The Agile Team That Committed to Failure for 18 Sprints Straight | Darryl Wright

Summary

Podcast Summary: Scrum Master Toolbox Podcast

Episode Title: The Agile Team That Committed to Failure for 18 Sprints Straight
Guest: Darryl Wright
Host: Vasco Duarte
Date: October 28, 2025

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Overview

In this episode, Vasco Duarte speaks with Agile Coach and Scrum Master Darryl Wright about an all-too-common phenomenon in Agile: teams repeatedly overcommitting and underdelivering. The discussion dives into the roots of "learned helplessness" within teams, why such destructive cycles persist, and what Scrum Masters can do to break the pattern and restore morale and effectiveness.

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Key Discussion Points

1. The Most Influential Book for Darryl (01:19–05:00)

• Book Recommendation:
  Darryl singles out Better Value Sooner, Safer, Happier by Jon Smart et al. as the book that most inspired his career.
• Why This Book?
  • It's packed with “real life experience” and authentic “war stories.”

    “It’s four or five decades or more of experience from people that have had their sleeves rolled up in the trenches...It’s so authentic, just the way they write it. You can tell they’ve got all the war stories, all the scars firsthand.” — Darryl (01:47)

  • The authors candidly share what failed in major Agile transformations as well as what works, creating a sense of relatability and learning.
• Illustrative Story:
  • At Barclays, Jon Smart’s team combated resistance to change (“laggards”) by publicizing "most improved teams" lists. Slowly, even the most resistant began asking how to get better.
  • “They started getting phone calls from people who were quite dedicated laggards who would say, ‘Hey, why am I on the bottom of this list?’...And then there’d be this moment, this little pause, this silence, and then the person would say, ‘Well, how do I get these improvements?’” — Darryl (03:41)

Key Insight: Social systems and subtle peer pressure can be more effective than direct mandates.

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2. The Case of the Team That Failed for 18 Sprints (05:35–09:16)

• The Situation:
  Darryl was invited to help a low-performing Agile team at a large energy retailer. The team’s morale and output were dire.
• Symptoms of Trouble:
  • The team was delivering far less than committed ("110 points committed, 30 delivered").
  • This pattern persisted for 18 sprints.
  • Team size and story estimation did not explain the discrepancy.
• The Core Discovery:
  • The team kept overcommitting because “the business needs that much.”
  • Despite the business never receiving the requested output, neither the morale nor the standing with the business improved; instead, both worsened.
  • “Why would the team say they can deliver 110 points when they’ve been delivering 30 points for 18 sprints?” — Darryl (06:58)
• The Vicious Cycle:
  • Unrealistic targets → Repeated failure → Loss of trust and morale → Even less delivery → Cycle repeats
  • Business distrust and team stress were at all-time highs.
  • “Every time the team gets pushed to commit to an unrealistic target, they then experience failure. That makes them more despondent, it makes them more hesitant…” — Darryl (08:15)
• Proposed Solution:
  Darryl suggested changing the next Sprint goal to 30 points (the team’s actual capacity):
  • “The good news is I know what the problem is and I can help... The bad news is that the Sprint goal for the next sprint is going to be 30 points.” — Darryl (07:21)
  • This suggestion was rejected because “the business needs 110 points.”

Key Insight: Ignoring empirical evidence for the sake of perceived business need only escalates dysfunction.

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3. Sources and Effects of Learned Helplessness (09:16–12:36)

• Who Perpetuates the Vicious Cycle?
  • Dysfunction had set in so deeply that even the team itself clung to impossible commitments.
  • The team’s attitude: “We just have to try…we know we can’t do it, we’ll never do it, but we just have to try.” — Darryl (10:02)
  • Vasco relates a similar experience where teams committed to unattainable goals “because we thought you wanted us to.” (10:37)
• The Puzzle of Adult Behavior:
  Vasco: “How can adult people…when they go to work, they have this kind of attitude?... It’s still a puzzle for me how this is possible.” (10:46)
• Reference to Maverick (Ricardo Semler):
  • Vasco recounts that Semler was similarly puzzled by how capable adults stifled their initiative at work.
  • The lesson: Changing the system, not just the people, is essential to breaking this dynamic.
• Deming’s Wisdom:
  • Darryl reminds us: “A bad system will beat a good person every time.” (12:32)

Key Insight: Organizational culture and systemic forces—not individual capabilities—often dictate team outcomes.

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Memorable Quotes

• Darryl Wright (01:47):
  “It’s so authentic, just the way they write it. You can tell they’ve got all the war stories, all the scars firsthand.”
• Darryl Wright (03:41):
  “They started getting phone calls from people who were quite dedicated laggards who would say, ‘Hey, why am I on the bottom of this list?’…Well, how do I get these improvements?”
• Darryl Wright (08:15):
  “Every time the team gets pushed to commit to an unrealistic target, they then experience failure. That makes them more despondent…”
• Vasco Duarte (10:46):
  “The mystery is how can adult people, who go out and have their own lives…when they go to work, they have this kind of attitude...and it’s still a puzzle for me.”
• Darryl Wright (12:32):
  “As Deming said, a bad system will beat a good person every time.”

