balancing work, family, and ambition. You can learn more about Claudia’s work and podcast here.

Here are three lessons from Claudia’s story that every entrepreneur should take to heart:

1. It’s Never as Big as It Feels

When you’re in the moment, everything feels like life or death. The truth? Most things aren’t. Whether it’s a funding hiccup, a lost customer, or a product delay, these moments rarely define the outcome. What matters is staying calm, putting one foot in front of the other, and moving forward. Claudia’s story in Critical Moments is a perfect example: what felt monumental in the moment was just a bump in the road in hindsight.

2. Resilience is the Job

Entrepreneurship is messy and full of uncertainty. The real work isn’t just building the product or closing the deal—it’s showing up, day after day, even when things feel impossible. Claudia speaks candidly about this in the podcast, recounting how she found the determination to keep going, even when the odds felt stacked against her.

3. Don’t Lose Perspective

The stakes always feel sky-high, but perspective changes everything. Claudia described her startup as her “third child.” That’s how attached she was. But years later, after growing companies, mentoring founders, and working in innovation at Yale Ventures, she sees things differently. Startups are important, but they’re projects—not life itself. This reflection is something she emphasizes in the episode, reminding us all that no single moment defines the journey.

Entrepreneurship will test you. It’s not about knowing the answers; it’s about staying in the game, adapting to the unknown, and finding a way forward. Claudia’s story is a reminder that the journey almost never goes how you think it will—and that’s okay. 🎙️

Listen to “A Very Vexing Issue” and other episodes here.

Shutting down a company is not something you prepare for when you start your company. You plan for growth, you rally a team, and you chase ambitious goals. But the reality is that most startups fail.

This week’s episode of Critical Moments features Josh March and Kasia Gora, co-founders of Sci-Fi Foods. They raised $45 million from top investors, including , to develop cultivated meat—meat grown from cells instead of animals—with the dream of changing how the world produces food. And while they were developing a great product — the progress was undeniable, the market evaporated for what they were building.

When it became clear that the end was inevitable, they didn’t retreat or hide. Instead, they leaned into leadership. They over-communicated with their employees, ensured investors stayed informed, and preserved the team’s collective dignity. Their guide, Graceful Exit, captures the lessons they learned along the way.

The key takeaway? Vulnerability is strength. It’s scary to be open, especially when sharing hard truths, but Josh and Kasia’s experience proves that honest communication builds trust—even in failure. They showed their employees respect by being transparent. Their investors appreciated their maturity and candor. And their decision to document everything offers invaluable insights to the rest of us.

For CEOs, the tension between optimism and realism is ever-present. We are paid to dream big and solve impossible problems. But knowing when to pivot—and when to stop—is one of the most challenging and essential skills.

Josh and Kasia’s journey is a reminder that failure isn’t the end of your story. It’s part of the story, and how you handle it speaks volumes about the leader you are.

The most striking part of our conversation? Despite the shutdown, Sci-Fi Foods’ core intellectual property now lives on as an open-access resource, ensuring future startups can build on their work. That’s leadership. That’s impact.

For those of us leading companies, it’s worth asking: Am I as intentional about how I’ll exit as I am about how I’ll grow?

This podcast episode isn’t just about shutting down. It’s about showing up—with grace, courage, and integrity.

I recently spoke with Emmanuelle Skala, formerly of Toast, Digital Ocean, and more, on my podcast Critical Moments. She shared a pivotal moment from her career when she did ’t get a promotion because she “was not very well-liked.” It was shocking feedback, especially for someone who’s truly one of the kindest and most generous people I’ve met. It turned out to be the wake-up call she needed.

Emmanuelle had always prioritized results. She believed her job was to grow the business—not to make friends. But what she learned is that relationships aren’t just a “nice-to-have” in leadership—they’re essential, no matter how great the results are.

She continued her rocketship journey and has had one of the most impressive careers of anyone I’ve met, so we should pay close attention to the lessons she shared:

1. Relationships Matter

Lots of people say this, but until you learn it the hard way, it’s hard to appreciate just how much they matter. Emmanuelle realized that while she was delivering exceptional results, her “my way or the highway” approach could alienate some peers. Taking time to understand colleagues’ perspectives doesn’t just smooth interactions—it improves outcomes.

