When Teams Lose Trust—How Scrum Masters Rebuild It One Small Change at a Time | Sara Di Gregorio

Summary

Scrum Master Toolbox Podcast
Episode: When Teams Lose Trust—How Scrum Masters Rebuild It One Small Change at a Time | Sara Di Gregorio
Host: Vasco Duarte | Guest: Sara Di Gregorio
Date: November 17, 2025

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Episode Overview

This episode explores what happens when teams lose trust—within themselves, with their company, or in the prospect of positive change—and how Scrum Masters can play a pivotal role in rebuilding it. Vasco Duarte and his guest, Sara Di Gregorio, an Italian Scrum Master focused on empathy and people-first practices, share stories and actionable approaches to navigating and healing team negativity. The central theme is the practical, people-centered work needed to foster trust and positivity, one small change at a time.

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Key Discussion Points & Insights

1. Sara's Path to Becoming a Scrum Master

• Sara’s Origin Story
  • Sara began her career at the luxury e-commerce company YOOX, working across multiple teams during an Agile transformation with ThoughtWorks.
  • Senior consultant Sunil Mundra saw Sara’s potential as a Scrum Master, highlighting her empathy, communication skills, and passion for improvement.
  • This recognition, combined with formal training, shaped her career focus:

    “He recognized in me the qualities that are essential for a Scrum Master, like empathy, strong communication, the passion for working with people, and a natural drive to support continuous improvement.” —Sara Di Gregorio [03:13]

• Power of Recognition
  • Vasco and Sara stress how important external validation and noticing others’ strengths can be in shaping careers.

2. The Challenge of Fostering Trust in Teams

• Recurring Failure: Negativity and Lost Trust
  • Sara describes a recurring difficult scenario: teams where trust has broken down, leading to a negative atmosphere and resignation.

    “When a team falls into a negative atmosphere where people have lost trust and believe that nothing can truly improve… these are very delicate situations.” —Sara Di Gregorio [06:12]

• Real Example: Individual Negativity Affecting Teams
  • Sara recounts working with a team member who lost trust in the company due to misunderstandings—not from malice, but lack of clarity.
  • The individual’s negativity became pervasive, affecting the team dynamic.

3. Emotional Impact and Responsibility as Scrum Master

• Personal Impact
  • Sara highlights the emotional toll negative team dynamics take on a caring Scrum Master.

    “It weighs on me because I feel responsible for it, because I genuinely care about the wellbeing of the team…” —Sara Di Gregorio [07:32]

• Continuous Effort and Experimentation
  • She discusses holding one-on-ones, energizing team meetings, and using humor or icebreakers in retrospectives to lighten the atmosphere and foster open communication.

4. The Power of Small Changes and Persistent Positivity

• Sara's Approach
  • Never give up; approach each day with openness, positivity, and trust in the process.
  • Experiment with small interventions—like starting with energizing greetings, or making people smile.

    “I truly believe that even the smallest changes can make a difference over time.” —Sara Di Gregorio [08:55]

• Reading the Room Every Day
  • Vasco underscores that each day, the “same” team might be facing new challenges; it's essential to listen to what’s happening now.

    “Every day you’re facing a different team... We need to be aware that we're always facing a new team and being ready to listen to what's going on today.” —Vasco Duarte [10:05]

5. Listening Beyond the Words

• Active Listening & Energy
  • Sara emphasizes the difference between hearing and truly listening—not just to what is said, but how people feel.

    “Sometimes we feel like listening but we are not really listening what the people are saying... it's not only about the content but you have to understand how they feel.” —Sara Di Gregorio [11:05]

  • She focuses on setting a positive tone, even with weather or light humor, to shift energy.

    “For me it’s very important to start the stand up saying, ‘Hi guys, how are you today?’ ...Only a very small smile. It's enough to say okay, it's something different from two minutes ago.” —Sara Di Gregorio [11:23]

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Notable Quotes & Memorable Moments

• Sara’s Turning Point:

  “I see you as a Scrum Master.” —Sunil Mundra to Sara Di Gregorio [02:32]
  (A moment of recognition that shaped Sara’s career.)

• Trust and Responsibility:

  “It weighs on me because I feel responsible for it, because I genuinely care about the wellbeing of the team...” —Sara Di Gregorio [07:32]

• Changing the Mood with Small Gestures:

  “Even the smallest changes can make a difference over time.” —Sara Di Gregorio [08:55]

• Listening and Energy:

  “Starting with a good tone of voice… something that makes them smile. For me, also only a very small smile, it's enough to say, okay, it's something different from two minutes ago.” —Sara Di Gregorio [11:23]

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Timestamps of Important Segments

• [02:06] Sara’s background & becoming a Scrum Master
• [06:04] The recurring challenge of broken trust and team negativity
• [07:32] Emotional responsibility as a Scrum Master
• [08:55] The power of small, persistent changes in culture and mood
• [10:05] Why every day brings a new team dynamic
• [11:05] Sara’s approach to listening and bringing energy to teams

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Conclusion & Key Takeaways

The episode delivers practical, emotionally intelligent insights for Scrum Masters dealing with demoralized or distrustful teams, focusing on:

• The necessity of persistent small changes and positive energy.
• The role of the Scrum Master as an active listener and champion of team wellbeing.
• Understanding that team dynamics are fluid and require daily attention.
• The value of recognition and support from colleagues in shaping our career journeys.

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This summary encapsulates the spirit and actionable wisdom of Sara Di Gregorio’s discussion, offering encouragement and practical tools for Scrum Masters facing challenging team dynamics.

Transcript

[A]

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 one more week of the Scrum Master Toolbox Podcast. And this week, joining us from beautiful Italy is Sara Di Gregorio. Hi Sara, welcome to the show.

[B]

Hi, thank you very much.

