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

“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 the book 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.

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Darryl Wright

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.

Jörn Hendrik Ast: The Double-Edged Sword of Commitment, An Agile Team’s Journey Through Innovation and Despair

Jörn Hendrik recounts a sobering team story centered around the development and eventual discontinuation of a seemingly promising app. This episode sheds light on the dangers of commitment without flexibility, the value of listening to feedback, and the importance of recognizing when to pivot. It’s a tale of commitment, disillusionment, and the hard-earned wisdom that sometimes, stopping is part of the journey to success.

Featured Book of the Week: Fearless Organization by Amy Edmondson

Dive into Amy Edmondson’s “Fearless Organization” with Jörn as he shares how this seminal work on psychological safety reshaped his approach to team management and workshop organization. This segment, explores the transformative power of psychological safety in the workplace, underpinned by practical insights from Jörn’s experience. Discover how breaking the silence on issues can propel teams towards better collaboration, innovation, and success. A must-listen for anyone looking to foster an environment where every voice is heard and valued.

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Jörn Hendrik Ask

Jörn Hendrik Ast, founded of New Work Heroes in 2018. He is an entrepreneur, podcaster, and author dedicated to innovating work through team collaboration, leadership, and personal development. He is coaching teams, producing podcast episodes, and continues to create impactful learning formats and books.

You can link with Jörn Hendrik Ask on LinkedIn and connect with Jörn Hendrik Ask on Threads.

Caterina Palmiotto: The Phantom Product Owner, How Lack of Decision-Making Impacts the Team and Kills Innovation

The Great Product Owner: The Collaboration Between PO and Team as Key to PO Success

In this segment, Caterina shares a story of a great Product Owner who worked closely with their team. The PO took the time to share the high-level vision and timeline for a new module, collected doubts and comments from the team, and presented user stories with enough information to start a discussion. The PO listened to all suggestions and was available every day to collaborate. The refinement process was done in two parts, with the second part focused on investigating technical aspects. The PO even participated in retrospectives and worked with the team to improve the product based on either technical or functional ideas by the team. Caterina emphasizes the importance of building this kind of productive collaboration between POs and their teams, with the help of Scrum Masters.

The Bad Product Owner: The Phantom PO, How Lack of Decision-Making Impacts the Team and Kills Innovation

In this segment, Caterina talks about a Product Owner who only wrote user stories but was unable to make decisions. The Product Owner always needed to report to his boss, which caused a delay in decision-making. This led to delays in the team’s work, resulting in not completing the story in the sprint. Additionally, the team lost trust in the PO, and did not have enough information or support from the PO to bring their contribution to the product through technical innovation. Eventually, the team started to make decisions on their own and stopped suggesting ideas to the PO. Caterina emphasizes the importance of Product Owners being able to make decisions and not causing delays in the team’s work.

Are you having trouble helping the team work well with their Product Owner? We’ve put together a course to help you work on the collaboration team-product owner. You can find it at bit.ly/coachyourpo. 18 modules, 8+ hours of modules with tools and techniques that you can use to help teams and PO’s collaborate.

About Caterina Palmiotto

Caterina started as a software developer but soon realized that she was passionate about team dynamics and communication, and embraced agility from the moment she saw it.

Caterina believes a team can be more than the sum of its parts and that growing the right culture is essential. When people are surrounded by good examples they will be motivated to do their best.  So the first step is doing your best to be a good example of the culture you want to nurture.

You can link with Caterina Palmiotto on LinkedIn.

Sean Dunn: develop teams and you will be successful

Many will say that helping team meeting commitments is how Scrum Masters best do their work. Seann shows us another side of the job: developing teams. Helping them develop their skills, their collaboration, and focus on outcomes, not outputs.
We discuss that knowing “why” is often more important than focusing on the work at hand, and we mention the book by Simon Sinek: Start with Why.

About About Sean Dunn

Sean is an Enterprise Agile Coach with IHS Global. He has been involved with agile development for 8 years as a developer, product owner, and agile coach. Prior to his exposure to agile development Sean spent 13 years in the Canadian Army. In fact, Sean is known to point out that the Army is far more agile than most people think.
That background in the Canadian Army influenced his view of Leadership and the role of Leadership in creating and developing great teams.
You can connect with Sean Dunn on LinkedIn, check out Sean Dunn on the Scrum Alliance or email him at sean.dunn@ihs.com
Check out Sean Dunn’s blog on leadership.

Neil Killick on information radiators, Little’s Law and Queuing Theory

Little’s Law is a relatively recent discovery in Queuing Theory. It was only proven in 1961, and still unknown to many in the software industry today.
Neil discusses why that simple theorem is so important in software projects, and how it can help you understand why over-commitment is so common, and bad for software development.

About Neil Killick

scrum_master_toolbox_podcast_Andy_Deighton Neil has been a software professional for over 18 years, mostly as a developer, before moving to management. He spent the last 5 years being a passionate Agile, Lean and Scrum coach, trainer and practitioner. Neil cares deeply about creating enjoyable, authentic workplaces in which human potential can thrive.
You can connect with Neil Killick on twitter. Neil Killick’s blog.

Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Internal Conference
Checklist
Internal Conference
Checklist
Download a detailed How-To to help measure success for your team
Motivate your team with the right metrics, and the right way to visualize and track them. Marcus presents a detailed How-To document based on his experience at The Bungsu Hospital
Download a detailed How-To to help measure success for your team
Read about Visualization and TRANSFORM The way your team works
A moving story of how work at the Bungsu Hospital was transformed by a simple tool that you can use to help your team.
Read about Visualization and TRANSFORM The way your team works
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Access three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
FREE! Audiobook Chapters: Overcome Team Resistance and Gain Leadership Buy-In
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
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