2. Authenticity Builds Trust

A lot of people try to keep their personal lives separate from their work lives. Some people can’t help but share everything (👋, it’s me!). But it’s not about going out for drinks or silly “get to know you exercises,” it’s really about sharing and being your authentic self. When you really allow people to know you, your strengths, weaknesses, interests, and who you really are — in Emmanuelle’s case a working mom trying to balance her family life with an unparalled professional drive — you create stronger bonds and deliver better results.

3. Feedback Is a Gift

A CEO’s job is to build a company that delivers the desired results and outcomes. When your team is ’t performing, I always ask the CEO if the team has clarity on roles, strategy, and performance. I encourage direct, clear RealTalk. High performers crave feedback — especially when it is constructive, but it has to come from a place of care. It was this radical candor that propelled Emmanuelle’s growth. Instead of resenting it, she sought coaching and introspection, and it helped transform her leadership approach.

The takeaway? Great leaders balance results with relationships. If you’re not actively building trust and understanding, you’re missing a key ingredient for success.

Emmanuelle’s story is a reminder that leadership is as much about the “how” as it is about the “what.”

👉 Want to hear more? Listen to the episode here.

But realities get in the way. All….the…time.

I want to share one of my favorite frameworks for setting goals and breaking through internal log jams. “Wouldn’t it be great if….”

Let’s give an example that you may have encountered.

It’s budget season and your investors are pushing for faster growth; your team is asking for more resources, and you’re stuck trying to balance your big dreams and the realties of your day-to-day. 

Often these are at odds. Your investors are pushing you to grow faster. Your team is likely being conservative and asking for more resources if they have to grow. 

And you are trying to balance your desire to build an amazing company and you probably don’t want to miss yet another annual plan..

So, how do you break through and get to something meaningful and innovative?

Try starting by finishing this sentence:

“Wouldn’t it be great if…”

Share your vision of what great is and what you really want and ignore the constraints or the realities of the current situation. 

For example, let’s say you grew 30% this year and your whole leadership team is telling you that 35% is the right goal for next year. But you know that the best companies are growing much faster than that.

“Wouldn’t it be great if we could grow at 50% or better next year?”

Your team may scoff or not believe it, but you’re not done yet.

You need to work backwards. “Now, what would need to be true for that to happen?”

Your sales leader might say, “we need 10 more reps.”

Your product leader might say “we need to triple engagement.”

Your success leader might say “we need to improve our NRR to 115%.”

This is where you now drill down into each of these and continue to work together to understand the possible.

Can you really add 10 more reps? Maybe not. But can you improve ACV by 15% by adding an upsell motion? How would you do that? You can give that goal to your sales leader as part of planning

Same with all parts of your leadership team. If you need to grow 50% next year and each team needs to have stretch goals to get there. Ask each of them to ask themselves the same questions..

When you ask yourself, "Wouldn't it be great if…," you’re giving yourself permission to think beyond the constraints of today. You’re allowing yourself to envision a future where the barriers you see now no longer exist. This isn’t about ignoring reality — it’s about freeing yourself from the mental blocks that prevent you from pursuing your most ambitious goals.

I use this all the time, both in my personal life and in business.

Years ago, my wife and I did this exercise together. I said, "Wouldn’t it be great if I didn’t have to ever ride NJ Transit again," and “I could attend every lacrosse game?” At the time, it seemed like a far-fetched idea. Commuting was a necessary evil, or so I thought. But instead of dismissing it as impossible, we started thinking about other ways to make it happen. Could we move closer to work? Could I find a job that allowed for remote work? Could we restructure our lives to eliminate the need for that daily grind?

By not getting stuck on immediate barriers, we opened up possibilities that we hadn’t considered before. And eventually, we made it happen. I no longer have to deal with NJ Transit, and I don’t miss it a bit, other than maybe a piping hot slice at Don Pepi’s. IYKYK.

So, next time you’re setting goals—whether in your personal life or in business—try asking, “Wouldn’t it be great if…?” You’re not ignoring reality; you’re giving yourself permission to see beyond the limits of today’s constraints. When you start with this mindset, you open up space for innovation, clarity, and purpose, aligning your team (or family) toward a vision that’s bigger than the immediate obstacles.

