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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

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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18:40

Why Lean Startup Isn't Dead (And When You Need...

Definitely, Maybe Agile ·

2025/07/31

Is the Lean Startup methodology dead? Peter and Dave tackle the growing criticism around MVP approaches and explore why this foundational model still has its place in modern product development. Drawing from George Box's famous insight that "all models are wrong, but some are useful," they discuss how tools evolve but don't necessarily become obsolete. With AI making prototyping faster and cheaper than ever, the conversation explores what's changed about experimentation and what hasn't. The h...

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19:09

Risk & Agile – Why Moving Fast Doesn’t Have to Break...

Definitely, Maybe Agile ·

2025/07/24

Can agile teams really move fast without breaking stuff? In this episode, Dave and Peter dig into one of the biggest tensions in modern software delivery: the push for speed versus the need to manage risk. They unpack the idea that when agile is done right, it actually helps reduce risk, not amplify it. You’ll hear stories and analogies (yep, including a messy kitchen and airplane cockpits) that bring this idea to life. Along the way, they highlight why teams that obsess over "faster delivery...

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27:20

Cybersecurity Insights with Peter Buckley

Definitely, Maybe Agile ·

2025/07/17

Former HSBC Canada CISO Peter Buckley shares practical cybersecurity advice for small and medium enterprises. Despite having fewer resources, SMEs face the same cyber threats as large corporations, ransomware and data breaches. Peter breaks down how organizations can manage 80% of their cyber risk through smart planning and leveraging existing tools, without requiring massive budgets or dedicated security teams. We explore how cybersecurity extends beyond technology into HR practices, organiz...

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14:07

There Are No Safe Bets in Business Anymore

Definitely, Maybe Agile ·

2025/07/03

In this episode, Dave and Peter explore why "safe bets" in business can be the riskiest moves today. They unpack the shift from long-term plans to fast, testable experiments, and why companies must embrace uncertainty to stay competitive. Topics include digital transformation pitfalls, cultural resistance to change, and the importance of alignment over tech. Key takeaways: Shorter cycles are essentialThere are no safe bets anymoreAlignment matters more than technologyFor more insights, visit ...

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30:47

AI and Knowledge Management with Derek Crager

Definitely, Maybe Agile ·

2025/06/19

In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock are joined by Derek Crager, a seasoned engineer turned AI entrepreneur who shares his journey from blue-collar work to building AI-powered knowledge management solutions. Derek discusses how AI is transforming workplace onboarding, knowledge transfer, and personal productivity, drawing parallels between today's AI revolution and the early days of the internet. Derek brings a practical perspective on implementing AI i...

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37:24

Building Remote Teams Through Culture with Leandro...

Definitely, Maybe Agile ·

2025/06/12

Talent acquisition remains stuck in the past while organizations have drastically evolved. "We still hire like it's 1999," explains Leandro Cartelli, CEO of Lana Talent, highlighting a critical disconnect between modern business needs and outdated hiring practices. In this episode, Dave and Peter explore with Leandro how successful teams are built through strategic cultural assessment rather than simple skill matching. The conversation reveals the difference between "cultural fit" and "...

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15:50

Why Executive Buy-In Needs Both Strategy AND Tactics

Definitely, Maybe Agile ·

2025/06/05

Getting executive buy-in for transformation requires more than vision – it demands clarity about what will actually change and how success will be measured. Leaders need concrete details about what will look different in their organization, not just high-level strategy. This episode explores balancing directive consulting with coaching. Modern transformations benefit from proven frameworks combined with coaching conversations that help leaders navigate challenges personally. We also examine m...

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33:28

Product Manager Impact with Shobhit Chugh

Definitely, Maybe Agile ·

2025/05/29

In this insightful episode of Definitely Maybe Agile, Shobhit, CEO and founder of Intentional Product Manager, shares his journey from engineer to McKinsey consultant to Google product manager, and now to coaching others in building fulfilling product careers. The conversation explores the challenges of breaking into product management, the critical differences between product managers and product owners, and how to demonstrate true value in an increasingly competitive field. This week´s take...

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200 results

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