Definitely, Maybe Agile

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.

  1. 3d ago

    What Happened to the Scrum Master Role?

    The Scrum Master role hasn't disappeared. It's been diluted, pushed outside the organization, or absorbed into everyone's job description. Peter Maddison and Dave Sharrock dig into what's actually happened to the Scrum Master and agile coach role as AI reshapes how teams work. They trace how a role that once had real impact got watered down as two-day certifications flooded the market, and why the deeper value was never the role itself but the culture of continuous improvement it was meant to build. Using Toyota's andon cord as a lens, they compare organizations that treat problems as learning opportunities against those just racing to get the line moving again. The stronger realization is understanding when continuous learning shifts from being a role-driven practice to a part of the culture. This week's takeaways: - The standalone Scrum Master role got diluted as it became widespread, and the certifications never guaranteed the facilitation and coaching skill the role actually required. - The real value was never the role, it was building a culture of continuous improvement, and that culture works best as a shared responsibility across a team rather than one person's job. - Toyota's andon cord shows the difference between organizations that treat a pulled cord as a signal to learn versus organizations that only care about getting the line moving again. Listen to the full episode at definitelymaybeagile.com Subscribe so you never miss an episode. Have a question or topic you'd like us to cover? Reach out at feedback@definitelymaybeagile.com

  2. Aug 6

    What Your AI Token Spend Is Actually Buying

    AI vendors are shifting from flat-fee pricing to consumption-based billing, and most organizations have no idea what their token spend is actually producing. Dave Sharrock and Peter Maddison break down what's driving the shift to AI token economics, why the old "$20 per user" budget model is breaking down, and why usage alone is the wrong thing to optimize for. They dig into the pattern showing up across organizations, where a small share of users account for half the token spend, and why chasing that number down misses the real question: what value did that spend create? The conversation covers KPI traps, model selection tradeoffs, and how to build the kind of honest, open culture that lets you actually govern AI spend without punishing your best people. This week's takeaways: - Token usage by itself is a bad KPI once your organization has moved past early AI adoption, because it stops measuring exploration and starts driving the wrong behavior. - The 10% of users driving 50% of the token spend aren't automatically the problem. Some are generating outsized value, and the only way to know is to ask them directly. - Managing AI cost well means pairing spend visibility and caps with an honest conversation about the value that spend is producing, not just sorting a table by usage. Listen to the full episode at definitelymaybeagile.com Subscribe so you never miss an episode. Have a question or topic you'd like us to cover? Reach out at feedback@definitelymaybeagile.com

  3. Jul 30

    Why AI Agents Need Room to Fail Before They Learn

    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 out its own strategy inside them. Peter and Dave connect this to the Virginia Satir change curve, the same dip in performance that shows up when an organization tries a new way of working, and to the difference between using AI to optimize what you already do versus using it to rethink the business itself. They also get into how experiments like Andon Labs' AI-run cafes and vending machines use small dollar constraints to let a model learn from failure without real financial risk. This week's takeaways: - A well-articulated objective with clear guardrails lets an AI agent find its own path to a solution, even one you didn't expect or fully understand. - Real learning, whether it's an AI agent or an organization adopting a new way of working, comes with an unavoidable dip in performance that can't be planned away. - The bigger opportunity with AI isn't squeezing more efficiency out of an existing process, it's using AI to test entirely different ways a business could operate. Listen to the full episode at definitelymaybeagile.com Subscribe so you never miss an episode. Have a question or topic you'd like us to cover? Reach out at feedback@definitelymaybeagile.com

  4. Jul 23

    AI Coding Speed Isn't Agile's Real Bottleneck

    AI can write code faster than ever, but Peter Maddison and Dave Sharrock argue that coding was never the actual bottleneck in software delivery. In this conversation about AI software delivery, Peter and Dave dig into why faster coding hasn't solved the two problems that always mattered: knowing whether what you built is actually valuable, and knowing what to build in the first place. They connect this back to sprint length, arguing it was never set by how hard the coding is, but by how fast an organization can learn and decide. As AI generates more options and even makes decisions on our behalf, the conversation turns to what happens when judgment can't keep pace with output, and why product owners and stakeholders still need real time to validate high-risk calls. This week's takeaways: - Coding speed was never the real constraint. The two problems that still matter are knowing if something is valuable and knowing what to build in the first place. - Sprint length should be set by your organization's decision and learning latency, not by how fast code can be written. - As AI generates more options and even makes decisions for you, leaders need time and context to validate high-risk calls, because judgment doesn't speed up as easily as output does. Listen to the full episode at definitelymaybeagile.com Subscribe so you never miss an episode. Have a question or topic you'd like us to cover? Reach out at feedback@definitelymaybeagile.com

