Bridging the Gap Between Agile Teams and Leadership | Josh Anderson

Bridging the Gap Between Agile Teams and Leadership | Josh Anderson

Substack Week: Bridging the Gap Between Agile Teams and Leadership With Josh Anderson

In this Substack Week episode, we explore the critical challenges and opportunities in the relationship between Agile teams and organizational leadership. Josh Anderson shares insights from his extensive experience in technology leadership and discusses how both sides can work together more effectively.

Understanding the Business-Team Divide

"We are part of the business, but many teams separate it out say, 'Oh, that's over there, that's not us.' No, that is us."

One of the most common challenges in organizations is the perceived divide between "the business" and development teams. Josh emphasizes that this separation is an anti-pattern that needs to be addressed. Teams must understand how they create value for customers and how their work connects to the organization's broader mission. The key is asking fundamental questions like "Why do we exist?" and focusing on delivering real value to customers rather than just building features or fixing bugs.

The Art of Communication with Leaders

"You have to reach across the aisle... speak in language that they understand, and of course the other side of the aisle has to understand that you may not understand all of the financial acumen or other things that they're throwing out."

Effective communication requires both sides to make an effort to understand each other. Josh highlights the importance of:

  • Using common language that everyone understands

  • Being willing to ask for clarification when needed

  • Explaining technical terms and concepts clearly

  • Focusing on business value rather than process details

  • Understanding that it takes approximately seven repetitions for new concepts to be fully absorbed

Learning from Anti-Mentors

"That experimental database of things I need to try is getting actively shrunk. So I'm starting to just cross off things. Okay, don't do that, don't do that, don't do that."

Josh introduces the concept of "anti-mentors" - learning valuable leadership lessons from challenging experiences with ineffective leaders. This approach helps:

  • Build a clear understanding of what not to do

  • Narrow down the field of potential leadership approaches

  • Create a stronger foundation for experimentation with new methods

  • Transform negative experiences into positive learning opportunities

The Leadership Laboratory

"Constantly experiment with things. But be super inclusive about those experiments that you're going to run and say, 'Hey, this is who we want to be.'"

Josh emphasizes treating leadership development like product development, using experimentation and feedback loops to improve continuously. Key aspects include:

  • Setting clear expectations about experiments and intended outcomes

  • Including team members in the process of change

  • Giving changes enough time to show results

  • Being open to adjusting based on feedback

  • Creating a safe environment for trying new approaches

Recommended Resources For Further Study

[The Scrum Master Toolbox Podcast Recommends]

🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥

Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people.

🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.

Buy Now on Amazon

[The Scrum Master Toolbox Podcast Recommends]

About Josh Anderson

With over two decades of experience in technology leadership, product innovation, and operational excellence, Josh has worked with many businesses and helped transform them into high-value, product-driven organizations. Josh is also a fellow podcaster at the Meta-Cast with Bob Galen.

You can connect with Josh Anderson on Substack.

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When Process Becomes a Prison, Breaking Free from Over-Rigid Agile Team Practices | Mateusz Komander

When Process Becomes a Prison, Breaking Free from Over-Rigid Agile Team Practices | Mateusz Komander

