How to Know Your Team Has Internalized Agile Values | Sara Di Gregorio

Summary

Podcast Summary: How to Know Your Team Has Internalized Agile Values

Scrum Master Toolbox Podcast
Host: Vasco Duarte | Guest: Sara Di Gregorio
Date: November 20, 2025

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Episode Overview:

This episode delves into the core question of how Scrum Masters can recognize when their teams have truly internalized Agile values. Sara Di Gregorio shares hands-on retrospective strategies, principles for fostering team engagement, and markers of real Agile success. The discussion is candid, practical, and focused on culture and growth, rather than just delivery metrics.

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Key Discussion Points & Insights

1. Retrospective Formats: Mixing Structure and Freedom

[01:11–05:14]

• In-person Value: Sara highlights the unique benefits of holding retrospectives in person, when possible, to enhance connection.
• Novel Experimentation:
  • Sara has shifted towards “free format” retrospectives using blank paper, sticky notes, and colored pens.
  • This approach starts with open questions, e.g., “What impacted you the most last week? How do you feel today?”
• Balancing Formats:
  • Structured retrospectives are essential and effective.
  • Introducing unstructured, open formats sparks deeper engagement and genuine reflection.
• Engagement Through Variety:
  • Changing the routine can encourage openness and more enriching conversations.

Notable Quote:

“Sometimes breaking the routine and creating spacing for true reflections bring out something deeper and more meaningful.”
— Sara Di Gregorio [04:40]

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2. Success as a Scrum Master: Beyond Deliverables

[06:01–09:56]

• Communication & Growth:
  • Success isn't only about team delivery. It’s equally about how the team communicates, collaborates, and grows.
  • Facilitating better communication directly enhances delivery outcomes.
• Active Participation:
  • A real mark of success is when teams see value in Scrum events and engage actively, not just out of obligation.
  • Examples:
    • Teams proactively ask for additional reflection time or propose discussions outside of scheduled retrospectives.
    • Mentioning the “goal” in planning signals growing alignment and purpose.
• Proactive Team Behavior:
  • Teams that initiate action — such as reminding others about timeboxes or leading by example in cross-team contexts — display Agile maturity.
  • Sara shares pride in witnessing her team independently championing Agile practices, e.g., advocating for timekeeping in meetings she’s merely attending as an observer.
• Healthy PO Interactions:
  • Regular feedback, open discussions, and a shared care for quality are essential signs that Agile values have been internalized.

Notable Moment:

“When I listen the teams saying, ‘Sara, can we have 30 minutes talking this sprint? Because we have something to say, so we have to reflect on something.’ Yes, of course. We don’t have to wait for the retrospective...”
— Sara Di Gregorio [07:01]

Notable Quote:

“A successful team is one that truly sees the value on Scrum events … they participate actively and understand why each event matters.”
— Sara Di Gregorio [06:35]

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3. Indicators of Culture and Maturity

[09:56–10:54]

• Success Manifested in Attitudes:
  • The team’s attitude towards each other, leadership, and the Scrum Master shows the health of the Agile culture.
  • Building an open environment where candid feedback, collaboration, and extra-reflective moments outside prescribed events are normalized is core.
• Building or Amplifying Culture:
  • Some teams already possess these traits and just need encouragement. Others develop them step by step with deliberate Scrum Masterwork.
• Retrospective Structures as Culture Tools:
  • Both structured and “white paper” retrospectives serve the evolution of team norms and reflection habits.

Host Reflection:

“It illustrates the importance of the kind of environment and culture that we are able to bring to the team ... talking openly, having reflection outside the retrospectives. All of those things.”
— Vasco Duarte [10:23]

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4. Scrum as a Way of Working, Not Just a Framework

[10:54–11:45]

• Enabling Change Through Empowerment:
  • When joining new teams, Sara stresses that she’s not there to enforce change, but to empower the team to decide for themselves — a mindset crucial to real Agile adoption.
• Sustainable Culture:
  • The long-term goal is for teams to be happy, communicative, and process-improving on their own.

