Frequently Asked Questions for CEO Coaching

What is CEO Coaching?

CEO coaching is a private, one-on-one relationship between a CEO and an experienced outside advisor who has no stake in the outcome.

It's not consulting — I won't tell you what to do. It's not therapy — we're not excavating your childhood. And it's not the kind of cheerleading that makes you feel good for an hour and changes nothing.

What it is: a regular conversation with someone who is completely objective, asks the questions nobody inside your company will ask, and helps you think through what's actually going on — clearly, honestly, and without an agenda.

Most CEOs of privately held companies have nobody in their immediate world who can do that. Their board has equity. Their leadership team has a reporting relationship. Their spouse has heard it all before.

CEO coaching fills that gap.

It's the thinking partner you didn't know you were missing — until you have one.

How long does a CEO Coaching engagement last?

The minimum engagement is six months — and there's a reason for that.

Real change doesn't happen in a session or two. The first few conversations are about building enough trust to get to the things that actually matter. After that, the work deepens. Patterns surface. Clarity builds.

Six months is where most people start to feel the difference — not just in how they think, but in how they lead, communicate, and make decisions.

After six months we reassess together. Some clients continue for years. Others have what they need and move on. Either outcome is fine — my goal is never to create dependency, it's to make myself unnecessary.

How is the CEO Coaching Process structured?

Simply.

We meet by phone — either twice a month or weekly, depending on what works best for you and where you are in your business. No video calls, no fancy platforms.

Just a phone call.

Before each conversation you'll have things on your mind — decisions you're wrestling with, people situations that aren't resolving, something that's been nagging at you. We start there.

I ask questions. You think out loud. Things that felt tangled start to clarify. By the end of the call you usually know what you actually think — which is most of the time all you need.

Occasionally something comes out of a session that you want to explore further on your own — a question worth sitting with, something worth writing down. That's your call, not mine. I don't assign homework. But some people find it useful.

Between sessions, you have my contact information. If something comes up that can't wait, you can reach me.

That's it. No complexity. No process for the sake of process. Just a regular conversation with someone who is paying close attention — and has no agenda other than your clarity.

How much does CEO Coaching cost?

Pricing depends on the frequency and structure of our engagement and is discussed during the discovery call.

What I'd ask you to consider is this: most CEOs of privately held companies spend significantly more than my fees on advisors who tell them what to do. This is different — and for the right person, the return isn't measured in dollars. It's measured in clarity, better decisions, and a company that reflects what you actually want it to be.

If cost is the primary consideration, we're probably not the right fit. If value is — let's talk.

What if I'm international? Can I still work with you?

I've worked with clients all over the world for the last 20 years.

My booking system makes it easy to find a time that works, and we can use an alternative communication platform/software if cell phone access is difficult or costly.

How do I prepare for my CEO Coaching sessions?

You don't need to prepare much — and that's intentional.

One thing I do ask: please complete the short pre-session questionnaire before we meet. It takes five minutes and means we hit the ground running, as it asked a few prompting questions about what's on your mind right now.  One-liners are okay.

Then you just show up.

Some clients jot down a few notes. Others arrive with nothing and let the conversation find its own direction. Both work fine.

What doesn't work is arriving with a polished presentation of how everything is going. Leave that for the board meeting. This is the one conversation where you don't have to have it together.

Can I reschedule a CEO Coaching session?

Of course. Life happens — especially at the CEO level.

I ask for 24 hours notice when possible, simply out of mutual respect for each other's time. If something comes up last minute, just reach out directly and we'll find another time.

Once you've committed to working together, you can add an assistant's email to your account so they can manage scheduling on your behalf — no reason this needs to land on your plate.

What I'd gently note: the sessions you're most tempted to reschedule are often the ones you need most. When everything is on fire is exactly when having an outside perspective matters. But that's your call, not mine.

What can I expect during a CEO Clarity Call?

A conversation. That's it.

No pitch, no presentation. Just a short questionnaire beforehand so we're not starting from zero — and then about 30 minutes together to see if this makes sense.

We'll get to know one another, and I'll ask you what's going on. You tell me as much or as little as you want. I set aside a full hour — some people need 20 minutes to know, others need the whole time. Either way, there's no clock pressure. I may ask a few questions that cut a little deeper than you expected — that's intentional, and it gives you a real taste of what the work actually feels like.

By the end you'll know two things: whether you got value from the conversation, and whether you want more of it.

If it's not the right fit, I'll tell you honestly — and if I can point you toward someone who might serve you better, I will.

No pressure. No follow-up sales sequence. Just an honest conversation between two people figuring out if there's something worth doing here.

Does CEO Coaching by phone really work?

Aside from the benefits of avoiding traffic, working by phone is much more effective than video and for some clients even better than face-to-face.

When talking about sensitive issues where you may feel vulnerable, not being seen helps us to get to the heart of the issue faster and with less discomfort.

I already have a mentor, board advisor, or therapist. How is this different?

Each of those relationships has a built-in constraint.

A mentor has their own experience and tends to tell you what they would do. A board advisor has equity — which means they have a stake in certain outcomes. A therapist is working in a different territory entirely.

What I offer is something most CEOs genuinely don't have: a regular conversation with someone who knows your business well enough to ask real questions, has no agenda, no equity, no reporting relationship, and no history with you that shapes what they say.

That combination is rarer than it sounds.

How do I know if I'm ready?

If you're asking that question, you probably are.

The clients who get the most out of this aren't in crisis — they're at an inflection point. Something has shifted, or is about to. The job has changed, the company has grown past what it used to be, or they've achieved what they set out to achieve and found themselves wondering what comes next.

Readiness isn't about having the bandwidth or the budget. It's about being willing to have honest conversations about what's actually going on. If you're there, the timing is probably right.

What kinds of issues do CEOs actually bring to sessions?

Decisions they can't talk through with anyone inside the company. A leadership team situation that isn't resolving. A board dynamic that's starting to create friction. The realization that the company has scaled faster than they have.

Sometimes it's strategic — should we take the investment, do we make this hire, is this the right direction. More often it's personal in ways they didn't expect — identity, energy, what they're actually optimizing for and whether that still makes sense.

The through-line is usually this: something is nagging at them that they can't quite get to the bottom of on their own. That's what we work on.

How will I know if it's working?

Rarely in a dramatic moment. Usually in hindsight.

You'll notice that a decision you would have agonized over for weeks took you two days. That a conversation you'd been avoiding happened — and went better than expected. That you're less reactive in situations that used to knock you off balance.

The clearest signal for most clients is simply this: they find themselves looking forward to the call. Not because it's comfortable — it isn't always — but because it's the one hour where they get to think about what's actually going on without performing for anyone.

That shift in itself tends to be measurable, even when the outcomes aren't.