What makes a good CEO coaching programme?

Why does this episode matter for CEO coaching?

Cameron Herold has coached CEOs for decades and grew 1-800-GOT-JUNK from two million to 106 million dollars in revenue as its COO. What makes this conversation useful isn’t the theory. It’s watching him diagnose real leaders in real time: the CEO who can’t find good people, the client who has no time to swim, the executive who’s run a 200-person company without ever being taught to lead one. Each one points at the same thing. What a good coaching programme is actually for.

What are the five takeaways for building a CEO coaching programme?

What did Cameron Herold say about CEO coaching?

These short excerpts show the episode’s most useful points in Cameron Herold’s own words.

“if a leader is making these excuses, it’s a really good sign that they’re hitting their ceiling and their opportunity is to go get coaching so that they can actually bust through that ceiling and continue to scale.”

What it means: the tell that you need a coach isn’t a crisis. It’s the moment a capable leader starts explaining why things can’t change. That’s the skill ceiling talking, and it’s exactly what a good programme is built to break.

“how many hours in your career have you ever been trained on doing proper job interviews?”

What it means: Cameron’s client had hired hundreds of people and still couldn’t find good ones. The problem was never the talent market. It was that he’d never been trained on the core skill. A good programme finds the gap you can’t see and fills it.

“he’d grown at 200-person company without ever really knowing how to be a leader. Because we never really spend time on that.”

What it means: scale hides skill gaps. You can run a large business on drive and instinct and still be missing the fundamentals. Coaching that only flatters you won’t catch that. Coaching that trains you will.

About the guest

Cameron Herold, known as the CEO Whisperer, is the founder of the COO Alliance and the Second in Command podcast. As COO he grew 1-800-GOT-JUNK from two million to 106 million dollars in revenue in six years. He learned to scale at College Pro Painters, where he had trained 120 franchise entrepreneurs by 1993 and later gave the reference that helped fund Kimbal Musk’s first startup, Zip2. He is the author of Vivid Vision, Double Double, Meetings Suck, Free PR, The Miracle Morning for Entrepreneurs and The Second in Command.

Frequently asked questions

What makes a CEO coaching programme worth the money?

A CEO coaching programme is worth it when it changes what your business can carry without you, not just how you feel. It surfaces skills you were never trained on, holds a mirror to your blind spots, and develops your leaders alongside you.

As Cameron Herold puts it, when a leader starts making excuses they’ve hit their ceiling, and that’s where coaching earns its cost.

Should a CEO coaching programme include the leadership team?

Yes. Coaching only the CEO leaves the layer beneath you stuck, and the business can grow only as fast as its managers. A good CEO coaching programme develops you and your senior team together, so alignment and capability rise at the same time.

Cameron Herold’s whole argument is “don’t just grow the CEO”: pro athletes have coaches, and so should your leaders.

How do you know when you need a CEO coach?

The clearest signal that you need a CEO coach is your own excuses. When a capable leader suddenly has no time, can’t find good people, or is working harder without getting further, that’s the ceiling talking.

Cameron describes it as a fly banging its head on the window when the door is open. A coach turns you 90 degrees so you can see it.

What should you look for in a CEO coaching programme in the UK?

Look for practical skill-building over motivation, an outside perspective that names your blind spots, and work that reaches your leadership team, not only you. The test is simple: does it teach you and your leaders how to do the job, or just tell you to try harder.

You can see how our CEO coaching programme works to judge the fit.

How does Monkhouse & Company help with CEO coaching?

Dominic Monkhouse built two 30-million-pound scale-ups and has since coached more than 200 founder-CEOs through exactly this shift: from being the person every decision runs through to leading a team that can carry the business. Every month you stay the single point of failure, the business is capped at your capacity, not its potential. If this episode struck a nerve, see how our CEO coaching programme works.

You might also read eleven proven ways to become a better CEO and why you need to master executive presence for strategic success. If what’s really holding the business back is the founder role rather than the CEO role, start with founder coaching.