The Agile Team That Committed to Failure for 18 Sprints Straight | Darryl Wright

Chris Sims: Middle Management, The Forgotten Layer in Agile Transformations Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Chris Sims recounts his experience with a rapidly growing startup that decided to adopt Scrum to address slowing delivery. When a VP championed the initiative, Chris provided training that generated excitement at the team level. However, they overlooked a critical component: the middle management layer. As teams embraced Scrum, they found themselves caught between multiple sources of direction—their direct managers, project managers, and newly established Product Owners with backlogs. This created confusion as middle managers, who weren't included in the transformation discussions, continued operating in their traditional ways. The result was teams appearing busy yet delivering slowly. Chris emphasizes the importance of considering how management roles evolve during agile transformations, deliberately redefining job descriptions, and helping managers find ways to bring value in the new structure rather than undermining it unintentionally. Self-reflection Question: In your organization's agile transformation, how are you addressing the needs and concerns of middle managers whose roles might be significantly impacted? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Chris Sims Chris Sims is a scrum trainer, agile coach, and recovering C++ developer who helps organizations improve their productivity and happiness. Chris is the founder of Agile Learning Labs and the co-author of two best-selling scrum books: The Elements of Scrum and Scrum: a Breathtakingly Brief and Agile Introduction. You can link with Chris Sims on LinkedIn, visit Chris Sims' Agile Learning Labs website.

23 Huhti 17min

Chris Sims: The Hidden Cost of "No Time for People Stuff" in Software Teams Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Chris Sims shares a challenging team situation involving strong personalities with conflicting opinions about how to approach their work. What began as small disagreements evolved into harmful behaviors including harsh criticisms and behind-the-back comments. As resentment grew, conflicts intensified, leading to a toxic environment that ultimately resulted in team members being dismissed. Chris highlights how the team's self-imposed belief that "we don't have time for this people-stuff" prevented them from addressing issues early. He recommends one-on-one coaching, exploring why people react as they do, using retrospectives to address latent conflicts, and explicitly discussing desired team culture with reference to the Scrum value of respect. Chris emphasizes that maintaining team health should take priority over productivity concerns, even during high-pressure situations. In this segment, we refer to the Core Protocols episode with Richard Kasperowski, and the Superchicken Paradox Ted Talk by Margaret Heffernan. Featured Book of the Week: The Elements of Scrum Chris shares his experience writing "The Elements of Scrum," a book he co-authored using Scrum principles and a story mapping approach. The process of writing the book became a significant learning experience for Chris. He also recommends "Sacred Hoops" by Phil Jackson, which explores how to manage teams of great professionals. Phil Jackson is renowned for his ability to get exceptional players to function effectively as a cohesive team, making this book particularly valuable for those managing talented individuals with strong personalities. Self-reflection Question: How might you better balance technical excellence with interpersonal dynamics in your high-performing teams? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Chris Sims Chris Sims is a scrum trainer, agile coach, and recovering C++ developer who helps organizations improve their productivity and happiness. Chris is the founder of Agile Learning Labs and the co-author of two best-selling scrum books: The Elements of Scrum and Scrum: a Breathtakingly Brief and Agile Introduction. You can link with Chris Sims on LinkedIn, visit Chris Sims' Agile Learning Labs website.

22 Huhti 16min

Chris Sims: When Terminology Creates Misunderstandings, The "Ideal Days" Story Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. In this insightful episode, Chris Sims shares a valuable lesson from his early days implementing XP and Scrum. Chris's team had established an effective workflow using relative estimation with "ideal days" rather than story points, achieving good predictability and velocity measurements. However, things took an unexpected turn when a skeptical VP discovered their tracking spreadsheet and misinterpreted their metrics as showing only 2.5 days of work per week. Despite Chris's best efforts to explain the concept of "ideal days," the misunderstanding tarnished the team's reputation. Chris emphasizes the importance of socializing your working methods with stakeholders and communicating in ways meaningful to leadership. Working "under the radar" can backfire, so transparency about your processes is crucial for organizational alignment and trust. Self-reflection Question: How transparent are you about your team's estimation methods with stakeholders who might not be familiar with agile terminology? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Chris Sims Chris Sims is a scrum trainer, agile coach, and recovering C++ developer who helps organizations improve their productivity and happiness. Chris is the founder of Agile Learning Labs and the co-author of two best-selling scrum books: The Elements of Scrum and Scrum: a Breathtakingly Brief and Agile Introduction. You can link with Chris Sims on LinkedIn.

