The Leadership Letter by Phil Hayes-St Clair

Being surrounded by supporters​
​The big problem with going it alone

READ ON PHILHSC.COM • 4 MINUTE READ • 16 SEPT, 2026

I knew I needed help before I knew what help meant.

I was leading a healthcare company during COVID that asked more of me each month than the one before it, and I had reached the point where the quality of my own thinking and my decisions was having an impact on my team.

What I wanted was one person in my working life with no agenda beyond me becoming a better leader and a better human. Everyone else around me had an opinion on what I should do next, and all of them had a stake in which way I moved.

A mutual friend introduced me to Andrew. I saw him speak at an event soon after and sat there thinking, I could work with this guy.

That was the extent of my diligence. I had no picture of what good coaching looked like, what I should expect of it, or how I would know whether it was working.

I did however have a much clearer view of what I didn’t want.

I didn’t want a set of questions that kept circling back to how things made me feel. Therapy has its place, and when I have needed it, I have gone there.

I didn’t want theory delivered by someone who hadn’t done my job and felt the constant low-level unease of having to make decisions where there is no good answer.

And I didn’t want progress measured in a series of handwaving statements. I wanted evidence that the investment was producing change I could measure.

Meet Andrew

Andrew is the youngest man to date to be accepted and serve in the Australian Special Air Service Regiment. He was also my first coach.

He understands high stakes, he has a great sense of humour and he holds a view I have since borrowed, that helping a leader find some peace is the main game, not a nice by-product of the work.

He also understands data and here’s an example.

The first thing he asked me to do was track my self-limiting beliefs. Write them down as they arrived, in the moment, through the week.

The exercise was uncomfortable for about a fortnight, and then it became the most useful thing I did. A belief you carry silently feels like a fact about the world. The same belief written down, dated, sitting alongside the four others you logged that week, starts to look very different.

Counting them gave us a baseline. Months later we could see how many I was logging, which ones had gone quiet, and which one had been under everything the whole time. That was the first quantifiable evidence I had that the work was doing something, and it changed what I thought coaching was for.

He never once asked how any of it made me feel. He asked what I intended to do about the pattern, and then he asked me the same question the following month.

What Andrew gave me was a system I could run without him, with numbers attached so I could see whether it was working.

This is one small example of the power of having a great coach.

150 conversations later

In the last 12 months I have spoken with more than 150 CEOs and their insight led to the design of a group coaching program for chief executives to deliver value and relationships that surprise even the most experienced leaders.

The CEO Lab includes confidential 1:1 time, a class of peers and a system called CLIMB that they can keep using long into the future.

The five-step CLIMB

Step 1: Chart where you are. You start by reflecting on where you are today before anyone offers an opinion about it, including me. You answer 54 questions across nine dimensions, covering energy and clarity, your most important relationships, identity and legacy, decision-making, trust inside your team, the systems and partnerships carrying your growth, women’s health, financial confidence, and what you want from coaching. Most CEOs arrive with a diagnosis already formed, usually a problem that has been living rent-free in their mind for months, and the scoring regularly disagrees with it. Each dimension also carries a written question, and the answers to those usually tell me more than the numbers do. The one that does the most work asks what the real work is, the thing you hope I won’t ask you about and probably will.

Step 2: Limit focus. We review the data and identify the one thing genuinely holding your organisation back. One rock, not five. This is where CEOs resist hardest, because every item on a list of five feels urgent and naming one of them as the constraint means consciously leaving four alone for a while. I wrote about that discipline in The power of subtraction.

Step 3: Invite perspective. This is where you bring your issue or opportunity to the five other CEOs in your class in a special weekly session called the CEO Spotlight. It’s here where you gain candid, thoughtful and confidential perspectives which you fold into your thinking. We use the four chairs from the counsel map I described in Four empty chairs. The Mirror, who reflects you back accurately. The Challenger, who finds the weakest assumption in your reasoning before the market does. The Elder, who has already lived with the consequences of the call you are about to make. The Peer, who can say ‘me too’ and mean it. The insights from these sessions are powerful and fold into the 1:1 sessions you have with me.

Step 4: Make the call. You decide, using the anatomy I set out in The anatomy of good decisions. Context before content, so the people around you know the filter before they know the options. Imperfect information as the default rather than the exception, because the alternative is waiting for a completeness that never arrives. Reasoning you can articulate, in plain words, to the people who need to help you deliver. And closing the loop out loud, so your team has the chance to fully comprehend the direction of the decision.

Step 5: Back-brief and move. You hand the work over properly, which is the part most of us get wrong and still call delegation. This means you describe the outcome rather than the task. You set the boundaries, which is where your control belongs and what makes the first step safe. Then you take the back-brief, where your team tells you the outcome and their plan in their own words, early enough for any misunderstanding to be caught and managed. I set that out in full in Delegate the outcome.

That’s CLIMB.

When it comes to the CEO Lab, each class meets twice a week for six weeks. One call is 1:1, where we work on the thing you would rather not say in front of five other CEOs. The other is the CEO Spotlight, where the class of CEOs work a live problem belonging to one of you. At the end of the six weeks you answer the same 54 questions again, against where you started and against the goal you set yourself in week one. Some dimensions will have moved a long way. One or two will not have moved at all. Both results are worth having, because you can see them rather than sense them.

And after the six weeks, your class keeps meeting once per month and alumni also get access to me for time-sensitive issues and get priority access to attend the annual CEO retreat, a special experience to help you get the recharge you need.

If this reads like a pitch…

If this reads like a pitch, you are reading it right and I would love your help.

The CEO Lab runs in classes of six, with a new class starting every three weeks from 28 September, and a break over Christmas. If it sounds like the environment you’ve been missing, book a clarity call and we will work out whether there’s a fit.

If you are here because somebody sent this to you, that person thinks you are carrying more than you are letting on. In my experience they are usually right.

And if you are not a CEO and not on track to become one, there's a good chance you know someone who is doing everything right and quietly finding it harder than it should be. If that's the case, send this email their way, tell me you did, and I will find a meaningful way to thank you for it.

See you next Wednesday and thanks for reading.

Phil Hayes-St Clair
CEO Coach

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