It's Decision Time: Why CEOs Stop Trusting Their Judgement

Nearly everyone who enters into a coaching program with me goes through the same thing before getting in touch: an unfamiliar decision, delayed by something clouding what should be a fairly straightforward call. This piece is about decisions, and what's actually on the other side of it. If any part of this article sounds familiar, get in touch before deciding not to.

Edward is not his real name. As with all client stories I share, names and identifying details have been changed to protect confidentiality.

Imagine riding the Tour de France with no stage finishes. No crowds lining the final kilometre, no line to cross at the end of the day, nobody waiting to tell you what you just did was extraordinary. Just the road continuing — the next stage already underway before the last one has properly ended, the real finish always another hundred metres further on than wherever you currently are. You'd still be riding well. You might even be leading. But how long could you feel good about it, with nobody ever there to tell you you'd arrived anywhere?

That's not a cycling problem. It's what running a business at the top of it can feel like, and it's the reason most of the people I work with eventually get in touch.

Edward runs a business with more moving parts than most people would want to hold in their head at once — several challenges in motion at any given time, each one still open when the next begins. He got in touch because he'd stopped trusting his own judgement. Not because anything had gone wrong. Nothing had. He simply couldn't remember the last time he'd felt certain about a decision and had started to wonder whether that meant he was losing his edge, or whether it was because nobody had told him otherwise in longer than he could recall.

He doesn't have a board to sit in front of. He doesn't have a boss to review his year. The business is his to run and his alone to judge, and the nature of what he does means one project is barely finished before three more are already moving. Stage after stage, no podium, no pause — so the feeling of having actually achieved something rarely lands before attention's already needed elsewhere.

Getting in touch was, by his own account, one of the harder things he's done. Not because the process is difficult — it isn't. Because saying "I don't trust my own judgement any more" out loud, even to someone whose entire job is to hear exactly that, felt like making it true. Almost everyone I work with tells me some version of the same thing: the hesitation before that first message was worse than anything that happened after it.

It's a strange kind of self-consciousness, when you think about it. The same person would book an optician the moment reading started giving them headaches, or hire a personal trainer without a second thought. Nobody treats that as an admission of failure. Coaching just happens to be the one form of expert help where asking still feels, to a lot of people, like confessing something.

What He Actually Needed

What we've worked on together was never about fixing his judgement — it was never broken. It was building in the thing his role structurally can't provide: a space to actually see the wins that are already there, rather than racing past them on the way to the next stage.

Session to session, that looks like fairly ordinary things. Somewhere to say out loud everything currently churning round his head, without needing an answer back — a kind of verbal mind-map that, just in the saying, tends to release whatever insight was stuck behind it. Someone pointing at results he'd already achieved and making him actually look at them, properly, instead of nodding and moving straight on. And, more than either of those: permission — real permission, not just the idea of it — to stop for a moment and let a win be a win, before the next stage starts.

There's more to it than relief, though. What's changed for him is how decisions get made in the first place. It's become a habit of reflection rather than a leap: pausing on what he's learned before, checking it against what's in front of him now, and finding the trust is already there in the pattern, even when the specific answer isn't. And when something genuinely new comes up — a decision with no precedent to lean on — he's found he can still draw on the last time he faced exactly that: no map, a decision made anyway, and a result that taught him the process itself could be trusted, even when the outcome couldn't be known in advance. None of that is available to you if you never stop to look at it. Pausing when a goal is actually met, rather than moving straight on to the next stage, is what turns an achievement into something you can learn from.

There's a name for this outside of coaching, and it comes from an unlikely place. In 1974, the tennis coach Tim Gallwey wrote The Inner Game of Tennis, built around a formula that's since travelled well beyond sport: Performance = Potential − Interference. His point wasn't that players lacked skill. It was that most of what blocks good performance is already sitting underneath it — the habits of mind that inhibit excellence, as he called them: self-doubt, over-effort, a mind too busy judging itself to let its own ability through.

Decision-making runs on the same formula. Nobody's judgement gets worse because the skill for it disappeared. What gets in the way is the interference stacked on top of it — the doubt, the overthinking, the second-guessing of calls that were sound to begin with. Take the interference out, and the judgement that was there all along shows up as decision quality.

Getting in touch with me in the first place was itself one of those decisions with no precedent — a path that felt like it sat outside his comfort zone, when it was really just a path he hadn't walked yet. It only felt uncomfortable because he didn't yet know what coaching actually was. Looking back, he calls it a no-brainer.