Winmark NETWORK Meeting

Executive Transitions - Why They Often Fail and How to Better Navigate to Success

About

Stepping into a new executive role is one of the highest-stakes moves a leader, and their organisation, can make. The numbers tell a sobering story: research consistently shows that more than 40% of executive transitions fail within the first 18 months. Behind that statistic sit real costs: lost momentum, unsettled teams, damaged reputations, and, too often, a talented leader whose potential never had the chance to land.

So why do so many transitions falter, and what separates the ones that succeed? In this session, Peter Jackson, former CEO of Hill Dickinson LLP, and Richard Turner, a CFO who has held senior finance leadership roles across multiple sectors and geographies, draw on decades of hard-won, first-hand experience to unpack what really goes wrong, and what genuinely works.

Together they'll explore the risks that both the incoming executive and the organisation face during a transition: the misaligned expectations, the unspoken assumptions, the first-90-days traps, and the relationship dynamics that can quietly derail even the most capable appointment. More importantly, they'll share practical, tested approaches for navigating these risks and moving through transition with clarity, confidence and control.

This won't be a lecture. It's a candid, interactive conversation, and every attendee is encouraged to bring their own "tips and tricks" to the table, the lessons, instincts and hard-earned wisdom that have helped them (or those around them) get a transition right, for both the individual executive and the organisation they join.

Whether you're preparing for your own next move, hiring into a critical role, or supporting leaders through change, you'll leave with sharper insight and practical tools to tilt the odds firmly in your favour.

Speaker

Peter Jackson

NED

Taha Capital

Speaker

Richard Turner

Portfolio CFO

Executive Transition Coach / Adviser

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