Executive Coaching for Founders: When Startup Skills Break

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I’ve built 3 companies, each of them was acquired by a public conglomerate.
In the process, I’ve made every mistake a founder can make.

I’ve hired wrong, fired wrong, and waited too long when I should have moved faster. I’ve been the smartest person in the room and the most oblivious one. Often in the same week, sometimes in the same meeting.

So when I speak with a founder and they say, “I don’t know why I’m having these problems,” I usually know exactly why. Because I’ve been there. And I know the way out.

Executive coaching for founders, at it’s best, helps you feel heard, feel seen, and feel comforted that you have a resource to help drive you forward, fast. You don’t need any smart person asking you thoughtful questions – you need a founder who became a coach, who recognizes what you’re experiencing because they experienced it too.

In other words, when it comes to executive coaching for founders, the reason you need a founder to speak with is because people who haven’t been entrepreneurs simply don’t understand the nuance of the personality.

Let me explain.

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The Founder Journey Has Stages (And Most People Skip Explaining the Hard One)

The first stage of the founder’s personality is what most people picture when they think of an early stage entrepreneur. You’re scrappy. You’re fast. You’re following every revenue opportunity that blinks in your direction. You make all the decisions because there’s no one else to make them, and because nobody will ever know or be able to articulate your business vision like you do.

I call it the jab-duck-jab phase. Everything is temporary and everything is agile. The product might be completely different in 6 months depending on what the market wants.

Stage 2 is when you begin to find product-market fit and business starts scaling. It’s exciting. You begin hiring, you start scaling. You feel great that you have a team firing on all cylinders and you are pinching yourself in disbelief that your vision is coming alive.

And then there’s Stage 3.
This is the stage nobody warns you about.

Because Stage 3 doesn’t feel like a different challenge than Stage 2. In fact, it feels like the same challenge. You’re just doing more of what worked.

Except the rules have completely changed and everybody’s realized it but you.

The start-up mode of Stage 1 requires agility, continuous change, and saying “yes, we can.” The scale-up mode of Stage 3 requires consistency, process and knowing when to say “no, we can’t.” The company was built as an extension of you, but for you to be successful in Stage 3, it needs to run more effectively without you at the center of everything.

Stage 1 rewards jab-duck-jab. Stage 3 punishes it.

That transition is the reason 99% of founders can’t scale.

Not because they aren’t smart.
Not because they aren’t working hard.
Because the patterns that got them to Stage 3 are now the ones preventing them from getting through it.

And that, my friend, is why executive coaching for founders is not a nice-to-have, it’s a must-have.
In fact, if you don’t believe me yet, you should read this article in Forbes: “For Founders, Coaching Is Here To Stay.“

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Why the Skills That Built Your Company Stop Working at Scale

Here’s the funny thing about the founder personality: it includes exactly the right patterns that help you scale your company. It isn’t a weakness. Until it is.

Your ability to make fast decisions works really well when you have 7 people at the company. At 35 employees, it makes you the bottleneck that slows everything down.

Following every promising revenue opportunity worked when you searching for product-market fit. It helped you move fast. At scale, chasing every revenue opportunity requires your team to do so many different things, it will cause you to move slowly.

Being the person who knows everything worked when the team was small. When the company gets big enough, knowing everything holds your team back.

Your patterns didn’t get worse. Your patterns didn’t even change.
The environment changed.

This is what I call the Pattern-Environment Loop. The behaviors that built the company are so deeply ingrained that most founders don’t even even see them as behaviors. It’s just who they are. And that’s exactly the problem. Because “who you are” is suddenly limiting the company’s growth.

The 0.1% of founders who break through this transition share one thing in common.
It’s not intelligence.
It’s not luck. (OK, maybe it’s a little luck).
It’s the willingness to challenge their own patterns before those patterns challenge their business’s potential.

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Why Founders Need to Talk to Other Founders

I’ve talked with entrepreneurs who are skeptical of executive coaching for founders. I get it.
They hired executive coaches before. Smart coaches. Credentialed coaches. Good people.

Their experience is always some version of the same thing: “Nice person, but they didn’t really understand me. It was like talking to somebody who only read about what it means to be an entrepreneur.”

Understanding founders only comes from having been a founder. The executive coach needs to know what it’s like when you can’t let go of decision-making and lose employees because of it. They need to understand how following a big revenue opportunity can hurt the company more than it helps it. And they need to have experienced sitting in front of investors explaining why growth stalled, and knowing, somewhere underneath the explanation, that you were the reason.

You can read about that. You can’t feel it the way you feel a memory.

When a coach has been through the founder experience themselves, the conversation is completely different. They’re not asking you questions from a framework – they’re recognizing a pattern you keep repeating. They can say “I know exactly what you’re describing, and here’s what’s usually happening underneath it” because they’ve been underneath it.

That’s not a small thing. It’s the difference between a diagnosis and a guess.
It’s the difference between executive coaching for founders that works, and the coaching that doesn’t.

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Why the Choice Isn’t Between a Coach and a Mentor — It’s Both

Most founders who’ve tried out executive coaching or mentoring describe the same issue, but from opposite viewpoints.

Pure coaching without founder experience feels like useless therapy. You’re getting better at understanding yourself, but nobody’s helping you use that understanding to scale your company.

