From Permission-Seeking to Forgiveness-Begging—Agile Team Evolution in Self-Management | Bernie Maloney

Summary

Scrum Master Toolbox Podcast: "From Permission-Seeking to Forgiveness-Begging—Agile Team Evolution in Self-Management" with Bernie Maloney

Host: Vasco Duarte
Guest: Bernie Maloney
Date: September 11, 2025

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Episode Overview

In this lively Success Thursday episode, Vasco Duarte welcomes back agile coach and Scrum Master Bernie Maloney for a deep dive into what meaningful success looks like for Agile teams and their facilitators. The conversation explores Bernie’s favorite retrospective formats and unpacks the practical evolution of teams from needing direction, to seeking permission, and ultimately, to self-management. The focus is on helping Scrum Masters foster an environment where teams expand their influence, experiment, and drive relentless improvement.

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Key Discussion Points & Insights

1. Bernie's Favorite Retrospective Formats ([01:20]–[04:59])

• Sailboat Retrospective:
  • Bernie prefers the simplicity of the sailboat format, focusing on "above the waterline, below the waterline" rather than complicating it with anchors, islands, and seagulls.
  • He credits a team manager in Shenzhen with adding a Likert pain scale (smiley faces) to the sailboat to emphasize the intensity of team feelings, greatly enhancing retrospective clarity.
  • Quote — Bernie Maloney ([02:18]):
    "That simple emoticon really gets people to understand the intensity of stuff that's there in a sailboat."
• What the Duck & LEGO Serious Play:
  • Drawing from the "Strategic Play and the Creative Facilitator’s Guide," Bernie recommends playful, hands-on formats like "What the Duck" using an eight-brick LEGO kit.
  • Physical activities help dissociate strong emotions, making it easier for team members to discuss challenging issues.
  • Quote — Bernie Maloney ([03:32]):
    "By creating an object outside of yourself and then talking about it, you're able to...step into that third position and see the whole situation."
• Creative Show & Tell:
  • Another creative tool is asking team members to sketch their thoughts or build physical representations (with LEGO, for example), and then explain them to the group.
  • Bernie finds show-and-tell formats powerful for surfacing information in retrospectives.

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2. Defining Success as a Scrum Master ([05:49]–[09:09])

• Success is enabling teams to thrive—even during challenges—by fostering self-direction and sustainable autonomy.
• Early Indicators:
  • Bernie teaches facilitation techniques like thumb voting (roman voting) and observes when teams independently adopt them, signaling self-direction.
  • Quote — Bernie Maloney ([06:27]):
    "When they come up for, they've got to do some decisions and they start organically on their own without me facilitating it...that's a clue to me that they're starting to become self directed."
• The Evolution to Self-Management:
  • Bernie wants teams to move from waiting for instructions, to seeking permission, and ideally to “begging forgiveness”—acting proactively within understood constraints.
• Diana Larson’s "Circles and Soup":
  • Used to coach teams on the concepts of control, influence, and adaptation to external factors.
  • Teams map what they control, what they influence, and what they have to accept, gradually expanding their locus of influence over time.
  • Quote — Bernie Maloney ([07:34]):
    "Part of our job is to coach those teams, to expand those circles, to get them to recognize that they've got more control than they thought they did."
• Coaching Managers:
  • Bernie highlights the need to also coach managers, especially those rooted in command-and-control leadership, towards creating "boundaries of safety" for teams to take risks and grow.
  • Quote — Bernie Maloney ([08:13]):
    "Another part of my success is getting those managers to start to expand those boundaries and then start to coach the teams instead of direct the teams."

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3. Pragmatic Tools for Continuous Team Progress ([09:09]–[11:13])

• Observation & Retrospectives:
  • Mapping influence circles regularly in retrospectives helps teams visualize and track their growing influence and ownership.
  • Quote — Vasco Duarte ([09:09]):
    "If we do that at a regular interval in the retrospectives...is the team believing that their domain of influence has grown or are they not?"
• Building a Backlog of Improvements:
  • Bernie emphasizes the importance of maintaining an "improvement backlog"—a prioritized list of organizational impediments—and focusing relentlessly on resolving the top issue.
  • Momentum is critical; teams must see systemic changes resulting from their input to avoid falling into "process theater" or disengagement.
  • Quote — Bernie Maloney ([10:28]):
    "If nothing changes, your team is going to get depressed. They're going to feel like this is just process theater and why are we doing it?"

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4. The Goal: Relentless Improvement ([11:14]–[11:24])

• Building on the earlier points, both host and guest advocate for a culture of "relentless improvement," ensuring feedback leads to real action and nurtures optimism and growth.
  • Quote — Vasco Duarte ([11:14]):
    "They get to this point of relentless improvement...a beautiful, beautiful phrase."

