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Hey there, agile adventurer, just a quick question. What if for the price of a fancy coffee or half a pizza, you could unlock over 700 hours of the best agile content on the planet? That's audio, video, E courses, books, presentations, all that you can think of. But you can also join live calls with world class practitioners and hang out in a flame war free and AI slop clean slack with the sharpest minds in the game. Oh, and yes, you get direct access to me, Vasko, your Scrum Master Toolbox podcast. No, this is not a drill. It's this Scrum Master Toolbox membership. And it's your unfair advantage in the agile world. So if you want to know more, go check out scrummastertoolbox.org membership. That's scrummastertoolbox.org Membership. And check out all the goodies we have for you. Do it now. But if you're not doing it now, let's listen to the podcast. Hello everybody. Welcome to our Wednesday the coaching day here on the podcast this week with Sara DiGregorio. Hey Sara, welcome back.
B
Ciao. Thank you.
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Ciao. And we are here to talk about coaching, but not from a theoretical point of view, rather from a very practical point of view. We're going to have a coaching conversation from Sara has a topic that she wants to discuss and we are both going to explore that topic and potentially come up with a few experiments to try when trying to tackle a topic like the one she has to share with us. So let's start with the topic. What is the topic? The area that you want to explore in today's episode? Sara?
B
I think that the retrospective can be a good example and we can talk about it. I think that so when I think about coaching, I always think about from to bring the team of the person from a point A to a point B. So we have to understand how we can do this path. Normally during the retrospective we can have different kind of teams. I make teams with a lot of things to talk about so many topics. And so the idea was so oh, but at the end we cannot talk about all the topics. So it was very important for me to under to make them understand that the aim of the retrospective is not to talk about a lot of topics, but to go deeper into some topics chosen by the team. So during the retrospective it's very important to ask questions to make clear the topic to understand why this topic is very important for the team.
A
So what have you tried to help? Let's imagine a team that you were working with that wanted to discuss 20 topics. Like everybody had two or three topics to talk about. What were some of the things that you have used and tried out to help the team narrow their focus?
B
Well, first of all, we voted the main topic we want to discuss about. And I explained, trying to explain that they have to vote the topics that they want to discuss about, not only the topic that are important for them, but you have to be open to discuss. Because for me something can be very important, but if I don't have nothing to say, could be made sometimes difficult to approach. So I try always to highlight it. So please, guys, you should vote the topics that you want to discuss. So I try to make a lot of questions, but when I see that the communication start and they are very connected, sometimes I go to the corner and I leave them discussing only for example, saying, guys, we are close to the, to the end of the time that we reserved for this discussion. So I try to help on respect timing and so on. But it's very important for me that when they start connecting and so they have a very intense, interesting discussion, I go to the corner and I only trying to listen, of course, I'm always there and try to help people that try to talk and are a little bit shy or I don't know. So it's always important to be there and try to facilitate, moderate the conversation.
A
One of the things, before we go further, one of the things that is really important for us as a skill is to know when to step back. So going to the corner, as you were just saying, but also when to step in, right? Like one of the things that you said at the start of this was when there's a lot of topics that may be topics of retrospective, I help the team focus on one or two or whatever number, but a small number of topics that they really want to discuss. So not topics that they have an opinion on, but like topics that they want to discuss, they want to have a collective agreement on, I guess could be a way to describe it. So that's one way to step in, right? Like when, when you say, hey, this is the role, we're going to select the topic, you select it. But it's we're going to select the topic, then we're going to discuss it, okay? So that's one way to step in. And then you talked about being able to step back when, when they are engaged, when they are connecting with each other, but even during that moment, right? Like they, they are engaged, they're connected with each other, but the conversation can go off course. Maybe one person starts taking over, maybe they lose sight of understanding the problem and they start immediately discussing solutions. Like there's a lot of potential reasons for us to step in. So what are some of the practices that you have used to kind of trigger yourself to step in when the conversation is perhaps for example, shifting to another topic without the team even noticing it necessarily?
