Writing
Essays on AI, enterprise technology, and software leadership.
Essays
Working with Robert
A short guide to how I think and work — meetings, email, product management fundamentals, KANBAN, North Star, the Popper problem-solving model, and when I bias toward action versus deferred commitment.
Digital Workplace and AI Future
The objections I hear today about AI-powered workplace tools sound remarkably like the ones I heard about cloud-first workplace tech in the early 2010s. A pattern.
Enterprise Product Management Coaching: The Assessment Framework
If you aren't assessing your product managers, you aren't developing them. A three-pillar framework — product, process, people — for coaching PMs in enterprise environments.
The Four Questions of Product Management in Enterprise IT
Marty Cagan's four questions — value, usability, feasibility, viability — still work when your customers sit three floors above you. But how you answer them changes.
The Dark Side of Innovation
The sunshine being sold to us says innovation is a panacea. It isn't. On the difficult, unglamorous work of actually building an innovative culture.
5 Lessons on Leadership from the Dungeon Master's Table
Everything I learned about leadership, I learned from D&D. Five lessons from years behind the Dungeon Master's screen.