Phil Le-Brun and Dr. Jana Werner both work inside Amazon, advising Fortune 500 leaders on transformation. But before Amazon, they spent decades in the trenches — Phil as International CIO of McDonald’s, Jana leading change in banking and logistics. Together they wrote The Octopus Organization (HBR Press) to explain why most companies are still running on a hundred-year-old factory model, and what the alternative looks like.
“We Want to Help You Make Your Own New Interesting Mistakes”
“We keep saying, as Phil likes to say, can we help you make your own new interesting mistakes and avoid the mistakes that we see again and again.”
Jana and Phil are both practitioners who have led large-scale changes — and made mistakes they’re now happy to share. Jana describes working with incredible, smart, thoughtful people inside large organizations who weren’t trusted, weren’t allowed to do the work they could do, and couldn’t be their best selves. She managed to turn teams considered underperforming into rock stars simply by listening and giving them space. Phil saw the same pattern at McDonald’s — incredible people who knew the answers but weren’t allowed to act on them. A disastrous standardization push from 2002 to 2004 taught him that top-down efficiency mandates don’t work. The CEO left, and Phil got the opportunity to tap into people lower in the organization, define a common mission, and start building from there.
In this BONUS Xmas Special episode, we explore what happens when we strip away the certifications and branded frameworks to recover the essential practices that make software development work. Building on Episode 2’s exploration of the Project Management Trap, Vasco reveals how the core insights that sparked the Agile revolution remain valid – and how real organizations like Spotify, Amazon, and Etsy embody these principles to thrive in today’s software-driven world. The answer isn’t to invent something new; it’s to amplify what’s already working.
Agile as an Idea, Not a Brand
“The script (sold as the solution) will eventually kill the possibility of the conversation ever happening with any quality.”
We establish a parallel between good conversations and good software development. Just as creating “The Certified Conversational Method™” with prescribed frameworks and certification levels would miss the point of genuine dialogue, the commodification of agile into Agile™ has obscured its essential truth. The core idea was simple and powerful: build software in small increments, get it in front of real users quickly, learn from their actual behavior, adapt based on what you learn, and repeat continuously. This wasn’t revolutionary – it was finally recognizing how software actually works. You can’t know if your hypothesis about user needs is correct until users interact with it, so optimize for learning speed, not planning precision. But when the need to certify and validate “doing Agile right” took over, the idea got packaged, and often the package became more important than the principle.
Four Fundamental Practices That Enable Living Software
“Every deployment was a chance to see how users actually responded.”
Software-native organizations distinguish themselves through core practices that align with software as a living capability. In this episode, we review four critical ones: First, iterative delivery means shipping the smallest valuable increment possible and building on it – Etsy’s transformation from quarterly releases in 2009 to shipping 50+ times per day by 2012 exemplifies this approach, where each small change serves as a learning opportunity. Second, tight feedback loops get software in front of real users as fast as possible, whether through paper prototypes or production deployments. Third, continuous improvement of the process itself creates meta-feedback loops, as demonstrated by Amazon’s “You Build It, You Run It” principle introduced by Werner Vogels in 2006, where development teams running their own services in production learn rapidly to write more resilient code. Fourth, product thinking over project thinking organizes teams around long-lived products rather than temporary projects, allowing teams to develop deep expertise and become living capabilities themselves, accumulating knowledge and improving over time.
Spotify’s Evolutionary Approach
“The Spotify model has nothing to do with Spotify really. It was just a snapshot of how that one company worked at the time.”
Spotify’s journey reveals a critical insight often missed in discussions of their famous organizational model. Starting with standard Scrum methodology pre-2012, they adopted the squad model around 2012 with autonomous teams organized into tribes, documented in Henrik Kniberg and Anders Ivarsson’s influential white paper (direct PDF link). But post-2016, internal staff and agile coaches noted that the “Spotify model” had become mythology, and the company had moved on from original concepts to address new challenges. As Kniberg himself later reflected, the model has taken on a life of its own, much like Lean’s relationship to Toyota. The key insight isn’t the specific structure – it’s that Spotify treated their own organizational design as a living capability, continuously adapting based on what worked and what didn’t rather than implementing “the model” and declaring victory. That’s software-native thinking applied to organization design itself.
Amazon’s Two-Pizza Teams and Massive Scale
“Amazon deploys code every 11.7 seconds on average. That’s over 7,000 deployments per day across the organization.” (see this YouTube video of this talk)
Amazon’s two-pizza team principle goes far deeper than team size. Teams small enough to be fed with two pizzas (roughly 6-10 people) gain crucial autonomy and ownership: each team owns specific services and APIs, makes their own technical decisions, runs their services in production, and manages inter-team dependencies through APIs rather than meetings. This structure enabled Amazon to scale massively while maintaining speed, as teams could iterate independently without coordinating with dozens of other teams. The staggering deployment frequency – over 7,000 times per day as of 2021 – is only possible with a software-native structure for the company itself, demonstrating that this isn’t just about managing software delivery but touches everything, including how teams are organized.
Why These Practices Work
“These practices work because they align with what software actually is: a living, evolvable capability.”
