Sara Di Gregorio: Facilitating Deeper Retrospectives—When to Step In and When to Step Back

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"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, but conversations stayed surface-level, never reaching the insights that drive real improvement. Sara recognized that the aim of the retrospective isn't to talk about everything—it's to go deeper on topics the team genuinely cares about.

So she started coaching teams to select just three main topics they wanted to discuss, helping them understand why prioritization matters and making explicit which topics are most important. But her real skill emerged in how she facilitated the discussions. When she saw communication starting to flow and team members becoming deeply connected to the topic, she moved to the corner and listened. She didn't abandon the team—she remained present, ready to help shy or quiet members speak up, watching the clock to respect timeboxes.

But she understood that when teams connect authentically, the Scrum Master's job is to create space, not fill it. Sara learned to ask better questions too. Instead of repeatedly asking "Why? Why? Why?"—which can feel accusatory—she reformulated: "How did you approach it? What happens?" When teams started blaming other teams, she redirected: "What can we influence? What can we do from our side?" She used visual tools like white paper, sharpies, and sticky notes to help teams visualize their discussion steps and create structured moments for questions.

Sometimes, when teams discussed complex technical topics beyond her understanding, she empowered them: "You are the main expert of this topic. Please, when someone sees that we're going out of topic or getting too detailed, raise your hand and help me bring the communication back to what we've chosen to talk about."

This balance—knowing when to step in with structure and when to step back and listen—is what transforms retrospectives from checkbox events into genuine opportunities for team growth.

Self-reflection Question: In your facilitation, are you creating space for deep team connection, or are you inadvertently filling the space that teams need to discover insights for themselves?

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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.