Leadership Coaching For Founders: When Startup Skills Break At Scale

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There’s a particular kind of founder who is really good at leading a start-up.

They’re decisive – and they can move fast because of it.
They’re comfortable with ambiguity because they’ve been operating in the grey zone for years.
They attract people who want to be led by someone who knows where they’re going and doesn’t hesitate to make it happen.

Like magic, their company gets bigger.

But the exact same qualities that made them a great founder, soon start working against them.

This is the founder’s trap.

It’s not about bad leadership. It’s about leadership that worked perfectly for one stage of growth, but doesn’t translate to the next one.

And that, my friend, is why leadership coaching for founders is vitally important.

Why the Skills That Built the Company Break It at Scale

In the early days, a founder’s instincts become the company’s operating system. Their strengths are the company’s strengths and their weaknesses the company’s challenges. There’s no time for process in those early stages, which is good because there’s usually no budget for bureaucracy. You hire people who can run fast and who trust you to point them in the right direction.

It works because it has to. There is no other choice.

Speed, decisiveness, and control are the features of the effective founder. They’re the characteristics that let a 10-person company out-innovate a 5,000-person competitor.

But when the company hits 30 people, then 50, then 100, those same traits that were the start-ups strengths become the companies biggest weaknesses.

And that’s because of the founder and the siloed environment they’ve created.

  • The founder who decides everything fast can easily become the bottleneck that slows everything down.
  • The founder who trusts their gut over data is often what defines the executive team’s limits – because no one’s analysis is ever going to beat the founder’s opinions. (Check out Senior Leadership Team Coaching for more on this subject.)
  • The founder who thrives in ambiguity, never defines the systems and processes that allow a company to scale .

The founder style of leadership doesn’t scale. That’s why leadership coaching for founders is critical once a company has grown to between 30 and 100 employees.

The Specific Ways Founders Get Stuck

Every founder has their version of the founders trap – I see it all the time in my leadership coaching business. Here are some of the ways founders get stuck:

They are unable to delegate at the level the organization needs. This isn’t about unwillingness. It’s about trust, and trust is built through pattern recognition. Founders have ample proof about how the pattern around their own judgment have succeeded. But the type of judgement and delegation that worked in a smaller sized company break down as the company grows. Most founders delegate in theory, but they pull back in practice. In the end, their executives learn to wait until the founder gives an opinion before they can move forward. That works for a 5 person company, not for a 50-person one.

They mistake the speed of startup decision-making for good decision-making. Fast decisions are necessary when information is scarce and survival is at stake. Fast decisions are dangerous when you have 80 people executing on them and the wrong call costs you 6 months of runway and a whole bunch of frustrated people. The decision-making muscle that served the founder well at 10 people will dramatically destroy a culture when it grows beyond 30 people.

They’ve built a culture in their own image. This sounds like a compliment. It isn’t. A culture built around the founder’s strengths is also built around their blindspots. If the founder avoids conflict, the culture can quickly become toxic. If the founder is a visionary with little interest in operations, the organization will be chaotic in it’s operational effectiveness. The leader’s limitations become the organization’s limitations. This is an important thing that leadership coaching for founders addresses.

They’ve never been managed well. Most founders didn’t climb a corporate ladder. They didn’t have a great manager who modeled what excellent leadership looks like (this usually happens often with women in leadership.) They learned to lead by leading – which means they developed a leadership style without any understanding of what’s working and what’s a problem. They have difficulty delegating effectively, they don’t know what they don’t know, and there’s no one close enough to tell them. That’s when they start hearing the voices of imposter syndrome in leadership.

Each of these pitfalls can cause revenue to plateau and a company to reach it’s growth potential earlier than expected. This is exactly why leadership coaching for founders is critical as the company grows.

What Leadership Coaching for Founders Actually Does

Leadership coaching for founders is important. Most founders don’t recognize this – or acknowledge it – because most founders I work with aren’t struggling leaders who need to be fixed. To the contrary. They’re usually high-performing leaders who’ve hit the limit of what their current leadership approach can do – and they want to push past it.

That’s the thing about this, leadership coaching for founders isn’t always about the founder asking for the coaching. Sometimes it comes from HR or another executive. Oftentimes it starts with executive team coaching.

Regardless of how it is initiated, work happens in a few specific areas.

Pattern recognition. The founder’s most powerful tool is also their biggest blind spot. Their leadership instincts are trained to succeed in the environment that existed when they built those instincts. That was earlier. The company is different now. The market is different. The team is different. Leadership coaching for founders helps them see which of their patterns are still assets and which have become liabilities. It is incredibly hard to make that distinction from inside your own head – no matter how smart and self-aware you are.

Letting the organization grow up. At some point, the founder has to stop being the operating system and become the guide. Their job transforms to the visionary who builds the right team, sets the strategic direction and gets the heck out of the way. This transition is rarely comfortable and almost never happens without intention. Coaching creates the space to do it in a quick and purposeful way.

Building the executive team the company actually needs. Founders often hire executives they feel comfortable with. These are usually people who operate the way they operate, who share their communication styles, who won’t challenge the founder too hard. The problem is that the executive team the founder is comfortable with is rarely the executive team the company needs. Leadership coaching for founders helps them see the gap and do something about it.

Getting honest feedback. The higher you are in an organization, the less honest feedback you get (check out The Iceberg of Ignorance.) Everyone in the company is cautious of how the founder perceives them. Direct reports manage up. The board is selective in what they say. Peers are not interested in rocking the boat. A leadership coach is the one person in your professional ecosystem who has no stake in your ego – and whose entire job is to give you the honest and straight-forward perspective no one else will.

When’s the Right Time to Start With Coaching?

Most founders come to leadership coaching when something is already broken. Maybe the executive team is misaligned. The culture has started to become toxic. Or growth has stalled in a way that doesn’t feel like it’s a market problem.

That’s fine. That’s when it’s most urgent and when there is a lot of motivation to do the work.

But the founders who get the most out of coaching are the ones who start before the breaking point. Leadership coaching for founders is most impactful when the company has scaled enough that the founder’s original approach is starting to show its limits – but no crisis has yet come about. At that point, the work is about helping mold the founder’s leadership abilities to meet the next challenges of the growing company.

The skills that helped you build the company are real. They deserve a ton of respect. But they also have their limitations.

If you’re a founder who’s wondering whether your leadership is helping the company grow, or whether it’s slowing it down down – that’s a conversation worth having. Leadership coaching for founders might be the right thing you need right now.

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Jeff Matlow is a leadership coach 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.