What this is

Transition Coaching is a structured process for founders at the end of a venture — or any leader at a significant career crossroads. The focus is practical: what do I do next, what are my real options, and how do I pursue the right one deliberately.

It's shorter and more tightly structured than ongoing coaching. Three sessions, preparation work, and synthesis running throughout. The goal is clarity and momentum, not an open-ended conversation.

Who it's for

Founders stepping away from a venture — whether that's a sale, a wind-down, or simply a decision to move on. And any senior leader facing a significant transition who wants a more structured approach than conventional career coaching provides.

If any of this sounds familiar, it's probably worth a conversation:

You're not sure how your experience reads to people outside the world you've been working in. Founders are often highly capable generalists who've spent their careers focused on where the work needs doing, not on where they're best suited. As one client put it: "I felt like I could do everything and nothing." Broad operational roles can look attractive but might not be right. Recruiters don't always know what to do with generalists.

The practical concerns feel awkward to name. Most founders don't end their journeys with life-changing wealth. What's more consistent is that they end them with commitments — families, mortgages, sometimes older parents — that weren't there at the start. In a world that prizes mission and purpose, it can feel uncomfortable to say "actually, I need X amount of money." It shouldn't. It's a legitimate and important input.

The experience has been bruising. Not always — but sometimes. Most founders I work with are high-functioning and action-oriented, more focused on what's next than on processing what happened. For others, the journey has knocked their confidence in ways they're not used to. Both are valid. The process meets people where they are.

What I bring

Towards the end of last year I went for lunch with an old client on the day he'd been let go by the company he started. I just listened: a frustrating and even unjust end to a ten year journey, and beyond that, unmapped territory.

Since then I've been working with founders at exactly these moments — either when the writing is on the wall, or post-exit and deciding what comes next. The process was built iteratively through a pilot with three founders, each at the end of their venture but with different stories to tell about it. It was shaped by those conversations, not designed in advance of them.

Discussions with experts and thought leaders in my network helped broaden the focus. Early versions concentrated heavily on the individual: leadership style, strengths, how they operate. The sharper version balances that with the practical: constraints, obligations, what the market actually looks like, and what realistic options exist within it. Both matter. Neither is enough on its own.

And I've learned that founders don't sit on their hands. None of the founders I've worked with waited until the end of the process to act on their insights. The process is designed to create clarity first — and then move with them.

AI runs throughout more explicitly here than in my other work — used to synthesise reflections, build leadership profiles, and help illustrate key decisions as they emerge. This means that between sessions, thinking doesn't sit still. It gets captured, shaped, and fed back.

How it works

Preparation — before the first session, you complete a set of structured inputs: a reflection exercise covering your ambitions, constraints, and where you've done your best work; targeted feedback from a small number of people who know how you operate; and a Hogan psychometric assessment covering leadership strengths, pressure behaviours, and what actually motivates you. Between sessions I'll ask you to reflect on your network, the paths available, and the conversations you've been having as you explore options.

Stage 1: Understanding how you operate — building a clear, grounded picture of where you're strongest, what environments suit you, what drives you, and where you're less likely to be at your best. Output: a professional profile and a sharper narrative about the value you bring.

Stage 2: Evaluating the landscape — turning attention outward. Together we map the realistic paths available and build a framework for evaluating them properly. Most founders aren't short of options at this stage. They're short of a disciplined way to assess them. Output: a decision framework that helps you compare opportunities against what actually matters to you.

Stage 3: Execution and momentum — sharpening how you tell your story, developing a targeted approach to the people and conversations worth having, and staying grounded through a search that will have its difficult moments. Output: clear next steps and a networking strategy.

The process is built to flex. Once there's clarity or a live opportunity, the sessions move with it — a job offer that's come in early, a difficult rejection worth unpacking, a pitch that needs sharpening.

What you get

• A grounded professional profile built from assessment data, structured reflection, and stakeholder feedback

• A decision framework for evaluating opportunities against what actually matters to you

• A clearer narrative about your experience and what it's worth in the market

• Three sessions, preparation work, and synthesis throughout