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 essential
• There are no safe bets anymore
• Alignment matters more than technology

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:

• 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

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:

• Document your band-aids with clear reasoning and next steps
• Protect team capacity to enable thoughtful decision-making
• Focus on system resilience rather than trying to prevent every failure

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:

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.

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:

• Data fragmentation persists - Organizations struggle with siloed data across systems, especially after mergers, blocking comprehensive analysis.
• AI augments human intelligence - "A doctor with AI will displace a doctor without AI" - the goal is removing grunt work so humans tackle higher-value analysis.
• Measure the "delight KPI" - Track how AI improves job satisfaction by enabling more data-informed work without technical bottlenecks.
• Cultural shift needs technical solutions AND organizational buy-in to overcome skepticism about AI in the workplace.

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:

• Creating capacity through new technologies doesn't mean downsizing teams—it means enabling organizations to address previously neglected but valuable work while maintaining knowledge pipelines.
• Team autonomy is crucial for effective change management—when teams have both direction and freedom to make decisions about their workspace, they can respond more effectively to urgent needs in the system.
• Organizations must recognize and protect "slack time" as a valuable resource rather than inefficiency—this time for maintenance, innovation, and thinking is essential for sustainable systems.

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:

• Product Owners have clearer progression paths toward leadership positions, but organizations must properly position and empower the role from the beginning to enable this growth.
• Scrum Masters develop highly valuable skills in facilitating delivery and optimizing organizational flow, but need to actively demonstrate their impact to create career advancement opportunities.
• Both roles require increasingly strategic thinking about business value and financial outcomes to progress into higher leadership positions within organizations.

In this episode of Definitely Maybe Agile, hosts Peter Maddison and David Sharrock dive into the world of Objectives and Key Results (OKRs). They explore how this increasingly popular framework helps organizations create alignment, measure progress, and foster autonomy while moving away from traditional KPIs. From the origins at Intel in the 70s to widespread adoption by tech giants like Google, Peter and David discuss the nuances of implementing OKRs effectively and why they're particularly well-suited for organizations operating in rapidly changing environments.

This week´s takeaways:

• Unlike KPIs which measure performance, OKRs measure progress and alignment to strategy. They should never be tied to individual performance metrics as this undermines their exploratory nature.
• Successful OKR implementation requires ongoing conversations, regular reviews, and a cultural shift. Many organizations underestimate the effort needed to maintain OKRs effectively.
• Effective OKRs should be limited in number (3-5 objectives with 3-5 key results each), represent stretch goals beyond business-as-usual, and serve as a prioritization mechanism for the organization.

When was the last time raising risk in your organization led to anything other than slowing down? Join hosts Peter Maddison and David Sharrock as they challenge conventional thinking about risk management in the age of rapid technological change. This episode reveals why traditional approaches might be putting your organization in greater danger.

Drawing from their battle-tested experience working with financial and technology organizations, Peter and David crack open the uncomfortable truth: many companies still treat risk management as a checkbox exercise rather than a competitive advantage. They reveal how the explosion of data analytics capabilities has rendered old "rule of thumb" approaches obsolete while simultaneously creating entirely new risk landscapes that most organizations are woefully unprepared to navigate.

This week's takeaways :

1. Risk management begins with identifying vulnerabilities, understanding potential impacts, and making informed decisions about how to handle them—whether through acceptance, avoidance, transfer, or reduction.
2. Effective risk management isn't just about frameworks and committees—it requires a cultural environment of psychological safety where risks can be openly discussed without fear.
3. The most effective approaches position oversight functions like architecture as service providers rather than gatekeepers, helping teams move forward safely rather than simply blocking progress.

Subscribe to "Definitely Maybe Agile" to transform how your organization approaches risk, digital transformation, and DevOps at scale.

In this insightful episode of "Definitely Maybe Agile," hosts Peter Maddison and Dave Sharrock welcome David Hirschfeld, founder and CEO of Tekyz Inc, to discuss the complexities of effective product management. A 35-year software development veteran and former physics student from UCLA, David brings a unique perspective shaped by leadership roles at tech giants like Computer Associates, Texas Instruments, Intel, and Motorola.

The conversation explores the critical balance between product market fit and product solution fit, with David emphasizing why focusing on customer problems rather than product features leads to greater success. Whether you're a startup founder, product manager, or development team leader, this episode with the host of the Scaling Smarter Podcast provides actionable insights for creating products that truly solve customer problems and generate sustainable revenue.

