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 organizations have forgotten the purpose of half their tools and processes.
From navigating the "permafrost layer" of middle management to understanding why AI initiatives often miss the mark, this conversation offers practical insights for anyone working to transform how organizations operate.
Three Key Takeaways:
Featured Guest: Barbara Whittmann - Founder, Digital Wisdom Collective
Contact: feedback@definitelymaybeagile.com
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 connection and psychological safety, your best people will walk.
Whether you're leading digital transformation or navigating organizational change, this episode delivers practical wisdom on building growth-oriented cultures where people actually want to stay.
This week´s Takeaways:
1. Hope Drives Change People with high hope find a way where there is no way. Leaders must tap into this to navigate uncertainty; it's not just positive thinking, it's the catalyst for transformation.
2. Psychological Safety Starts at the Top Growth-oriented cultures need leaders brave enough to say "maybe it's my team" instead of pointing fingers. Cross-functional honesty beats departmental defensiveness every time.
3. Influence > Position Leadership is influence, nothing more, nothing less. You don't need a title to create change; just the will to advocate for your team and drive positive impact.
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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 off your purpose. Hussein also challenges the wall-poster approach to company values and explains why living your principles matters more than declaring them.
Three Key Takeaways:
Topics Covered:
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🚨 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:
The Three Critical Steps:
Whether you're an Agile Coach, Scrum Master, Product Manager, or Engineering Leader dealing with organizational resistance, this episode gives you practical strategies to move forward when structural change isn't an option.
Resources Mentioned:
About Definitely Maybe Agile: Join Peter Maddison (XodiacInc) and Dave Sharrock (IncrementOne) as they discuss the complexities of adopting new ways of working at scale. Real conversations about digital transformation, agile, and DevOps challenges, no sugar-coating, just practical insights.
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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:
Three Key Takeaways:
Connect with us: Website: https://definitelymaybeagile.com/ LinkedIn: https://www.linkedin.com/company/definitely-maybe-agile-podcast Email: feedback@definitelymaybeagile.com
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:
Key Takeaways:
✅ Traditional customer journey mapping optimizes a narrow, linear experience when customers want many different paths
✅ Privacy and ethics matter more as experiences become hyper-personalized
✅ What was too costly before is now feasible, changing the game for customer experience
Perfect for product managers, CX professionals, and digital transformation leaders.
Connect: definitelymaybeagile.com | feedback@definitelymaybeagile.com
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 from augmenting existing teams rather than downsizing them. Plus: why most AI initiatives fail and how to find the real business problems worth solving.
This week´s Takeaways
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 wisdom around OKRs and goal-setting, explaining why they often create an illusion of performance while masking real problems.
The conversation explores why goals, targets, and OKRs backfire and what actually works instead. Radhika introduces her tried-and-tested alternative: a framework for puzzle-setting and puzzle-solving called OHLs (Objectives, Hypotheses, and Learnings). This approach helps companies develop a mindset that equips teams to experiment, learn, and adapt in a disciplined way, ultimately delivering far better results than traditional goal-setting methods.
The discussion dives deep into crafting detailed, hypothesis-driven vision statements that actually help teams make decisions, rather than fluffy corporate speak that sounds inspiring but provides no guidance. Radhika explains how to balance vision debt against short-term survival needs using her three-question puzzle-solving framework.
Key Takeaways:
Free Resource: Download the OHLs template and toolkit: https://www.radicalproduct.com/toolkit/#OHLToolkit
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:
If you're wrestling with where to apply AI in your organization without breaking what already works, this episode offers a practical framework for thinking through the trade-offs.
Resource:
Questions or thoughts? Reach us at feedback@definitelymaybeagile.com
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 how well they're currently performing.
Warren shares a compelling healthcare case where well-intentioned technology actually destroyed employee experience by preventing human connections, plus insights on why leadership becomes more critical during agile transformations.
Key Takeaways:
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 hosts dig into common misapplications of Lean Startup principles, from "MVPs" that take months to build to organizations that skip the crucial feedback loops. They also explore when incremental learning isn't enough and you need those bigger strategic pivots.
