Skipp Williamson: Why Transformations Go Off Track

Skipp Williamson has spent decades working with organisations on one of the most persistent challenges in business: execution. As founder of Partners in Performance, she has seen first-hand how even the most compelling strategies can unravel when delivery falls short. In this conversation, Skipp explores why execution risk is often underestimated at board level, and how major projects can drift off course despite appearing on track. She explains the difference between the "pageantry" of project management and the realities of delivery, and why traditional reporting often obscures more than it reveals. The discussion examines how boards can strengthen oversight without crossing into management, including what to look for in critical projects and how to identify early warning signs. Skipp also shares practical insights on capability, accountability and the importance of leading indicators, alongside lessons from large-scale transformations, AI programs and decarbonisation efforts. Key Takeaways: The illusion of control — how reporting and dashboards can mask emerging risks in major projects. Project failure dynamics — why initiatives drift off course long before problems are visible. Board oversight in practice — probing assumptions, testing readiness and knowing where to focus. Leading versus lagging indicators — shifting from retrospective reporting to forward-looking insight. Transformation at scale — aligning strategy, execution and accountability across complex organisations. AI and execution discipline — applying lessons from past transformations to new technology investments. Decarbonisation as delivery challenge — turning ambition into achievable action.