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 takes to build something that holds.
The Why Change Fails series
- The Five Breakpoints Leaders Miss
Why transformations fail: five predictable breakpoints behind stalled change and stalled AI programs, and the question that detects each one early.
- The Stewardship Gap
Change fades after launch because keeping it alive is nobody's job. How to sustain change in an organization by closing the stewardship gap.
- Designed to Stall
A stalled transformation is usually designed that way: the choices that make failure the path of least resistance, and how to see them before launch.
- The AI Mirror
Why AI projects fail after the pilot: the deployment exposes the organization around it. What it reveals, and what to fix first.
- Before It Breaks
How to make change stick in an organization: seven disciplines leaders apply before the launch, not after the stall.
- The Leader the Work Requires
Leading transformational change: what the leader believes about the people they lead, and whether they act on it when it costs something.
The research behind the framework
Sources across consulting firms, academic institutions, and business media, organized by breakpoint and searchable by publisher.
Explore the evidence →The Work in Practice
- Your AI Agent Won't Save You
Why AI agents fail in production: the five breakpoints that decide an enterprise AI deployment before the technology gets the blame.
- The Win Rate Illusion
Your sales win rate measures the signature, not the customer's result. Two illusions revenue teams stopped questioning, and what they cost.
- The Flaw in Forward Deployment
The forward deployed engineer model solves the wrong problem for enterprise AI. Technical capability isn't the constraint; the organization is.
- The Altitude Problem
AI governance challenges start upstream of governance. Why the conversation happens at the wrong altitude, and where the problem sits.
- When Good Enough Isn't
Watermelon metrics: the dashboard is green and the results aren't. What your success rate is hiding, and why the system is built not to notice.
The Work at a Personal Level
- The Interview Audit
Questions to ask before accepting a leadership role: how to screen an organization for whether your mandate can succeed, before you say yes.