Memorable Exchange:

“Scrum isn’t just a process to follow, but it’s a way of working ... you will choose what you want to change.”
— Sara Di Gregorio [11:01]

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Notable Quotes & Moments

| Timestamp | Speaker | Quote/Highlight | |-----------|---------|-----------------| | 04:40 | Sara Di Gregorio | “Sometimes breaking the routine and creating spacing for true reflections bring out something deeper and more meaningful.” | | 06:35 | Sara Di Gregorio | “A successful team is one that truly sees the value on Scrum events ... they participate actively and understand why each event matters.” | | 07:01 | Sara Di Gregorio | “Sara, can we have 30 minutes talking this sprint? Because we have something to say, so we have to reflect on something.” | | 09:36 | Sara Di Gregorio | “Some years ago, a colleague of mine in a meeting with other people...say, guys, we have to respect the time box. So I feel so happy.” | | 10:23 | Vasco Duarte | “It illustrates the importance of the kind of environment and culture that we are able to bring to the team ...” | | 11:01 | Sara Di Gregorio | “Scrum isn’t just a process to follow, but it’s a way of working ... you will choose what you want to change.” |

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Timestamps for Important Segments

• [01:11] – Discussion on retrospective formats: structured vs. unstructured
• [06:01] – What “success” means as a Scrum Master
• [07:01] – Teams taking initiative for reflection
• [09:36] – Maturity indicators: proactivity and timeboxing
• [10:23] – Host reflection on building culture
• [11:01] – “Scrum is a way of working” philosophy

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Tone and Language

Sara speaks with warmth, humor, and a hands-on, empowering attitude. Vasco supports with affirming, reflective comments, facilitating a conversational and genuinely insightful exchange.

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Takeaways

• Retrospective formats should be varied to unlock deeper team engagement.
• True Agile success is grounded in communication, proactivity, and a culture of reflection, not just delivery metrics.
• Scrum Masters succeed when their teams own the process, seek improvement independently, and demonstrate Agile values naturally—even outside formal ceremonies.

This episode offers practical strategies, motivational moments, and clear guidance for any Scrum Master seeking to measure and nurture real Agile maturity in their team.

Transcript

[Vasco Duarte]

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.

[Host/Co-host]

Do it now. But if you're not doing it now.

[Vasco Duarte]

Let'S listen to the podcast.

[Host/Co-host]

Hello everybody. Welcome to our success. Thursday, the big question of the week. Of course, this week with Sara DiGregorio. Hey Sara, welcome back. So before we dive into success, which is really the big question of the week, let's talk about retrospectives. We were talking about it yesterday and we'll talk about it today, but from a different angle. Share with us what what's your favorite agile retrospective format and why?

[Sara Di Gregorio]

Okay, so first of all, I know that a lot of us are working from home, but for the person that like me, can work half from home and half from the office, could be very valuable to have the retrospective in office. Because for me, the retrospective is one of those key moments where being in the same room can make a big difference. Of course, when it's possible, when it's not possible, we can have other, we can do other experiments and so on. I usually like to start retrospective with a simple, funny icebreaker to help people disconnect from the their day. Okay, the week and reconnect with the team. Because as I always say to the team I work with, guys, you are very lucky to have a moment to discuss with your team about how we can improve. Because it's not something that we have to say, okay. It's because not in all the companies we have. These people is so lucky. Lately I've been experimenting free format. But after trying many structured approach together, I thought that could be a good idea to start with a white paper and a lot of sticky notes Sharpies. So what we do, just a paper, pens of different colors and starting with an open conversation, sometimes we start guiding the retrospective by data or metrics. But other times it's how the team is feeling that day. So I start, guys, what did impact you mostly during the last week? How do you feel today? I've been seeing great response from the team. So it was an experiment that I tried. After a lot of structured retrospective that I think that are very important to do and to follow, and I always try to do, sometimes in this format and sometimes in the structured format, they are more engaged. This is what I saw more open and more present in the conversation. Maybe because it was something new. So instead of starting always with the same different but same structured conversations format, I said, okay, white paper, pens, everyone can write, of course, following a structured conversation. So who want to start? Okay, but everyone has the possibility to write in the white paper. I'm not saying that the structural format don't work because as I said before, they are very useful for me. But sometimes breaking the routine and creating spacing for true reflections bring out something deeper and more meaningful.

[Host/Co-host]

It definitely opens the space for something that is not yet predicted. Right. Like in the coaching conversation, we were just talking about how important it is to have a kind of a direction to know where you're going and so on. But it's also important for us to be aware of things that are not structured, that don't have a specific direction, but allow people to express what's going on for them.

[Sara Di Gregorio]

Right, Exactly.

