Context Engineering and the Roles AI Is Rewriting

Definitely, Maybe Agile

Definitely, Maybe Agile
Context Engineering and the Roles AI Is Rewriting
Apr 16, 2026 Season 3 Episode 216
Peter Maddison and Dave Sharrock

AI is changing how products get built. That part isn't news. But it's also changing who needs to do what - and that's a conversation most organizations haven't had yet.

In this episode, Peter and Dave dig into one of the more interesting tensions emerging in 2026: as coding agents take on more of the actual development work, the thing that drives quality output isn't just better tooling. It's better context. Clear, structured, well-owned context that tells agents what you're actually trying to build, who it's for, and what can't be compromised.

Which raises a real question. Who owns that? Where does it live? And what happens when it's missing - which, let's be honest, it usually is?

They get into the rise of "context engineering" as a role, why the name creates its own problems, and what this shift means for product owners, product managers, and the long-standing gap between business and technology teams.

Key takeaways from this episode:

  • Most organizations have never truly written down their product intent in a structured, usable way. AI is making that gap impossible to ignore.
  • Good context drives better outcomes from agents - and the work of capturing, structuring, and maintaining that context needs a clear owner.
  • Start asking: what context exists to guide your products? Where is it stored? Who creates it? Who picks it up and moves it through the system?
  • The business and technology divide matters more now, not less. You can't afford to throw things over the wall anymore. The two groups need to work closely together, not in parallel.
  • What's new here isn't the idea. It's the urgency. These are transformations organizations have been attempting for years. AI is just forcing the issue.

Want to continue the conversation?

If this episode brought up questions about how your teams are navigating the shift to agentic development - or where context ownership actually sits in your organization - reach out at feedback@definitelymaybeagile.com. We'd love to hear what you're seeing.

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