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Timestamps for Important Segments

• Book that Inspired Darryl: 01:19–05:00
• Barclays & “Most Improved Teams” Story: 03:07–04:54
• Setting the Scene: The Failing Team: 05:35–08:37
• Analyzing the Vicious Cycle: 08:15–09:16
• Who Maintains Dysfunction? 09:27–10:09
• Learned Helplessness Examples: 10:09–11:30
• Semler, Maverick, and Adult Initiative: 11:30–12:32
• Deming’s Maxims: 12:32–12:45

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Final Thoughts and Takeaways

• The commitment to failure is often a systemic, not personal, issue rooted in mismatched expectations and repeated negative cycles.
• Changing team behavior means addressing the surrounding context and systems, not just “motivation.”
• Scrum Masters can best help by exposing local realities (actual team velocity), advocating for sustainable commitments, and pushing for system-level change.
• Recognize learned helplessness early and act to break the downward spiral before it becomes entrenched.

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For more actionable Agile advice and stories from the trenches, visit scrummastertoolbox.org.

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.

[C]

Welcome to our Team Tuesday. This week we have with us Daryl Wright. Hey, Daryl, welcome back.

[B]

Hi Vasco.

[C]

So, Daryl, on Tuesdays we talk about teams and how sometimes they create their own problems. But before we dive into that, tell us, what's the book that most inspired you in your career as a Scrum Master?

[B]

Thanks. I love this question. So there have been so many books and it is hard to narrow it down to just one. But if I was just to really pick one, I would go with Better Value Sooner, Safer, Happier by John Smart and a few others. An incredible book and I love this book so much for a number of reasons. The first one is that it's real life experience. It, you know, it's four or five decades or more of experience from people that have had their sleeves rolled up in the trenches going. We have tried all of these things that didn't work and we're going to tell you about all of those. And then we've got all these things that do work and we're going to tell you about all of those. And it's so authentic just the, the way they write it. You can tell they've got all the war stories, all the scars firsthand. So I love that about that. And I've even seen some of the authors live presenting and they're so genuine. They open with, let me tell you about all the things we've stuffed up in major agile transformations all around the world. We'll regale you with all these stories of we tried this, it didn't work and this is why, this is what works instead. So, so Empowering. So, yeah, I love it.

[C]

Remember one story that you think kind of crystallizes what you really like about that book?

[B]

Yes. So when the lead author, John, was working at Barclays bank and, you know, they'd been pivoting, and over a number of years, they were starting to build up a whole bunch of areas in the organization that were really starting to show improvements, that were really starting to benefit. And of course, if anyone is familiar with the change adoption curve, you'll know that at the end of the curve, you'll have some late majority and even some laggards who they don't want to change and they resist. And even with all the social proof in the world, they're not going to change. And so they were wondering, how do we do anything about this? And so what they did was they started circulating and publishing lists of the most improved teams. And so as teams made changes, they made improvements. They would tell the transformation body about the improvements that they'd made. And so they made a list of the teams in order of the most improved teams and started circulating it. And so after a while, actually, pretty quickly they started getting phone calls from people who were quite dedicated laggards who would say, hey, why am I on the bottom of this list? And they would say, oh, did you have some improvements that we didn't know about? Could you tell us about those? And then we can move you where you need to be on the list. And then there'd be this moment, this little pause, this silence, and then the person would say, well, how do I get these improvements.

[C]

For example, of creating demand?

[B]

Yes, yes. And I just thought that was just fantastic. Such a great way to.

[C]

This kind of illustrates that we're always working in a social system, even when we're just developing software. All right. And talking about social systems. One social system we often work with is the team, whatever that means, in whatever context that might be. But, Daryl, I'm sure you have one context and one team in mind. Tell us that context so that we may understand what the team was facing and then walk us through those little behaviors or patterns that emerged that eventually destroyed the team.

