The 90-Minute Retrospective Disaster That Taught Me Servant Leadership | Juliana Stepanova

Summary

Scrum Master Toolbox Podcast: The 90-Minute Retrospective Disaster That Taught Me Servant Leadership | Juliana Stepanova

Date: February 2, 2026
Host: Vasco Duarte
Guest: Juliana Stepanova, Agile Coach & Scrum Master (Germany)

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Episode Overview

This episode centers on a pivotal learning moment in Juliana Stepanova's early career as a Scrum Master—a failed 90-minute retrospective that ultimately led her to embrace and understand the essence of servant leadership in agile teams. Through honest reflection, Juliana discusses the importance of adaptability, facilitation, and empowering teams to take ownership of their improvement processes.

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Key Discussion Points & Insights

1. Juliana’s Journey to Becoming a Scrum Master

[01:25–03:56]

• Former engineer and consultant, Juliana observed inefficiencies and resource waste in traditional workplaces.
• Discovery of Scrum in 2014 led her to pursue the Scrum Master path to "organize the process and work with people" for more meaningful outcomes.
• Received her first Scrum Master role just two weeks after certification, seeing this as a sign she was on the right path.

2. The Retrospective Disaster: Story of Failure

[04:45–05:31]

• Juliana recounts a major personal failure during her first year:
  • She meticulously prepared a "brilliant” retrospective with structured activities designed around her view of the recent sprint.
  • The session lasted 90 minutes.
  • Team feedback: "It was the worst retro ever."

“At the end I asked my team how was the retro and they say it was the worst retro ever.”
— Juliana Stepanova [05:24]

• The experience led to disappointment but set the stage for critical learning.

3. Lessons Learned: From Directing to Enabling

[05:37–09:48]

• Juliana realized her preparation was based on her own assumptions, not the team’s needs.
• The retrospective delivered results, but not in a way that engaged or motivated the team.
• Key shift: Start asking the team what topics they want to address and how they want to work, rather than imposing predetermined exercises.
• Moved from "leader" to "servant leader," learning to facilitate from behind rather than direct from the front.

“I behave myself as a leader, but not servant leader. … As a servant leader, you [are] asking, you [are] communicating … how they would like to work on it, to give them a bit like freedom to choose on which points.”
— Juliana Stepanova [08:13]

4. Practical Takeaways: Improving Retrospective Facilitation

[09:48–11:50]

• Juliana now prepares multiple backup exercises and adapts in the moment based on the team’s energy and needs, especially using tools like Miro for online retros.
• Starts every retrospective with open questions to surface the team's expectations.
• Sets clear boundaries to ensure constructive discussions but lets the team’s priorities drive the session.

“I start usually with the questions, with open questions. What the people expect to do, what they would like as a to have as a result to align with their mood and actually to cut off. If for example the person come to blame somebody, I will say, okay, it's not the topic and not their context of our meeting today.”
— Juliana Stepanova [10:41]

5. The Importance of Facilitation Skills in Agile Coaching

[11:50–12:20]

• Even a perfectly planned retro may not meet the team's needs.
• Effective facilitation is about responding to the team’s evolving requirements, listening, and being able to pivot.

“Even if you have a great perfectly organized and prepared retrospective, that does not mean that that's what the team needs at that time and what they need will emerge in the interaction.”
— Vasco Duarte [11:53]

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Notable Quotes & Memorable Moments

• On Learning from Failure:
  “Actually, failure, it's a normal part of the life and work, and the only one point that really need to be done is to analyze and to learn from failure.”
  — Juliana Stepanova [04:45]

• On Servant Leadership:
  “As a servant leader, you [are] asking, you [are] communicating ... how they would like to work on it, to give them a freedom to choose on which points.”
  — Juliana Stepanova [08:13]

• On Retrospective Flexibility:
  “I have like really backup version like twice. If I have like, I don't know, five tools, I will prepare at least 10 of them to have ability to change.”
  — Juliana Stepanova [10:23]

