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.

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explains Leandro Cartelli, CEO of Lana Talent, highlighting a critical disconnect between modern business needs and outdated hiring practices.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 perspectives
• Remote work requires intentional investment - comprehensive onboarding and dedicated connection-building are non-negotiable
• Treat talent acquisition strategically - connect hiring with development plans and performance expectations for real business impact

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 concepts
• Blend Consulting with Coaching - Combine proven frameworks with personal coaching conversations
• Measure System Change - Focus on meaningful indicators rather than activity metrics

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:

• Master the "What if I wasn't here?" question - The most powerful way for product managers to stand out is by clearly articulating what wouldn't have happened without their involvement, moving beyond just keeping engineers busy
• Prioritize product-market fit above all else - If you don't have at least 40% of customers who would "crawl to you" if you took the product away, that should be your only focus until achieved
• Balance execution with strategic thinking - Use the three horizons framework and deliberately make important long-term work urgent by creating commitments and deadlines, while leveraging AI to handle routine tasks faster

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:

• Systems Over Silos: Toyota's integrated management system creates both vertical alignment (connecting corporate objectives to frontline work) and horizontal alignment (ensuring cross-functional collaboration).
• Value-Creating Managers: Middle management layers should be redefined as value creators and people developers rather than eliminated or reduced.
• Improvement at the Gemba: Real progress happens by focusing improvements at the "gemba" (where work actually happens) with leadership's primary role being to remove burdens from frontline workers.

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:

• The Machine That Changed the World - by James P. Womack- https://www.goodreads.com/book/show/93903.The_Machine_That_Changed_the_World_
• Managing Our Purpose - by Mark Reich- https://www.lean.org/store/book/managing-on-purpose/
• Our Least Important Asset - by Peter Capelli- https://www.goodreads.com/book/show/75492283-our-least-important-asset?from_search=true&from_srp=true&qid=IGIsI50s8q&rank=1

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:

• Leaders can create environments where flow happens - Establishing boundaries like protected focus time (e.g., 9 AM to noon) allows team members to accomplish meaningful work before daily meetings begin.
• The "two-problem" approach to creativity - Having more than one challenge to work on simultaneously can unlock creative solutions, as your subconscious mind works on one problem while you actively engage with another.
• Remote work requires different "colors on your palette" - Different work modes (remote, hybrid, in-office) excel at different tasks, with in-person collaboration being particularly valuable for creative ideation and whiteboarding sessions.

Books Mentioned:

• "Flow" by Mihaly Csikszentmihalyi - https://www.goodreads.com/es/book/show/66354.Flow
• "The Net and the Butterfly" by Olivia Fox - https://www.goodreads.com/book/show/30024684-the-net-and-the-butterfly
• "Atomic Habits" by James Clear - https://www.goodreads.com/book/show/40121378-atomic-habits

Every technical system harbors its share of quick fixes and band-aids – those temporary solutions we implement with the best intentions of returning to fix properly "someday." But what happens when that day never comes?

Peter Maddison and David Sharrock dive deep into what they call "longstanding risks" – the accumulated technical debt that results from prioritizing expediency over completeness. Through a relatable example of a memory-leaking service that gets automatically restarted rather than properly fixed, they unpack the hidden costs of these decisions. The conversation reveals how seemingly minor shortcuts can gradually transform robust systems into fragile, unmaintainable messes.

The hosts share a compelling analogy about a utility company that saved money by skipping tree trimming around power lines for just one year – only to face significantly higher costs from the resulting infrastructure damage. This perfectly illustrates how short-term thinking about technical maintenance creates expensive long-term consequences. They offer practical recommendations including proper documentation of temporary fixes, avoiding team overload, and maintaining good system hygiene.

What makes this episode particularly valuable is the mindset shift it advocates: moving from attempting to prevent all possible failures to building systems that remain resilient when inevitable problems occur. As Sharrock references from safety expert Sidney Decker's work, sometimes the best approach is focusing on what makes your system work well rather than obsessively eliminating every risk. Whether you're managing complex technical systems or leading transformation efforts, these insights will help you balance pragmatic solutions with long-term system health.

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:

1. Revisit and reinforce your work definition process regularly, as changing roles and organizational shifts can erode even the most robust systems over time.
2. Use the "full kit" concept as part of your definition of ready, and be willing to say no to work that doesn't meet these criteria.
3. Work is ready to start when it's the team's top priority, has a clearly defined problem to solve, and the team can confidently estimate it within their typical delivery range.