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

Scrum Master Toolbox Podcast: Agile storytelling from the trenches

Release Date: 10/28/2025

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

Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes.

 

"As Deming said, a bad system will beat a good person every time." - Darryl Wright

 

Darryl was called in to help a struggling team at a large energy retailer. The symptoms seemed straightforward—low morale, poor relationships, and chronic underdelivery. But as he asked questions, a heartbreaking pattern emerged. The team had been "committing" to 110 story points per sprint while consistently delivering only 30. For 18 sprints. 

When Darryl asked why the team would commit to numbers they couldn't possibly achieve, the answer was devastating: "The business needs that much." This wasn't a problem of skill or capability—it was learned helplessness in action. Sprint after sprint, the team experienced failure, which made them more despondent and less effective, creating a vicious downward spiral. The business lost trust, the team lost confidence, and everyone was trapped in a system that guaranteed continued failure. 

When Darryl proposed the solution—committing to a realistic 30 points—he was told it was impossible because "the business needs 110 points." But the business wasn't getting 110 points anyway. They were getting broken promises, a demoralized team, stress leave, high churn, and a relationship built on distrust. Darryl couldn't change the system in that case, but the lesson was clear: adult people who manage their lives perfectly well outside work can become completely helpless inside work when the system repeatedly tells them their judgment doesn't matter. As Ricardo Semler observes in Maverick!, people leave their initiative at the door when organizations create systems that punish honest assessment and reward false promises.

 

Self-reflection Question: Is your team committing to what they believe they can achieve, or to what they think someone else wants to hear? What would happen if they told the truth?

Featured Book of the Week: Better Value, Sooner, Safer, Happier by Jonathan Smart

Darryl describes Better Value, Sooner, Safer, Happier by Jonathan Smart as a treasure trove of real-life experience from people who have "had their sleeves rolled up in the trenches" for decades. What he loves most is the authenticity—the authors openly share not just their successes, but all the things that didn't work and why. 

One story that crystallizes the book's brilliance involves Barclays Bank and their ingenious approach to change adoption. Facing resistance from laggards who refused to adopt Agile improvements despite overwhelming social proof, they started publishing lists of "most improved teams." When resisters saw themselves at the bottom of these public lists, they called to complain—and were asked, "Did you have improvements we didn't know about?" The awkward pause would follow, then the inevitable question: "How do I get these improvements?" Demand creation at its finest. 

Darryl particularly appreciates that the authors present at conferences saying, "Let me tell you about all the things we've stuffed up in major agile transformations all around the world," bringing genuine humility and practical wisdom to every page.

 

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🔥In the ruthless world of fintech, success isn't just about innovation—it's about coaching!🔥

Angela thought she was just there to coach a team. But now, she's caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn't just about the product—it's about the people.

 

🚨 Will Angela's coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue.

 

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About Darryl Wright

 

Darryl is an Agile Coach and Instructor dedicated to helping organisations and leaders be both successful and humane. He has over two decades in IT delivery and business leadership, he champions Agile ways of working to create thriving workplaces where people are happy, productive, and deliver products customers truly love.

 

You can link with Darryl Wright on LinkedIn, and visit Darryl's website at www.organa.com.au.