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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

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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25:08

Why Dedicated Teams FAIL (And What Actually Works...

Definitely, Maybe Agile ·

2025/10/16

🚨 Struggling to implement Agile because you can't get dedicated cross-functional teams? You're not alone. In this episode, Dave Sharrock and Peter Maddison tackle one of the BIGGEST challenges facing late-adopter organizations: how to increase productivity and deliver value when dedicated teams just aren't in the cards. In this episode, we explore: Why the "dedicated team first" approach often crashes in traditional organizationsThe hidden dysfunctions and perverse incentives that keep teams

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29:02

How AI is Transforming UX and Agile Teams with Nick...

Definitely, Maybe Agile ·

2025/10/09

In this episode, hosts Peter Maddison and Dave Sharrock sit down with Nick Cawthon to explore how generative AI is revolutionizing the relationship between UX, design, and agile development. Key Topics: Embedding UX research into agile sprints, balancing short-term feedback loops with long-term strategic insightsThe "electric bicycle" analogy: How AI gives teams superpowers but can also accelerate you in the wrong directionWhy Nick believes he'll never use Figma again, shifting from design to...

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17:59

The Hidden Problem With Customer Journey Mapping

Definitely, Maybe Agile ·

2025/10/02

Customer journey maps have been the standard for years. But what if they're built for a world that no longer exists? Dave and Peter challenge the linear, step-by-step approach to understanding customer experience. From showers on Emirates flights to adaptive payment systems, they explore why our traditional mapping tools might be keeping us from seeing breakthrough opportunities. What We Cover: Why traditional journey maps focus on the "critical path" and miss everything elseThe shift from co...

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34:00

One Pizza Teams vs Two Pizza Teams: When Size...

Definitely, Maybe Agile ·

2025/09/25

Can AI really shrink your development teams from two pizzas to one? Peter and Dave explore the promise and reality of smaller teams in the age of AI agents. While AI can handle documentation, test automation, and other "hygiene" tasks teams often skip, the real question isn't whether you can reduce team size, it's whether you should. They dig into when one-person teams make sense (startups and greenfield projects), when they don't (complex legacy systems), and why the biggest gains might come...

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36:29

Product Diseases and Vision-Driven Development with...

Definitely, Maybe Agile ·

2025/09/18

In this episode, Dave and Peter sit down with Radhika Dutt, author of "Radical Product Thinking: The New Mindset for Innovating Smarter," to explore why iteration-obsessed product development is failing organizations. Radhika shares hard-learned lessons from her 25-year career across diverse industries and five acquisitions, introducing the concept of "product diseases" like hero syndrome, pivotitis, and obsessive sales disorder that plague modern product teams. She challenges conventional wi...

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16:19

AI Agents: Friend or Foe?

Definitely, Maybe Agile ·

2025/09/11

When should you let AI agents loose on your processes, and when should you keep them on a tight leash? Peter and Dave explore the messy reality of using agentic AI for process improvement. They dig into why the processes you can easily map might not be the ones where AI agents add the most value. From recruitment pipelines that need human intuition to DevOps workflows that demand zero variation, not every process is created equal when it comes to AI intervention. This week's takeaways: Catego...

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36:04

What Your Employees Are Really Thinking with James...

Definitely, Maybe Agile ·

2025/09/04

What happens when you look beyond survey data to understand what's really driving your organizational culture? James Warren, founder of Share More Stories, reveals how analyzing employee and customer stories at scale uncovers the hidden "how" and "why" that traditional data misses. His most surprising discovery? Trust has become the single most predictive emotion across all industries. Companies with high trust create lasting loyalty, while low-trust organizations remain vulnerable no matter ...

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208 results

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