• On Team-Driven Improvement:
  “What they need will emerge in the interaction … as we start the retrospective.”
  — Vasco Duarte [11:54]

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Important Segment Timestamps

• [01:25] — Juliana’s background and road to Scrum Mastery
• [04:45] — Introduction of the “Fail Monday” retrospective disaster story
• [05:31] — Team’s candid feedback: “worst retro ever”
• [06:45–08:13] — Identifying the need to shift from leader to servant leader
• [09:48–11:50] — Modern approach to retrospective facilitation and team alignment
• [11:53] — Importance of facilitation and adaptive retrospectives

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Summary

Juliana Stepanova’s story is a real-world lesson in humility, adaptability, and growth as a Scrum Master. Her “90-minute retrospective disaster” was not a technical failure but a failure of alignment and empathy—it taught her the true nature of servant leadership: facilitating the team's self-discovery, not dictating it. Now, Juliana approaches every retrospective as a dynamic interaction, grounded in servant leadership principles and agile flexibility, ensuring that each session is driven by the team’s voice and needs.

This episode is essential listening for Scrum Masters, Agile Coaches, and anyone interested in elevating their facilitation practices beyond checklists and exercises, toward true team empowerment.

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.

[B]

Hello everybody. Welcome to one more week of the Scrum Master Toolbox Podcast. And this week joining us from Germany is Juliana Stepanova. Hey Juliana, welcome to the show.

[C]

Thank you for inviting me.

[B]

Absolutely. So Juliana is an Agile coach and Scrum Master with a focus in her work on transformation through people and processes rather than the other way around. She helps teams and leaders create clarity, build trust and create value with purpose. Her work combines structure with empathy and is always focused on real collaboration and meaningful results. So Juliana, that was a short intro. Tell us a little bit more about yourself and how did you end up becoming a Scrum Master?

[C]

It's really interesting question because I have got this question so many times and it's like the most question that I usually get after that actually what Scrum Master is or what is the role. And my answer in the short is I have really very big luck to become a Scrum Master. I was previously an engineer and working for about five years in consulting company and I saw a lot of resource waste, how the process is not going on like the work was built just to do some work and that's all. And I find myself really impatient to help keep people, to organize the process, to work with the people and not only doing job for nothing or for money for salary. And as I have choose to start working somewhere else up to my consulting company, I was thinking what I can do most or best for me or for people in this particular area. And I remember in one of the project I faced up with the Scrum and that time it was not so popular. It was about 2014 and I actually like put it in my memory like a bookmark. Okay. It's really something interesting that I can get into. And I start to looking around the Scrum, Scrum Master role. What is the process? What is the methodology, how I can get there? And I was passing exam and really with a big luck, I have got an offer for the job in 14 days to start.

[B]

That's really nice.

[C]

And that was like, like really the sign for me. Okay, I'm doing everything right. It's a good idea. Let's start to do it. Of course it was not easy, but actually this is like the way how I was introduced into the Scrum Master role.

[B]

And this attempt or desire to help others is very common within our profession. I would say it's probably a very even perhaps the most common trait in the people we interview here on the podcast. And when we think about that, of course we always want to help people, but sometimes, for whatever reason, we are just not able. And today's Fail Monday here on the podcast. And we explore a story of failure. Not because we want to dwell on failure, but just because we want to understand what might have gone differently from our expectations and what can we learn to apply in the future. So, Juliane, when you think about that story of a difficult moment you had as a Scrum Master, tell us that story first and then we'll dive into the takeaways. But tell us that story first.

[C]

Actually the failure, it's a normal part of the life and work and only one point that really need to be done. It's to analyze and to learn from failure. And when I'm just thinking, of course I have many examples, but I don't want to go deeper on the company level or the team level. And I will tell you my personal failure as a Scrum Master. It was on the first year there was this role and I prepared, in my opinion, like brilliant retrospective everything like in a book with different exercises, with content to the sprint. And it was really like 90 minutes. And at the end I asked my team how was the retro and they say it was the worst retro ever.

