Tag
Leadership
6 essays
Filed under6 filed
Goal Translation Infrastructure: Encoding What Your Organization Actually Wants
Your Capability Map says a workflow is Agent Ready. Now what does the agent optimize for? OKRs were designed for humans. Agent Actionable Objectives are the translation layer that's been missing.
The Organizational Capability Map: Deciding What Your AI Agents Should Actually Own
Most AI deployments fail not because the technology doesn't work, but because nobody decided which workflows agents should actually own. The Organizational Capability Map is a framework for making that call.
The Intent Gap: Why Your AI Agents Are Optimizing for the Wrong Thing
Klarna's AI agent saved $60M then backfired. The problem wasn't the AI. It was the gap between what agents optimize for and what organizations actually need.
When Measuring Impact Gets in the Way of Actually Having Impact
Teams hit every metric—green dashboards, perfect scores. But customers were frustrated and critical incidents kept happening. Here's why: people spent more time proving they had impact than actually having it. Measurement systems don't just fail, they twist the work they measure.
Why Technical Debt Isn't a Technical Problem
Southwest Airlines lost $825 million in ten days because of a crew scheduling system from the 1990s. Pilots had warned management for years. This wasn't a technical failure—it was a leadership failure. Technical debt isn't a technical problem. It's a business problem disguised as an IT issue.
Three Questions Before Any Technology Decision
A company spent $20M on software that didn't work. They picked tools first, then tried to solve problems. After 20 years at Microsoft, I learned to ask three questions before any tech decision. Start with problems, not solutions.