AI Assisted Coding: Transactional AI Development - Commit, Validate, and Rollback With Sergey Sergyenko

AI Assisted Coding: Transactional AI Development - Commit, Validate, and Rollback With Sergey Sergyenko

AI Assisted Coding: Treating AI Like a Junior Engineer - Onboarding Practices for AI Collaboration

In this special episode, Sergey Sergyenko, CEO of Cybergizer, shares his practical framework for AI-assisted development built on transactional models, Git workflows, and architectural conventions. He explains why treating AI like a junior engineer, keeping commits atomic, and maintaining rollback strategies creates production-ready code rather than just prototypes.

Vibecoding: An Automation Design Instrument

"I would define Vibecoding as an automation design instrument. It's not a tool that can deliver end-to-end solution, but it's like a perfect set of helping hands for a person who knows what they need to do."

Sergey positions vibecoding clearly: it's not magic, it's an automation design tool. The person using it must know what they need to accomplish—AI provides the helping hands to execute that vision faster. This framing sets expectations appropriately: AI speeds up development significantly, but it's not a silver bullet that works without guidance. The more you practice vibecoding, the better you understand its boundaries. Sergey's definition places vibecoding in the evolution of development tools: from scaffolding to co-pilots to agentic coding to vibecoding. Each step increases automation, but the human architect remains essential for providing direction, context, and validation.

Pair Programming with the Machine

"If you treat AI as a junior engineer, it's very easy to adopt it. Ah, okay, maybe we just use the old traditions, how we onboard juniors to the team, and let AI follow this step."

One of Sergey's most practical insights is treating AI like a junior engineer joining your team. This mental model immediately clarifies roles and expectations. You wouldn't let a junior architect your system or write all your tests—so why let AI? Instead, apply existing onboarding practices: pair programming, code reviews, test-driven development, architectural guidance. This approach leverages Extreme Programming practices that have worked for decades. The junior engineer analogy helps teams understand that AI needs mentorship, clear requirements, and frequent validation. Just as you'd provide a junior with frameworks and conventions to follow, you constrain AI with established architectural patterns and framework conventions like Ruby on Rails.

The Transactional Model: Atomic Commits and Rollback

"When you're working with AI, the more atomic commits it delivers, more easy for you to kind of guide and navigate it through the process of development."

Sergey's transactional approach transforms how developers work with AI. Instead of iterating endlessly when something goes wrong, commit frequently with atomic changes, then rollback and restart if validation fails. Each commit should be small, independent, and complete—like a feature flag you can toggle. The commit message includes the prompt sequence used to generate the code and rollback instructions.

This approach makes the Git repository the context manager, not just the AI's memory. When you need to guide AI, you can reference specific commits and their context. This mirrors trunk-based development practices where teams commit directly to master with small, verified changes. The cost of rollback stays minimal because changes are atomic, making this strategy far more efficient than trying to fix broken implementations through iteration.

Context Management: The Weak Point and the Solution

"Managing context and keeping context is one of the weak points of today's coding agents, therefore we need to be very mindful in how we manage that context for the agent."

Context management challenges current AI coding tools—they forget, lose thread, or misinterpret requirements over long sessions. Sergey's solution is embedding context within the commit history itself. Each commit links back to the specific reasoning behind that code: why it was accepted, what iterations it took, and how to undo it if needed. This creates a persistent context trail that survives beyond individual AI sessions. When starting new features, developers can reference previous commits and their context to guide the AI. The transactional model doesn't just provide rollback capability—it creates institutional memory that makes AI progressively more effective as the codebase grows.

TDD 2.0: Humans Write Tests, AI Writes Code

"I would never allow AI to write the test. I would do it by myself. Still, it can write the code."

Sergey is adamant about roles: humans write tests, AI writes implementation code. This inverts traditional TDD slightly—instead of developers writing tests then code, they write tests and AI writes the code to pass them. Tests become executable requirements and prompts. This provides essential guardrails: AI can iterate on implementation until tests pass, but it can't redefine what "passing" means. The tests represent domain knowledge, business requirements, and validation criteria that only humans should control. Sergey envisions multi-agent systems where one agent writes code while another validates with tests, but critically, humans author the original test suite. This TDD 2.0 framework (a talk Sergey gave at the Global Agile Summit) creates a verification mechanism that prevents the biggest anti-pattern: coding without proper validation.

