“We can’t continue to do this. Something has to change.” – Carmela Then
Carmela shares a story of organizational chaos that will resonate with many Agile practitioners. She joined a company where teams would jump straight into writing requirements without pausing to understand what they were trying to achieve. Vendor deliverables were thrown “over the fence” to internal technology teams with the assumption that everyone would magically know what to do. For almost a year, this pattern continued: teams writing stories on the fly while building, creating massive rework, confusion, and burnout.
The Product Owner faced constant stakeholder disappointment, having to explain what wasn’t delivered and why. Then came the breakthrough moment—the PO reached out and said, “We can’t continue to do this.” Carmela introduced a structured approach: workshops that brought business stakeholders and subject matter experts together to walk through end-to-end business processes. She implemented story mapping—visualizing the journey from beginning to end, with each major step broken into smaller, actionable stories.
Critically, she built in feedback loops: playback sessions where the team validated their understanding with stakeholders before committing to development. The result? Teams could now distinguish between well-understood work they could start immediately and the “hairy” items that needed more investigation. The Product Owner could make informed prioritization decisions, and the entire team gained visibility into the bigger picture.
Self-reflection Question: How often does your team pause to map the full end-to-end journey before diving into requirements, and what might you be missing by skipping this step?
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About Carmela Then
Carmela is a Senior Business Analyst with 15+ years in financial and mining sectors. A Certified and Advanced ScrumMaster, she excels in leading agile initiatives, delivering business value, and aligning technical outcomes with strategic goals.
In this powerful conversation, former fighter pilot Christian “Boo” Boucousis reveals how military precision translates into agile business leadership. We explore the FLEX model (Plan-Brief-Execute-Debrief), the critical difference between control-based and awareness-based leadership, and why most organizations fail to truly embrace iterative thinking.
From Cockpit to Boardroom: An Unexpected Journey
“I learned over time that it doesn’t matter what you do if you’re always curious, and you’re always intentional, and you’re always asking questions.” — Christian “Boo” Boucousis
Christian’s path from fighter pilot to leadership consultant wasn’t planned—it was driven by necessity and curiosity. After 11 years as a fighter pilot (7 in Australia, 4 in the UK), an autoimmune condition ended his flying career at age 30. Rather than accepting a comfy job flying politicians around, he chose entrepreneurship. He moved to Afghanistan with a friend and built a reconstruction company that grew to a quarter billion dollars in four years. The secret? The debrief skills he learned as a fighter pilot. By constantly asking “What are you trying to achieve? How’s it going? Why is there a gap?” he approached business with an agile mindset before he even knew what agile was. This curiosity-driven, question-focused approach became the foundation for everything that followed.
The FLEX Model: Plan-Brief-Execute-Debrief
“Agile and scrum were co-created by John Sutherland, who was a fighter pilot, and its origins sit in the OODA loop and iteration. Which is why it’s a circle.” — Christian “Boo” Boucousis
The FLEX model isn’t new—fighter pilots have used this Plan-Brief-Execute-Debrief cycle for 60 years. It’s the ultimate simple agile model, designed to help teams accelerate toward goals using the same accelerated learning curve the Air Force uses to train fighter pilots. The key insight: everything in this model is iterative, not linear. Every mission has a start, middle, and end, and every stage involves constant adaptation. Afterburner (the company Christian now leads as CEO) has worked with nearly 3,800 companies and 2.8 million people over 30 years, teaching this model. What’s fascinating is that the DNA of agile is baked into fighter pilot thinking—John Sutherland, co-creator of Scrum, wrote the foreword for Christian’s book “The Afterburner Advantage” because they share the same roots in the OODA loop and iterative thinking.
Why Iterative Thinking Doesn’t Come Naturally
“Iterative thinking is not a natural human model. Most of the time we learn from mistakes. We don’t learn as a habit.” — Christian “Boo” Boucousis
In this fascinating conversation about complex adaptive systems, Simon Holzapfel helps us understand why traditional planning and control methods fail in knowledge work — and what we can do instead.
Understanding Ecosystems vs. Systems
“Complex adaptive systems are complex in nature and adaptive in that they evolve over time. That’s different from a static system.” — Simon Holzapfel
Simon introduces the crucial distinction between mechanical systems and ecosystems. While mechanical systems are predictable and static, ecosystems — like teams and organizations — are complex, adaptive, and constantly evolving. The key difference lies in the interactions among team members, which create emergent properties that cannot be predicted by analyzing individuals separately. Managers often fall into the trap of focusing on individuals rather than the interactions between them, missing where the real magic happens. This is why understanding your organization as an ecosystem, not a machine, fundamentally changes how you lead.
“I used to come into class with a lesson plan — doop, doop, doop, minute by minute agenda. And then what I realized is that I would just completely squash those questions that would often emerge from the class.” — Simon Holzapfel
Simon shares his transformation from rigid classroom planning to embracing emergence. As a history and economics teacher for 10 years, he learned that over-planning kills the spontaneous insights that make learning powerful. The same principle applies to leadership: planning is essential, but over-planning wastes time and prevents novelty from emerging. The key is separating strategic planning (the “where” and “why”) from tactical execution (the “how”), letting teams make local decisions while leaders focus on alignment with the bigger picture.
“Innovation Arrives Stochastically”
“Simply by noticing the locations where you’ve had your best ideas, we notice the stochasticness of arrival. Might be the shower, might be on a bike ride, might be sitting in traffic, might be at your desk — but often not.” — Simon Holzapfel
Simon unpacks the concept of stochastic emergence — the idea that innovation cannot be scheduled or predicted in advance. Stochastic means something is predictable over large datasets but not in any given moment. You know you’ll have ideas if you give yourself time and space, but you can’t predict when or where they’ll arrive. This has profound implications for managers who try to control when and how innovation happens. Knowledge work is about creating things that haven’t existed before, so emergence is what we rely on. Try to squash it with too much control, and it simply won’t happen.
