How did I get to be a Coach to CEOs?

So how did you do it? How did you get to be a coach to CEOs? That's the question I get asked the most often. How did I go from research and design to working with CEOs? [Read on: Reinvention]​

From Visionary to Leader (and back again)

Hi Reader

One of the biggest challenges I’ve seen founders face is navigating the leap from a scrappy, hands-on visionary to the strategic leader a growing company needs. It’s a pivotal moment, and it comes with its own set of hurdles, especially when it comes to team management.

During a recent webinar with the team at KeySearch, "From Founder to CEO: Strategic Insights for a Smooth Transition", I shared my thoughts on the most common mistakes founders make during this transition and how to overcome them.

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The Leadership Challenge as Teams Scale

Many founders hit a major inflection point when their companies grow to around 100–200 employees. The leadership team they built during the early days, when the company was lean and nimble, starts to face the strain of scaling. Subject matter experts in areas like growth, product, or tech, essential to the company’s initial success often aren’t equipped to lead at this next level.

This stage requires a shift. As the founder-CEO, your job is no longer to hold everything together yourself. It’s about assembling a team of leaders what I call “mini-CEOs” who can think strategically, manage larger teams, and help drive the business forward.

Why Subject Matter Expertise Isn’t Enough

Your early team members were likely hired for their deep expertise. They knew their craft inside and out and helped get the company to where it is today. But being great at growth hacking or product design doesn’t necessarily mean they’ll thrive as leaders of large teams.

It’s a tough realization for many founders: the people who got you here may not be the people to take you to the next stage. That doesn’t mean you need to let them go; often, it’s about transitioning roles or supporting their growth into leadership. And sometimes, it means bringing in fresh talent with the skills and experience to lead in ways your team hasn’t had to before.

The Role of the Founder-CEO

As a founder-CEO, your vision is critical. But you can’t and shouldn’t do it all. Holding onto every decision and every role limits your team’s ability to grow and, ultimately, your business’s ability to scale. Hiring leaders who can run key areas of the business frees you to focus on where you add the most value.

These “mini-CEOs” should:

• Drive their areas with both strategic vision and operational excellence.
• Manage teams effectively, freeing you from the day-to-day.
• Share the load of leadership, so you can focus on the bigger picture.

Don’t Get Stuck

One of the most common mistakes I see is founders holding onto roles or people that no longer fit. It’s hard to let go, but clinging to the familiar only holds you back. The key to scaling isn’t doing more, it’s empowering others to take the reins in their areas of expertise.

Your Next Step If you’re in the middle of this transition, ask yourself:

• Are my early team members equipped to lead at this stage?
• Do I have the right leaders in place who can act as “mini-CEOs”?
• Am I holding onto roles or decisions I should delegate?

Let me know how you’re tackling this challenge. I’d love to hear your thoughts and don’t forget to check out the full webinar for more insights on making the leap from founder to CEO.

​Watch the Webinar Here.

Here’s to scaling smartly!

Thank you and catch you soon,

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