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. 6D AGO

    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 work. They cover five key predictions: AI moves from tools to organizational capability: Organizations that invest in literacy, governance, and data foundations will pull ahead of those just sprinkling AI on top and hoping for the best.Critical thinking beats prompt engineering: The real competitive advantage won't be writing clever prompts. It'll be knowing when to pause, think through the problem, and decide if you even need the AI in the first place.Product delivery becomes non-negotiable: After 20 years of pushing Agile principles, AI might finally force organizations to actually adopt them (even if they're reluctant to call it "Agile").Businesses return to fundamentals: Just like the dot-com bubble, we're heading toward a moment where the market will care more about revenue, customers, and sustainability than hype.Reskilling becomes a structural investment: Organizations will need to figure out what roles actually look like in an AI-enabled world and invest in growing their people, not just replacing them.At the end, Peter and Dave pick which prediction is hardest to measure (spoiler: it's critical thinking) and commit to revisiting these in March to see how wrong they were. If you've been wondering where all this AI stuff is actually heading, this episode cuts through the noise with grounded, practical predictions you can actually use. Related episodes: AI and Knowledge Management with Derek Crager: https://www.buzzsprout.com/1643821/episodes/17360635Product vs. Process Innovation: https://www.buzzsprout.com/1643821/episodes/7953100There Are No Safe Bets in Business Anymore: https://www.buzzsprout.com/1643821/episodes/17433034Reach out: feedback@definitelymaybeagile.com

    25 min

  2. DEC 12

    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 Essentials, to explore how self-awareness shapes better leadership. They dig into why even talented leaders struggle with identity shifts, how generational expectations are changing the workplace, and why the best coaches focus on small tweaks rather than complete overhauls. From the reluctant engineer-turned-manager to the chef who can't slow down, this conversation gets real about the grief of letting go of old identities and the messy work of looking in the mirror. This week´s takeaway:  Your gifts become your blind spots when overused. That strength that got you promoted? It might be working against you now. The key is recognizing when speed becomes recklessness, when confidence becomes rigidity, or when expertise becomes tunnel vision.Identity shifts are a grieving process. Moving from individual contributor to leader to leader of leaders isn't just a promotion. It requires letting go of the identity you've built your career on, and that loss is real. Give yourself (and others) permission to struggle with it.Skip the woo-woo, ask "why" instead. Self-reflection doesn't have to feel soft or abstract. Simple questions like "Why did I react that way?" or "What role am I playing in this?" are pragmatic tools that work in any meeting, with any team.

    35 min

  3. DEC 4

    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 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 employees as customers. He walks through real examples of iterative onboarding improvements, the importance of understanding jobs to be done in hiring, and why talent density matters more than filling seats quickly. The conversation explores compensation dynamics, the value of matchmaking over recruiting, and how small experiments can build momentum for broader HR transformation. Whether you're leading people operations or navigating organizational change, this episode offers practical insights on making HR less transactional and more intentional. Key Takeaways: Start with discovery, not solutions – Before building HR processes or solutions, take time to interview employees, understand their stories and experiences, and map out what's actually obstructing outcomes. Even 10 minutes of discovery beats rushing to a result.HR as a matching exercise, not a numbers game – Recruitment and people management generate real value when viewed as careful matchmaking between what work a company offers and what employees are looking for, rather than just transactional headcount filling.Make HR less transactional – Slow down important conversations around hiring, onboarding, and employee experience. These decisions deserve the same rigor companies apply to external product development, not just checkbox processes.

    41 min

  4. NOV 27

    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, 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 competitors. You'll learn: Why documenting your product strategy matters (and why most PMs skip it)How to prompt AI to be critical, not just complimentaryThe danger of accepting AI outputs without evaluationTemperature settings, context windows, and other practical techniquesWhat to do with the time you get back (hint: talk to real customers)Dave and Peter also share a key practice: write down what you expect before you prompt. This simple step helps you critically evaluate AI responses instead of accepting them at face value. If you're a product manager, product owner, or anyone building digital products, this conversation will help you use AI as a tool for better thinking, not just faster output.

