Work That Holds
Seventy percent of large initiatives fail. Most of the remaining thirty percent deliver something less than what was promised. The conditions for both outcomes were set before the work began.
Work That Holds is a publication for senior leaders who want an honest read on why that happens and what it actually takes to build something that holds.
The Why Change Fails series
- The Five Breakpoints Leaders Miss
The five predictable failure patterns that derail large-scale change and why they are almost always visible before they become costly.
- The Stewardship Gap
Why leaders who understand change conceptually still fail to produce it and what separates intent from structural ownership.
- Designed to Stall
The organizational design decisions that make failure the path of least resistance and how to recognize them before they are built in.
- The AI Mirror
What your AI deployment reveals about the organization around it.
- Before It Breaks
Seven disciplines for leaders who want to build something that holds, applied before the launch, not after the stall.
- The Leader the Work Requires
What the leader actually believes about the people they lead and whether they will act on it when it costs something: the question the rest of this series couldn't reach.
The Work in Practice
- Your AI Agent Won't Save You
The five breakpoints explain why enterprise AI deployments fail before the technology gets blamed.
- The Win Rate Illusion
Two illusions the sales industry stopped questioning and the measurement system that sustains both.
- The Flaw in Forward Deployment
Why the Forward Deployed Engineer model solves the wrong problem, and what a complete model requires.
- The Altitude Problem June 30
The AI governance conversation is happening at the wrong altitude. The deeper problem is upstream.