Rebuilding Agile Team Connection in the Remote Work Era | Sara Di Gregorio
Scrum Master Toolbox Podcast: Agile storytelling from the trenches
Release Date: 11/18/2025
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...
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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...
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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...
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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,...
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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...
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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...
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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...
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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...
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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...
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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_outlineSara 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: http://bit.ly/SMTP_ShowNotes.
"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 truly present. The spontaneous coffee machine conversations that built relationships and surfaced important information had vanished.
So Sara started experimenting. She introduced 5-minute chit-chat sessions at the start of every meeting: "Guys, how are you today? What happened yesterday?" She created "coffee all together" moments—10-minute virtual breaks where the team could drink coffee or have aperitivos together, sometimes three times per week. She established weekly feedback sessions every Friday morning—30 minutes to recap the week and understand what could improve.
These weren't just social niceties; they were deliberate efforts to recreate the human connections that remote work had stripped away. Sara recognized that mechanized interactions—"here are the things I need you to do, let's talk next steps"—kill team dynamics. Teams need moments where they relate to each other as people, not just as functions.
The experiments worked because they created space for genuine connection, allowing the team to maintain the trust and collaboration that makes effective teamwork possible, even when working remotely.
In this episode, we refer to Non-Violent Communication concepts and practices.
Self-reflection Question: How are you creating moments for your remote or hybrid team to connect as people, not just as colleagues executing tasks?
Featured Book of the Week: Nonviolent Communication by Marshall Rosenberg
Sara credits Nonviolent Communication by Marshall Rosenberg (translated in Italian as "Words are Windows, or They are Walls") as having a deep impact on her career. The book explores how to listen without judging, how to ask the right questions, and how to observe people to understand their real needs. But above all, it teaches how to communicate in a way that builds connection rather than creating barriers.
For Sara, the book was remarkably practical—she didn't just read it, she experimented with the techniques afterward. She explains: "I think that without this mindset, it's easy to fall into reactive communication, trying to defend, justify, or give quick answers. But that often blocks real understanding." The book helped her shift from reacting to connecting, which completely changed the quality of her conversations.
As a Scrum Master working with people every day—facilitating meetings, mediating conflicts, supporting teams—the way we communicate determines whether we open dialogue or close it. Sara found that taking time to reflect instead of giving quick answers transformed her ability to help teams discover dependencies, improve dialogue, and address communication issues. For anyone in the Scrum Master role, this book provides essential skills for building the kind of connection that makes true collaboration possible.
In this segment, we also refer to the NVC episodes we have on the podcast. Check those out to learn more about Nonviolent Communication
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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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About Sara Di Gregorio
Sara is a people-centered Scrum Master who champions trust, collaboration, and real value over rigid frameworks. With experience introducing Agile practices, she fosters empathy, inclusion, and clarity in every team. As an Advanced Scrum Master, she helps teams grow, perform, and deliver with enthusiasm and purpose.
You can link with Sara Di Gregorio on LinkedIn.