After all, the most rewarding outcomes often come from goals that once seemed impossible—until you dared to imagine otherwise.

One day, a guy on my team came into my office, closed the door, and asked me straight up for the truth about what was happening. He told me to just share the truth of what I needed from him and not to sugarcoat it.

He called it “RealTalk™”—and yes, he included a trademark! 

It struck me then how refreshing it was to have a framework that allowed for real honesty and allowed me to frame the needs of the business and not make it feel personal. Since that day, I’ve come to cherish RealTalk™.

So, what is it? Simply put, RealTalk™ is when you tell the person you’re working with exactly what you really need and what you really mean. It’s direct, candid, and specific. Sure, it can feel uncomfortable at times, but it’s a crucial tool for effective leadership and team success.

Think about it. How can you expect to get what you need if you aren’t willing to share it? Too many leaders dodge the tough conversations, tiptoeing around issues and hoping for the best. This rarely ends well. More often than not, it leads to frustration, unmet expectations, and stagnation.

RealTalk™ is a gift—a way to ensure your team knows exactly where they stand, what’s expected of them, and how they can improve. It’s about clarity, honesty, and having the guts to be straightforward.

Let me share a couple of examples from my own journey.

1. The Marketing Leader

I had a marketing leader who I loved, but wasn’t delivering the results we desperately needed. We were not hitting our goals, and there was a noticeable disconnect between our discussions and the actual execution. Because we had such a strong personal relationship, I was hesitant to tell them that they just weren’t cutting it.

Starting that conversation wasn’t easy, but it had to happen. I sat down with them and laid it all out—clear as day. I explained our goals, what was currently happening, and where the gaps lay. No sugarcoating. Just straightforward examples of where we were falling short.

To my surprise, they were not only receptive but grateful. They hadn’t fully grasped the disconnect and really appreciated the clarity. We brainstormed a new strategy, set clear expectations, and agreed on a game plan. The results improved significantly in the following months. That tough conversation turned out to be a pivotal moment.

2. The CTO

There was another case at a different company, with our CTO. The team was missing deadlines, and the quality was slipping. I knew this conversation would be a challenge because they were incredibly passionate about their work, and I hadn’t had as much experience on the engineering side of things.

But I didn’t back down from the hard truths. I told them exactly what was happening, how it was impacting the company, and what needed to change. It wasn’t just about pointing fingers; it was about being honest about expectations and listening to their perspective, too.

Once again, the response was positive. They were thankful for the honesty and agreed that we needed to change things up. We set new goals together, and the improvement was immediate.

RealTalk™ isn’t about being harsh or overly critical. It’s about honesty and clarity. It’s about equipping your team with the information they need to succeed and helping them understand what’s expected. This kind of communication builds trust, fosters growth, and leads to better outcomes for everyone involved.

In my experience, employees value RealTalk™. They want to know where they stand and how they can improve. They want to be safe and successful. If you don’t share the truth, how can they be either?

So, the next time you hesitate before having a difficult conversation, remember the power of RealTalk™. Be direct, be honest, and be specific. It’s one of the most powerful tools in your leadership toolkit, and it can truly make a difference.

I am not sure I buy that there is an ideal “work/life balance” but I do know that there are ways to make a meaningful effort. I was fortunate to have a great teacher when it came to finding that balance—my dad.

My dad was also an entrepreneur, a clinical psychologist who worked tirelessly to build his private practice. He wasn’t home for dinner most nights. But what he did create rituals that made the time we had together special.

One of my favorite rituals was our Saturday morning breakfasts. On Saturdays when we were very young, my dad would take my brother and me to the hospital cafeteria. We loved the food—bacon, eggs, and pancakes—and he loved the time with us. It was a win-win. For him, it was also a chance to meet doctors and build a referral base for his practice. To this day, I have a strong affinity for hospital cafeteria food. Weird? Maybe. But those memories are priceless.

As we got older, those breakfasts became dinners on Tuesday nights. Our mom would work late on Tuesdays (here’s a post about what I’ve learned from my mom.) and my dad would bring home dinner for my brother and me. It was always the same thing from the same place. Tuna Grinders for he and my brother and a cheese pizza for me from Excellent Pizza in Warwick, RI. I remember it so well. The three of us would sit together, eat, and connect. It was like clockwork.

