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PODCAST

Definitely, Maybe Agile

Peter Maddison and Dave Sharrock

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.

business management

All Episodes

41:27

AI Won't Fix a Structural Problem with AJ Bubb

Definitely, Maybe Agile ·

2026/04/09

A lot of organizations are betting that AI will make their teams faster. Some of them are right. Most are solving the wrong problem. AJ Bubb, founder of MxP Studio and host of Facing Disruption, joins Peter and Dave to talk about what actually happens when AI lands in a development team without fixing the system around it. If engineers can't get approvals, can't get access, and spend half their day in meetings, AI just means they produce more output the organization still can't handle. That's...

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19:46

Project vs. Product: Finding the Operating Model That...

Definitely, Maybe Agile ·

2026/04/02

Most organizations are running some version of a project operating model or a product operating model - or, more honestly, an uncomfortable mix of both. In this episode, Peter Maddison and Dave Sharrock get into what actually separates these two approaches, where the tensions show up, and why copying what works somewhere else rarely lands the way you expect. They dig into how the nature of your work - ordered versus unordered, stable versus volatile - should shape how you plan, who holds deci...

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22:02

Who Decides? Sorting Out Product Managers, Project...

Definitely, Maybe Agile ·

2026/03/26

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 or...

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28:20

AI Agent Governance in Production with Logan Kelly

Definitely, Maybe Agile ·

2026/03/19

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...

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35:55

AI in the Real World, Not the Demo

Definitely, Maybe Agile ·

2026/03/12

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 ...

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19:08

Two Speeds, One Organization

Definitely, Maybe Agile ·

2026/03/05

Something is shifting inside organizations right now, and it's creating a split that's hard to ignore. AI is compressing the time it takes to generate, validate, and prototype ideas. Some people inside your org are moving at a completely different speed than the systems built to support them. Peter and Dave are calling it the great decoupling, and it's already happening whether you've noticed it or not. In this episode, they dig into why acceleration in one part of a system creates pressure e...

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36:56

AI and Automation with David Kilzer

Definitely, Maybe Agile ·

2026/02/26

A few times in tech, two streams collide, and everything changes. David Kilzer has spent 50 years putting automation to work in manufacturing and distribution around the world, and he thinks we're at one of those moments right now. The convergence of AI and humanoid robotics, in his view, is the biggest shift humankind has faced since fire. In this episode, David joins Peter and Dave to unpack where automation ends, and AI begins, why confusing the two creates brittle systems, and what organi...

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39:13

Flow Over Efficiency with Steve Pereira

Definitely, Maybe Agile ·

2026/02/19

Peter Maddison and Dave Sharrock sit down with Steve Pereira, founder of Visible Flow Consulting, to talk about something most organizations get backwards: the obsession with efficiency at the expense of actual flow. Steve works with large companies to improve operational performance through value stream mapping and continuous delivery. But the conversations he keeps having aren't about cutting costs. They're about untethering capable people from the systems that are quietly holding them back...

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22:29

AI Foghorns and the New Rules of Innovation

Definitely, Maybe Agile ·

2026/02/12

The marketplace is full of AI noise, but what does it actually mean for how organizations innovate and learn? Dave and Peter revisit the classic pioneers-settlers-town planners model and discover something unexpected: AI has reversed the flow. Where organizations once looked up the chain for scaling lessons, now large enterprises are watching small explorers to understand disruption, while entrepreneurs stitch together emerging technologies to solve real problems today. The old playbook doesn...

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29:17

Beyond On-Time, On-Budget with Deborah Kaminetzky

Definitely, Maybe Agile ·

2026/02/05

You know that expensive software system your company bought that everyone... stopped using? Deborah Kaminetzky sees this pattern constantly. Projects delivered on time and on budget that still fail because nobody wants to touch them. Deb brings a unique lens to technology implementation. She's a former attorney turned project management consultant who specializes in what she calls the "messy middle" – the space between buying software and actually getting value from it. Her secret? Translatio...

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30:43

Why Predictability Beats Features with Ivan Gekht

Definitely, Maybe Agile ·

2026/01/29

What happens when you need to ship software in environments where failure isn't just expensive, it's catastrophic? Ivan Gekht, CEO of Gehtsoft, joins Peter and Dave to challenge how we think about agile delivery in high-stakes, regulated systems. Forget the innovation lab. Ivan argues that real innovation happens 10 minutes at a time, every day, at your desk. He shares why learning without outcomes is just an expensive distraction, why retrospectives reveal more than sprint planning ever will...

