Managing Expectations in the AI Era
How to have honest conversations with stakeholders about AI productivity — what actually changes, what doesn't, and how to set realistic expectations.
Sprints, story points, and velocity metrics were never a perfect fit for complex software work. Now that LLMs have changed the shape of a development day entirely, the gap between how most teams plan and how work actually gets done has become impossible to ignore. This series covers the tools, habits, and operating models that work better.
How to have honest conversations with stakeholders about AI productivity — what actually changes, what doesn't, and how to set realistic expectations.
How to run a Shape Up betting table — the planning meeting where pitches get selected and cycles begin or quietly collapse.
AI makes implementation cheaper and judgment more valuable. Learn how engineering roles, hiring, and team design are changing.
How to review AI-generated code effectively, what failure modes to watch for, and how to maintain quality standards as code volume increases.
How to write specifications that produce useful LLM output, covering interface definitions, edge cases, and why the spec is your highest-leverage artifact.
A practical introduction to Shape Up - the planning methodology built on appetite over estimation, fixed time with flexible scope, and small autonomous teams.
How to write Shape Up pitches that give engineering teams real clarity - problem definition, appetite, solution shaping, rabbit holes, and no-gos explained.
Technical debt is inevitable. What matters is whether you manage it deliberately. A practical framework for prioritisation and stakeholder communication