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"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 subtle but powerful. When teams come to her with specific requests outside the regular schedule—"Can we have 30 minutes to talk and reflect mid-sprint?"—she knows something has shifted. When teams want to reflect outside the retrospective cycle, it means they've internalized the value of continuous improvement, not just going through the motions. She listens for the word "goal" during sprint planning.
When team members start their planning by talking about goals, she feels a surge of recognition: "Okay, for me, this is very, very, very important." Success shows up in unexpected places. One of her colleague's teams pushed back during a cross-team meeting, saying "We're going out of the timebox" and suggesting they move the discussion to a different time. That kind of proactive leadership and accountability signals maturity. It means the team isn't just attending Scrum events because they have to—they truly understand why each event matters and actively participate to make them valuable.
When Sara first met a team, they asked if she wanted to change things. She said no. What she focuses on is how people improve and understand the process better. For her, it starts with the people—when people change and understand the value, that's when real changes happen in the company. It's about helping people feel good and be guided well, because when they're working well, that's when transformation becomes possible. As Sara reminds us, Scrum isn't just a process to follow—it's a way of working that teams must embrace, understand, and make their own.
Self-reflection Question: Are your teams coming to you asking for reflection time outside scheduled events, and what does that tell you about how deeply they've internalized continuous improvement?
After facilitating many structured retrospectives, Sara started experimenting with an unstructured format that brought new energy to team reflection. Instead of using predefined frameworks, she brings white paper, sticky notes, and sharpies of different colors. She opens with a simple question: "Guys, what impacted you mostly during the last week? How do you feel today?" Sometimes she starts with data and metrics; other times, she begins with how the team is feeling.
The key is creating open space for conversation rather than forcing it into a predetermined structure. What Sara discovered is remarkable: "They are more engaged, more open, and more present in the conversation, maybe because it was something new." Instead of the same structured format every time, the unstructured approach breaks the routine and creates space for true reflections that bring out something deeper and more meaningful. It allows people to express what's genuinely going on for them, not just what fits into a predefined template.
Sara doesn't abandon structured formats entirely—she alternates between structured and unstructured to keep retrospectives fresh and engaging. She also recommends, if you work hybrid, trying to schedule unstructured retrospectives for days when the team is in the office together. The physical presence combined with the open format creates an environment where teams can be more vulnerable, more creative, and more honest about what's really happening. The unstructured retrospective isn't about chaos—it's about trusting the team to surface what matters most to them, with the Scrum Master providing light facilitation and space for authentic reflection.
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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.