Coaching Teams Trapped Between Agile Aspirations and Organizational Control | Alex Sloley

Summary

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Scrum Master Toolbox Podcast Episode Summary

Episode Title: Coaching Teams Trapped Between Agile Aspirations and Organizational Control
Guest: Alex Sloley
Host: Vasco Duarte
Date: October 22, 2025

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Episode Overview

In this Wednesday "Coaching Challenge" episode, Vasco Duarte and guest Alex Sloley explore the tension faced by new Agile teams when their aspirations to work autonomously are restricted by entrenched organizational controls. Alex shares his experience coaching a pilot Scrum team in a large organization that is new to Agile. The discussion focuses on the challenges of enabling true team empowerment amidst authoritative structures, and how a coach can respond with empathetic experimentation rather than prescriptive solutions.

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Key Discussion Points & Insights

1. Introducing the Coaching Challenge

• [01:11-02:16]
  • Vasco sets the stage for an experiment- and systems-oriented coaching conversation.
  • Emphasis is placed on incremental learning via experiments over seeking final solutions:
    • “The idea of experiments is that the solution doesn't necessarily need to look like what you may expect because insights will bring new knowledge and new knowledge will bring new experiments.” (Vasco, 01:44)

2. Alex’s Coaching Context: Highly Controlled Agile Pilot

• [02:16–04:27]
  • Alex describes his current work with a 10-person Scrum team, the first Agile team in a 1,500-employee organization.
  • The team is eager and open to Agile but faces constant organizational obstacles:
    • “The org keeps coming back and saying stuff like no, no, no, you can't do that. Because in this org we don't allow that…They’re really like putting all these systemic organizational impediments on the team.” (Alex, 03:12)
  • Restrictions include mandated estimation methods, prescriptive work breakdowns, and role-based work limitations (e.g., enforced RACI models).

3. Organizational Control and Its Impact:

• [04:27-07:06]
  • Vasco explores the concept of learned helplessness:
    • “When we defer to authority, we are implicitly accepting that there's a better way of doing things. But … we are also deferring to authority the responsibility of the success of that way of working.” (Vasco, 05:48)
    • Teams following orders may find comfort in relinquishing responsibility: “It's very comfortable to be in the position where you can just say, hey, I did what you told me.” (Vasco, 06:44)
  • Vasco cautions that this pattern, while comfortable, is self-destructive.

4. Diagnosing Team Dynamics

• [07:06-09:13]
  • Alex reflects on whether learned helplessness is affecting the team, acknowledging he hadn't considered it before.
  • The need for deeper understanding—what’s truly driving the team’s behavior—is highlighted by both.

5. Coaching Experiments to Foster Team Ownership

• [07:44-09:13]
  • Vasco suggests experiments to probe the team’s sense of agency:
    • “Just ask, hey, how do you...how do you think we should do it?” (Vasco, 07:50)
    • Watch for answers that deflect responsibility: "We were told to do it this way."
  • Encourages facilitating possibilities and observing reactions, to surface root issues of fear or comfort.

6. Planning a Safe, Small Experiment

• [09:13-10:05]
  • Alex agrees on running a retrospective experiment:
    • “In the next retrospective, I could actually design a retrospective around asking those kinds of open ended questions about what the team thinks they are empowered to do versus what management is asking them to do.” (Alex, 09:26)
  • Advocates for experiments that are “small, safe, and...good enough for now.”

7. Considering Internal Team Power Structures

• [10:05-11:14]
  • Vasco urges attention to intra-team hierarchies:
    • “There is a power structure inside the team that has importance and influence over everything the team as a system does.” (Vasco, 10:32)
  • Suggests mapping which members lean in or out, both during and after retrospectives, for further insight.

8. Building on Experiments: Delegation & Decision Authority

• [11:14-12:05]
  • Alex proposes a follow-up experiment:
    • Using “delegation cards or decision making cards” to examine team vs. organizational authority safely.
    • “I think that could be a really interesting and safe way to talk about those kinds of topics.” (Alex, 11:38)
  • Both agree on the practice of “small, safe, and good enough for now” experiments as the foundation for progress.

