Coaching Teams Trapped Between Agile Aspirations and Organizational Control | Alex Sloley
Scrum Master Toolbox Podcast: Agile storytelling from the trenches
Release Date: 10/22/2025
Scrum Master Toolbox Podcast: Agile storytelling from the trenches
AI Assisted Coding: From Designer to Solo Developer - Building Production Apps with AI In this special episode, Elina Patjas shares her remarkable journey from designer to solo developer, building —an AI-powered study tool with 1,500+ users and paying customers—entirely through AI-assisted coding. She reveals the practical workflow, anti-patterns to avoid, and why the future of software might not need permanent apps at all. The Two-Week Transformation: From Idea to App Store "I did that, and I launched it to App Store, and I was like, okay, so… If I can do THIS! So, what else can...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Sara Di Gregorio: Coaching Product Owners from Isolation to Collaboration 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: . The Great Product Owner: Using User Story Mapping to Break Down PO Isolation "One of the key strengths is the ability to build a strong collaborative relationship with the Scrum team. We constantly exchange feedback, with the shared goal of improving both our collaborating and the way of working." - Sara Di Gregorio Sara considers herself fortunate—she...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Sara Di Gregorio: How to Know Your Team Has Internalized Agile Values 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: . "Scrum isn't just a process to follow, it's a way of working." - Sara Di Gregorio For Sara, success as a Scrum Master isn't measured by what the team delivers—it's measured by how they grow. She knows that if you facilitate team growth in communication and collaboration, delivery will naturally improve. The indicators she watches for are...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Sara Di Gregorio: Facilitating Deeper Retrospectives—When to Step In and When to Step Back 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: . "When they start connecting and having an interesting discussion, I go to the corner, and I'm only trying to listen." - Sara Di Gregorio Sara faces a challenge that many Scrum Masters encounter: teams that want to discuss too many topics during retrospectives without going deep on any of them. The team had plenty to talk about,...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Sara Di Gregorio: Rebuilding Agile Team Connection in the Remote Work Era 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: . "The book helped me to shift from reacting to connecting, which completely changed the quality of conversation." - Sara Di Gregorio When COVID forced Sara's team into full remote work, she noticed something troubling—the team was losing real connection. Replicating in-office meetings online simply didn't work. People attended meetings but weren't...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Sara Di Gregorio: When Teams Lose Trust—How Scrum Masters Rebuild It One Small Change at a Time 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: . "I continue to approach this situation with openness, positivity, and trust, because I truly believe that even the smallest changes can make a difference over time." - Sara Di Gregorio Sara faced one of the most challenging situations a Scrum Master can encounter—a team member who had lost all trust in change, creating a...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
BONUS: Flawless Execution — Translating Fighter Pilot Precision to Business Results In this powerful conversation, former fighter pilot reveals how military precision translates into agile business leadership. We explore , the critical difference between control-based and awareness-based leadership, and why most organizations fail to truly embrace iterative thinking. From Cockpit to Boardroom: An Unexpected Journey "I learned over time that it doesn't matter what you do if you're always curious, and you're always intentional, and you're always asking questions." — Christian...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Alidad Hamidi: When Product Owners Facilitate Vision Instead of Owning It 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: . The Great Product Owner: Co-Creating Vision Through Discovery "The best product owner I worked with was not a product owner, but a project manager. And she didn't realize that she's acting as a product owner." - Alidad Hamidi The irony wasn't lost on Alidad. The best Product Owner he ever worked with didn't have "Product Owner" in her title—she was a...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Alidad Hamidi: Maximizing Human Potential as the Measure of Success 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: . "Does my work lead into maximizing human potential? Maximizing the ability of the human to use their potential and freedom." - Alidal Hamidi Alidad calls himself a "recovering agility coach," and for good reason. For years, he struggled to define success in his work. As an enterprise coach, he plants seeds but never sees the trees grow. By the time...
info_outlineScrum Master Toolbox Podcast: Agile storytelling from the trenches
Alidad Hamidi: The Tax Agile Teams Pay for Organizational Standards 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: . "If you set targets for people, they will achieve the target, even if that means destroying the system around them." - W. Edwards Deming (quoted by Alidad) The tension is familiar to every Scrum Master working in large organizations: leadership demands standard operating models, flow time metrics below specific numbers, and reporting structures that fit...
info_outlineAlex Sloley: Coaching Teams Trapped Between Agile Aspirations and Organizational Control
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 team says, oh, we want to try to do things this way, and the org keeps coming back and saying stuff like, no, no, no, you can't do that, because in this org, we don't allow that." - Alex Sloley
Alex shares his current challenge working with a 10-person pilot Scrum team within a 1,500-person organization that has never done Agile before. While the team appears open-minded and eager to embrace agile ways of working, the organization continuously creates impediments by dictating how the team must estimate, break down work, and operate. Management tells them "the right way" to do everything, from estimation techniques to role-based work assignments, even implementing RACI matrices that restrict who can do what type of work. Half the team has been with the organization for six months or less, making it comfortable to simply defer to authority and follow organizational rules. Through coaching conversation, Alex explores whether the team might be falling into learned helplessness or simply finding comfort in being told what to do—both positions that avoid accountability. His experimental approach includes designing retrospective questions to help the team reflect on what they believe they're empowered to do versus what management dictates, and potentially using delegation cards to facilitate conversations about decision-making authority. Alex's key insight is recognizing that teams may step back from empowerment either out of fear or comfort, and identifying which dynamic is at play requires careful, small experiments that create safe spaces for honest dialogue.
Self-reflection Question: When your team defers to organizational authority, are they operating from learned helplessness, comfort in avoiding accountability, or genuine respect for hierarchy? How can you design experiments to uncover the real dynamic at play?
[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.
[The Scrum Master Toolbox Podcast Recommends]
About Alex Sloley
Alex believes that a great Scrum Master can have a long and lasting impact on people and teams. He is a global agile and product management evangelist, author of The Agile Community, and frequent international speaker. A former Microsoft leader with 15 years' experience, he now trains, coaches, and drives transformations worldwide. Certified across Scrum, ICAgile, and Kanban, Alex energizes communities, guides leaders, and—yes—enjoys good beer.
You can link with Alex Sloley on LinkedIn.