What I look for in someone before we start working
Coaching isn't for everyone, and it's certainly not for the people who want it most. Three things I quietly assess before saying yes.
A common assumption: the people who want coaching the most are the ones who'll get the most out of it.
In my experience: not really.
The people who get the most out of this work are usually people who are already moving — already half-changing their life on their own, already running into the wall they need help getting over, already mostly capable of doing it without me but stuck on the part they can't see from the inside.
Wanting coaching, by itself, isn't a signal. Wanting to change something specific, and being willing to put the weight of the actual decision on yourself rather than on the process, is.
Here are three things I'm quietly checking for before I say yes.
1. They've already named the thing
Not perfectly. Not eloquently. But they can point at it.
"I'm working too much" is fine. "I keep avoiding the conversation with my co-founder" is fine. "I don't know who I am outside of this job" is fine. "I want to leave but I can't afford to leave" is fine.
What's not fine is "I just want to be more productive." That's a defended sentence. It tells me they don't want to look at what's underneath, and the work, when we start, will be about getting them to look. That's not impossible — but it's a longer engagement, and I have to know that going in.
2. They're not outsourcing the decision
The people who do well in this work treat me as a thinking partner, not as an oracle.
If the implicit contract is "tell me what to do," we're going to disappoint each other. Not because I don't have opinions — I have many — but because the changes that hold are the ones you've authored. If you wait for me to give you permission to leave the job, you'll find a reason to come back next quarter.
What I want, instead, is someone who shows up willing to think hard, in real time, alongside me. Who can hold a hypothesis lightly. Who can disagree with me when I'm wrong. Who treats the sessions as a place to do their own thinking better, not as a place where I do the thinking for them.
3. They have somewhere to put the work
This sounds practical, but it's the one most people underestimate.
Coaching produces changes you have to actually live. New decisions. Conversations you've been avoiding. A different relationship to your week. If the rest of your life is structured so that nothing can change — if the calendar is fully booked, if every relationship is load-bearing, if there is no slack anywhere — then we'll talk about good ideas every two weeks and none of them will land.
I'd rather work with someone whose life has a little air in it. Not a lot. Just enough room for the answer to actually take hold.
What this means in practice
It means I qualify out of conversations more than people expect.
It means the application form on /start is not a marketing tool — it's a real filter. I read every one. I reply to most of them honestly, even if the honest reply is "I don't think this is the right time for us to work together, and here's what I'd do first."
It means the people I do say yes to are people I expect to do excellent work with. Not because I'm so good — but because the fit is so right that the work was already mostly going to happen, and I'm just there to make it land cleanly.
That's the kind of coaching I want to do. And it's the kind that justifies what it costs.