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Definitely, Maybe Agile

Definitely, Maybe Agile

By: Peter Maddison and Dave Sharrock
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Adopting new ways of working like Agile and DevOps often falters further up the organization. Even in smaller organizations, it can be hard to get right. In this podcast, we are discussing the art and science of definitely, maybe achieving business agility in your organization.© 2026 Definitely, Maybe Agile Economics Management Management & Leadership
Episodes
  • Who Decides? Sorting Out Product Managers, Project Managers, and Product Owners
    Mar 26 2026

    Product manager. Product owner. Project manager. Three roles that often exist in the same organization, sometimes in the same meeting, and frequently stepping on each other's toes. In this episode, Dave and Peter break down what actually separates these roles, why the confusion happens, and what it costs when the lines blur in the wrong ways.

    They dig into the difference between a project-centric operating model and a product operating model, and why that distinction matters more than most organizations realize. They also get into a concept Peter uses with clients: product owners reduce decision latency, project managers reduce reporting latency. It sounds simple, but the implications reach into how teams are funded, how authority is distributed, and why some transformations stall halfway.

    The conversation covers real patterns from the field, including what happens when a technical project manager spends most of his time coordinating 14 dependency groups just so a product owner can get a decision made, and what it looks like when a project-centric funding model quietly undermines a product operating model that was never quite finished.

    They also touch on where AI fits into all of this, and where it currently falls short as a bridge between these two worlds.

    Three key takeaways from this episode:

    1. It's not either-or. Both project management and product management are necessary. The goal is to use each skill set in the right place, not to eliminate one in favor of the other.
    2. The relationship between product managers and project managers works best as a true peer-to-peer dynamic. Hierarchy between the two tends to break things down quickly.
    3. Be clear about decision-making authority. If your product owners don't actually have the autonomy to make decisions, the role isn't working. And if your project managers exist primarily to satisfy a funding model that doesn't match your operating model, that's a signal to look at finishing what you started.

    If this is a conversation your team needs to have, share this episode with them. And if you're finding value in Definitely Maybe Agile, follow the show on your favorite podcast platform so you never miss an episode. New conversations drop every week.

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    22 mins
  • AI Agent Governance in Production with Logan Kelly
    Mar 19 2026

    Most organizations are somewhere between experimenting with AI agents and quietly hoping nothing breaks in production. Logan Kelly, CEO of Waxle AI, has spent a lot of time in that gap, and he thinks governance is the piece most teams are walking past too quickly.

    In this episode, Logan joins Peter and Dave to talk about what agentic governance actually looks like in practice, why a single consistent layer beats a pile of point solutions, and how to keep developers moving fast without letting things go sideways when it counts.

    This week's takeaways:

    • Let your teams experiment. That's how you learn what agents can actually do. Just don't skip governance on the way to production.
    • Governance doesn't have to be a gate. The best version layers in without friction, and gives everyone in the organization visibility, not just the dev team.
    • If a developer has to do extra work to implement a governance feature, that's a design problem. Good governance should work for the developer, not the other way around.
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    28 mins
  • AI in the Real World, Not the Demo
    Mar 12 2026

    Most conversations about AI focus on what it can do in a controlled setting. This one doesn't. Callum Sharrock spends his days deploying AI systems in real environments, watching them succeed and fail in ways no simulation predicted, and reporting what he finds. His conclusion? The trend line is steeper than most people realize, and snapshot thinking is getting a lot of organizations into trouble.

    Peter Maddison and Dave Sharrock dig into why reliability, not capability, is the real adoption bottleneck right now. They talk through what happens when non-deterministic models get applied to problems that need deterministic answers, why validation and testing are becoming more important than writing the code itself, and how the calculus around decision making is changing fast. If you can build and test something in the time it takes to debate whether to do it, the meeting starts to look like the problem.

    They also get into what this means for developers, for leaders, and for anyone trying to figure out where to actually invest their energy right now. The barriers to building have never been lower. That makes the question of what to build more important than ever.

    This isn't a conversation about AI hype. It's about what's actually happening at the frontier, and what it means for the way organizations make decisions.

    This Week's Takeaways:

    1. The barriers to building have never been lower - figuring out what's worth building is now the real work
    2. Leadership is shifting toward agency and rapid decision-making, away from top-down strategy setting
    3. If you can run the experiment in the time it takes to schedule the meeting about it, run the experiment

    If this episode resonated, follow Definitely Maybe Agile wherever you listen to podcasts so you never miss a conversation. And if you know someone spending two hours debating whether to test an idea they could just build, send this one their way. There are plenty more episodes worth your time at definitelymaybeagile.com.

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    36 mins
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