The founder coaching guide: leadership development for scaling founders

How coaching helps founders in growth businesses

I came to coaching the long way round. I had twenty-six years experience as a founder, managing director and chief operating officer first – running agencies, scaling a listed technology group from £31.5m to £83m, leading teams through acquisitions, integrations and leadership transitions – and only then formally training as a coach. I’ve been coaching founders and operational leaders since 2021 and the reason I trained properly rather than coaching based on my operator CV was simple: I wanted to do this work to the standard I’d want if I were the founder sitting on the other side of the conversation.

This guide is the honest version of what founder coaching is, how it’s different from the adjacent roles (advisor, mentor, therapist, consultant), when it’s the right tool, what a session actually looks like, how to choose a coach and most importantly when to step away from coaching. If you’re a founder weighing up whether coaching is the right investment of your time and money, this page is written for you.

What founder coaching actually is

Coaching is a structured, confidential conversation between a founder and a trained coach, usually on a regular rhythm, designed to help the founder think more clearly, decide more wisely and grow as the person leading the business.

The defining feature of coaching – the thing that makes it different from advising, mentoring or consulting – is that the coach doesn’t bring the answers. The coach brings questions, a framework for thinking and disciplined attention. The answers come from the founder because the founder is the one who has to live with them.

This sounds counter-intuitive to founders the first time they hear it. Why pay somebody to ask questions? Isn’t it faster if they just tell you what they’d do?

The short answer is that the work a founder most needs help with isn’t the kind of work that responds to being told. Decisions about how you lead, how you show up, how you handle pressure, how you manage your own reactions, how you sit with the uncertainty of a hard week – these aren’t problems where somebody else’s answer maps cleanly onto your life. The work has to be yours. My job as a coach is to make the work happen faster and more reliably than it would if you were doing it alone.

The distinction: coaching, advising, mentoring, therapy

These four words get used interchangeably and they shouldn’t be. The roles do different work and it’s a problem when they get mixed up.

A coach works on the founder. The subject of the conversation is you – how you’re leading, how you’re thinking, how you’re holding the weight of the role. The business shows up as context not as the central subject. A coach will almost never tell you what to do about the business. They will help you work out what you want to do about the business and why.

An advisor works on the decisions in front of the founder. The subject of the conversation is the business – which way to jump on this fundraise, how to think about this acquisition, how to structure this exec team. An advisor is expected to bring pattern-matched views from their own experience. (I also work with founders as an advisor, separately from coaching – but the two are different engagements and I’m clear with founders about which mode we’re in.)

A mentor is someone a little further along the path you’re on, usually with a more informal, less structured relationship. Mentoring sits between coaching and advising – a mentor will sometimes ask good questions and sometimes give direct advice. In my experience it’s generally looser by design.

A therapist works on psychological issues, often with a clinical purpose. Therapy is the right tool if what you’re facing is a mental health concern, a trauma, or a pattern of life that extends beyond the work context. Coaches are not therapists, and a good coach will tell you directly if what you actually need is therapy. Only work with a qualified therapist – not a coach. I am not a qualified therapist but I know some good ones.

The cleanest way to think about the difference between coaching and therapy: therapy is often oriented backwards toward understanding and healing things from the past. Coaching is oriented forwards toward what you want to do and who you want to become from here. The two overlap, but they’re doing different work.

Why an operator-coach hybrid is different

There are plenty of excellent coaches who have never run a scaling business. There are also plenty of ex-operators who call themselves coaches without ever having been trained in the craft. Both can work but the founders I coach tell me the combination is what they were actually looking for.

What the combination means in practice is that I can sit in a conversation about a board dynamic, a restructure, a commercial crisis or an acquisition and understand the texture of what you’re describing – without falling into the trap of giving you the answer I’d have given as a COO. I’ve been inside those rooms. I’ve made those decisions. I’ve lived with the consequences. That fluency lets coaching work on the real situation rather than on a sanitised version of it and it keeps me honest about the difference between coaching (the work is yours) and operator advice (the work is mine).

