Leadership By Design 2026
Hilarious Tales of Failure: What a Year of Building With AI Taught Me
None of us feel like experts right now, and the loudest voices online are making that worse. I want to fix that for 30 minutes.
A year ago I started building an AI product-management assistant, mostly to teach myself what these tools could actually do. It’s been genuinely messy: agents that confidently reported things that weren’t true, a scheduled job that died silently through a server reboot, a “fix” that looked more precise and quietly made things worse. I’ll walk through the real failures, not the highlight reel, and the one principle that’s kept the whole thing usable through all of it: the human has to own the loop, not just be somewhere inside it.
If you’ve felt behind on AI, or suspicious of everyone who claims they’re not, this talk is for you. Bring your hands. We’re getting them dirty.
