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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Product Owner Patterns – The Great and the Bad | Ellen Grove

Product Owner Patterns – The Great and the Bad | Ellen Grove

Ellen Grove: The Messenger Anti-Pattern, When Product Owners Lack Authority Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: Building Shared Understanding, The Collaborative Product Owner Pattern Ellen describes an exemplary Product Owner (PO) who actively engaged with customers, often bringing the team along to meet users. This practice fostered a shared understanding of customer needs and amplified creativity within the team. A great PO promotes collaboration and ensures that the team is aligned with the product vision, enabling innovative solutions and meaningful outcomes. The Bad Product Owner: The Messenger Anti-Pattern, When Product Owners Lack Authority A poor PO, Ellen explains, is one who lacks decision-making authority. In one case, a PO served merely as a messenger for the CEO, repeatedly deferring to higher-ups for answers. This lack of empowerment hindered team progress and frustrated the development process. Ellen underscores that Scrum Masters play a crucial role in supporting POs to ensure they can fulfill their responsibilities effectively. Self-reflection Question: How can you support Product Owners to strengthen their ability to make informed decisions? [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

10 Jan 16min

The Power of "Why", Modeling Coaching Behavior for Agile Teams | Ellen Grove

The Power of "Why", Modeling Coaching Behavior for Agile Teams | Ellen Grove

Ellen Grove: The Power of "Why", Modeling Coaching Behavior for Agile Teams Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen defines success for Scrum Masters as the team developing a stronger sense of agency and self-sufficiency. When teams begin asking better questions and demonstrate ownership of their processes, it indicates growth and maturity. Scrum Masters must model this behavior by being thoughtful, curious, and consistently asking "why" to encourage a coaching mindset. This approach enables teams to think critically and solve problems collaboratively. Self-reflection Question: How can you model the behavior you want to see in your team during retrospectives and beyond? Featured Retrospective Format for the Week: Retromat Ellen recommends using Retromat, a versatile online tool that provides a variety of retrospective formats to match the specific needs of your team. Ellen values mixing up retrospective formats to keep sessions engaging and contextually relevant. She stresses the importance of paying attention to all steps of a retrospective process, ensuring teams reflect, ideate, and act effectively. [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

9 Jan 16min

The Dual Work of Agile, Managing Projects and Change Simultaneously | Ellen Grove

The Dual Work of Agile, Managing Projects and Change Simultaneously | Ellen Grove

Ellen Grove: The Dual Work of Agile, Managing Projects and Change Simultaneously Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen shares her insights on managing organizational change effectively. She explains how Scrum and Lean Change Management offer tools to make the "change work" visible alongside project work. By putting infrastructure in place to support this dual focus, stakeholders and teams can gain transparency and clarity. Ellen emphasizes that lasting change requires collaboration and visibility, not isolation. Self-reflection Question: How can you make the "change work" more visible in your organization? [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

8 Jan 15min

Why Feedback Loops Are Essential for Agile Teams | Ellen Grove

Why Feedback Loops Are Essential for Agile Teams | Ellen Grove

Ellen Grove: Why Feedback Loops Are Essential for Agile Teams Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen shares a story about coaching a team in a public sector enterprise working on a website project. Despite their commitment to Agile, the team’s disconnect from user feedback led them to build features that missed critical functionality. This stealthy anti-pattern—assuming "what should be done and why" without user input—resulted in wasted effort and budget. Ellen emphasizes the importance of direct feedback loops with real users, even for internal products. Self-reflection Question: How can you ensure your team receives continuous feedback from real users to avoid building the wrong product? Featured Book of the Week: Humble Inquiry by Edgar Schein Ellen highlights "Humble Inquiry," a transformative book that stresses the importance of relationships over tasks in solving problems. The book encourages leaders to build trust and respect through better questioning techniques. It challenges readers to rethink their interactions and adopt a stance of curiosity, fostering collaboration and understanding. [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

7 Jan 14min

Managing Change in Complex Organizational Cultures | Ellen Grove

Managing Change in Complex Organizational Cultures | Ellen Grove

Ellen Grove: Managing Change in Complex Organizational Cultures Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen reflects on her early experiences as a Scrum Master, facing challenges in an environment that resisted the introduction of Scrum. She shares valuable lessons about handling external resistance, managing personal expectations, and avoiding emotional burnout when navigating organizational change. Ellen emphasizes the importance of focusing on what can be influenced and detaching from outcomes beyond one’s control. Self-reflection Question: How do you maintain focus and resilience when dealing with resistance to Scrum in your organization? [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 Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

6 Jan 14min

Throwing Features Over the Fence, The Disconnected PO | Robert Finan

Throwing Features Over the Fence, The Disconnected PO | Robert Finan

Robert Finan: Throwing Features Over the Fence, The Disconnected PO Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: Fostering Quick Feedback Loops With Story Mapping Robert describes a great Product Owner as someone who immerses themselves in the team, fostering collaboration and ensuring quick market feedback.  By using tools like Story Mapping, these POs help teams focus on value while staying engaged and open to learning. The Bad Product Owner: Throwing Features Over the Fence, The Disconnected PO Bad Product Owners remain distant, throwing requirements “over the fence” without participating in the team’s efforts. This disconnect often leads to misalignment and poor outcomes.  For Scrum Masters and Agile Coaches, Robert suggests investigating the root cause of this distance and addressing it collaboratively. [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 Robert Finan Robert has been working in IT for over 25 years, with the last decade spent deeply engaged in “messy” real-world Agile transformations. He documents his experiences in the Agile Drill Sergeant webcomic. You can link with Robert Finan on LinkedIn.

3 Jan 14min

Promoting Agile Team Growth Through Experiments And Small Focused Changes | Robert Finan

Promoting Agile Team Growth Through Experiments And Small Focused Changes | Robert Finan

Robert Finan: Promoting Agile Team Growth Through Experiments And Small Focused Changes Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Robert defines Scrum Master success as driving impactful team improvements through small, focused changes.  By maintaining a backlog of improvement ideas and encouraging teams to experiment, Robert highlights the importance of measurable progress in both behavior and collaboration. Featured Retrospective Format for the Week: Sailboat Retrospective Robert recommends the Sailboat format, especially when working with new teams. By exploring current realities, future goals, and risks, this format provides rich insights and fosters alignment. The focus on improvement ensures actionable outcomes that resonate with team members. [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 Robert Finan Robert has been working in IT for over 25 years, with the last decade spent deeply engaged in “messy” real-world Agile transformations. He documents his experiences in the Agile Drill Sergeant webcomic. You can link with Robert Finan on LinkedIn.

2 Jan 14min

Flexible Change Processes, How To Adopt Agile With An Agile Approach | Robert Finan

Flexible Change Processes, How To Adopt Agile With An Agile Approach | Robert Finan

Robert Finan: Flexible Change Processes, How To Adopt Agile With An Agile Approach Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Robert discusses how top-down, project managed Agile transformations often fail to account for the complexity of change. By focusing on flexibility, inspect/adapt cycles, and bringing comfort to the change process, Scrum Masters can guide organizations away from one-size-fits-all solutions and toward the sustainable improvement that is the hallmark of Agile. Self-reflection Question: How can you bring comfort to the change process in your organization? [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 Robert Finan Robert has been working in IT for over 25 years, with the last decade spent deeply engaged in “messy” real-world Agile transformations. He documents his experiences in the Agile Drill Sergeant webcomic. You can link with Robert Finan on LinkedIn.

1 Jan 12min

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