    20 min

  5. NOV 20

    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 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 to move beyond "toy apps" to create real business value with AI. Key topics covered: • Why organizations need an AI strategy before investing in tools • The critical importance of end-user proficiency with LLMs • How cross-functional collaboration enables AI success • Why annual planning cycles may be holding your AI initiatives back • The parallels between agile adoption and AI transformation • Moving from efficiency gains to true value creation Whether you're leading AI initiatives, managing agile transformations, or wondering why your organization's AI investments aren't paying off, this conversation offers practical frameworks for thinking about organizational readiness in the age of generative AI. THREE KEY TAKEAWAYS: 1. End-user proficiency is everything.  2. Define the sandbox before choosing the toys. 3. Innovation in planning matters as much as innovation in products.  Contact us: feedback@definitelymaybeagile.com #GenerativeAI #AgileTransformation #OrganizationalChange #AIReadiness #DigitalTransformation #LLM #CrossFunctionalTeams #Innovation

    41 min

  6. NOV 13

    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 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 efficiency and customer experience, and why starting with internal-facing AI tools is the safest path to transformation. Discover the surprising truth about which customer satisfaction metric actually predicts loyalty (hint: it's not what most companies are measuring), and why customer expectations for AI are shaped more by bad experiences with other companies than by anything your organization does. THREE KEY TAKEAWAYS: 1. AI for Everyone, Not Just Customers: AI can transform your entire organization, from helping frontline agents with real-time guidance, to giving managers instant analysis capabilities, to enabling executives to make data-driven strategic decisions. The most successful implementations use AI across all levels: customers, agents, managers, and executives. 2. Start Internal, Then Scale Outward: Begin with internal tools that help agents, managers, and executives first. This builds confidence, allows teams to experience the technology firsthand, and creates incremental improvements that build organizational trust. By the time you roll out customer-facing AI, your entire team understands and trusts the system. 3. The best predictor of customer loyalty isn't satisfaction scores or Net Promoter Score, it's the Customer Effort Score. Ask customers, "How much effort was required for you to get what you needed?" after each interaction. Low-effort experiences drive loyalty, and this metric gives you actionable insights into where to improve your service processes. CONTACT US: Email: feedback@definitelymaybeagile.com Definitely Maybe Agile explores the complexities of adopting new ways of working at scale, covering digital transformation, agile practices, and DevOps in enterprise environments. #AI #CustomerService #Banking #DigitalTransformation #ContactCenter #CreditUnions #CustomerExperience #Glia #FinancialServices #AgileTransformation

    43 min

  7. NOV 7

    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, 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: Meet Organizations Where They Are - Don't force rigid methodologies or terminology. Use the organization's own language and focus on solving their actual problems rather than trying to "fix" them with prescribed frameworks.The Power of Cohorts - Change isn't an individual effort. Building a cohort of four people creates redundancy, moral support, and a self-reinforcing dynamic that can create ripples throughout the organization.Communication is Critical - We don't invest enough in helping leaders develop communication skills. Leaders need ongoing support, coaching, and safe spaces to develop their ability to listen, speak up, and collaborate effectively.Featured Guest: Barbara Whittmann - Founder, Digital Wisdom Collective Contact: feedback@definitelymaybeagile.com

    39 min

  8. OCT 30

    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 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. 🔔 Subscribe to never miss an episode of Definitely Maybe Agile! 💬 What's your biggest leadership challenge? Tag us with #DefiniteMaybeAgile

    48 min
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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.

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  • Creator
    Peter Maddison and Dave Sharrock
  • Years Active
    2021 - 2025
  • Episodes
    204
  • Rating
    Clean
  • Copyright
    © 2025 Definitely, Maybe Agile
  • Show Website
    Definitely, Maybe Agile