What is startup coaching?

Startup coaching is one-to-one work with a founder or leadership team on the decisions, judgment and relationships that determine whether a young company survives. It differs from consulting, which delivers answers, and from mentoring, which passes on one person's playbook. Coaching works on how the founder thinks, so the answers hold after the coach leaves.

The term covers a lot of ground, and some of what gets sold under it is worth very little. Here is how to tell the difference.

The category is a mess, and that costs you money

"Startup coaching" is not a protected term. Nobody governs it. The person selling it to you might have run three companies, or might have finished a weekend certification and built a website last month. Both will use the same words.

The market splits roughly three ways.

There are operators who coach. People who have actually built and sold things and now work with founders. Expensive, opinionated, and they will disagree with you.

There are trained coaches without operating history. Real craft, real listening skill, genuinely useful for some people. Their limit shows up the moment you need someone who knows what a bad term sheet looks like.

And there is the growing pile of people who read a few books and are hoping you cannot tell. You can, usually inside twenty minutes, if you ask the right question. I have put that question further down.

I am in the first group and I am not neutral about it. My view is that lived experience beats credentials, and I will push back on anyone who treats a certificate as the bar. That said, I have met certified coaches with no founder background who are better at this than plenty of ex-CEOs. The scars matter. They are not the only thing that matters.

What is actually being bought

Strip away the labels and startup coaching tends to be one of four things.

A place to think. The founder has nobody to say the true version to. Every other relationship has a stake in the answer. This is the most common reason people come, though it is rarely the reason they give on the first call.

Pattern recognition. You are hitting a wall. Someone who has seen forty companies hit the same wall can tell you which of the four usual causes it is. This is where operating history earns its fee.

Pressure that you cannot generate alone. Somebody who notices you did not do what you said, and asks about it. Founders are surrounded by people who will not chase them.

Repair work. Something has already broken. The co-founder relationship, the exec team, your health, your marriage. This is the most common actual reason and the least commonly stated one.

Most engagements start as the second and turn into the first or the fourth by month three.

What it looks like inside my practice

Mine is deliberately demanding. Sessions, writing between sessions, homework. Radical transparency from you, constructive candour from me. I stopped offering free discovery calls to unqualified leads because the work only functions when both people take it seriously from the start.

A typical engagement runs six to twelve months. Sessions every two weeks, an hour to ninety minutes. Between them, you write. Most of the value shows up in the writing, because that is where you find out what you actually think.

I work with scaling founders, CEOs and corporate leaders. Not first-time founders at idea stage, and not people looking for general life advice. That is not snobbery about stage. It is that the work I do assumes you already have a company with real weight in it, and without that weight the sessions turn abstract.

[PETER: this article needs one client engagement described start to finish, anonymised. What they arrived with, what it turned out to be, where they landed. That single passage will do more than everything above it.]

The varieties, and which ones mean anything

You will see a lot of labels. Some are real distinctions and some are marketing.

Business growth coaching usually means revenue, channels and the machinery of scaling. Real category, though it often shades into consulting.

Business strategy coaching means working on where the company is going and why. Whether this is coaching or advisory depends entirely on whether the person is drawing answers out of you or handing them over.

Life business coaching is the acknowledgement that the founder's life and the founder's company are one system. I think this is correct and I built my practice on it. It is also the label most likely to be used by someone with nothing behind it.

Executive coaching is the corporate cousin. Usually paid for by the company, which shapes what can be said.

Agile coaching is a different job entirely. That is process work with engineering and product teams, about how they ship. If someone offers you both in the same breath, ask which one they have actually done.

The label matters far less than the person. I have seen founders get more from a good coach with the wrong label than from a badly-matched one with the right one.

What it costs, and what it is worth

Rates run from a few hundred to several thousand per session depending on who you are hiring and what they have done. Nobody publishes this clearly, which is its own signal.

The more useful question is what a bad six months costs you. A co-founder split handled badly can end the company. A hire you kept eighteen months too long costs you the team's respect and a year of momentum. A founder who burns out takes the company down with them, and I say that as someone who nearly did it.

Against those numbers the fee is rarely the real question. The real question is whether the person you are hiring is any good.

How to pick well

Three tests that will tell you more than any website.

Ask them to describe a client they failed. Everyone who has done this seriously has one. If they cannot name it, they are new or they are managing you. Both should cost them the work.

Ask what happens between sessions. If the answer is nothing, you are buying a fortnightly conversation. Pleasant, occasionally useful, rarely enough to change how you operate.

Notice whether they disagree with you in the first meeting. The whole value of this relationship is someone who does not need you to like them. If they spend the intro call agreeing, you have learned what the next six months will be.

And one thing to bring yourself: write down the real problem before you talk to anyone. Not "I want to grow as a leader." The actual sentence, the one you have not said out loud. If you cannot write it, that is information.

Common questions

How is startup coaching different from having an advisor?
An advisor gives you their opinion on your business and often holds equity. A coach works on your judgment and holds nothing. Advisors are good when you need domain knowledge. Coaches are for when the constraint is you.

When is it too early for a coach?
If you are pre-product with two people and no revenue, your problems are almost all solvable by shipping. Spend the money on the product. This work starts paying once you have people, weight and decisions you cannot take to anyone.

What happens in a first session?
In mine, we establish what is actually going on, which is usually not what was written in the enquiry. Expect to be asked what you have not told anyone. Expect to leave with something to write before we speak again.

Can coaching help a founding team, not just one founder?
Yes, and the co-founder relationship is where I see the most damage. The pattern is almost always the same: two people who stopped saying the true thing to each other a long time ago and built the company around the gap.

The short version

Startup coaching is worth a great deal or nothing at all, and the variable is the person, not the category. Ask them about a failure, ask what happens between sessions, and pay attention to whether they are willing to disagree with you before you have paid them anything.

If you want to work out whether this is the right time, get in touch.