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Memorable Quotes

• Vasco Duarte:
  • “The idea of experiments is that the solution doesn't necessarily need to look like what you may expect because insights will bring new knowledge and new knowledge will bring new experiments.” (01:44)
  • “When we defer to authority, we are implicitly accepting that there's a better way of doing things...” (05:48)
  • "Just tell me what to do’ pattern is quite self destructive because obviously the best you can do is then know what keys to press. And software development is really not about the typing." (08:27)
  • “There is a power structure inside the team that has importance and influence over everything the team as a system does.” (10:32)
• Alex Sloley:
  • “I'm confident that if these impediments didn’t exist, the team would be wildly successful if they were just allowed and empowered and autonomous, allowed to do their own thing. And it's making me crazy. I’m getting frustrated. So now I’m at a dilemma like what do I do?” (03:48)
  • “I like my experiments to be small and I like them to be safe and I like them to be just good enough for now.” (09:48)
  • “Maybe I facilitate a session where we use something like delegation cards or decision making cards...I think that could be a really interesting and safe way to talk about those kinds of topics.” (11:36)

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Important Timestamps

• [01:44] – Philosophy of experimentation in coaching
• [03:12] – Concrete examples of systemic impediments
• [05:21] – Vasco probes team history and authority deference
• [06:44] – "It's very comfortable to be in the position where you can just say, hey, I did what you told me."
• [08:27] – Why blindly following can be self-destructive
• [09:26] – Retrospective experiment design idea
• [10:32] – The significance of internal power structures
• [11:36] – Delegation cards as an experiment

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Tone & Style

The conversation is open, thoughtful, and practical. Both host and guest model the reflective, systems-thinking approach they advocate. The emphasis is on empathy for teams, curiosity about systemic constraints, and continuous, safe experimentation.

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Takeaways for Scrum Masters and Agile Coaches

• Model experiments, not solutions:
  • Approach constraints as opportunities to learn incrementally.
• Surface underlying team dynamics:
  • Use open-ended retrospectives and small interventions to understand learned helplessness or comfort in deference.
• Respect power structures:
  • Attend to who holds influence within teams and how that affects change efforts.
• Iterate with safety:
  • As Alex repeats: experiments should be “small, safe, and good enough for now.”

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This episode is a must-listen for coaches facing the frustration of eager Agile teams blocked by entrenched organizational mechanisms. The strategies and mindsets discussed offer pragmatic, compassionate paths forward.

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 Wednesday the Coaching Challenge episode. This week with Alex Slowly. Hey Alex, welcome back.

[C]

Hey Vasco, how you doing?

[B]

All good, all good. So I'm looking forward to this conversation. So Alex is going to talk to us about a problem that he's either faced recently or he's facing right now. And our goal today for you out there listening is to model both the idea of what a coaching conversation might look and feel like, as well as the idea of experimentation rather than solutioneering. We are looking for experiments to learn more and to progress in our understanding of the system, eventually to come to a solution. But the idea of experiments is that the solution doesn't necessarily need to look like what you may expect because insights will bring new knowledge and new knowledge will bring new experiments. And that way we always evolve the way we look at a specific situation or system. So Alex, share with us, what's the challenge or topic you want us to talk about today?

[C]

Yeah, I mean, I'm working with a small team right now and it's a small team, Scrum team, and they're kind of new and they don't have a lot of experience in the Agile space. And that kind of reflects the agile experience overall of the organization that this small team is in. This is their very first Agile team. They've never had an Agile team before and this is their little pilot team. The entire company is about 1500 people and this little scrum team is about 10 people. I've been working with this small team, helping them get better at doing their ways of Scrum and I think they want to Be agile. They want to embrace this agile thing. And I find them to be quite open minded and open to experiments. But what keeps happening is that the organization puts impediments in the way of the team. The team says, oh, we want to try to do things this way. There are ways of working. We want to try this, we want to try that. The org keeps coming back and saying stuff like no, no, no, you can't do that. Because in this org we don't allow that. In fact, we're going to tell you how to do these things the right way. And it's stuff like everything from the org telling the team how they're supposed to estimate, telling them how they're supposed to break down the work, telling them who can do what roles based work. And they're using terms like oh, the scrum team needs a racy so everybody on the team can only do certain types of. And they're really like putting all these systemic organizational impediments on the team. I'm confident that if these impediments didn't exist, the team would be wildly successful if they were just allowed and empowered and autonomous, allowed to do their own thing. And it's making me crazy. I'm getting frustrated. So now I'm at a dilemma like what do I do?

[B]

By the way, love the way you describe the context and what is happening. One of the things we talked about it yesterday, actually one of the things that can happen sometimes is that teams get into this state of learned helplessness. Right. Like for example, when a manager comes to you. And this is especially true if we're talking about people who are starting their career or in the beginning of their career who are much more deferring to authority at that point. Although generations change and it might not be exactly like that in your case. So when I hear you describe this story, my experience expectation is that this is probably younger people that are maybe in the beginning or early stages of their career for whom the organization's authority is very important. Is that so? Is that how you see it?