B
Yes, for example, when they talk about technical stuff. So sometimes there are things that I cannot understand from a technical point of view. What I say is, guys, you are the main expert of this topic. So please, when someone understands that we are going out of topic or I don't know, we are very detailed, please raise your hand and help me on bringing the communication back to be focused on what we chosen to talk about it. This could be one thing. I give them the responsibility for technical stuff when it's something that is non technical. Of course, when I see that they are going a little bit out of the topic, I come back into the discussion and try to do some stuff, step back. What can help sometimes is to have a white paper, some Sharpies and try to to visualize and have some steps on what we are talking about. For me, it's always very important to give white papers, sticky notes and so on because they can write some questions on the sticky notes and we can talk about them when it's the correct moment. Because from a coaching point of view, for me it's important to create space for questions to create a structured moment to talk about the topic. So there are a lot of things to pay attention to that we should pay attention attention like so connection that we are focused on the topic, that we are doing the right questions instead of why, why, why? Because normally we are very used to say why is this happening? We can change also the question and say in other ways. So how did you approach it? What happens? So also to help people to reformulate the questions. So sometimes when I saw that the guys tried to I are very direct, I always try them to say, okay, can we exclude. Explain better your question because it helps the other people to answer and to find a solution. Because the idea of course of the retrospective is to find a small action, something that we can go that we can achieve in one sprint. Okay, so it's important to do the right questions. And for me, as a scrum master, I try to keep always the team into the right path.
A
One of the cool things that you mentioned that I think is really critical is the ability to ask questions that instead of kind of directing teams, they create space for Reflection. Right. Like, for example, an example would be, so I hear you say that. And whatever that is that you hear them say, did I understand correctly? Is this what you're trying to describe? And then bring that back to the original topic. So one very common anti pattern is, I hear you say that if only this other team would act differently, all your problems would be solved. Is this what you're saying?
B
Exactly.
A
And sometimes people get into this kind of, oh, yeah, it's their fault. Oh yeah, it's their fault. And then the problem for us as grandmaster is that the moment that becomes kind of the accepted narrative is that the team, our team can't do anything about it because everything is on the other team. Right. And then the problem becomes, how do you change them? And that's not a good idea because we don't have power over others. Right. We only have power over us. So. And then we can bring that discussion back to, is this how you feel that if only others would change, then all your problems would be solved? And probably they'll say, no, no, no, no, that's not what we're trying to say. And then we can bring it back to the topic with things like, okay, so what are the things we can influence that would help solve this problem? Right. Like, and, and I think that being attentive as you described, being attentive to what's going on, helping them to verbalize could be through conversation. Sometimes it's better to actually do silent writing, like give everybody post its and ask them to write it instead. And I think it's very important for us to be aware that this, there's. I call it a fragile focus in retrospectives where during certain moments the team is really focused on understanding and solving the challenges they have, but it's fragile. It can easily derail. And kind of listening to the conversation and asking these clarifying questions can help bring the focus back to that topic that we decided together that we wanted to cover.
B
Exactly. I think that is the point. And it's very important to give them space, but at the same time to help them rephrase the questions and so on. And it's very important to, instead of talking about the other teams, to say, okay, what can we influence? What can we do from our side? So I always try to. Absolutely.
A
Yeah, yeah, yeah. Retrospectives aren't good if all we are doing is talking about what others need to do instead of what we need to do. Great stuff. Thank you for sharing that with us, Sara.
B
You're welcome.
A
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Podcast: Scrum Master Toolbox Podcast: Agile storytelling from the trenches
Host: Vasco Duarte
Guest: Sara Di Gregorio
Date: November 19, 2025
This episode dives deep into the practical facilitation of Scrum retrospectives, focusing on the nuanced judgment Scrum Masters must exercise—knowing when to actively guide a conversation and when to step back and allow the team to self-organize. Vasco and Sara use real-world coaching scenarios to explore strategies for helping teams focus, engage deeply, and generate actionable outcomes during retrospectives.
The conversation is practical, reflective, and highly relatable for current Scrum Masters, mixing hands-on tips with thoughtful discussion. Both Sara and Vasco maintain a tone of professional camaraderie, focused on real-world challenges and solutions, with gentle humor and mutual respect for the Scrum Master’s craft.
This episode offers actionable advice for Scrum Masters on deepening the impact of retrospectives, focusing on facilitating meaningful conversations and cultivating team responsibility for progress. Sara and Vasco stress the importance of balancing intervention with allowing organic discussion, ultimately aiming for retrospectives that spark genuine improvement owned by the team.