AI Talent & Careers
The changing jobs, skills, incentives, training, compensation, and career choices created by AI-native software development.
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Should You Take That Job or Should You Stay
Executive Deck ↗Exec summary ↗Listen ↗A comprehensive guide for developers weighing an offer, leaders trying to retain talent, and executives wondering why their best people keep leaving. The diagnostic that reveals whether an engineering org has actually adopted AI or just bought the tools.
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I Think I Know Where Your High Performers Are
Executive Deck ↗Exec summary ↗Listen ↗Your heaviest AI users are probably your best people. That’s the easy part. The harder question, the one that actually matters, is who still is not really using it. Go find out. It’s going to be an awkward conversation.
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The People Conversation
Executive Deck ↗Exec summary ↗Listen ↗Every executive conversation I have starts the same way. Tooling budgets. Adoption dashboards. Training roadmaps. All of it oriented around the technology. None of it oriented around the people. Anywhere from twenty minutes in to the relationship or 20 months, someone asks the real question. How do we know our people can actually do this? […]
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If Your Engineers Only Get Thirty Minutes to Learn, That Is Not Their Failure. It Is Yours.
Executive Deck ↗Exec summary ↗Listen ↗You called to talk about AI adoption. But you do not know your value streams, your engineers get thirty minutes a week to learn, and you are still defending manual QA that produces no ROI. That is not an adoption problem. That is a leadership problem you built and now own.
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Congratulations: You Just Reinvented Peter Gibbons from Office Space
Executive Deck ↗Exec summary ↗Listen ↗A 2025 parody exploring how enterprise AI adoption recreated Office Space. Your measurement systems train top performers to do just enough. That is not their failure. It is yours.
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Stop Asking for “Advanced” AI Training
Executive Deck ↗Exec summary ↗Listen ↗Advanced AI training is a status marker, not a learning objective. Discover what you actually need to know based on your role and current skill level.
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Dear Jim in Detroit — Don’t Punish Your Top AI Dev
Executive Deck ↗Exec summary ↗Listen ↗An open letter to engineering managers: why punishing your fastest AI adopters creates a lose-lose situation. Here’s what to do instead.
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What Got You Here Won’t Keep You Here: A Letter to VPs of Engineering
Executive Deck ↗Exec summary ↗Listen ↗VPs of Engineering: your playbook is obsolete. Here’s how AI changes everything about how you lead, measure, and develop your organization.
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What Got You Here Won’t Keep You Here: A Letter to Engineering Directors
Executive Deck ↗Exec summary ↗Listen ↗Engineering directors have 18 months to prove they can transform teams for AI. The market in 2028 will have directors with proven transformation track records. Will you be one of them?
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What Got You Here Won’t Keep You Here: A Letter to Mid and Late-Career Developers
Executive Deck ↗Exec summary ↗Listen ↗Mid and late-career developers: AI isn’t here to replace you. But developers who use AI will replace those who don’t. Here’s how to adapt.
Corporate fiction
Three books. One operating problem. No clean hero.
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