“When you have three nonlinear functions working at the same time within a system, you have almost no ability to predict its future state beyond just some of the shortest time series data.” — Simon Holzapfel
Simon uses the three-body problem from physics as a powerful metaphor for organizational complexity. In physics, when you have three bodies (like planets) influencing each other, prediction becomes nearly impossible. The same is true in business — think of R&D, manufacturing, and sales as three interacting forces. The lesson: don’t think you can master this complexity. Work with it. Understand it’s a system. Most variability comes from the system itself, not from any individual person. This allows us to depersonalize problems — people aren’t good or bad, systems can be improved. When teams understand this, they can relax and stop treating every unpredictable moment as an emergency.
Coaching Leaders to Embrace Uncertainty
“I’ll start by trying to read their comfort level. I’ll ask about their favorite teachers, their most hated teachers, and I’ll really try to bring them back to moments in time that were pivotal in their own development.” — Simon Holzapfel
How do you help analytical, control-oriented leaders embrace complexity and emergence? Simon’s approach is to build rapport first, then gently introduce concepts based on each leader’s background. For technical people who prefer math, he’ll discuss narrow tail distributions and fat tails. For humanities-oriented leaders, he uses narrative and storytelling. The goal is to get leaders to open up to possibilities without feeling diminished. He might suggest small experiments: “Hold your tongue once in a meeting” or “Ask questions instead of making statements.” These incremental changes help managers realize they don’t have to be superhuman problem-solvers who control everything.
Giving the Board a Number: The Paradox of Prediction
“Managers say we want scientific management, but they don’t actually want that. They want predictive management.” — Simon Holzapfel
Simon addresses one of the biggest tensions in agile adoption: leaders who say “I just need to give the board a number” while also wanting innovation and adaptability. The paradox is clear — you cannot simultaneously be open to innovation and emergent possibilities while executing a predetermined plan with perfect accuracy. This is an artifact of management literature that promoted the “philosopher king” manager who knows everything. But markets are too movable, consumer tastes vary too much, and knowledge work is too complex for any single person to control. The burnout we see in leaders often comes from trying to achieve an impossible standard. In this segment, we refer to the episodes with David Marquet.
Resources for Understanding Complexity
“Eric Beinhocker’s book called ‘The Origin of Wealth’ is wonderful. It’s a very approachable and well-researched piece that shows where we’ve been and where we’re going in this area.” — Simon Holzapfel
Simon recommends two key resources for anyone wanting to understand complexity and ecosystems. First, Eric Beinhocker’s “The Origin of Wealth” explains how we developed flawed economic assumptions based on 19th-century Newtonian physics, and why we need to evolve our understanding. Second, the Systems Innovation YouTube channel offers brilliant short videos perfect for curious, open-minded managers. Simon suggests a practical approach: have someone on your team watch a video and share what they learned. This creates shared language around complexity and makes the concepts less personal and less threatening.
The Path Forward: Systems Over Individuals
“As a manager, our goal is to constantly evaluate the performance of the system, not the people. We can always put better systems in place. We can always improve existing systems. But you can’t tell people what to do — it’s not possible.” — Simon Holzapfel
The conversation concludes with a powerful insight from Deming’s work: about 95% of a system’s productivity is linked to the system itself, not individual performance. This reframes the manager’s role entirely. Instead of trying to control people, focus on improving systems. Instead of treating burnout as individual failure, see it as information that something in the system isn’t working. Organizations are ever-changing ecosystems with dynamic properties that can only be observed, never fully predicted. This requires a completely different way of thinking about management — one that embraces uncertainty, values emergence, and trusts teams to figure things out within clear strategic boundaries.
Recommended Resources
As recommended resources for further reading, Simon suggests:
Simon Holzapfel is an educator, coach, and learning innovator who helps teams work with greater clarity, speed, and purpose. He specializes in separating strategy from tactics, enabling short-cycle decision-making and higher-value workflows. Simon has spent his career coaching individuals and teams to achieve performance with deeper meaning and joy. Simon is also the author of the Equonomist newsletter on Substack, where he explores the intersection of economics, equality, and equanimity in the workplace.
In this episode, Chrissy shares a critical learning moment from her career when she attempted to juggle both Product Owner and Scrum Master roles simultaneously. This dual role led to a situation where the team began “sandbagging” their estimates due to underlying conflicts with leadership. The situation culminated when a team member completed a supposedly two-month project in just two days, destroying team credibility and ultimately leading to the team’s dismissal.
Self-reflection Question: How do you ensure you maintain your authentic voice as a Scrum Master while balancing multiple stakeholder needs?
The Scrum Master Toolbox Podcast Recommends…
🔥 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.
Chrissy came to Scrum-Mastering via Product Management and a deep love of seeing teams work together. She spent 15 years in the New York tech scene and is currently an Associate Principal in Business Agility with Turnberry Solutions. She also has her own company where she coaches and helps businesses and technologists with their development.
Ramya faced resistance when introducing change in an organization bound by outdated timesheet practices. By implementing capacity sheets, she reframed the discussion around team availability instead of tracking hours, convincing the Delivery Manager and customer of its benefits. This success highlights the power of leading by example and addressing resistance with practical, team-centric solutions.
Self-reflection Question: How can you use simple tools to address resistance and demonstrate the value of change in your team?
The Scrum Master Toolbox Podcast Recommends…
🔥 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.
Ramya is an Enterprise Agile Coach from India who focuses on organizational growth and agility through human-centric coaching. She co-hosts two podcasts: Agile Coaching Round Table and Career Storyteller (on YouTube).
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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