Shows / Definitely, Maybe Agile
Definitely, Maybe Agile
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.
Episodes
- Definitely, Maybe Agile
AI in the SDLC Is Only as Good as Its Context
AI in the software delivery lifecycle is moving faster than any process you can write down. A model that works today may be wrong in a month or two. Dave…
- Definitely, Maybe Agile
Outcomes Over Output with Mik Kersten
AI can now produce output faster than most organizations can absorb it. Mik Kersten explains why the move from output to outcome has become a leadership job…
- Definitely, Maybe Agile
Is Spec-Driven Development Just Big Upfront Design?
Spec-driven development with AI is getting a lot of attention. Peter and Dave ask when that structure actually helps you, and when it slows you down. They…
- Definitely, Maybe Agile
How to Validate AI Output Before You Trust It
AI agents will tell you everything works. Here is how to validate AI output when the mistakes are ones no human would ever make. Peter and Dave compare notes…
- Definitely, Maybe Agile
Why AI Agents Don't Belong on Your Org Chart
Giving AI agents names and a spot on the org chart makes people feel less accountable for the work, and it squeezes the agent into a role it doesn't need. Dave…
- Definitely, Maybe Agile
AI Changes The Real Bottleneck with Bernie Maloney
AI speeds up building. It doesn't speed up deciding. The real bottleneck has moved to management, and organizations don't see it yet. In this episode, Peter…
- Definitely, Maybe Agile
Why Faster Isn't Better with Dave West
Don't abandon Agile for AI. The real bottleneck isn't speed of delivery, it's organizational decision-making and clarity about value. Dave West, CEO of…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
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…
- Definitely, Maybe Agile
AI Adoption Starts With How People Think, Not Which Tools They Pick - with Royce Sin
Royce Sin spent a decade at HSBC automating things nobody asked him to automate. He didn't ask for permission. He just did it, showed people the results, and…
- Definitely, Maybe Agile
What Organizations Get Wrong About Junior Engineers and AI
As AI handles more of the foundational work, entry-level engineering roles are disappearing. Peter Maddison and Dave Sharrock examine why that trend is…
- Definitely, Maybe Agile
AI in the room, helping non-technical teams actually use it
Conference season is back, and so are the real conversations. In this episode, Peter Maddison and Dave Sharrock catch up after a busy stretch of travel and dig…
- Definitely, Maybe Agile
Why Your SDLC Is Broken with Andre Kaminski
Most organizations think they're doing AI. They've bought the licenses, rolled out the tools, and told the team to start using Copilot. But adding AI on top of…
- Definitely, Maybe Agile
Intent Is Not Enough
Agreeing on an idea doesn't mean you both understood the same thing. Dave Sharrock and Peter Maddison dig into why shared context breaks down in practice, and…
- Definitely, Maybe Agile
Why AI and PowerPoints Are Quietly Killing Your Product Intent
It doesn't happen all at once. A great idea comes out of a strategy session. Someone turns it into a PowerPoint. Another person summarizes that PowerPoint with…
- Definitely, Maybe Agile
Do You Actually Have a Capacity Problem?
Most organizations think they have a capacity problem. They usually don't. What they have is a work-in-progress problem. And those two things call for very…
- Definitely, Maybe Agile
Context Engineering and the Roles AI Is Rewriting
AI is changing how products get built. That part isn't news. But it's also changing who needs to do what - and that's a conversation most organizations haven't…
- Definitely, Maybe Agile
AI Won't Fix a Structural Problem with AJ Bubb
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…
- Definitely, Maybe Agile
Project vs. Product: Finding the Operating Model That Actually Fits
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…
- Definitely, Maybe Agile
Who Decides? Sorting Out Product Managers, Project Managers, and Product Owners
Product manager. Product owner. Project manager. Three roles that often exist in the same organization, sometimes in the same meeting, and frequently stepping…
- Definitely, Maybe Agile
AI Agent Governance in Production with Logan Kelly
Most organizations are somewhere between experimenting with AI agents and quietly hoping nothing breaks in production. Logan Kelly, CEO of Waxle AI, has spent…
- Definitely, Maybe Agile
AI in the Real World, Not the Demo
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…
- Definitely, Maybe Agile
Two Speeds, One Organization
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…
- Definitely, Maybe Agile
AI and Automation with David Kilzer
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…
- Definitely, Maybe Agile
Flow Over Efficiency with Steve Pereira
Peter Maddison and Dave Sharrock sit down with Steve Pereira, founder of Visible Flow Consulting, to talk about something most organizations get backwards: the…