Plus, they make the case for Wardley mapping as an underutilized tool for spotting step-change opportunities that incremental approaches might miss.
Key Takeaways:
Whether you're questioning your current approach to product development or looking for ways to balance tactical execution with strategic vision, this episode offers a pragmatic perspective on using the right tools for the right challenges.
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" often end up with systems that are, well, kind of fragile.
Whether you're navigating compliance hurdles, trying to foster psychological safety, or just figuring out how to move fast without chaos, this conversation brings a grounded, practical take on how agile and risk can work together, not against each other.
This week’s takeaways:
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, organizational culture, and the power of community collaboration.
Three Key Takeaways:
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:
For more insights, visit definitelymaybeagile.com, subscribe, and follow us on social media. Questions or feedback? Reach out at feedback@definitelymaybeagile.com.
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 in enterprise environments, focusing on his company's voice-powered AI assistant "Pocket Mentor" that helps organizations capture tribal knowledge and streamline employee onboarding. The conversation explores the challenges of extracting expertise from subject matter experts, the importance of having clear business outcomes when adopting AI, and advice for students navigating career choices in an AI-driven world.
Key Takeaways:
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 "cultural add," and how one retail company reduced their 80% turnover rate by half, saving millions through targeted assessment questions.
Leandro breaks down why remote team success hinges on comprehensive onboarding (which drives 80% better retention) and intentional connection building beyond work tasks. Without deliberate efforts like virtual team activities and structured check-ins, remote work becomes "just a slogan" rather than a successful strategy.
Key Takeaways:
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 measuring system change rather than just activity, understanding that progress is non-linear and involves experimentation cycles.
Key Takeaways
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 takeaways:
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, who spent 23 years at Toyota before joining the Lean Enterprise Institute, to examine how Toyota's legendary Hoshin Kanri system transforms strategic thinking into coordinated action.
This week´s takeaways:
Mark explains the fundamental difference between most companies' approach to strategy and Toyota's integrated management system. Unlike conventional top-down cascading goals, Hoshin Kanri creates alignment throughout the organization. The discussion explores practical aspects of strategy execution: separating strategic initiatives from daily management, structuring cross-departmental collaboration, and developing people at all levels. Whether you're struggling with siloed departments, disconnected leadership, or strategies that never fully materialize, this episode offers a blueprint for creating systems that align vision with execution while developing organizational capability.
Resources:
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 unique background spanning Hollywood film production and tech startups, Steven shares fascinating insights about achieving flow states in remote and hybrid work environments.
Steven's journey from IBM software engineer to Hollywood executive (where he helped manage franchises like Die Hard and Wolverine at studios including DreamWorks and 20th Century Fox) provides a refreshing perspective on team productivity and creative collaboration. He explains how the film industry has long mastered the transitions between remote, hybrid, and in-person work—knowledge that proved invaluable when the pandemic forced tech teams into distributed environments.
The conversation explores the neuroscience of creativity, practical leadership approaches to foster flow states, and how Steven's experiences led him to create a platform specifically designed to help remote workers overcome procrastination while maintaining wellbeing. This is one not to miss!
Key Takeaways:
Books Mentioned:
Quick fixes turning into permanent problems? You're not alone.
In this episode of Definitely Maybe Agile, Peter Maddison and Dave Sharrock tackle "longstanding risks" – those temporary solutions that somehow become permanent fixtures in our systems. From memory-leaking services to utility companies skipping maintenance, they explore how small shortcuts create massive long-term costs.
This Week's Takeaways:
Perfect for engineering leaders, DevOps teams, and anyone managing complex technical systems. Subscribe for more insights on scaling agile practices and building maintainable systems.
In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock explore the critical question: "How do we know when work is ready to start developing?" They discuss the challenges of translating business requirements into technical implementation, the importance of having the right people in collaborative discussions, and practical approaches to defining "ready" work. Peter shares recent experiences with organizations struggling with this exact problem, while Dave highlights how trust between business and technology teams impacts the handoff process. They explore visual collaboration techniques, the concept of "full kit," and practical ways to determine if work is truly ready to begin.