This week´s takeaways:

• The most valuable customer conversations happen when you ask about their problems, not your product features.
• Successful product management requires understanding both the perceived impact of a problem and its actual cost to customers.
• Successful founders and product managers are those who love understanding customer problems and spend their time learning about customer challenges.

In this engaging episode of "Definitely Maybe Agile," hosts Peter Maddison and David Sharrock welcome Marcelo Calbucci, author of "The PR FAQ Framework." Marcelo shares his expertise from 25+ years at companies like Amazon and Microsoft, plus his extensive startup experience.

The conversation explores the Press Release and Frequently Asked Questions (PR FAQ) framework developed at Amazon around 2004. This approach helps teams clarify vision and strategy before jumping into execution, addressing a common problem in software projects. Unlike PowerPoint presentations that can create an "illusion of clarity," the PR FAQ document promotes alignment and ownership through collaborative creation.

This week´s takeaways:

• Why most PR FAQs actually lead to "no" decisions (which is valuable)
• How the framework balances strategic thinking with practical considerations
• The importance of involving multiple stakeholders (sometimes 20+ people)
• How PR FAQs can be used at different product lifecycle stages

The hosts draw parallels to lean startup methodology, while Marcelo explains why PR FAQ encourages "thinking before shooting" rather than the "build first, learn later" approach. The discussion highlights how clear, collaborative documentation can prevent misalignment and create shared ownership of initiatives.

You can check out Marcelo's website and book here: The PRFAQ Framework

In this episode of Definitely Maybe Agile, Peter Maddison and Dave Sharrock dive into the nuances of intake funnels and definitions of ready—key concepts for ensuring work progresses effectively. They explore how traditional project delivery mindsets differ from product-driven approaches, emphasizing the need for adaptability, continuous learning, and decision points that prevent wasted effort.

From setting clear entry criteria to measuring throughput and pivoting when needed, they break down how teams can structure their workflows to prioritize value-driven outcomes. Whether you're refining your backlog, managing stakeholder expectations, or optimizing delivery processes, this episode provides practical insights to help you navigate uncertainty while keeping momentum.

This week´s takeaways: 

• Clear intake process – Define criteria to assess idea readiness before execution.
• Product vs. project mindset – Embrace uncertainty and pivot as needed.
• Measure progress – Use checkpoints and throughput tracking to prioritize work.

Tune in to learn how to balance discipline with flexibility and ensure your work moves forward with intention!

 In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock explore the evolution of Agile methodologies. They discuss how Agile represents solutions to persistent problems that may be rebranded but address fundamental needs. The hosts examine why Agile has faced criticism, drawing parallels to Lean's journey from buzzword to established methodology, while exploring the challenges organizations face in implementation.

This week´s takeaways: 

• The fundamental problems Agile addresses remain constant, even as attitudes toward the methodology evolve.
• Organizations often struggle with Agile implementation due to legacy architecture, leadership buy-in, and organizational context.
• Like Lean before it, Agile is transitioning from a hyped methodology to becoming part of a broader toolkit.

Ready for more insights?  Follow Definitely Maybe Agile on your favorite podcast platform and join Peter and David as they tackle the complexities of digital transformation at scale. New episodes drop regularly!

In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock explore the critical role of documentation, terminology, and process definition in scaling organizational success. They discuss how leading companies like Netflix build strong cultures through well-defined terms and principles rather than rigid processes. The hosts dive deep into how architectural decisions, cultural transformation, and team empowerment all stem from having a shared organizational language. Through real-world examples and references to modern practices, they examine the balance between principle-based leadership and necessary process documentation in creating high-performing organizations.

This week´s takeaways:

• Shared terminology drives better communication and decision-making across teams and departments.
• Principles empower teams more effectively than rigid processes and controls.
• Leading with principles while maintaining essential process documentation creates the right organizational balance.

In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock explore the evolution of quarterly planning from traditional PI planning events to more streamlined modern approaches. They discuss how effective quarterly planning reveals organizational dependencies, aligns priorities across teams, and helps maintain focus on delivering value. The hosts share insights on avoiding common pitfalls like over-planning future work and emphasize the importance of maintaining flexibility while ensuring clear direction for immediate execution.