Pure mentoring without coaching feels like someone else’s answers to your questions. It’s sometimes useful, but you’re just listening to their judgment instead of developing your own. Regardless of the mentors experience, I guarantee it was different than yours.

What founders actually need is someone who moves between both executive coaching and mentoring in the same conversation. Someone who can sit with you in the fogginess of entrepreneurialism and help you get clarity, and, at the same time, who can say, “here’s what I did when I had the same issue, and here’s what I’d do differently now.”

When I work with founders, I don’t fit neatly into either the executive coaching or mentoring box, because that wouldn’t be helpful to you. Coaching and mentoring aren’t mutually exclusive approaches. They’re tools for different moments in the same conversation – sometimes in the same sentence.

When executive coaching for founders including mentoring, you’ll get further, faster, than the founder who chooses one or the other.

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Executive Coaching For Founders: 5 Signs You’re Ready.

If you’ve ever wondered whether you need executive coaching for founders, there are 5 signs that can help you quickly make the decision. You don’t need all 5 to be happening. If only 2 or 3 of these are true, you have a problem that can use coaching and mentoring.

Your people are quitting. When people keep leaving, that’s a big red flag. My guess is, they feel like they have no room to grow, no autonomy, and/or they think you’re the bottleneck. Will they say this? Sometimes, but usually not. How will you find out? Executive coaching for founders (it’s my entire point here!)

You’re working harder but the company isn’t moving faster. Your clocking in more hours than anybody else at the company, but the growth isn’t matching your effort. In almost every situation like this, the founder is the bottleneck problem.

Every important decision still runs through you. Even though you have employees who are good at what they do. Even though you’ve said multiple times that you want them to own their work. You still are involved in almost every decision because that’s what helped build your company. That’s the pattern your environment rewards.

You know you need to delegate more. You’ve been saying it for awhile, but nothing has actually changed. That’s not problem with difficulty delegating – that’s an identity problem that’s deeper than delegation.

The thing that made you successful is now the thing limiting the company. Maybe you can feel it happening, but you can’t quite figure out exactly what it is. You just know something is holding you back. Something is keeping your company from becoming something bigger than you. And the way you try to address it (with more control) is exactly the thing that will make it worse.

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What to Look For When You Want Executive Coaching as a Founder

Executive coaching for founders should have a higher barrier to entry than other types of leadership coaching. Not because founders are more important, but because the specific transition you’re navigating requires a specific kind of understanding. Most coaches don’t understand it at all.

So here’s what I want you to do:

Look for someone who has actually built something — someone who has been in the muck. You want a coach who has struggled with the desire to control, when the company needs them to let go. You want to find a coach who has made the identity shift themselves and can describe what it actually feels like, not what some random book says it feels like.

Also, and this is important, look for someone who pushes back. Assuming you’re an entrepreneur, you need that. A good coach doesn’t just validate your current story – they help you examine it to find out what is working in your favor and what isn’t. If every session ends with you feeling confirmed rather than challenged, you’re not getting what you need.

And, finally, look for someone who can be both a coach and a mentor. Executive coaching for founders is about sharing real experience to help you figure out what to do with what you need.

Founders who can grow their companies the fastest are the ones who get coaching and mentoring in the same relationship. That combination isn’t common. But when you find it, it’s the right fit.

And this is the part where you probably should read about my story.

If you want to find out what’s actually happening within your leadership blindspots — specifically which patterns are limiting you — the Leadership Diagnostic Workshop is where to start. It’s free. It’s 90 minutes. And most founders who go through it say the same thing: “I knew something was off. I just didn’t know it was that.”

Frequently Asked Questions About Executive Coaching for Founders

Q: What’s the difference between executive coaching for founders and regular leadership coaching?
Founder-specific executive coaching focuses on the transition from Stage 1 to Stage 3 — from jab-duck-jab to consistent scale. General leadership coaching builds skills. Executive coaching for founders addresses identity: the behaviors that helped you build your company are now the same behaviors that are limiting it. Changing those behaviors requires more than skill-building. It requires a fundamental shift in how you see your own role.

Q: Do I need executive coaching or mentoring?
Probably both. Executive coaching without founder experience leaves you with insight and no map. Mentoring gives you someone else’s answers instead of developing your own judgment. The most effective relationships for founders combine both — someone who can do the pattern work with you and draw on real founder experience in the same conversation. In that sense, executive coaching for founders is somewhat of a misnomer. It should probably be called executive coaching and mentoring for founders.

Q: How do I know if I’m ready for this?
If 2 of the 5 signs above are true, trust me, you’re ready. The most common trigger that you can benefit from executive coaching for founders is when you feel that something is off, and you don’t know what. It’s highly possible that the thing that made you successful is now the thing limiting your growth. That’s the Pattern-Environment Loop knocking on your door.

Q: How long does executive coaching for founders typically last?
Most times I work with founders, it’s usually for 6+ months. We’ll start with understanding your patterns, how they are benefitting you, how they are working against you and how you repeat the same mistakes. After that, we start building new patterns. Finally, we create the systems that allow you to maintain your trajectory, even when things get hard.

Q: What’s the best way to start?
Good question. The Leadership Diagnostic Workshop is a free 90-minute session that will allow you to see the specific patterns shaping how you’re leading right now. No pitch. No commitment required. Just a clear picture of what’s actually going on before you decide on anything.

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Jeff Matlow is a leadership coach, mentor and 3x entrepreneur who helps senior leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He’s spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.