Why has founder CEO succession become one of the most stressful and consequential decisions a board can make?

In this episode of The Boardroom Path, host Ralph Grayson speaks with Evgeny Shadchnev, founder of Makers, author of Startup CEO Succession and coach to founder CEOs, about how to navigate leadership transitions when the stakes feel deeply personal and financially critical. Drawing on his own journey from founder CEO to coach, Evgeny explains the crucial shift from building a product to building the company that builds the product, and why behaviours that work in a five‑person team become harmful in a seventy‑person organisation.

Against a backdrop of rising CEO turnover even at high‑performing companies, as boards lean into more proactive succession planning rather than waiting for crisis, Evgeny and Ralph explore how boards can spot early warning signs, support founders through burnout and identity shifts, and create a safe, trusted space for honest conversations. From job specs that look ahead to where the “puck” is going, to the pitfalls of rushed transitions and lateral moves into chair roles, this conversation offers a practical roadmap for founders, investors and aspiring NEDs.

Evgeny Shadchnev: Evgeny Shadchnev is the founder and former CEO of Makers, one of the UK’s leading coding bootcamps, where he helped tackle the tech talent shortage by training complete beginners to become software developers. After leading Makers through its growth and his own CEO succession, he became a certified professional coach specialising in founder CEO transitions, working with entrepreneurs and boards on the personal and organisational challenges of leadership change. He is the author of Startup CEO Succession: A Founder’s Guide to Leadership Transition and hosts the Startup CEO Succession podcast, where he interviews founders, successor CEOs and investors about real‑world succession stories.

Ralph Grayson: Ralph Grayson is a Partner in the Board Practice at Sainty Hird & Partners, bringing extensive experience in board-level recruitment, assessment, and advisory services. With a deep understanding of the corporate governance landscape, Ralph specialises in guiding senior executives as they transition into impactful boardroom careers. His thoughtful approach, combined with a passion for developing effective leaders, enables him to facilitate insightful conversations that equip aspiring and newly appointed Non-Executive Directors with the tools they need to succeed. Through The Boardroom Path, Ralph leverages his extensive professional network and expertise to empower listeners on their journey into the boardroom.

Episode Insights:

• The founder’s job is to keep the company alive and find product–market fit, while the CEO’s job is to build and lead the organisation that builds the product.
• Behaviours that are life‑saving in a five‑person startup, such as having an opinion on everything, often become micromanagement and a blocker once the team scales.
• Early, ongoing conversations about the CEO job spec, the company’s future needs and the founder’s preferences reduce the risk of crisis‑driven, rushed transitions.
• Trust and informal dialogue between founder, chair and investors are as important as formal board meetings in handling succession with maturity and respect.
• Lateral moves (for example, founder to chair or functional role) only work when the founder is genuinely qualified for the role and willing to get out of the new CEO’s way.

Action Points:

1. Clarify the founder vs CEO job over time: Schedule regular discussions between the founder, chair and board about how the CEO role is evolving over the next two to three years. Map what the company will need from its leader, compare that with the founder’s strengths and preferences, and document a living CEO job spec that is revisited annually rather than only in moments of crisis.
2. Normalise early succession conversations: Build CEO succession into the board’s “good hygiene” agenda, alongside cash flow and risk. Treat it as an ongoing strategic topic, not a signal of imminent removal, so that founders can talk openly about burnout, changing life priorities and future roles without fear that one conversation will trigger an immediate process.
3. Invest in trusted relationships on the board: Ensure there is at least one board member – ideally the chair – with whom the founder has a deep, trusted relationship. Encourage informal check‑ins between meetings so concerns about fit, performance or wellbeing surface early and privately, rather than erupting in formal sessions where they are harder to handle constructively.
4. Design the succession process as a shared project: When a CEO transition becomes likely, treat it as a collaboration between outgoing CEO and board. Co‑create the forward‑looking job description, agree who leads the search, and define how the current CEO will contribute without over‑controlling the process. This shared ownership reduces defensiveness and keeps the company’s long‑term interests at the centre.
5. Plan the founder’s next chapter deliberately: Support the founder in clarifying what comes after the CEO role before any transition is finalised. Encourage them to take time to rest, reflect and explore options such as coaching, new ventures, advisory roles or different executive positions, rather than grabbing the first opportunity. A clear, attractive “next step” makes it easier for the founder to let go and for the board to communicate a confident story to investors.

The Boardroom Path is the essential podcast for aspiring and newly appointed Non-Executive Directors (NEDs) navigating the journey from executive leadership to the boardroom. Hosted by Ralph Grayson, partner at Sainty Hird & Partners, each episode offers insightful conversations with industry leaders, seasoned board directors, and governance experts. Our guests share practical strategies, valuable perspectives, and actionable advice on how to effectively transition into board roles, maximise your impact, and build a rewarding NED career. 

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The Boardroom Path is produced by Story Ninety-Four in Oxford, UK.