When my brother and I left home for college and started our own lives, my dad made it a point to call us every Tuesday night. Sometimes it was just a voicemail; sometimes we’d have a long conversation. But it was every Tuesday night, without fail, from the day I left for college in 1990 until he passed away in 2015.

These rituals weren’t just about staying connected—they were about teaching me what it means to be a dad, a husband, a brother, and an entrepreneur. They showed me that I could try to find that elusive “balance” and have meaningful moments with my family.

And you can bet that I’ve continued these rituals with my own sons. When they were young, every Saturday morning we’d go out for breakfast. Now that they’re older and off at college, I try to talk to them every Tuesday night. It’s a simple thing, but it keeps us connected, no matter where life takes us.

Another ritual that’s been crucial for maintaining balance in my marriage is our Saturday night date night. When our boys were little, my wife was home with them all week while I worked long hours. We needed to carve out time for each other, so we made Saturday night our night. We hired a babysitter every week, no matter what. Sometimes we’d rush to our favorite restaurant and grab a seat at the bar; other times we’d just go grocery shopping together. The activity didn’t matter as much as the fact that we were together, uninterrupted.

Rituals like these are what keep me grounded. They create a sense of continuity and connection that helps balance the chaos of being a CEO. They’re a reminder that no matter how busy work gets, there’s always time for the people and things that truly matter.

So, if you’re struggling to find balance, consider establishing your own rituals. They don’t have to be complex or time-consuming. They just need to be consistent and meaningful. Whether it’s a weekly breakfast, a regular phone call, or a standing date night, these rituals can help you find that elusive balance between work and home life.

I’ve been the CEO of three companies over the past 16 years, and a senior executive for years before that. I was always hungry to learn how to be a great CEO. I sought out coaches, mentors, friends, podcasts, blog posts, HBR pdfs, and more. I was acutely aware that I could always be better at my job and that it would be a non-stop learning experience. As a CEO, there is always some new problem to solve or opportunity to capture.

At the same time, I was wrestling with how my job fit into the rest of my life – as a husband, father, son, brother, and friend. How could I be the person that I want to be to the others in my life? How would I achieve my professional ambitions AND my personal goals? 

We bring the rest of our lives to our jobs every day. We are complex beings and all working on something. Both my parents and my brother are clinical psychologists, and growing up, almost no topic was off limits at the dinner table. I’ve known from the start that how we feel is as important as how we act and behave. In fact, they're inextricably tied. As a result, I'm very comfortable asking hard questions to get to the ground truths of how we feel. I hope it's made me a better husband, father, a better leader, and a better person.

Across all of these, what I always valued most was practical advice, based on real experience, communicated clearly and directly. There's no substitute for having “been there and done that,” and I continue to place real value on advice from people who have been there before and are able to talk truly honestly about the journey.

I’ve come to believe in a balanced approach where ambition meets well-being, so you don’t just achieve your goals: you enjoy the journey, too.

These different pieces come together to form the core tenets of how I coach CEOs and executives:

• Start with the Truth: Face the truth as it is, rather than how we want it to be. This involves honestly evaluating ourselves, recognizing our strengths, and recognizing areas where we can improve. As a fellow operator, you can count on direct, honest feedback from me. I will hold you accountable.

• Wouldn't It Be Great If: I encourage you to dream beyond your current limitations. Imagine what could be possible if we momentarily ignored the current constraints and set goals based on your hopes, dreams, visions, and often investor and market expectations.

• Frameworks & Working Backwards: Practical tools and frameworks can help turn aspirations into tangible outcomes. By planning strategically and working backwards from our goals, we’ll outline clear, actionable steps to success.

• Honest Communication & Strong Relationships: Success also hinges on how well we connect with and lead others. Candor builds trust within teams and networks. Teams follow leaders, and it all starts here.

• Have Fun, Life is Short: Enjoy the journey! You are more than your work. How can you craft a life that balances all the sides of you, and have fun doing it? Integrating joy and positivity into the pursuit of excellence makes the process as rewarding as the outcomes.

Coaching is an opportunity for me to be a helpful partner in your journey. It’s about sharing the lessons I’ve learned and helping others to not just envision their success but actively prepare for and achieve it. 