[B]

Yes. Look, this one is a little heartbreaking. I was asked to go in and help. There was a situation. It was a. It's a large energy retailer, and they had a team. They said, we need you to come in and help this team. You know, they're just not. They're not delivering, they're not performing. It's. It's all going badly wrong. Come in and help. And so I said, okay, so I came in and I'm starting to ask some questions. So what's going on with the team? And you know, oh, so the team, they're low morale, they don't have good relationships and they're not delivering. And I said, okay, well when you say not delivering, tell me more about that. And I got told, well, for example, last Sprint, they committed to delivering 110 points worth of work and they delivered 30. And I said, oh, okay, 110 points. That, that sounds like quite a lot. Is it a really big team? I said, no, no, no, but it was a dozen people. And I said, oh, okay, well, are they using really store small, really small stories to do their. Their estimation? Is that why the numbers were so big? No, no, no, no, no normal sized stories. Okay, well they. Why would they commit to 110 points worth if. And then they only delivered 30? That seems really strange. What happened to Sprint before that? I said, oh, it was similar. And I went, wait a minute, what, what do you mean it was similar? Has this been going on for a while? How long has this been going on for? And I said 18 sprints. And I went, what? Okay, what? Why would the team say they can deliver 110 points when they been delivering 30 points for 18 sprints? And they said, oh, because the business needs that much. And I said, okay, when have you talked to a few people? Yes, that's what's going on. So I came back and I said, okay, so I've got good news and I've got bad news. And I said, oh, great, what's the good news? And I said, the good news is I know what the problem is and I can help. And they went, oh, fantastic. Thanks so much. Oh, Darryl, we're so glad we got you. Oh, wait a minute, what's the bad news? And I said, the bad news is that the Sprint goal for the next sprint is going to be 30 points. And I went, oh, no, you can't do that. And I said, why not? And I said, oh, because the business needs 110 points. I said, but the business is not going to get 110 points. They haven't been getting it for 18 sprints. I said, let me ask you a question. What's the relationship between the team and the business? What's that like? Oh, it's terrible. The business doesn't trust them. And I said, okay, and what's the morale like in the team? I said, oh, it's terrible. Everyone keeps going off on stress leave. And you know, there's a high churn in the team and everything. And I said, okay, can you see that? The reason is because the team are being pushed to provide completely unrealistic commitments and targets that they cannot possibly meet. The way that this is done creates a vicious cycle. Every time the team gets pushed to commit to an unrealistic target, they then experience failure. That makes them more despondent, it makes them more hesitant. And so then they're even less likely to meet it the next time. And it just gets worse and worse and worse. And every time the business push them to do this and then they don't do it, the business loses trust, they lose confidence. It's just a downward spiral. What we want to do is to change that vicious cycle into a virtuous cycle. We want to create an up spiral.

[C]

Did anything change?

[B]

Well, unfortunately on this example, I got told, no, you can't change it. It's just the business.

[C]

So it was the team who wanted to stick to the idea of over promising and under delivering. It was not the business, it was the team itself.

[B]

Yeah.

[C]

The team was kind of a self inflicted wound.

[B]

Yes, yes.

[C]

Was this the whole team or was this like specific roles within the team that were kind of wanting to, quote, unquote, deliver what the business wants or promise?

[B]

Unfortunately, because this had been going on for a while, there was just this sense of kind of learned helplessness within the Learned helplessness.

[C]

Yeah, yeah.

[B]

And they were just like, we just have to try. And we know we can't do it, we'll never do it, but we just have to try. We're just going to say it because we just have to.

[C]

You know, I remember a story of a team and I was working with them. This only happened one Sprint, thank God. But, but that, that was what. What happened with the Sprint planning? They committed, I don't recall anymore how many stories. Let's say 15 stories. And then they delivered three. And then I asked, wait a minute, but were you aware when we were doing Sprint planning that you would not be able to deliver? And they said, yes. So why did you commit to 15 story, whatever the number was? And they said, because I thought. Because we thought you wanted us to.

[B]

Yeah.

[C]

For me, the mystery is how can adult people, you know, who go out and have their own lives, they get married, they have kids, they build houses, buy houses, get cars, eventually grow old, get retired, have a full life. When they go to work, they have this kind of attitude. And it's still a puzzle for me how this is possible.

[B]

Yes. As far as I can tell it's that learned helplessness they start out, you know, oh no, I'm going to say something, I'm going to speak up, I'm going to say that's not right. But they get told no, and eventually they just learn there's no point fighting it. I'm just going to turn up, collect my paycheck. And that's just all it is.

[C]

Many years ago I read this book called Maverick by Ricardo Semler, and that's one of the things that he talks about. He expresses his own, I think, puzzlement as to why people get into that kind of learn helplessness, as you called it. And that is actually a great story because he ends up creating a totally different company, Semco, which works on totally different principles and so on. So the book is a great read anyway. But he starts from that acknowledgment that these people who are completely independent and with initiative adults out there, when they come in, they kind of leave all of that at the door, right? And there's a lot of stories that are in that book. So I really recommend. But it really is our job to figure out how can we change the system around the team so that they don't continue to behave in this Learned helplessness perspective 100%.

[B]

As Deming said, a bad system will beat a good person every time.

[C]

Oh, I love a Deming quote. Thank you for bringing that, Daryl.

[B]

Thank you for he's the most quotable person ever for sure.

[C]

And thank you for sharing that story with us.

[B]

Thanks so much, Besco.

[A]

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[C]

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