[Host/Co-host]

Absolutely. Great, great tip. Now we turn our attention to what success means for us. Of course, we run retrospectives because we want to help teams succeed and we want ourselves to succeed as well. But for that to happen, we need to define what it is. So, Sara, what does success mean for you as a Scrum Master?

[Sara Di Gregorio]

Well, for me, as a Scrum Master, the success is not only measured by what the team delivers. I'm not saying that is not important, but it's not the only thing. Because for me, it's very important to understand how the team grows, how they improve the communication, the collaboration. Because if we facilitate the team on the growth in improving communication, conversation, for sure the delivery will improve. So the team, if the team communicates very well, the delivery will be impacted from this. I think that for me, as a Scrum Master, this is very important. And a successful team is one that truly see the value on Scrum events. So. So when I see that they don't just attend because they have to do, because they have these events on their agenda, but they participate actively and understand why each event matters, for me it's, I think the big success I can imagine for my role. For example, when the team asks me to run the retrospective because they still they need to reflect and improve. Or they use the sprint planning. And that's for me first of all to be aligned on a goal. For me, when I listen the teams saying, sara, can we have 30 minutes talking this sprint? Because we have something to say, so we have to reflect on something. Yes, of course. We don't have to wait for the retrospective or for example, okay, guys, so today we can start planning is a new planning. And I listen people saying the word goal. Okay? For me this is very, very, very important. I also see the success when the team is proactive, when they lead by example. Even in crossing meeting. For example, by helping other teams stick to time boxes or pushing to end a meeting with clear outcomes. It should maturity and accountability. For example, some years ago, a colleague of mine in a meeting with other people, it was not leaded by me, so I was only a listener and interrupter. After, at the end of the meeting say, guys, we have to respect the time box. So I feel so happy. I said, okay. So it was so it was a good achievement.

[Vasco Duarte]

It's a proud moment, I bet.

[Sara Di Gregorio]

Yes. And another thing is how the team interact with the product owner. So as you can understand, for me it's very important the communication from. From all the points. So a team that regularly seek for feedback, open discussion or care about the quality. And for me this is very. So it's means for me that I pass them a lot of. So the important that the communication us in all the steps.

[Host/Co-host]

I really like how you're focusing on the attitude that the team shows in their interactions with each other, with others and with yourself. Because it really kind of exemplifies. It illustrates the importance of the kind of environment and culture that we are able to bring to the team. I mean, sometimes it's already there and which is great. We just need to amplify it. Other times it isn't there and we need to build it step by step. Like what you described just a moment ago when you were talking about the need to have structured and unstructured retrospectives because they fulfill different purposes. Right. So I think this is a really great example and illustration of those small little things that we need to be paying attention to that show the culture that is in the team and help us to. To achieve the right type of culture. Right? Like interaction, collaboration, talking openly, having reflection outside the retrospectives. All of those things.

[Sara Di Gregorio]

Yeah, no, that's because what I always say to the teams I work with is that Scrum isn't just a process to follow, but it's a way of working. When I met one team for the first time some years ago, one of the person that I met told me well, what do you want to do with us? Do you want to change things? And I said no, I don't want to change anything. You will choose what you want to change. So for me it's very important that now after a lot of years that I work with these people, I improved a lot the communication, they are happy happy about the process. All right, because I hope you like.

[Vasco Duarte]

Before you hit next episode.

[Host/Co-host]

This podcast is powered by people like.

[Sara Di Gregorio]

Saying something when members who wanted more.

[Vasco Duarte]

Than just inspiration into the company and real connection to people who are practicing.

[Sara Di Gregorio]

It's important that people every day we're.

[Vasco Duarte]

Talking access to 700.

[Sara Di Gregorio]

Have to be in a high level strategy, talking things.

[Vasco Duarte]

When you live workshops, courses, deep dive interviews, other teams, books and if you're into no estimates, pioneers of no estimates in those you just gave us quite.

[Host/Co-host]

A few quotable things there. The one that I really like, coaching.

[Vasco Duarte]

Your product owner courses, you name it, way of working, you'll get invites.

[Host/Co-host]

Really great multiple phrase there. Thank you for sharing that with us practitioners.

[Sara Di Gregorio]

You're welcome. Plus thank you.

[Vasco Duarte]

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[Host/Co-host]

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[Podcast Outro Announcer]

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