The effectiveness of software-native approaches stems from their alignment with software’s true nature. Traditional project approaches assume we can know requirements upfront, estimate accurately, build it right the first time, and reach a meaningful “done” state. Software-native approaches recognize that requirements emerge through interaction with users, estimation is less important than rapid learning, “right” is discovered iteratively rather than designed upfront, and “done” only happens when we stop evolving the software. When Etsy ships 50 times per day, they’re optimizing for learning where each deployment is a hypothesis test. When Amazon’s teams own services end-to-end, they’re creating tight feedback loops where teams feel the pain of their own decisions directly. When Spotify continuously evolves their organizational model, they’re treating their own structure as software that should adapt to changing needs.
The Incomplete Picture and the Question of Universal Adoption
“If these approaches work, why aren’t they universal?”
We’re not trying to paint a unrealistically rosy picture – these organizations aren’t perfect. Spotify has had well-documented challenges with their model, Amazon’s culture has been criticized as demanding and sometimes brutal, and Etsy has gone through multiple strategic shifts. But what matters is that they’re practicing software-native development at scale, and it’s working well enough that they can compete and thrive. They’re not following a playbook perfectly but embodying principles and adapting continuously. This raises the critical question that will be explored in the next episode: if these approaches work, why do so many organizations still operate in project mode, and why do “agile transformations” so often fail to deliver real change? Understanding the resistance – what we call The Organizational Immune System – is essential to overcoming it.
Vasco Duarte is a thought leader in the Agile space, co-founder of Agile Finland, and host of the Scrum Master Toolbox Podcast, which has over 10 million downloads. Author of NoEstimates: How To Measure Project Progress Without Estimating, Vasco is a sought-after speaker and consultant helping organizations embrace Agile practices to achieve business success.
The Great Product Owner: Strategic, Customer-Obsessed, and Vision-Driven
“The PO role in the team is strategic. These POs focus on the customer, outcomes, and strategy. They’re customer-obsessed and focus on the purpose and the why of the product.” – Karim Harbott
Karim believes the industry fundamentally misunderstands what a Product Owner should be. The great Product Owners he’s seen are strategic thinkers who are obsessed with the customer. They don’t just manage a backlog—they paint a vision for the product and help the entire team become customer-obsessed alongside them.
These POs focus relentlessly on outcomes rather than outputs, asking “why are we building this?” before diving into “what should we build?” They understand the purpose of the product and communicate it compellingly.
Karim references Amazon’s “working backwards” approach, where Product Owners start with the customer experience they want to create and work backwards to figure out what needs to be built. Great POs also embrace the framework of Desirability (what customers want), Viability (what makes business sense), Feasibility (what’s technically possible), and Usability (what’s easy to use). While the PO owns desirability and viability, they collaborate closely with designers on usability and technical teams on feasibility.
This is critical: software is a team sport, and great POs recognize that multiple roles share responsibility for delivery. Like David Marquet teaches, they empower the team to own decisions rather than dictating every detail. The result? Teams that understand the “why” and can innovate toward it autonomously.
Self-reflection Question: Does your Product Owner paint a compelling vision that inspires the team, or do they primarily manage a list of tasks?
The Bad Product Owner: The User Story Writer
“The user story writer PO thinks it’s their job to write full, long requirements documents, put it in JIRA, and assign it to the team. This is far away from what the PO role should be.” – Karim Harbott
The anti-pattern Karim sees most often is the “User Story Writer” Product Owner. These POs believe their job is to write detailed requirements documents, load them into JIRA, and assign them to the team. It’s essentially waterfall disguised as Agile—treating user stories like mini-specifications rather than conversation starters. This approach completely misses the collaborative nature of product development.
Instead of engaging the team in understanding customer needs and co-creating solutions, these POs hand down fully-formed requirements and expect the team to execute without question. The problem is that this removes the team’s ownership and creativity. When POs act as the sole source of product knowledge, they become bottlenecks.
The team can’t make smart tradeoffs or innovate because they don’t understand the underlying customer problems or business context. Using the Desirability-Viability-Feasibility-Usability framework, bad POs try to own all four dimensions themselves instead of recognizing that designers, developers, and other roles bring essential perspectives. The result is disengaged teams, slow delivery, and products that miss the mark because they were built to specifications rather than shaped by collaborative discovery. Software is a team sport—but the User Story Writer PO forgets to put the team on the field.
Self-reflection Question: Is your Product Owner engaging the team in collaborative discovery, or just handing down requirements to be implemented?
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 Karim Harbott
Karim is a consultant, trainer, and non-executive director. He bridges the gap between strategy, business agility, digital transformation, innovation, AI, and board governance. He is a Certified Scrum Trainer, and is the author of The 6 Enablers of Business Agility.
Tom and Mary Poppendieck have authored several books over the years about what needs to change in how we develop software to be able to meet the demands of the market, competition, and the growth in complexity of technology businesses. A recurring pattern they have witnessed is that people keep trying to discover a “silver bullet”. We explore why that is a bad idea and some of the changes in product development that make it an impossible quest.
Read on for the details, and all the links shared during the show.
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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