21 Huhti 21min

BONUS: Maria Chec Explores the Divide Between Agile Leaders and Practitioners In this BONUS episode, we explore Agile leadership with Maria Chec, author and host of Agile State of Mind. Maria shares insights from her analysis of Miro's Agile Survey, revealing a concerning disconnect between how Agile leaders and practitioners experience agile methodologies. We explore the roots of this divide, discuss practical approaches to bridging the gap, and consider the implications of recent industry developments like the PMI-Agile Alliance merger. Maria offers valuable perspectives on creating truly collaborative environments where frameworks serve the teams, not the other way around. The Disconnect Between Leaders and Practitioners "Practitioners feel pressured to comply with agile practices when they don't seem to add value." Maria highlights a stark divide revealed in Miro's survey of 1,200 agile practitioners and leaders. When asked if agile is living up to its original values, leaders and practitioners gave drastically different responses. For example, 69% of practitioners felt processes and tools overshadow individuals in their organizations, while only 43% of leaders shared this view. Similarly, 58% of practitioners believed documentation was prioritized over delivering final products, compared to just 39% of leaders. These disparities point to a fundamental disconnect in how agile is experienced at different organizational levels, with practitioners often feeling frameworks are imposed rather than collaboratively implemented. When Frameworks Become the Problem "The framework is too rigid... The framework is too complex... We have to change too much to use the framework." The issue isn't with agile frameworks themselves but how they're applied, Maria argues. Leaders often implement frameworks like SAFe without sufficient practitioner input or adaptation to organizational context. This creates an anti-pattern of "magical thinking" where companies believe they can install off-the-shelf solutions that worked elsewhere without considering their unique circumstances. The practitioners, who must live with these frameworks daily, experience frustration when rigid implementations fail to address their actual needs. Conway's Law comes into play here – the structure imposed by leadership often doesn't align with how teams naturally need to collaborate based on the systems they're building. The Role of Psychological Safety "Can I really admit that something the leadership made me do is not working for me? Will I be the only one admitting it?" This disconnect reveals deeper issues around psychological safety and trust within organizations. Many practitioners fear speaking up about framework problems, especially when they've just endured yet another organizational transformation. Maria emphasizes that without psychological safety, feedback loops break down, preventing the continuous improvement that's central to agile philosophy. Leaders must create environments where teams feel safe to provide honest feedback about what's working and what isn't, without fear of being singled out or dismissed. Without this safety, frameworks become rigid implementations rather than adaptable approaches that evolve with team needs. Reconnecting Through Gemba Walks "Be there where the value is created and know what's going on." To bridge the gap between leadership vision and practitioner reality, Maria strongly recommends Gemba walks – a concept from Lean and Toyota where leaders go to where value is created. This practice helps leaders understand the actual work being done and build relationships with team members. Maria references Project Aristotle at Google, which found that trust and psychological safety are fundamental to team success. She also notes the importance of leaders articulating a meaningful mission to inspire teams, sharing her experience at a taxi-hailing app where the CEO's vision of reducing urban parking needs made her feel she was "building something for the future." Leaders should regularly spend time where the actual work happens Teams need to understand how their work contributes to a larger purpose Open communication channels must be genuine, not just symbolic In this segment, we refer to Management 3.0 and Managing For Happiness by Jurgen Appelo. The PMI-Agile Alliance Merger and the Future of Agile "Have we really found better ways? Why are Agile Alliance and PMI merging?" The recent merger between the Project Management Institute and Agile Alliance represents a surprising development in the industry. Maria takes an optimistic view, wondering if this indicates PMI recognizing that agile is truly the way forward. She acknowledges the perception that "Agile is dead" discussions highlight a crisis in the movement, but suggests the merger might be an opportunity to influence project management with agile values. She emphasizes how AI is creating massive changes that require experimentation and adaptation – precisely what agile approaches enable. This industry shift offers agile practitioners the chance to shape how traditional and agile methodologies might complement each other in the future. The merger could be seen as closing a circle or as an opportunity for cross-pollination "Agile is dead" discussions reflect growing pains rather than true failure Rapid technological changes with AI require more experimentation, not less Breaking Down Silos with "Glue Roles" "What are the 'glue roles' that you need in your organization?" Maria introduces her concept of "glue roles" – positions that help break down silos and foster collaboration regardless of what they're called. Whether they're RTEs (Release Train Engineers), Agile Coaches, or Technical Project Managers, these roles can transform organizational effectiveness when focused on enabling teams rather than enforcing processes. She observes that nature constantly changes, yet we expect our companies to remain static. This mindset prevents the adaptation necessary for true agility. Instead, organizations need individuals who can facilitate communication, remove barriers, and help teams collaborate effectively across boundaries. Focus on the function of collaboration rather than rigid role definitions Adapt roles to organizational needs rather than forcing organizational change to fit frameworks Use these roles to foster psychological safety and open communication Learning Through Experimentation "We need to experiment." Looking toward the future, Maria emphasizes the importance of experimentation in the face of rapid technological change, particularly with AI. She notes that while tech professionals are often thought to be early adopters, AI tools like ChatGPT are being embraced across all industries. The accelerating pace of change means we can no longer plan years ahead with certainty – what we use today may be obsolete in two years. This reality makes agile approaches even more relevant, as they embrace change rather than fight it. She encourages agile practitioners to openly discuss how they use these new tools, adapting their practices rather than clinging to outdated methods. The accelerating pace of change makes long-term planning increasingly difficult AI is already transforming work across all industries, not just tech Agile principles of adaptation and experimentation are more relevant than ever About Maria Chec Maria Chec is a seasoned Agile leader, ProKanban Trainer, and creator of Agile State of Mind. With over a decade of experience, she specializes in transforming teams through SAFe, OKRs, and process optimization, achieving remarkable productivity gains. Maria's mission is empowering teams to thrive through collaboration and adaptability. You can link with Maria Chec on LinkedIn and subscribe to Maria Chec's Substack.