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Notable Quotes & Memorable Moments

• On creative retrospectives:
  Bernie Maloney ([03:32]):
  "Using Legos is a great way to get your teams talking...you're able to, like we talked about yesterday, Vasco, step into that third position and see the whole situation."

• On observing team self-direction:
  Bernie Maloney ([06:27]):
  "That's a clue to me that they're starting to become self directed. I can actually back off."

• On expanding circles of influence:
  Bernie Maloney ([07:34]):
  "Part of our job is to coach those teams, to expand those circles, to get them to recognize that they've got more control than they thought they did."

• On tackling systemic impediments:
  Bernie Maloney ([10:28]):
  "Surface all the things that are getting in the team's way, but put them in an improvement backlog and focus on only one thing...If nothing changes, your team is going to get depressed."

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Important Timestamps

• 01:20 – Bernie introduces his favorite retrospective formats.
• 05:49 – Definition of success as a Scrum Master.
• 07:34 – Discussion of "Circles and Soup" for expanding team influence.
• 09:09 – Concrete methods for tracking team's area of control.
• 10:28 – Importance of improvement backlog and avoiding process theater.
• 11:14 – The concept of relentless improvement.

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Takeaways for Listeners

• Success for an Agile coach or Scrum Master is not in perpetual presence but in building capable, self-directed teams and managers who support continuous improvement.
• Simple, creative retrospectives foster honest conversations and break down emotional barriers.
• Regularly mapping and expanding team influence is crucial for motivation and organizational change.
• Focus relentlessly on resolving top issues raised in retrospectives to maintain momentum and prevent disengagement.
• Coaching extends beyond the team—empowering managers to support, not dictate, unlocks further organizational agility.

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For more creative retrospective formats, check out Bernie's YouTube channel.
Relevant books: "Strategic Play and the Creative Facilitator’s Guide" and Diana Larson’s work.

Transcript

[A]

Hey there, agile adventurer, just a quick question.

[B]

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[A]

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[B]

Hello, everybody. Welcome to our Success Thursday. This week we have with us Bernie Maloney. Hey, Bernie. Welcome back.

[C]

Thank you, Vasco.

[B]

So Success Thursday is of course where we explore success for us as grandmasters. But before that, share with us. Bernie, what's your favorite retrospective format and why?

[C]

So I've got a couple. So the one that I will go to probably more often than not is sailboat because it's really simple, but you can add some layers on. Now I, I tend to keep sailboat, very simple. Sailboat above the wall, above the waterline, below the waterline. I don't put in things like anchors and islands and seagulls and things like that. I keep it really kind of simple. One thing that I will do, and this is something I learned from a client. So I love when clients teach me things. I was in a workshop in. This was in Taipei. No, no, it was in Shenzhen. So I was in China and I was teaching in English, but we had a live translator there and I was doing a sailboat retrospective about the workshop and the manager of the team came up and drew smiley faces. So, you know, a Likert pain scale with, you know, big smile up at the top and you're kind of in the middle and then kind of a flat like around the waterline and then a big frowny face down at the bottom, you know, so a 5, a 5 degree Likert pain scale. And that simple emoticon really gets people to understand the intensity of stuff that's there in a sailboat. So it's something quick, it's easy, it's got loads of layers. Like I can use sailboat plus a two or three other things and run a hackathon at the drop of a hat. So sailboat is one of my favorite retrospectives. Another one that I like is what the Duck. So now that comes out of a book that I reference on Team Tuesday, Strategic Play and the Creative Facilitators Guide. There's an eight brick LEGO kit you can go on ebay, you can go on Amazon. They cost about $10 here in the US the last time I check. You can go build them yourself for less than that. Something to know. Engineers love Legos. So you can do a whole bunch of facilitation just with that eight brick LEGO kit. Or if you want to go a little bit further, you can go invest about $20 in a Lego kit, send it to everybody on your team, and then when you're doing a retrospective, have them build something that represents what you're talking about and then describe it. What you're actually doing is something that comes out of therapy. It's called dissociation. So by creating an object outside of yourself and then talking about it, you're able to, like we talked about yesterday, Vasco, you're able to step into that third position and see the whole situation. So you've got less of the direct emotional attachment. We see this in children's therapy where they might use puppets to describe difficult things. So using Legos is a great way to get your teams talking. In fact, if you're looking for creative retrospective formats, I've got a YouTube video powered by teams.com YouTube with four creative retrospective formats. Another one that I picked up from Karina Balduf and Retromat was just doing a sketch. Okay. And then having people show it. So doing a show and tell with either something physical like Legos or a sketch is a great way to really tease out a whole bunch of information in a retrospective. So those are my two favorites.