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24:30

Five AI Predictions for 2026

Definitely, Maybe Agile ·

2025/12/18

As we close out 2025, Peter and Dave are making predictions about what's coming in 2026, especially around AI, organizational change, and how teams actually work. They cover five key predictions: AI moves from tools to organizational capability: Organizations that invest in literacy, governance, and data foundations will pull ahead of those just sprinkling AI on top and hoping for the best.Critical thinking beats prompt engineering: The real competitive advantage won't be writing clever promp...

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35:18

Blind Spots and Better Leaders with Jill Macauley

Definitely, Maybe Agile ·

2025/12/12

What happens when your greatest strength becomes your biggest blind spot? In this episode, Peter and Dave sit down with Jill Macauley, COO of Behavioral Essentials, to explore how self-awareness shapes better leadership. They dig into why even talented leaders struggle with identity shifts, how generational expectations are changing the workplace, and why the best coaches focus on small tweaks rather than complete overhauls. From the reluctant engineer-turned-manager to the chef who can't slo...

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40:54

Rethinking HR as a product with Josh Hill

Definitely, Maybe Agile ·

2025/12/04

In this episode, Peter Maddison and Dave Sharrock sit down with Josh Hill, an HR innovator who's challenging the traditional transactional approach to people management. Josh shares his unconventional journey from the Australian military to progressive HR, where he's pioneering the concept of "work as a product" at marketing agency Tier 11 and through his recruiting venture, Super Hired. Josh explains how HR teams can shift from rushing to solutions toward discovery-led approaches that treat ...

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19:43

AI Tools for Product Managers: Beyond Just Writing...

Definitely, Maybe Agile ·

2025/11/27

Product managers and product owners are drowning in documentation, vision statements, roadmaps, and backlogs. But what if AI could handle the heavy lifting, freeing you up to actually talk to customers? In this episode, Dave and Peter explore how large language models are changing product management. They go beyond the obvious use cases (like generating user stories) to discuss upstream opportunities: building product strategy, validating market positioning, and testing ideas against competit...

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40:40

Generative AI Readiness with Justin Trombold

Definitely, Maybe Agile ·

2025/11/20

In this episode, Peter Maddison and Dave Sharrock welcome Justin Trombold, President and Founder of Antison Advisors, to discuss the parallels between agile transformation and generative AI adoption in organizations. Justin shares insights from his work helping companies navigate generative AI readiness, revealing that the biggest challenges aren't technical; they're organizational. From end-user proficiency to cross-functional collaboration, the conversation explores why companies struggle ...

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43:07

How AI is Transforming Banking Customer Service with...

Definitely, Maybe Agile ·

2025/11/13

In this episode, Peter Maddison and Dave Sharrock welcome Rick Delisi, Lead Research Analyst at Glia and co-author of "The Effortless Experience" and "Digital Customer Service," to discuss how AI is transforming customer service in banking and credit unions. Rick reveals why the future of contact centers isn't about eliminating human interaction; it's about automating the routine so humans can focus on building real relationships. Learn how banks are breaking the age-old trade-off between ef...

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38:44

Empowering Organizations from the Inside with Barbara...

Definitely, Maybe Agile ·

2025/11/07

Welcome to Definitely Maybe Agile! In this episode, Peter Maddison and Dave Sharrock sit down with Barbara Whittmann, founder of the Digital Wisdom Collective, to explore how real organizational change happens from the middle out. Barbara shares her 25 years of experience fixing broken digital transformation projects and reveals why the "juicy middle" of organizations holds the key to sustainable change. We dive deep into mindset training, building internal ecosystems, and why most organizati...

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48:23

Navigating Change Through Leadership and Culture with...

Definitely, Maybe Agile ·

2025/10/30

When Hanna Bauer's publishing business faced a perfect storm of budget cuts, industry disruption, and the ebook revolution, she learned that Six Sigma processes weren't enough. The real transformation required leading with heart. In this raw conversation, Hanna shares the wake-up call that changed everything: a top employee resigning to take a pay cut elsewhere. This crisis revealed the truth about organizational change; you can have all the right processes, but without genuine human connecti...

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38:32

Stay Close to Your Customers (And Your Why) with...

Definitely, Maybe Agile ·

2025/10/23

Hussein Hallak, serial entrepreneur and author of The Dark Art of Life Mastery, joins Peter Maddison and Dave Sharrock to talk about what really keeps entrepreneurs in the game. It's not resilience or grit, it's clarity about why you're doing this in the first place. The conversation covers the shift from pre-COVID to post-COVID startup communities, why watching customers do their work beats asking them what they want, and the critical difference between handing off your product and handing o...

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215 results

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