19 Huhti 40min

Richard Brenner: Hypothesis-Driven Product Ownership, The Experimental Mindset Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: The Experimenter Richard describes great Product Owners as "experimenters" who understand that everything they do is a hypothesis requiring validation. The best POs establish feedback loops early, actively engage with users and clients, and approach product development with a scientific mindset. Richard shares an experience working with a "coaching PO" who excelled at involving everyone in defining what needed to be done.  This PO was inspiring and helped the team participate in both building and decision-making processes. Richard emphasizes that the relationship between PO and team must be a true partnership—not hierarchical—for success to occur. Great POs facilitate team involvement rather than dictating direction, creating an environment where collaborative problem-solving thrives. In this segment, we refer to the Role Expectation Matrix Retrospective, and the Product Owner Sprint Checklist, a hands-on coaching tool for anyone interested in helping PO's prepare and lead successful Sprints with their teams. The Bad Product Owner: The Tech Visionary Disconnected from Users Richard recounts working with a high-level sponsor, a medical doctor interested in technology, who hired multiple development teams (up to four Scrum teams) to build a product. While technically knowledgeable, this PO had very concrete ideas about both the technology and solution based on assumptions about client needs.  The team developed impressive technology, including a domain-specific language (DSL), and felt they were performing well—until they delivered to actual clients. Only then did they discover users couldn't effectively use the software, requiring a complete rethinking of the UX concept. This experience taught Richard the critical distinction between the customer (the sponsor/PO) and the actual end users, demonstrating how even technically sophisticated Product Owners can miss essential user needs without proper validation. Self-reflection Question: How might you help Product Owners in your organization balance their vision with the practical realities of user needs and feedback? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Richard Richard is a versatile technology leader with experience as a Software Engineer, Product Owner, and Agile Coach. Passionate about building software that excites, he thrives at the intersection of technology, change, and leadership. Lately, he's focused on Collaborative Modeling, bridging disciplines to drive innovation and create meaningful impact. You can link with Richard Brenner on LinkedIn.