  5. Jul 9

    Why Change Triggers Your Organization's Immune System

    Organizational change resistance isn't dysfunction, it's a system doing exactly what it was built to do. Peter and Dave break down why structures, incentives, and leadership behavior create that resistance, and how AI is now exposing it faster than ever. Dave and Peter dig into what they call the organizational immune system: the structures, incentives, and habits that keep a company stable, and that fight back the moment you try to change them. They use the Boeing and McDonnell Douglas merger as a case study in how a shift in incentives can erode a culture built over decades, and how long it takes to rebuild that trust once it's gone. The conversation moves into how AI adoption doesn't fix broken systems, it amplifies the weak spots organizations have been avoiding for years, and forces conversations that used to be easy to put off. They close with a look at how value stream mapping can make an organization's hidden dependencies visible, so leaders can work with the immune system instead of fighting it. This week's takeaways: - Organizational structures exist to stabilize behavior, so treating them as barriers to simply remove often creates new problems you didn't expect. - Real change comes from adjusting incentives and giving people permission to experiment, not from stripping away the systems that hold the organization together. - AI adoption doesn't repair a broken process, it amplifies existing weak spots and forces the difficult conversations organizations have been putting off. Listen to the full episode at definitelymaybeagile.com  Subscribe so you never miss an episode.

  6. Jul 2

    Organizational Honesty in Agile Teams

    Organizational honesty starts with information: can your team actually see what's happening, and can they say it without fear of pushback? Dave and Peter dig into why teams shade the truth when a deadline is on the line, and what actually creates room for honesty instead. They talk about the difference between activity data and real information, why cheap, near real-time visual management beats a hand-curated status report, and why the structure of a status meeting decides whether bad news gets absorbed or gets shot down. They also get into why understanding how work flows end to end matters more than staring at a single date on a calendar. This week's takeaways: Cheap, near real-time visual management pulled straight from your work management systems gives people something honest to talk about instead of a filtered report.Structure in status conversations matters because it lets people absorb bad news and adjust instead of reacting defensively, which makes it safer to bring problems forward next time.Understanding how work actually flows end to end, not just watching a deadline date, is what shows you where the real bottlenecks and constraints are.Listen to the full episode at definitelymaybeagile.com  Subscribe so you never miss an episode.  Have a question or topic you'd like us to cover? Reach out at feedback@definitelymaybeagile.com

  7. Jun 25

    AI Is Speeding Up Delivery. Are You Building the Right Thing?

    AI is making it faster and cheaper to ship features. That doesn't mean you should ship more of them at once. Peter and Dave dig into a pattern they're both starting to see: organizations using AI-assisted development as a reason to bring back big upfront planning and large project releases. The logic makes a certain kind of sense. If AI can build faster, why not design bigger? But that reasoning skips the part that actually mattered when teams moved to product delivery in the first place: validating that you're building what customers actually need. The conversation covers why large releases make it harder to learn what's working, why feature parity with competitors is a trap, and what "North Star context" actually means when you're coordinating AI agents. The core argument: the planning layer is back in vogue for good reason, but the delivery layer still needs to be small and iterative. Cheaper to build doesn't reduce business risk. It just makes it easier to build the wrong thing faster. This week's takeaways: AI augmentation speeds up building and releasing features, but it doesn't replace the need to validate whether those features are what customers actually want.A big picture plan is useful as context for AI agents and delivery teams, but over-specifying every step upfront wastes time on details that will change anyway.The goal isn't projects vs. product delivery. It's combining a clear long-term direction with small, measurable, iterative delivery tied to real outcome metrics.Listen to the full episode at definitelymaybeagile.com  Subscribe so you never miss an episode.  Have a question or topic you'd like us to cover? Reach out at feedback@definitelymaybeagile.com

  8. Jun 18

    Data, AI, and Knowing When to Let Go - with Tommy Cotter

    Tommy Cotter is Director of Data Products at Benzinga, a financial media company building the data infrastructure that sits behind trading platforms and investment apps used by millions of people daily. He's been navigating the shift to AI-assisted workflows in a space where speed and accuracy aren't just nice to have - getting it wrong has real consequences. In this episode, Peter and Dave talk with Tommy about what it actually looks like to build data products responsibly in a fast-moving AI environment. They get into where humans still need to be in the loop, how compliance has become a competitive signal, and why being nimble matters more than picking the perfect architecture from day one. Three things to take away from this conversation: Self-agency is real now. If you have a strong conviction about a product or problem, the barrier to building something has never been lower. That's a genuine shift from even five years ago.Security and compliance are no longer just internal concerns. In a world where AI startups spin up overnight, having invested in SOC2 or GDPR signals to customers that you're a legitimate, trustworthy operation. It's a market differentiator.Humans still belong in the system. Not everywhere, but in the right places. For low-risk, deterministic processes, let AI run. For anything client-facing or accuracy-critical, keep a human in the loop. Knowing the difference is the skill.If this conversation sparked something for you, send us your thoughts at feedback@definitelymaybeagile.com. And if you haven't already, hit subscribe so you don't miss the next one.

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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.

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  • Creator
    Peter Maddison and Dave Sharrock
  • Years Active
    2021 - 2026
  • Episodes
    231
  • Rating
    Clean
  • Copyright
    © 2026 Definitely, Maybe Agile
  • Show Website
    Definitely, Maybe Agile