Why Bold Transformation Fails and How to Lead Through It
A strategic guide for leaders ready to fix the patterns slowing progress and quietly derailing change.
Even the boldest strategy will stall if the leadership system underneath can’t support it.
According to the Boston Consulting Group, just 30% of companies navigate transformation successfully. Most transformation efforts don’t fail because the strategy is wrong or the people aren’t capable, but because of unseen friction, misalignment, and drift that rarely get named.
They fail in the messy middle, where leadership intent meets organisational drag, and no one quite names what’s happening.
If you're leading transformation and it feels harder than it should, this is why.
This guide shows you how to spot the hidden patterns that derail change and what to do to shift them.
Why Bold Transformation Fails is a practical, strategic guide for leaders to uncover
The 4 invisible patterns that quietly stall transformation, even in capable teams
A proven diagnostic to identify what’s slowing you down
Real-world case insights from leadership teams who broke the cycle
The 3 systemic shifts that turn alignment into action
Drawing on over a decade of experience working with global leaders and businesses, this guide provides a lens that you can apply with your team immediately to deliver your most important and complex transformations.
About the Author
Hey, I'm Lily Woi
I’m a People & Culture Catalyst who helps senior leadership teams lead through complexity by shifting how they operate. I work at the intersection of strategy, culture, and leadership and am known for being deeply human, sharply strategic, and refreshingly practical.
Over the past decade, I’ve worked across global organisations, scaling startups, and complex legacy institutions, coaching leadership teams through high-stakes transformations, systemic culture change, and cross-functional misalignment that no amount of slide decks could solve.
But I didn’t start as a coach. I’ve led multimillion-pound transformation programmes, and I’ve been in the rooms where clarity goes missing. I know what it’s like to feel the weight of a stalled transformation, even when the people are great and the strategy looks sharp.
That’s why my work isn’t about quick wins or performance theatre. It’s about helping teams lead differently, in the moments that matter most.
© 2025 Lily Woi Coaching Limited. All rights reserved.