- Definitely, Maybe Agile
AI Foghorns and the New Rules of Innovation
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…
- Definitely, Maybe Agile
Beyond On-Time, On-Budget with Deborah Kaminetzky
You know that expensive software system your company bought that everyone... stopped using? Deborah Kaminetzky sees this pattern constantly. Projects delivered…
- Definitely, Maybe Agile
Why Predictability Beats Features with Ivan Gekht
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…
- Definitely, Maybe Agile
Five AI Predictions for 2026
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…
- Definitely, Maybe Agile
Blind Spots and Better Leaders with Jill Macauley
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…
- Definitely, Maybe Agile
Rethinking HR as a product with Josh Hill
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…
- Definitely, Maybe Agile
AI Tools for Product Managers: Beyond Just Writing User Stories
Product managers and product owners are drowning in documentation, vision statements, roadmaps, and backlogs. But what if AI could handle the heavy lifting…
- Definitely, Maybe Agile
Generative AI Readiness with Justin Trombold
In this episode, Peter Maddison and Dave Sharrock welcome Justin Trombold, President and Founder of Antison Advisors, to discuss the parallels between agile…
- Definitely, Maybe Agile
How AI is Transforming Banking Customer Service with Rick Delisi
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…
- Definitely, Maybe Agile
Empowering Organizations from the Inside with Barbara Whittmann
Welcome to Definitely Maybe Agile! In this episode, Peter Maddison and Dave Sharrock sit down with Barbara Whittmann, founder of the Digital Wisdom Collective…
- Definitely, Maybe Agile
Navigating Change Through Leadership and Culture with Hanna Bauer
When Hanna Bauer's publishing business faced a perfect storm of budget cuts, industry disruption, and the ebook revolution, she learned that Six Sigma…
Definitely, Maybe AgileStay Close to Your Customers (And Your Why) with Hussein Hallak
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…
Definitely, Maybe AgileWhy Dedicated Teams FAIL (And What Actually Works Instead)
🚨 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…
Definitely, Maybe AgileHow AI is Transforming UX and Agile Teams with Nick Cawthon
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…
Definitely, Maybe AgileThe Hidden Problem With Customer Journey Mapping
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…
Definitely, Maybe AgileOne Pizza Teams vs Two Pizza Teams: When Size Actually Matters
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…
Definitely, Maybe AgileProduct Diseases and Vision-Driven Development with Radhika Dutt
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…
Definitely, Maybe AgileAI Agents: Friend or Foe?
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…
Definitely, Maybe AgileWhat Your Employees Are Really Thinking with James Warren
What happens when you look beyond survey data to understand what's really driving your organizational culture? James Warren, founder of Share More Stories…
Definitely, Maybe AgileWhy Lean Startup Isn't Dead (And When You Need Something Bigger)
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…
Definitely, Maybe AgileRisk & Agile – Why Moving Fast Doesn’t Have to Break Things
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…
Definitely, Maybe AgileCybersecurity Insights with Peter Buckley
Former HSBC Canada CISO Peter Buckley shares practical cybersecurity advice for small and medium enterprises. Despite having fewer resources, SMEs face the…
Definitely, Maybe AgileThere Are No Safe Bets in Business Anymore
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…
Definitely, Maybe AgileAI and Knowledge Management with Derek Crager
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…
Definitely, Maybe AgileBuilding Remote Teams Through Culture with Leandro Cartelli
Talent acquisition remains stuck in the past while organizations have drastically evolved. "We still hire like it's 1999," explains Leandro Cartelli, CEO of…
Definitely, Maybe AgileWhy Executive Buy-In Needs Both Strategy AND Tactics
Getting executive buy-in for transformation requires more than vision – it demands clarity about what will actually change and how success will be measured…
Definitely, Maybe AgileProduct Manager Impact with Shobhit Chugh
In this insightful episode of Definitely Maybe Agile, Shobhit, CEO and founder of Intentional Product Manager, shares his journey from engineer to McKinsey…
Definitely, Maybe AgileFrom Vision to Execution with Mark Reich
Why do so many organizational strategies end up as posters on walls rather than driving real change? In this episode, Dave and Peter dive deep with Mark Reich…
Definitely, Maybe AgileFlow States in Remote Teams with Steven Puri
In this episode of Definitely, Maybe Agile, hosts Peter Maddison and David Sharrock welcome Steven Puri, Founder and CEO of The Sukha Company. Drawing from his…