Definitely, Maybe Agile
Definitely, Maybe Agile
Peter Maddison and Dave Sharrock
Why AI Agents Need Room to Fail Before They Learn
17 minutes Posted Jul 30, 2026 at 5:00 pm.
Welcome To Definitely Maybe Agile
AI Experiments And OAuth Frustration
What Autonomy Really Changes
Articulate The Objective Clearly
Measuring Success In Messy Work
AlphaGo Style Learning With Guardrails
The Satir Curve Of Change Costs
Beyond Optimization Toward Business Rethink
Context Windows Takeaways And Wrap
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Giving an AI agent real autonomy means accepting it will fail early and often before it gets good, the same curve organizations hit during any real change. Peter Maddison brings a stuck OAuth problem to the table: an AI agent that kept going in circles and couldn't find its way through. That leads into a conversation from Dave Sharrock's local AI meetup about an AlphaGo-style approach to AI agent autonomy: instead of specifying every step, you define hard constraints and let the model work o...