[B]

Well, there's a lot of stuff there to unpack. And we'll put the link to Dissociation, what it means, and maybe the link to the Strategic Playbook. Of course, every one of the retros and Bernie's YouTube channel in the show notes. But of course we're also talking about success. It is success Thursday, after all. And we do all of these retros and a lot more things in order to achieve that success, which is often represented by a high performing team. Successful outcome for the organization and the team. But we need to know what that success means for us because we need to map, to track our way to that successful outcome. So let's define it. Bernie, when you think about your role as an agile coach and as a scrum master, how do you define success for yourself?

[C]

At a broad level, it's having a situation in which a team can thrive and do their best work, even when it's challenging. Now some of the early indicators that I have for success, my goal when I come in and work with a team is to not be there forever. So I actually want the team to start to become self directed and to do their own stuff. So one of the first things that I will do is I will teach thumb voting or roman voting, some people call it, as a facilitation technique. And I'll try and teach it really well. And then I, I wait, I wait to see when the team starts adopting some of the stuff that I have injected. And thumb voting is one of the first things that I'll see a team do. Like when they come up for, they've got to do some decisions and they start organically on their own without me facilitating it. Using something like thumb voting that I've taught them, that's a clue to me that they're starting to become self directed. I can actually back off. So that's one of my early measures of success. Ah, this team is starting to get it. When I see them stepping out of waiting for direction and at least stepping into seeking permission, that's another sign of progress. I actually would love to get them into begging forgiveness, like understanding what the constraints are around them. And that's, that's something I try and get teams to understand. Diana Larson called calls this circles and soup. So at the inner circle is what the teams think they have control over. Outside of that is another circle that they think they have some influence over. And then there's the soup that they live in that they just have to live with. And part of our job is to coach those teams, to expand those circles, to get them to recognize that they've got more control than they thought they did, they've got more influence than they thought they did. And so as I see them starting to stretch those boundaries in an organization and starting to take initiative, that's, that's another sign of success. Look, honestly, every management team that I have worked with wants the teams to succeed. Now the managers, the leaders, they may need some coaching and leadership because they may only know about command and control as a leadership style. And so they're being very highly directive with their teams. And so part of my job is to coach those managers. And this is Typically line managers, first level managers, maybe second level managers. As you get into executives, they're already there. They know they have to delegate, they know they have to set direction and let the team go. But nobody and I referenced this when I talked about Peshawaria's too many bosses, too few leaders. There's. There's no structure to coach these people into these skills. And so that's part of what I do as a Scrum Master. How do those leaders start to set those boundaries of safety within which a team can experiment and then get those lessons? So another part of my success is getting those managers to start to expand those boundaries and then start to coach the teams instead of direct the teams. So those are some of the things that I look for as the more I do that, the more self directed the whole organization becomes and the more I can back off and go find another client.

[B]

The circles and soup example, I think makes it very concrete, one way for us to observe that the team is becoming more self directed because we see that what's under their influence keeps expanding. And if we do that at a regular interval in the retrospectives, where are these things and just do the mapping within the circles and try to understand, is the team believing that their domain of influence has grown or are they not? Because that might be a possibility. There are changes happening all the time and that is a very important, even very practical and pragmatic cue for us to help the team understand that, hey, this thing was in our control before, why is it not now and what can we do about it?

[C]

A very concrete way that a Scrum Master can help is again, going through retrospect. If you go into any organization, there's going to be a ton of stuff that's getting in the way of the teams being productive. And in retrospectives, part of what we're doing is we're surfacing, how could we improve? And some of that's going to be systemic in the organization. So early on, teams are like, yeah, we want to be self directed and yeah, this stuff is getting our way. If nothing changes, your team is going to get depressed. So one of the things I coach Scrum masters towards doing is build up a backlog of things that need to be fixed. So as you surface things in a retrospective, great. Surface all the things that are getting in the team's way, but put them in an improvement backlog and focus on only one thing. Focus on the top thing and keep focusing on whatever the top thing is until it changes. If nothing changes, your team is going to get depressed. They're going to feel like this is just process theater and why are we doing it? And they're going to fall back into waiting for direction. But if they see that their inputs start to change the overall organizational system, that's where they're going to have a little bit of hope. And they're going to keep chipping away at that sort of stuff.

[A]

Yeah, absolutely.

[B]

And they get to this point of relentless improvement, which is a phrase somebody used here on the podcast. And I, I very happily stole that because I think it's a beautiful, beautiful phrase.

[C]

I love that phrases as well. I've got a, an, an example, if you want, of getting a manager to recognize how they, they needed to change.

[B]

Thank you very much for sharing all of those stories with us, Bernie.

[C]

Okay, thank you.

[A]

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[B]

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