[A]

So it's a pleasure to hear the Italian accent on the English language. Sara is a people centered Scrum Master who champions trust, collaboration and real value over rigid frameworks. She has experience introducing agile practices in different organizations and 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. Sara, that was a short intro, necessarily short of course, but I'm sure you have a little bit more details to give us about your story, your background and how did you end up becoming a Scrum Master?

[B]

Well, I started my journey at ux, the luxury e commerce Italian company where I was working across multiple teams. At that time we were collaborating with ThoughtWorks, the consultant company that was helping us introducing the Scrum framework. Well, at that time I had the opportunity to work closely with Sanil Mundra, a senior consultant. He's Indian and working with ThoughtWorks, specialized in agile transformation. What happens that? One day during a conversation he said something that really stayed with me and he said, sara, I see you as a Scrum Master. So I said, wow. Well, it was such a special moment for me, not only because of what he said, but because it comes from someone with such deep experience in agility and organizational changes. So I was curious and then I asked him why he saw me as a Scrum Master. Why so that in me? Well, he explained that based on his experience he recognized in me the qualities that are essential for a Scrum Master, like empathy, strong communication, the passion for working with people, and a natural drive to support continuous improvement. That feedback helped me to reflect a lot and eventually embrace this path, which has since become my professional passions. So I've started doing some training course with Dusape, Desimone and other trainers that were working for Agile 42 at that time. Well, I discovered that is what I wanted to do. It's not easy to embrace this path, but working with people and see the improvements we do every day gives to me a lot of good energy. So now I'm very happy that Sunil helped me on starting this new path.

[A]

This sounds so like I remember this happening to so many of the member, the podcast guests that have kind of passed through. Right. Like they weren't necessarily going to school to learn how to be a Scrum Master. I mean, is not that old that it would be part of the, let's call it establishment. Right. But like when somebody notices. Right. And this is why it's so important for us also as Scrum Masters to notice what's going on around us because we can help shape somebody's future by observing what they are strong at. And so sometimes it's hard for us to see what we are strong at. But an external observation can trigger this. Oh yeah, and I really enjoy it, so I will follow it. But of course it isn't always easy. As you said, it is a difficult career path, but it's also very important one. That's my opinion at least. But because it's difficult, there's a lot of times when we struggle. And that's okay. Everybody struggles. That's why we have the Monday episode, as always, about failures, because failures are also incredible opportunities for learning. So, Sarah, share with us. When you think about your career as a Scrum Master, what is that moment of failure that you want to share with us? We'll dive into the takeaways and the learnings later, but first tell us that story.

[B]

Okay, so I don't have a single failure story to tell, but there is one type of situation that I always find particularly challenging. Well, when a team falls into a negative atmosphere where people have lost trust and change and believe that nothing can truly improve. For me, this is very, very important because when there are personal or character based dynamics tensioned into a team of personal, these I think are very delicate situations.

[A]

Can you remember like one specific situation that kind of illustrates what you're describing?

[B]

Yes. For example, I was working with a Team where a person was like losing a bit of trust in the company because of some, some misunderstanding. I think it's not because of the company or because of less transparency, but because sometimes there was some misunderstanding and I saw this person very negative and it was very sad for me working with this team and see negative atmosphere into the team. And for me it weighs a lot on my shoulders. I don't know what to say. It weighs on me because I feel responsible for it, because I genuinely care about the well being of the team, of the person I work with, and because I know how deeply the environment can affect both the work and the people. So we try to have a lot of talks with the team, some one to one and I always try to bring a lot of energy with me during the meetings. So for example, during the retrospective we tried to have some funny icebreakers to talk about what happens during what happens during the day, but from a funny point of view and also trying to experiment new things. For me, the important thing in this situation is to don't give up and so to try to work with the whole team. 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. And for me, it's very important to establish a good environment into the team.

[A]

What you said is really important, that it's really important to understand the where the team is at and also where certain individuals are at. We can't always affect it because it might be created for whatever reasons. I mean, people have private lives and they might be down because of what is going on in their private lives. And that's totally beyond our even ability to understand unless there are our friends already. Right? But it's important to have that in mind because a big change in the level of motivation or kind of, how do you say, openness by any of the team members can have a huge impact on the whole team. Like one of the things I often tell Scrum masters I coach is that every day you're facing a different team. It's the same people, but it's a different team because something has changed, whatever that is, somebody's life is upended by whatever reason or some big change in the company just happened or whatever. And we need to be aware that we're always facing a new team and being ready to listen what is going on today. And I find that, for example, the daily standups can be an excellent place for us to listen to what is going on and to understand what might be going on that particular day that wasn't there before. This is just my perspective. How about you, Sarah? Like when you think about listening to the team, understanding where they are working, what are kind of some of the techniques, the approaches you use to kind of always be listening and sensing where the team is at every day.

[B]

Yes, I think that listening is the word because sometimes we feel like listening but we are not really listening what the people are saying. So because it's not only about the content but you have to to to understand how they feel. So for me it's very important to start the stand up saying hi guys, how are you today? So from one time bringing energy because it's different. Like okay, so good morning, how are you? Oh, I'm depressed. So for me it's very important starting sometimes for me it's difficult because I'm not every day with full energy. But in this moment I try to do my best to be an energized people. So starting with a good tone of voice. So like good morning guys, how are you? It's sunny. It's a sunny day or yes, it's raining, but tomorrow will be better. I don't know. So something that make their smiling and for me also only very small smile. It's enough to say okay, it's something different from two minutes ago.

[A]

Yeah, absolutely. And then that's a great reflection for us to have even every day. Right. Like what kind of energy did I bring today to the interactions with the team? It's a great story. Thank you for sharing that, Sara.

[B]

You're welcome.

[A]

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[B]

Slack.

[A]

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