Learning from Poor Leadership

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 book: Turn the Ship Around by David Marquet

• Josn’s The Leadership Lighthouse Newsletter on Substack

• The Meta-Cast Podcast with Josh and Bob Galen

• And take a look at KAZI.IO - Josh's consulting business

[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.

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[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.