Mateusz Komander: When Process Becomes a Prison, Breaking Free from Over-Rigid Agile Team Practices 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. Working with an airline scheduling tool development team, Mateusz encountered a situation where rigid processes became a self-imposed prison. Instead of adapting to challenges, the team's response to missed deadlines was to add more process layers, particularly around testing.  The daily standups became status reports rather than collaboration opportunities, with team members focused on appearing busy rather than supporting each other. Through careful intervention, Mateusz helped transform their daily meetings to focus on future collaborations and mutual support needs. Self-reflection Question: How can you identify if your team's processes are serving as protective measures or becoming barriers to effective collaboration? Featured Book of the Week: Managing for Happiness by Jurgen Appelo Mateusz recommends "Managing for Happiness" by Jurgen Appelo as an essential read for Scrum Masters. This book stands out for its practical combination of tools and real-life examples, helping create better environments for teams' daily work. Its inspirational approach makes it particularly valuable for Scrum Masters looking to introduce new practices and ideas to their teams. In this segment, we also refer to Emotional Intelligence, by Daniel Goleman.  [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Mateusz Komander  Mateusz, is a Scrum Master at Heineken, and brings expertise from biotech and airline industries, excelling in Agile delivery and transformations. Skilled in Management 3.0, he fosters self-managed, innovative teams. Mateusz just launched a podcast on organizational transformation, Mateusz highlights how understanding team dynamics beyond the Scrum framework enhances collaboration and effectiveness. You can link with Mateusz Komander on LinkedIn.

11 Feb 14min

The True Purpose of Scrum, Enabling Individuals And Interactions | Mateusz Komander

The True Purpose of Scrum, Enabling Individuals And Interactions | Mateusz Komander

Mateusz Komander: The True Purpose of Scrum, Enabling Individuals And Interactions 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, Mateusz shares a valuable learning experience from his early days as a Scrum Master in a biotech company. With a small team of five people, he initially believed he could improve upon existing practices by modifying the Scrum framework. However, by skipping crucial ceremonies like daily standups, planning sessions, and retrospectives, hidden team conflicts emerged.  This experience led Mateusz to a crucial realization: Scrum isn't merely about process management, but rather about facilitating meaningful connections and interactions between team members while enabling empirical management. Self-reflection Question: How might your current understanding of Scrum's purpose be limiting your effectiveness as a Scrum Master? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Mateusz Komander  Mateusz, is a Scrum Master at Heineken, and brings expertise from biotech and airline industries, excelling in Agile delivery and transformations. Skilled in Management 3.0, he fosters self-managed, innovative teams. Mateusz just launched a podcast on organizational transformation, Mateusz highlights how understanding team dynamics beyond the Scrum framework enhances collaboration and effectiveness. You can link with Mateusz Komander on LinkedIn.

10 Feb 15min

BONUS The Evolution of Agile Leadership: Embracing the Therapeutic Turn with Ari-Pekka Skarp

BONUS The Evolution of Agile Leadership: Embracing the Therapeutic Turn with Ari-Pekka Skarp