[B]

Aha. So it went completely different from what you expected.

[C]

Exactly. So I was a little bit disappointed at the time. But of course learning, analyzing, taking actions, it helped. And then was the focus for me to ask more the team what they want because I prepared, in my opinion, how I. I saw the sprint, how I think I could help them to find points to improve. But actually it's not my job, my job to help them to find this to Interact their communication to start thinking about the improvements and not pushing them into my exercises what I think is best fit.

[B]

Yeah. So if I get you right, what you're saying is you started to prepare the retrospective with care and attention and with the desire to help, but it didn't land. And then when you talked with the team, you discovered that you had focused on something that was not what they wanted to focus on. Is that what happened?

[C]

So actually it's more about the tools and exactly the focus. Because as a scrum master, of course I'm not in there daily basis with the team and get everything and I have like an overview, like a bigger picture and sometimes this small stuff that happens in the team, it's coming just not coming on my table. And the solution was to ask them, okay, we have retrospective, what topics do you would like to discuss? Or of course I have like my list with the points with some problems or improvement stuff. But I ask then more my team where they would like to focus, how they would like to proceed in retrospective, of course with this frame that is given. But I give them the freedom to choose the best way. Like low hanging fruits. Really.

[B]

Okay, so if I hear you right, then what you're saying is it wasn't necessarily that the tools were bad or inadequate. It was just that the way the team expected to be in that retrospective was different from what you expected from them and there wasn't maybe like you were not aligned with the team. Is that how you would put it? How would you put it?

[C]

I would put it in the servant leadership. So I in this failure example, I behave myself as a leader, but not servant leader. So I prepared everything we go through. And actually it was a good result of retrospective. But team would do so prefer to do something else. And as a servant leader, you asking you communicating on the particular stuff how they would like to work on it, to give them a bit like freedom to choose on which points. Because if I put some exercise which not fit at the best or even not promote some conversation in the team, the exercise will be done, but the results could be better.

[B]

Okay, so what I'm thinking about is you're looking at that experiment, that workshop, that retrospective as a facilitation failure. So not necessarily the retrospective was wrong, but that in the retrospective things went or rather the retrospective was executed according to the plan, but it did not tackle the topics or even it didn't go through the topics in a way that the team could relate to, could feel that they were contributing to the conversation.

[C]

Yes, you are Right.

[B]

So when you think about setting up a workshop these days, right. Like based on that learning experience, what do you do to make sure that of course I'm guessing at least you have the flexibility to change the exercises, but to make sure that you allow the team to bring their perspective into the the retrospective. How do you do that today?

[C]

So in the backup case I have like prepared. So I mostly work with the Miro in the online workshops and I have like prepared exercises for backup if it's offline. In the real life I have like different exercises or tools in my head or written so it's prepared and I see mostly there mood of the group, how they behave and I can change iteratively some other tools or questions, put it in the different direction or different time. So I have like really backup version like twice. If I have like, I don't know, five tools, I will prepare at least 10 of them to have ability to change. And I start usually with the questions, with open questions. What the people expect to do, what they would like as a to have as a result to align with their mood and actually to cut off. If for example the person come to blame somebody, I will say, okay, it's not the topic and not their context of our meeting today to really set the boundaries, it's where the leadership comes. But set the boundaries and say that this is not a part of this workshop or meeting, but to see what is expectation to align and to have like in the main values of the whole team to see that they are on the same stage.

[B]

Yeah, absolutely. And this story shows how important it is for us to grow and become great facilitators. Because it is true that even if you have a great perfectly organized and prepared retrospective, that does not mean that that's what the team needs at that time and what they need will emerge in the interaction. Right. Like we will find out what the team needs in that particular time as we start the retrospective. It was a great story. Thank you for sharing that with us. Juliana.

[C]

Thank you very much.

[A]

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[B]

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