When founder coaching is the right tool

Here are five patterns where I’ve found coaching is consistently valuable for founders of scaling businesses.

1. The founder-to-CEO transition. The skills that got the business to £3m – like being in everything, doing most things personally, moving fast on instinct – are not the skills that will get it to £15m. Somewhere in the middle the founder has to become a different kind of leader and that’s a transition coaching is purpose-built for. The business is asking for a version of the founder that doesn’t exist yet and coaching is the space where that version gets built.
2. Letting go. At every stage of a scaling business, the founder has to let go of something – a function they used to run, a decision they used to make, a relationship they used to own. The letting-go is rarely rational. It’s almost always emotional even when it doesn’t feel that way. Coaching is where the emotional work of letting go happens, so that the operational work of delegating can actually land.
3. The weight of the role. Founders are carrying the psychological load of a whole business, often without a peer to share it with. That load doesn’t always look like burnout – sometimes it looks like short temper, sometimes it looks like avoidance, sometimes it looks like drift. Coaching is a structured place to put the weight down for an hour, look at it properly and then pick it back up in a way that’s more manageable.
4. A particular relationship that isn’t working. Maybe with a co-founder, a key hire, an investor, a board member. These conversations are hard to have clearly inside the business because every possible sounding board has their own stake in the answer. A coaching call is the one place where you can think about the relationship without the politics getting in the way.
5. A quiet sense that you’re not leading the way you want to. You’re doing the job and the business is fine. But you’ve noticed that the way you show up at work is a little more reactive, a little more tired, a little less like the version of yourself you’d want your team to see. Coaching gets to work on that gap before it becomes something more expensive.

I also work with members of founders’ leadership teams, which is often where coaching has the fastest visible impact on the business. A senior hire who is being set up to grow into a bigger role – for example a Head of Delivery who is going to become a VP of Operations or a new COO stepping into the seat for the first time – is a perfect candidate for structured coaching alongside the operational work they’re doing.

What actually happens in a coaching session

Founders who haven’t been coached before are often curious about what a session is actually like. The honest version is less mystical than it sounds and more useful than it looks from outside.

My sessions run for one hour. They start with a check-in – what’s on your mind, what happened since the last session, what you want to use this time for. I listen more than I speak in the first part of the conversation, partly because listening is the job and partly because what a founder brings in the opening minutes is almost never the thing the session ends up being about.

Then the session narrows. My job is to help you find the specific piece of the problem that matters most, name it clearly, and sit inside it long enough to see things you wouldn’t have seen on your own. That might involve questions you find uncomfortable. It almost always involves silences – long ones – because some of the best thinking you’ll do in the session happens in the space I leave rather than in the words I say.

Toward the end of the session, the conversation turns to action – not action in the sense of tasks, but in the sense of what you want to be different next week because of what you’ve understood in this hour. Sometimes that’s a specific conversation you’ve committed to have. Sometimes it’s a practice like a way of paying attention that you’re going to try. Sometimes it’s just a clearer view of the decision you were circling, and permission to take your time with it.

Good coaching feels as though something has settled after the session. The problem that walked into the room is usually still there but the founder is meeting it differently.

How to choose a founder coach

Coaching is a market with a huge range of quality and the things that matter aren’t always the obvious ones. Here’s what I’d actually pay attention to if I was a founder looking for a coach.

Formal training, not just experience. Coaching is a craft that can be taught. Look for coaches who have gone through a substantive training programme and work within the code of ethics of a professional body. My own training is the Human Technics Advanced Certificate in Executive Coaching, accredited by the University of the West of England, the International Coaching Federation (ICF) and the Institute of Leadership. I work within the ICF Code of Ethics. Accreditation isn’t a guarantee of quality on its own, but the absence of any credible training is a warning sign: it usually means the coach has decided they don’t need training because they’re “naturally” a good coach.

