Definitely, Maybe Agile

Peter Maddison and Dave Sharrock
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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.

  1. What Your Employees Are Really Thinking with James Warren

    -3 J

    What 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, 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: Trust beats everything: Trust is now the most predictive emotion across industries. High-trust cultures create sustainable advantage while low-trust organizations stay vulnerable to competitorsLeaders must change too: In agile transformations, leadership becomes more important, not less. Leaders need to model vulnerability and change alongside their teamsStories reveal hidden patterns: Traditional data tells you "what" happened but stories tell you "why" it happened, uncovering emotional drivers surveys completely miss

    36 min
  2. Why Lean Startup Isn't Dead (And When You Need Something Bigger)

    31 JUIL.

    Why 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 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: Lean thinking remains relevant: Lean Startup is still a valuable operational tool for continuous learning and incremental improvement, but it works best when properly implemented with complete feedback loopsYou need multiple models: Organizations need both incremental change capabilities (like Lean Startup) and strategic step-change tools (like Wardley mapping) to navigate complexity effectivelyAI commoditizes development, not strategy: While AI tools make prototyping easier and faster, they don't replace the need for good product thinking, user experience design, or asking the right strategic questionsWhether 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.

    19 min
  3. Risk & Agile – Why Moving Fast Doesn’t Have to Break Things

    24 JUIL.

    Risk & 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 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: Learning continuously is more powerful than just moving quicklyTeams should feel safe to say “something doesn’t feel right”Focus on what’s working, not just what’s broken

    19 min
  4. Cybersecurity Insights with Peter Buckley

    17 JUIL.

    Cybersecurity 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 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: Have a Plan: Create and regularly test an incident response plan that outlines what to do when things go wrong, who to call, and how to communicate with stakeholders.Make It Collaborative: Use tabletop exercises and casual team conversations about "what if" scenarios to build risk awareness while fostering team building.Build Community: Connect with industry peers to create a network of contacts you can call during a crisis and share resources with non-competing organizations.

    27 min
  5. There Are No Safe Bets in Business Anymore

    3 JUIL.

    There 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, 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 definitelymaybeagile.com, subscribe, and follow us on social media. Questions or feedback? Reach out at feedback@definitelymaybeagile.com.

    14 min
  6. AI and Knowledge Management with Derek Crager

    19 JUIN

    AI 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 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: Focus on Business Outcomes Over Buzzwords - Don't implement AI just to check a box or follow trends. Instead, identify specific business problems (like inefficient onboarding or knowledge retention) and then explore how AI can provide practical solutions to those challenges.AI Excels at Knowledge Augmentation and Accessibility - AI's greatest strength lies in making organizational knowledge instantly accessible 24/7, without judgment, and at a consistent quality level. This is particularly valuable for onboarding new employees and capturing tribal knowledge from subject matter experts before it walks out the door.Take Time to Learn and Evaluate Before Jumping In - The AI wave mirrors the early internet adoption curve and will continue evolving over the next 10-15 years. Organizations and individuals have time to thoughtfully evaluate AI solutions rather than rushing to adopt the first available option, emphasizing the importance of learning practical applications before implementation.

    31 min
  7. Building Remote Teams Through Culture with Leandro Cartelli

    12 JUIN

    Building 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 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: Culture encompasses both fit and add - assess how candidates navigate existing dynamics while bringing fresh perspectivesRemote work requires intentional investment - comprehensive onboarding and dedicated connection-building are non-negotiableTreat talent acquisition strategically - connect hiring with development plans and performance expectations for real business impact

    37 min
  8. Why Executive Buy-In Needs Both Strategy AND Tactics

    5 JUIN

    Why 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. 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 Close the Vision-Reality Gap - Executives need concrete details about organizational changes, not just strategic conceptsBlend Consulting with Coaching - Combine proven frameworks with personal coaching conversationsMeasure System Change - Focus on meaningful indicators rather than activity metrics

    16 min
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À propos

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.

Informations

  • Création
    Peter Maddison and Dave Sharrock
  • Années d’activité
    2021 - 2025
  • Épisodes
    189
  • Classification
    Tous publics
  • Copyright
    © 2025 Definitely, Maybe Agile
  • Site web de l’émission
    Definitely, Maybe Agile