This week´s takeaways:
In this insightful conversation with Suzanne El-Moursi, co-founder and CEO of BrightHive, Peter and Dave explore how organizations are addressing the growing gap between data volume and analytical capacity. Suzanne reveals that while 90% of the world's data was created in just the last two years, only about 3% of enterprise employees are data professionals, creating a massive bottleneck where business teams must wait in line for insights from central data teams.
BrightHive's solution is an "agentic data team in a box" – seven AI agents that work in unison to handle the entire data lifecycle from ingestion to governance to analytics. Unlike typical AI solutions, these agents operate at the metadata layer to ensure quality, compliance, and meaningful insights without replacing human expertise.
The conversation covers compelling use cases across industries – from helping resource-constrained organizations extend their analytical capacity to unifying fragmented data landscapes resulting from mergers and acquisitions. Perhaps most striking is Suzanne's vision for measuring AI's impact through what she calls the "delight KPI" – are employees finding their work more fulfilling when augmented by these tools?
Key Takeaways:
In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock explore how increasing technological capabilities—particularly AI and modern development tools—are changing the landscape of organizational change management. They discuss the implications of newly created capacity, the value of team autonomy, and the importance of balancing efficiency with innovation.
This week´s takeaways:
In this episode of Definitely Maybe Agile, hosts Peter Maddison and David Sharrock tackle an often overlooked but critical topic: career progression for Scrum Masters and Product Owners. They explore how organizations initiate these crucial Agile roles but frequently fail to consider their long-term evolution within the company structure.
The discussion contrasts the divergent career trajectories of these two roles. For Product Owners, a clearer path exists from managing individual products to becoming Chief Product Owners and potentially Line of Business managers, though challenges arise when the role lacks proper autonomy or is treated as a part-time responsibility. Meanwhile, Scrum Masters face a more ambiguous journey, with traditional progression into Agile coaching roles becoming increasingly limited in many organizations despite the valuable skills they develop.
Peter and Dave highlight the critical importance of demonstrating value and making contributions visible, particularly for Scrum Masters whose impact often remains behind the scenes. They also discuss how understanding financial aspects of the business becomes increasingly crucial as professionals advance in either career path.
Key Takeaways:
Empowering Organizations from the Inside with Barbara Whittmann
38:44
Navigating Change Through Leadership and Culture with Hanna Bauer
48:23
Stay Close to Your Customers (And Your Why) with Hussein Hallak
38:32
Why Dedicated Teams FAIL (And What Actually Works Instead)
25:08
How AI is Transforming UX and Agile Teams with Nick Cawthon
29:02
The Hidden Problem With Customer Journey Mapping
17:59
One Pizza Teams vs Two Pizza Teams: When Size Actually Matters
34:00
Product Diseases and Vision-Driven Development with Radhika Dutt
36:29
AI Agents: Friend or Foe?
16:19
What Your Employees Are Really Thinking with James Warren
36:04
Why Lean Startup Isn't Dead (And When You Need Something Bigger)
18:40
Risk & Agile – Why Moving Fast Doesn’t Have to Break Things
19:09
Cybersecurity Insights with Peter Buckley
27:20
There Are No Safe Bets in Business Anymore
14:07
AI and Knowledge Management with Derek Crager
30:47
Building Remote Teams Through Culture with Leandro Cartelli
37:24
Why Executive Buy-In Needs Both Strategy AND Tactics
15:50
Product Manager Impact with Shobhit Chugh
33:28
From Vision to Execution with Mark Reich
34:15
Flow States in Remote Teams with Steven Puri
38:15
The Hidden Cost of Temporary Fixes
17:02
When Do You Start Work?
18:43
How AI Agents Are Transforming Enterprise Data Work with Suzanne El-Moursi
41:47
AI, Change Management, and Team Autonomy
17:20
Career Paths for Scrum Masters and Product Owners
20:48