Experience in the founder world, not just the corporate one. Coaching a founder of a scale-up is different from coaching a senior manager at a FTSE 100. The stakes are more personal, the context is messier, the weight is carried differently. A coach who has worked primarily with corporate executives may be excellent but may not know the shape of founder life well enough to meet you where you are.

An operator background (or at least operator fluency). You don’t need a coach who’s been a CEO. But you do need a coach who can sit in the room with a founder talking about a board meeting, an exec-team restructure or a commercial crisis and understand the context of what’s being described, not treat every business decision as an abstract case study. Operator fluency lets the coaching work on the real situation rather than on a sanitised version of it.

Somebody whose questions you actually feel in the first conversation. Every good coach offers a chemistry session – a first conversation that’s free and that lets you test the relationship. In that hour pay attention to whether the coach’s questions move you. Do you find yourself thinking about something differently by the end of the call? Do you feel a little uncomfortable (in a useful way)? If the call felt pleasant but unmemorable, the coach probably isn’t the right fit for the work you need to do.

Clarity about what they won’t do. A good coach is open about the boundaries of coaching. They won’t diagnose. They won’t tell you what to do about a specific business decision (that’s advisory work). They won’t work with somebody who needs clinical mental health support rather than coaching. If the coach pretends to do everything, be cautious.

When coaching isn’t the right tool

When what you actually need is advice. If the problem in front of you is “should I structure this acquisition as a share deal or an asset deal?” you don’t need a coach – you need an advisor or a lawyer. Coaching can help you work out what you want to achieve with the deal, but it’s not the tool for the mechanics of the decision. If that’s where you are, my advisory or consultant COO services are likely to be a better fit than coaching.

When the problem is clinical. If you’re experiencing something that a good coach would recognise as a mental health concern – sustained low mood, anxiety that’s interfering with day-to-day life, trauma, anything that sits beyond the work context – coaching isn’t the right tool. A good therapist is. A coach who keeps coaching you when the work has moved into clinical territory is not a good coach.

When you’re not willing to be the subject. Coaching only works if the founder is prepared to do the work – to look at themselves honestly, to answer hard questions, to sit with discomfort. Some founders aren’t ready for that,or aren’t ready for that yet. Coaching with a reluctant founder produces frustration on both sides. It’s better to start when you’re willing.

How I work as a founder coach

I work with a small number of founders and senior operators at any one time. Coaching sessions are one hour long, on a fortnightly or monthly rhythm, delivered remotely – which means I work with clients across the UK, Europe and the US in their own time zones. Engagements usually run over an initial six months with a review at the end where we decide whether to continue.

Every engagement starts with a chemistry session – a first conversation where the point is to find out whether the work between us is going to be useful. If it’s not, I’ll say so. There are other good coaches, and part of the job is making sure you’re with the right one even when that isn’t me.

The founders and operators I coach tend to be leading scaling businesses between £1m and £15m revenue typically with 10 to 125 people. That’s the context I know best from my operator career and it’s where the coaching work lands most cleanly against the challenges you’re actually carrying.

Further reading

These articles go deeper into the themes that come up most often in my coaching work with founders of scaling businesses.

• Founder to CEO: how to make the shift — the hardest move most founders ever make, and the five shifts that actually work.
• The founder’s paradox: letting go without losing control — why the letting-go conversation is never really about delegation.
• Why congruence is the most underrated leadership trait — the leadership quality nobody talks about but every team can feel.
• Reflective leadership: the practice most founders skip — the highest-leverage habit most founders never build.

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Next step. If something in this guide has landed with you, book a chemistry session. We’ll spend the time in a real coaching conversation – not a sales call – and at the end of it you’ll have a clearer view of whether coaching is the right tool for what you’re carrying and whether I’m the right person to do it with.

Work with me as a founder coach →