BONUS: Beyond Process, How Psychology is Reshaping Modern Leadership with Ari-Pekka Skarp In this BONUS episode, we dive deep into the evolving landscape of Agile leadership with Ari-Pekka Skarp, an experienced Agile Coach, Psychotherapist, and Organizational Psychologist. Drawing from his unique blend of expertise, Ari-Pekka shares his lessons learned on how leadership has transformed over the past decades and what the future holds for Agile organizations. The Evolution of Agile and Social Complexity "We replaced authority with collaboration, this was revolutionary." The journey of Agile adoption over the past 16 years has been marked by two significant developments: technological advancement and increasing social complexity. Ari-Pekka reflects on how Scrum introduced a revolutionary "shared" aspect of collaborative work, fundamentally changing how hierarchies are established in modern organizations. This shift represents a departure from traditional command-and-control structures towards more collaborative approaches. The Therapeutic Turn in Leadership "Nowadays we are almost talking about the leaders as some sort of therapist." One of the most significant shifts in organizational dynamics has been the "therapeutic turn" in leadership. Where leaders were once expected to be commanders, today's leaders must embody the qualities of a therapist - demonstrating empathy, emotional intelligence, and a deep understanding of their team members' well-being. This transformation reflects broader societal changes, with mental health awareness becoming increasingly central to workplace dynamics. The Rise of Humanistic Leadership "We need a more humanistic leadership, but what does that look like in practice?" As organizations become more networked and complex, the need for humanistic leadership approaches becomes evident. Ari-Pekka shares his experience as an organizational psychologist, highlighting how traditional role definitions often fall short in addressing modern workplace challenges. The integration of tools from family therapy and other psychological disciplines is becoming crucial for effective leadership. The Future of Organizations "In order to compete you have to have a very well functioning organization!" Looking ahead, Ari-Pekka emphasizes the importance of viewing organizations through a psychological lens. He argues that organizational mental health culture and the psychological aspects of work are becoming critical competitive advantages. This perspective extends beyond processes and tools to encompass the holistic growth and well-being of people within organizations. A New Paradigm for Work "The biggest change was from a mechanistic world-view to a more humanistic world-view." As Agile evolves beyond its origins as a protest movement, Ari-Pekka explores how organizations are increasingly forming around purposes rather than just profits. He advocates for generative planning processes that foster creativity and human flourishing, suggesting a shift toward viewing work and organizations as social processes rather than mechanical systems. Leading Through Conversations "Why don't we look at work, organizations as social processes?" The conversation concludes with a powerful metaphor of leaders as gardeners, nurturing growth and development through meaningful conversations. This approach represents a fundamental shift in how we think about leadership and organizational development, emphasizing the importance of creating environments where people can thrive. In this segment, we refer to the work of Esko Kilpi, a thought leader and business philosopher who helped introduce complexity to the Agile community. About Ari-Pekka Skarp Ari-Pekka is a highly experienced Agile Coach, Psychotherapist, and Organizational Psychologist with over 20 years of experience working with organizations. As an author of several books on topics such as Complexity, the mind, and Mindfulness, Ari-Pekka blends deep psychological insight with practical expertise to help leaders and teams navigate the evolving landscape of work. You can link with Ari-Pekka on LinkedIn and connect with Ari-Pekka on Twitter.

8 Feb 49min

The Pressure Conduit, aka The Tornado Product Owner | Chrissy Fleming

The Pressure Conduit, aka The Tornado Product Owner | Chrissy Fleming

Chrissy Fleming: The Pressure Conduit, aka The Tornado Product Owner 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: Customer Advocate and Team Partner A great Product Owner brings customer insights directly to the team and shares access to customers, fostering deeper understanding of user needs. They maintain transparency about their knowledge limits and involve the team in both problem and solution spaces, ensuring comprehensive understanding before diving into solutions. The Bad Product Owner: The Pressure Conduit, aka The Tornado This anti-pattern emerges when Product Owners simply transmit leadership's volatility to the team, becoming mere messengers of pressure rather than true product leaders. They fall into "tornado mode," acting as order takers without questioning the "why" behind requests or protecting the team's ability to deliver value each sprint. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Chrissy Fleming  Chrissy came to Scrum-Mastering via Product Management and a deep love of seeing teams work together. She spent 15 years in the New York tech scene and is currently an Associate Principal in Business Agility with Turnberry Solutions. She also has her own company where she coaches and helps businesses and technologists with their development. You can link with Chrissy Fleming on LinkedIn.

7 Feb 16min

The Role of Trust and Fun in High-Performing Agile Teams | Chrissy Fleming

The Role of Trust and Fun in High-Performing Agile Teams | Chrissy Fleming

Chrissy Fleming: The Role of Trust and Fun in High-Performing Agile 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. For Chrissy, success as a Scrum Master means fostering high-performing teams that solve valuable problems. She emphasizes that while this sounds simple, it requires building trust, establishing accountability, and maintaining a commitment to continuous improvement. A key indicator of success is when teams naturally have fun together, reflecting their comfort and psychological safety. Featured Retrospective Format for the Week: Simple and Team-Led Chrissy advocates for simple retrospective formats that encourage team participation, particularly those led by team members rather than the Scrum Master. She recommends using tools like Easy Retro and MURAL for remote sessions, emphasizing the importance of individual reflection time before group discussion and creating a safe space by acknowledging personal mistakes. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Chrissy Fleming  Chrissy came to Scrum-Mastering via Product Management and a deep love of seeing teams work together. She spent 15 years in the New York tech scene and is currently an Associate Principal in Business Agility with Turnberry Solutions. She also has her own company where she coaches and helps businesses and technologists with their development. You can link with Chrissy Fleming on LinkedIn.

