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CEO and Founder Coaching

CEO coaching solves an availability problem before it solves a skills problem.

CEO and founder coaching — a founder reviewing a printed board pack alone at a desk after hours, Canada

Free call first, then the $1,500 Bottleneck Diagnostic

Key takeaways

  • A founder has a board that wants confidence, a team that wants certainty, and nobody whose job is to disagree with them in private. That is what this fills.
  • Big decisions get rehearsed before the meeting, not reviewed after it.
  • Direct challenge is part of the deal. If you hire an outside counterpart and get agreement, you have bought nothing.
  • What happens to the company after you is part of the conversation, whether or not you raise it.

CEO coaching solves an availability problem before it solves a skills problem. A founder of a company between $500k and $50M has a board that wants confidence, a leadership team that wants certainty, a spouse who has heard it all already, and nobody whose job is to disagree with them in private. That gap is where the worst decisions get made. This engagement fills it.

What this covers

  • One confidential counterpart who is not on the cap table, the payroll or the board
  • Founder-transition work: moving from doing the work to owning the system that does it
  • Board and investor decisions rehearsed in a 90-minute session before the meeting, not reviewed after
  • CEO coaching and founder coaching in one engagement rather than sold as two
  • Direct challenge written into the scope before the first session
  • Sessions monthly or every 2 weeks, 90 minutes, timed to the board calendar
  • Written decision log after every session, kept by the CEO and nobody else

Who this is for

Founders and CEOs whose company has outgrown the way it used to run. The tell is always the same: revenue grew, headcount grew, and your calendar looks exactly like it did two years ago. The company scaled. The habits did not.

Your exit, your succession, the horizon you are working towards: that is part of the conversation whether you raise it or not. A transition you have not planned is one somebody else will plan for you.

How it works

The Bottleneck Diagnostic opens the work: interviews inside the company, a look at how decisions actually move, and a written finding delivered to you. Sessions then run monthly or every two weeks, ninety minutes each. Board and investor decisions get rehearsed in the session before you take them into the room.

Direct challenge is written into the scope. The first uncomfortable session should not be a surprise.

What we work on

The last three tasks you still do yourself, which are almost always the three you enjoy. How long decisions take to get made, which in owner-led companies is the most common problem and the least measured. Whether your second layer is weak or simply never allowed to decide. Board preparation. And your own pattern under pressure, which is the slowest item and usually the real one.

Alternatives

If the problem is your co-founder rather than the company, mediation for business partners. If the team below you cannot yet carry decisions, executive team coaching or leadership development consulting. If the structure itself is wrong, organizational design consulting.

CEO and Founder Coaching at a glance
First stepA free 30-minute call
ThenThe Bottleneck Diagnostic, $1,500, fixed
After thatScoped and priced from what the diagnostic finds
DeliveryVirtual, or on site by arrangement
Built forOwner-led companies, $500k–$50M revenue
If we are not the fixWe say so on the call

Next step

How to start

Book a free call. We talk for about thirty minutes about your company and what is stuck. If it sounds like something we can help with, the next step is the Bottleneck Diagnostic, a fixed piece of work at $1,500 that tells you in writing what is actually holding the company back. Any work after that is scoped and priced from what the diagnostic finds. If it turns out we are not the right fit, we will tell you on the call.

Start with a free call

Thirty minutes about your company and what is stuck. If we can help, the next step is the $1,500 Bottleneck Diagnostic. If we cannot, we will say so.