Technology Transformation · AI
You're Coaching the Wrong Team
Transformations stall because they coach the team that receives the work instead of the team that shapes it, and AI rollouts are making the same mistake with context.
Perspectives
Working conclusions on enterprise IT, AI transformation, and the business of operating at scale — drawn from years in the room where these decisions actually get made. My thinking, in writing.
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You're Coaching the Wrong Team
Transformations stall because they coach the team that receives the work instead of the team that shapes it, and AI rollouts are making the same mistake with context.
AI Transformation · Automation
The Job Was Never the Unit of Work
AI pays off when you automate a specific moment in a workflow, not an entire job, and the narrow scope that delivers the return is also what keeps it under control.
AI Transformation · Implementation
The AI Implementation Gap Nobody Wants to Own
Most AI implementations underperform not because the technology is wrong, but because the organization deploying it never understood what problem it was actually solving.
Strategy · PE Ownership
The Board Said Modernize. They Meant Something Else.
When a PE-backed board mandates modernization, the word almost never means what the technology team hears — and closing that gap is the only work that matters.
AI Transformation · Operationalization
Agentic AI Won't Fail on the Algorithm. It'll Fail on the Org.
Operationalizing agentic AI fails not because the technology is immature, but because organizations haven't done the slower, harder work of understanding what they're actually asking it to do.
IT Leadership · Service
The Network Is Up. Nobody Cares.
IT organizations that measure success by uptime are solving the wrong problem — the job is not keeping infrastructure running, it's making the people depending on it effective.
PE · IT Strategy
Why the Recommendations Were Right and Nothing Changed
The most expensive consulting failures aren't caused by bad advice. They're caused by advice that was technically correct and organizationally impossible.