6 Feb 18min

From Tasks to Outcomes, An Agile Cultural Transformation Story | Chrissy Fleming

From Tasks to Outcomes, An Agile Cultural Transformation Story | Chrissy Fleming

Chrissy Fleming: From Tasks to Outcomes, An Agile Cultural Transformation 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. Chrissy shares her experience transforming a sales-led organization from task orientation to outcome focus. By partnering with the head of tech and implementing OKRs, they created meaningful conversations about team goals and progress. Through initiatives like Demo Days and the creation of team "houses," they successfully shifted the organizational culture while ensuring teams felt ownership of their future. Self-reflection Question: How can you create meaningful opportunities for your teams to shape their own identity and future? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Chrissy Fleming  Chrissy came to Scrum-Mastering via Product Management and a deep love of seeing teams work together. She spent 15 years in the New York tech scene and is currently an Associate Principal in Business Agility with Turnberry Solutions. She also has her own company where she coaches and helps businesses and technologists with their development. You can link with Chrissy Fleming on LinkedIn.

5 Feb 15min

The Impact of Unaddressed Conflict on Agile Team Health | Chrissy Fleming

The Impact of Unaddressed Conflict on Agile Team Health | Chrissy Fleming

Chrissy Fleming: The Impact of Unaddressed Conflict on Agile Team Health 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. Chrissy shares a compelling story about a newly formed team working on retention that struggled with toxic behavior. The presence of a hostile team member created an environment where healthy conflict became impossible, leading to either unhealthy confrontations or complete avoidance. Despite attempts to address the situation, the lack of trust prevented team members from addressing the destructive behavior, ultimately resulting in the team's dissolution. Self-reflection Question: How do you currently handle toxic behavior in your team, and what steps could you take to build the psychological safety needed for addressing conflicts openly? Featured Book of the Week: How Toddlers Thrive by Tove Klein How Toddlers Thrive by Tove Klein explores brain function and human behavior, drawing surprising parallels between toddler development and adult interactions. Chrissy recommends it for its valuable insights into emotional intelligence and human nature, reminding us that in Agile environments, we're fundamentally dealing with human beings and their emotions. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Chrissy Fleming  Chrissy came to Scrum-Mastering via Product Management and a deep love of seeing teams work together. She spent 15 years in the New York tech scene and is currently an Associate Principal in Business Agility with Turnberry Solutions. She also has her own company where she coaches and helps businesses and technologists with their development. You can link with Chrissy Fleming on LinkedIn.

4 Feb 16min

The Hidden Cost of Combined Scrum Master and Product Owner Roles | Chrissy Fleming

The Hidden Cost of Combined Scrum Master and Product Owner Roles | Chrissy Fleming

Chrissy Fleming: The Hidden Cost of Combined Scrum Master and Product Owner Roles 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 episode, Chrissy shares a critical learning moment from her career when she attempted to juggle both Product Owner and Scrum Master roles simultaneously. This dual role led to a situation where the team began "sandbagging" their estimates due to underlying conflicts with leadership. The situation culminated when a team member completed a supposedly two-month project in just two days, destroying team credibility and ultimately leading to the team's dismissal. Self-reflection Question: How do you ensure you maintain your authentic voice as a Scrum Master while balancing multiple stakeholder needs? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Chrissy Fleming  Chrissy came to Scrum-Mastering via Product Management and a deep love of seeing teams work together. She spent 15 years in the New York tech scene and is currently an Associate Principal in Business Agility with Turnberry Solutions. She also has her own company where she coaches and helps businesses and technologists with their development. You can link with Chrissy Fleming on LinkedIn.

3 Feb 13min

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