I believe in a balanced approach where ambition meets well-being, ensuring that you’re not only achieving your goals but also enjoying the path to them.

It isn’t about pushing you through a boot camp; it’s about walking with you, understanding your unique needs, and providing the tools and support to help you excel. It’s about being greater than yesterday, not through pressure, but through partnership and accountability. 

So, how can I help?

Here’s a straightforward, no-nonsense guide for you. It’s a practical, been-there-done-that framework, built on a ton of reps and lessons learned, that should help you

We’ll go through a five-page presentation that’ll help you solve specific problems and make sure you communicate clearly and get results.

Slide 1: Problem Statement

Objective: Pinpoint and clearly state the problem. This is about getting everyone on the same page right from the start.

• Summarize the Problem: What's the big issue here? Spell it out simply and directly.

• Provide Context and Background: What led us here? A quick backstory can help everyone understand the journey.

• Explain the Impact: How is this affecting us? Be clear about the consequences.

Examples (just to give you an idea):

• Customer Retention: "Our customer retention has tanked by 15% from last year, hitting our recurring revenue hard."

• Sales Pipeline: “We’re looking at a pipeline that’s 40% shy of where we need to be for the next two quarters.”

• Hiring Plan: “We’re not hiring fast enough to keep up with our growth, leaving us short-handed in crucial areas.”

Slide 2: Data That Shows the Problem

Objective: Show the hard facts. This slide is all about letting the data do the talking to highlight the severity and trends of the issues. I like to have at least three to five if possible. 

• Present Data: Use clear, easy-to-understand graphs and charts.

• Visual Aids: Think line graphs for trends, heat maps for demographics, bar charts for benchmarks.

Examples:

• Customer Retention: A line graph of monthly retention rates, a heat map of churn by customer segment.

• Sales Pipeline: A funnel chart of pipeline stages, a line graph of lead trends.

• Hiring Plan: A bar graph of planned vs. actual hires, a pie chart showing gaps in departments.

Slide 3: Learnings from the Data

Objective: Extract and highlight insights. What’s the data telling us? This is where we learn from what the numbers are showing.

• Summarize Key Learnings: Pull out the critical insights that will inform our actions.Ideally these flow directly from the data in slide 2.

Examples:

• Customer Retention: High churn mainly in the first year, negative feedback tied to pricing changes.

• Sales Pipeline: Poor lead generation in new markets, low conversion rates at early stages.

• Hiring Plan: Biggest gaps in tech roles, high rejection rates due to competitive offers.

Slide 4: Action Plan

Objective: Lay out a practical, actionable strategy based on what we've learned. This is the "what are we going to do about it" slide.

• Outline the Action Plan: What specific steps will we take to tackle these issues? Again, these should be obvious flowing from the data and learnings. The story should be coming together here.

Examples:

• Customer Retention: Start a loyalty program for new customers, revisit pricing strategies, target communications for renewals.

• Sales Pipeline: Push marketing in underperforming areas, boost training for sales qualifications, create an upsell strategy.

• Hiring Plan: Offer better signing bonuses, partner with staffing agencies, streamline the hiring process.

Slide 5: What Does Success Look Like

Objective: Define clear, measurable goals. How will we know we've succeeded? This slide sets the benchmarks.

• Define Goals, Metrics, and Timelines: What are our targets and by when do we want to hit them?

Examples:

• Customer Retention: Boost retention back to 85% in a year, cut churn by 50% in six months.

• Sales Pipeline: Meet pipeline targets fully in the next two quarters, improve conversion by 30% in six months.

• Hiring Plan: Fill all tech roles in three months, reduce hiring time by 50%, increase offer acceptance by 25%.

Conclusion

This framework isn't just about making good slides; it's about how you organize, prioritize, and communicate. It's a practical approach that can transform the way you work and lead to real results. By clearly defining problems, analyzing data, learning from it, and setting a clear action plan with success metrics, you're not just presenting; you're actively managing and leading your team towards improvement. Remember, it's not about the slides—it's about the clarity and action they bring to your work.

Let's Make This Even Better!

Your insights and experiences are invaluable. If you have any feedback, comments, or questions about this share. Every piece of input helps me improve and provide you with the most effective tools and strategies. Drop me a line anytime – I’m all ears and eager to hear from you!