Definitely, Maybe Agile
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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.
202 Episodes
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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 ...
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...
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 ...
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...
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...
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...
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...
🚨 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 ...
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...
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...
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...
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...
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...
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 ...
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...
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...
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...
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 ...
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...
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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