18 Huhti 20min

Richard Brenner: Contracting for Success,  Establishing Clear Agile Coaching Outcomes Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Richard reflects on his evolution in defining success as a Scrum Master and Agile Coach. Initially, he believed that if his team was successful, he was successful—but soon realized this perspective was incomplete. Top management wanted tangible evidence of coaching impact, which became problematic without clearly defined metrics. Richard now advocates for establishing a coaching agreement at the beginning of any engagement, with both management and teams defining what success looks like for the coach. He emphasizes the importance of dual-sided accountability as a natural outcome of proper contracting, using metrics that matter to the organization such as flow metrics and outcome metrics to demonstrate coaching value. Self-reflection Question: How are you measuring your own success as a coach or Scrum Master, and have you created explicit agreements with both teams and management about what success looks like? Featured Retrospective Format for the Week: Solution Focused Retrospective Richard recommends the Solution Focused Retrospective from the book "Solution Focused Coaching for Agile Teams." While traditional retrospective formats from books like "Agile Retrospectives" typically open a topic and dig deeply into the problem space, the solution-focused approach suggests spending only a short time discussing problems before pivoting to designing the desired future state. This format focuses on identifying the next step and emphasizing what positive outcomes the team wants to achieve, rather than dwelling on what's wrong. Richard values this approach for its ability to maintain a positive, forward-thinking mindset within teams. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Richard Richard is a versatile technology leader with experience as a Software Engineer, Product Owner, and Agile Coach. Passionate about building software that excites, he thrives at the intersection of technology, change, and leadership. Lately, he's focused on Collaborative Modeling, bridging disciplines to drive innovation and create meaningful impact. You can link with Richard Brenner on LinkedIn.

17 Huhti 16min

Richard Brenner: When Individual Performance Metrics Block Agile Transformation Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Richard shares an experience of implementing Agile methods in a large organization that initially showed promising signs with management "pull" for change. The transformation began well with cross-functional teams created through self-selection workshops. However, unexpected resistance emerged during the kick-off day, particularly from a line manager and his team. When investigating the source of this resistance, Richard discovered that the company's bonus structure was tied to individual performance metrics, fundamentally conflicting with Agile's team-oriented approach.  This insight led to developing a pilot for a team-focused performance management system. After three months, the team held a retrospective with all stakeholders, where management demonstrated remarkable leadership by empowering teams to redesign their structure when the initial setup wasn't working. This flexibility allowed even the most vocal critics to become part of the solution. Self-reflection Question: In what ways might your organization's reward structures be unintentionally blocking successful Agile adoption? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Richard Richard is a versatile technology leader with experience as a Software Engineer, Product Owner, and Agile Coach. Passionate about building software that excites, he thrives at the intersection of technology, change, and leadership. Lately, he's focused on Collaborative Modeling, bridging disciplines to drive innovation and create meaningful impact. You can link with Richard Brenner on LinkedIn.

16 Huhti 17min

Richard Brenner: How Small Signs of Cynicism Can Destroy Agile Team Cohesion Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Richard shares a powerful story about how team dysfunction often starts with small steps. During a joint retrospective with three agile teams, Richard witnessed a moment where a team member made a cynical comment toward a manager who was attempting to participate. This revealed a damaged relationship between management and the team, creating tension that Richard initially chose to ignore. Looking back, he would now immediately address such comments and tackle the "elephant in the room." Richard explains how seemingly minor behaviors like cynicism or passive-destructive actions (such as consistently being late to stand-ups) can significantly impact team health. He recommends establishing conflict resolution protocols early and using impact feedback without judgment to address these issues before they escalate. In this segment, we refer to Lysa Adkins' conflict resolution protocol.  Self-reflection Question: What small signs of dysfunction might you be overlooking in your team that could develop into larger problems? Featured Book of the Week: Solution Focused Coaching for Agile Teams Richard recommends "Solution Focused Coaching for Agile Teams" by Ralph and Veronika. This book describes the solution-focused approach to many common situations that Agile coaches face in their work. Richard values this resource for its practical guidance on addressing challenges through a positive, solution-oriented perspective rather than dwelling on problems. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator. Check Full Program [Scrum Master Toolbox Podcast Recommends] About Richard Richard is a versatile technology leader with experience as a Software Engineer, Product Owner, and Agile Coach. Passionate about building software that excites, he thrives at the intersection of technology, change, and leadership. Lately, he's focused on Collaborative Modeling, bridging disciplines to drive innovation and create meaningful impact. You can link with Richard Brenner on LinkedIn.

15 Huhti 15min