[C]

I would say that is accurate in terms of like how long some of these people have been in the organization. Like half the team has only been in the organization for like six months or less and the other half of the team has been there for longer. So it's more about like how long they've been in the org versus like their actual age.

[B]

Okay. Because the other thing that comes to mind if we think about this is when we defer to authority. And I'm now thinking about as a team member, when we defer to authority, we are implicitly accepting that there's a better way of doing things. But, and this is the dangerous part, when we do that and it's not our way, we, we are also deferring to authority the responsibility of the success of that way of working. Right. Like so as a team member, if I, let's just use this as an example. If I listen to the project manager who tells me this is how you estimate and then I estimate the way the project manager tells me, I'm also implicitly saying it's not my problem, I'm just going to do what you're telling me. Oh, and by the way, if it fails, I can point the finger at you and say this is how you told me to do it. This is a very comfortable position for the team though not be blue eyed about this. It's very comfortable to be in the position where you can just say, hey, I did what you told me. Because the other person has no defense against that. They can just tell, oh, but you forgot this, or maybe this part needs to be different, whatever. And that cycle just repeats over and over again. And then the team stands back and says, oh, but it's not my fault, you told me how to do it. So do you feel that the team might be getting into this kind of dynamic or do you see something else happening?

[C]

Yeah, I mean I haven't really considered that. So now I'm starting to reflect on that and I'm taking a pause and I'm thinking about it and I'm thinking that could be true. So I mean, I guess I would.

[B]

Have to.

[C]

Discover a little bit more about what's going on, maybe try to delve into what's truly driving this behavior and why they're doing it. So I'm starting to think about this stuff now. So that's an interesting idea.

[B]

So if you think that this might be a possibility, a couple of experiments that you could run to try to assess is this really that way would be to just ask, hey, how do you. And now talking to the team, how do you think we should do it? Because if the answer that comes, well, we were told to do it this way. It can be either submissiveness or that position of comfort. Right. It's not my problem, just I'm just typing here, you know, just tell me what to do. Like this, just tell me what to do. Pattern is quite self destructive because obviously the best you can do is then know what keys to press. And software development is really not about the typing. Right. Like in Newsflash, if people think that software development is about the typing, AI is coming for your job. Right. Like software development is about generating ideas, it's about building off on each other's ideas and creating something much bigger than the original request might have even intimated as possible. Right. So it might be good to have conversations with the team members about, hey, what if we tried, hey, have we tried this? Just kind of creating the idea of possibility and then seeing how the team reacts. Because if the team is constantly stepping back, it might be out of fear or out of comfort. Both of these are perfectly possible. But when you think about this idea of maybe having this type of conversation experiments with the team, how does it feel for you, Alex?

[C]

Yeah, I mean, I think you're sparking in me an idea that I could try a small experiment maybe. And the small experiment I think I would try is to perhaps ask some open ended questions in our next retrospective, which is next week by the way. In the next retrospective I could actually design a retrospective around asking those kinds of open ended questions about what the team thinks they are empowered to do versus what management is asking them to do. I think that would be an interesting experiment to try. I like my experiments to be small and I like them to be safe and I like them to be just good enough for now. They don't have to be like good experiments. So I think I could probably do that in our team retrospective.

[B]

Yeah, absolutely. That sounds like a great idea. And perhaps one thought to potentially seed conversation ideas for you is to try to assess where are the different team members? Right. Like just mental notes as to which team members are leaning into the conversation that you're starting, which team members are stepping back and then also trying to figure out post retrospective in the power hierarchies that are within the team, where are those different team members? Because let's not forget, and this is something for us to always have in mind as coaches and scrum masters, is that there is a power structure inside the team that has importance and influence over everything the team as a system does. And assessing not only the individual reactions, but also the power structure. Reactions to certain ideas can be very insightful, not necessarily because they give us solutions, because they might not, but also to understand where might be kind of angles to continue the conversation after the retrospective.

[C]

Yeah, that's definitely sparked another experimental idea in my brain about like maybe I facilitate a session where we use something like delegation cards or decision making cards, where we have conversations about decision making authority in the team in the organization. I think that could be a really interesting and safe way to talk about those kinds of topics.

[B]

Awesome. That's the goal of these type of conversations. Just generate ideas for experiments because we don't need to get stuck. We can always try something else. Yep.

[C]

And I just always make sure that my experiments are small, safe, and good enough for now.

[B]

And good enough for now. That's a great way to put it. Thank you for having that conversation with us, Alex.

[C]

My pleasure.

[A]

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[B]

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