Why CEO Coaching Isn't What You Think
Scaling founders make their biggest decisions with the least honest support. CEO coaching exists to fix that.
Somewhere between my seed round and $150 million raised, the coffees stopped.
Early on, I had founder friends at exactly my stage. Someone six months ahead could tell me precisely what was coming.
Then the companies diverged. Some died. Some stalled. Mine kept going, and one day I looked around and realised the people I could be completely honest with had thinned out to almost nobody. Not because of any falling out. Arithmetic.
Nobody warns you about this, because it sounds like a complaint from someone winning. It's actually a common problem for scaling founders: the more successful you become, the fewer people can help you.
What most people think CEO coaching is
Google "CEO coaching" and you'll find leadership development frameworks, communication skills, delegation models. Useful for functional executives. Mostly beside the point for you.
Because what a scaling CEO is missing isn't a skill. It's a person: someone with no agenda, no stake in your answer, and enough scar tissue to recognise where your situation is heading.
Here's why that person gets harder to find precisely when you need them most.
The support curve runs backwards
Part of it is just numbers. Thousands of founders raised a seed round the year you did; far fewer reached Series B; fewer still get beyond it. The peers you started with fall away. Later-stage CEOs don't often show up at founder meetups. You've outgrown your community, and the next one is much harder to find.
The rest is what scale does to the people still around you. Being a founder is like walking around with two hammers duct-taped to your hands. A passing comment, something like "have we thought about enterprise?", and three weeks later someone's built a deck. Your musings get heard as directions, so you learn to stop musing out loud. Your board has its own agenda, and you know it. Other CEOs at your stage are busy, and often quietly competitive.
You end up making the biggest decisions of your company's life with less honest support than you had when the decisions were smaller. On paper, you're the least alone person in the building. In practice, the room where you can say anything has emptied out.
The three conversations you can't have with anyone in the room
Coaching venture-backed CEOs, I've noticed the conversations that actually move things forward come in three shapes. What they have in common: each one is nearly impossible to have with someone who has a stake in your answer.
"What should I do?"
The 51/49 decisions. A founder I coach, who I'll call Priya, spent four sessions on one question: expand to the US or double down on Europe. Everyone around her had an opinion, and every opinion came attached to an interest. Her board wanted growth, her team wanted stability, her co-founder wanted the thing they'd argued about last month.
You don't need another opinion. You need someone who'll help you map what each path requires, what breaks under each one, and what you'd have to believe for either to work. Priya chose Europe. It might still turn out to be wrong, but it's the first big decision in two years she says she'd make the same way again tomorrow.
"How do I do this?"
You already know what needs to happen. You need to move your technical co-founder out of the CTO role, or restructure a team, or push back on an unreasonable board member. The question isn't whether. It's how to do it without breaking the relationship, the team, or the momentum.
These conversations are about sequencing and words. Literally: what do you say, in what order, to whom first. You can't rehearse them with the people involved, and that's usually everyone you trust.
"Am I crazy?"
You're considering something bold and everyone thinks it's risky. Before you make a bet-the-company decision, you need someone to stress-test your thinking who isn't invested in you being right or wrong.
Sometimes the answer is yes, you're missing something, and the conversation saves you from an expensive mistake. Sometimes the idea survives the pressure and you move with real conviction instead of manufactured confidence.
Try this before the week is out
You don't need a coach to start working on this. You need honesty about where your support actually stands. Three questions:
Who was the last person you were completely honest with about the company? Not mostly honest. Completely. If the answer is "no one" or "my partner, at 11pm, badly," that's your data point.
Which decision are you currently re-litigating in your head? The one you keep reopening at odd hours. That's usually a "what should I do?" conversation you haven't had with anyone.
When did you last hear someone describe a problem you're facing and think: they actually get it? If it's been more than a year, you haven't lost your peers. You've outgrown them, and nothing has replaced them yet.
Where a CEO coach fits (and where one doesn't)
I'm obviously not neutral here — I coach CEOs full-time. So let me concede the honest objection: plenty of founders scale without a coach. A great mentor, a genuinely safe co-founder relationship, or a peer group with real trust can cover a lot of this ground.
When I was a CEO, I looked for a coach myself. There were plenty of founder coaches around; I struggled to find one who'd actually sat in the chair. That gap is the reason I do this work now, and it's the test I'd give you whether you talk to me or anyone else: has this person felt the specific pressure of your job, or just studied it?
I did eventually make friends with later-stage founders, by the way. They're generous when I catch them. But a text back between board meetings isn't the same as someone who blocks out hours for your company every week, holds the full context, and picks up the thread exactly where you left it.
Most scaling founders carry this alone for far longer than they need to. I did, and it cost me decisions I'd like back.
Find your person. Start there.
Asher Ismail specialises in CEO coaching for venture-backed founders scaling from Seed through exit. Having raised $150M+ and scaled multiple companies from 0 to 250+ people, Asher combines hard-won founder experience with systematic approaches to help CEOs develop the decision-making skills their companies need.