This week´s takeaways:

• Clear, sequenced priorities shared across teams - focus on completing initiatives before starting new ones
• Detailed planning for immediate work (1-2 months), with less detail for future months
• Active dependency management to identify and address bottlenecks early

In this thought-provoking episode of Definitely Maybe Agile, hosts Peter Maddison and Dave Sharrock explore how successful organizations deliver value in today's complex environment. Discover why project success demands both effective execution and tangible business outcomes. The hosts examine the crucial differences between ordered and unordered problem spaces, revealing when to apply Agile versus traditional project management approaches. Learn practical insights about balancing execution with outcomes, and why the most successful organizations master both methodologies. Essential listening for project managers, Agile practitioners, and technology leaders navigating modern delivery challenges.

This week's takeaways:

• Organizations succeed by flexibly switching between agile and traditional project management based on context
• Success comes from delivering tangible business value alongside traditional project execution
• Match your methodology to the problem: ordered problems suit traditional approaches, while complex problems need agile methods

In this episode of Definitely Maybe Agile, Peter Maddison and David Sharrock explore the nuances of product backlogs in agile environments. They discuss the tension between emergent backlogs and fixed feature sets, the importance of backlog management, and various prioritization techniques, including "buy a feature" and impact-effort matrices.

This week's takeaways:

• Separate tactical (near-term) and strategic backlogs to reduce psychological pressure and maintain focus - avoid creating extensive long-term backlogs that will likely become irrelevant.
• Stakeholder prioritization must be balanced with technical constraints and team capabilities - product owners should communicate changes in delivery order transparently to maintain trust.
• Regular backlog refinement should include archiving rejected items instead of deleting them, helping teams avoid repeatedly addressing the same requests while keeping the active backlog manageable.

Ready to scale your agile practices? Tune in to more episodes on your favorite platform.

Join Peter Maddison and David Sharrock in this thought-provoking episode of Definitely Maybe Agile as they explore the evolution of leadership decision-making in modern organizations. They dive deep into how traditional leadership models are being challenged by today's business environment and discuss the crucial shift from control-based to collaborative decision-making approaches.

This week´s takeaways: 

•  Executive decision-making challenges often stem from two distinct factors: emotional intelligence issues (dealing with unprepared stakeholders) and critical thinking problems (legitimate exploration of complex issues). 
•  The traditional "highest paid person's opinion" (HiPPO) approach to decision-making is becoming increasingly dangerous in today's rapidly changing business environment, where the speed of market changes demands faster and more distributed decision-making processes. 
•  Modern leadership requires a fundamental shift from centralized control to distributed authority, with leaders focusing on creating frameworks that enable lower-level decision-making while maintaining visibility of outcomes. 

🎧 Want to Transform Your Leadership Approach? Subscribe to Definitely Maybe Agile on your favorite podcast platform

In this episode of Definitely Maybe Agile,  Peter Maddison and David Sharrock explore the evolving complexities of calculating the total cost of ownership (TCO) in modern software development and delivery.

This week´s takeaways:

• TCO fundamentals remain unchanged, but the environment for calculating and applying TCO has become more complex.
• Organizations must distinguish between strategic proprietary development and commoditized solutions, using tools like Wardley mapping to identify where to invest versus reduce costs.
• Understanding and defining system boundaries is crucial for accurate TCO calculation - using approaches like value chain mapping, value stream mapping, or domain-driven design helps identify hidden costs and dependencies.

Subscribe to Definitely Maybe Agile on your favourite platform and join Peter and David as they unpack the challenges of digital transformation at scale.

In this thought-provoking episode of the Definitely, Maybe Agile podcast,  Peter Maddison and David Sharrock dive deep into the evolving world of enterprise data management and its impact on modern organizations. From data hygiene to governance, discover how the definition of corporate data has dramatically shifted in recent years and what it means for your business.

This week´s takeaways:

• How regulatory compliance is reshaping data management practices
• The critical balance between quantitative and qualitative data in decision-making
• The impact of AI and LLMs on data analysis and sentiment tracking

Whether you're a technology leader, data professional, or business executive, this episode provides insights into navigating the complex intersection of data governance, team structure, and business value. Learn why traditional approaches to data management may be insufficient for today's challenges and what successful organizations are doing differently.