The Two Cardinal Rules: Architecture and Verification

"I would never allow AI to invent architecture. Writing AI agentic coding, Vibecoding, whatever coding—without proper verification and properly setting expectations of what you want to get as a result—that's the main mistake."

Sergey identifies two non-negotiables. First, never let AI invent architecture. Use framework conventions (Rails, etc.) to constrain AI's choices. Leverage existing code generators and scaffolding. Provide explicit architectural guidelines in planning steps. Store iteration-specific instructions where AI can reference them. The framework becomes the guardrails that prevent AI from making structural decisions it's not equipped to make. Second, always verify AI output. Even if you don't want to look at code, you must validate that it meets requirements. This might be through tests, manual review, or automated checks—but skipping verification is the fundamental mistake. These two rules—human-defined architecture and mandatory verification—separate successful AI-assisted development from technical debt generation.

Prototype vs. Production: Two Different Workflows

"When you pair as an architect or a really senior engineer who can implement it by himself, but just wants to save time, you do the pair programming with AI, and the AI kind of ships a draft, and rapid prototype."

Sergey distinguishes clearly between prototype and production development. For MVPs and rapid prototypes, a senior architect pairs with AI to create drafts quickly—this is where speed matters most. For production code, teams add more iterative testing and polishing after AI generates initial implementation. The key is being explicit about which mode you're in. The biggest anti-pattern is treating prototype code as production-ready without the necessary validation and hardening steps. When building production systems, Sergey applies the full transactional model: atomic commits, comprehensive tests, architectural constraints, and rollback strategies. For prototypes, speed takes priority, but the architectural knowledge still comes from humans, not AI.

The Future: AI Literacy as Mandatory

"Being a software engineer and trying to get a new job, it's gonna be a mandatory requirement for you to understand how to use AI for coding. So it's not enough to just be a good engineer."

Sergey sees AI-assisted coding literacy becoming as fundamental as Git proficiency. Future engineering jobs will require demonstrating effective AI collaboration, not just traditional coding skills. We're reaching good performance levels with AI models—now the challenge is learning to use them efficiently. This means frameworks and standardized patterns for AI-assisted development will emerge and consolidate. Approaches like AAID, SpecKit, and others represent early attempts to create these patterns. Sergey expects architectural patterns for AI-assisted development to standardize, similar to how design patterns emerged in object-oriented programming. The human remains the bottleneck—for domain knowledge, business requirements, and architectural guidance—but the implementation mechanics shift heavily toward AI collaboration.

Resources for Practitioners

"We are reaching a good performance level of AI models, and now we need to guide it to make it impactful. It's a great tool, now we need to understand how to make it impactful."

Sergey recommends Obie Fernandez's work on "Patterns of Application Development Using AI," particularly valuable for Ruby and Rails developers but applicable broadly. He references Andrey Karpathy's original vibecoding post and emphasizes Extreme Programming practices as foundational. The tools he uses—Cursor and Claude Code—support custom planning steps and context management. But more important than tools is the mindset: we have powerful AI capabilities now, and the focus must shift to efficient usage patterns. This means experimenting with workflows, documenting what works, and sharing patterns with the community. Sergey himself shares case studies on LinkedIn and travels extensively speaking about these approaches, contributing to the collective learning happening in real-time.

About Sergey Sergyenko

Sergey is the CEO of Cybergizer, a dynamic software development agency with offices in Vilnius, Lithuania. Specializing in MVPs with zero cash requirements, Cybergizer offers top-tier CTO services and startup teams. Their tech stack includes Ruby, Rails, Elixir, and ReactJS.

Sergey was also a featured speaker at the Global Agile Summit, and you can find his talk available in your membership area. If you are not a member don't worry, you can get the 1-month trial and watch the whole conference. You can cancel at any time.

You can link with Sergey Sergyenko on LinkedIn.

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You Can't Make a Flower Grow Faster—The Oblique Approach to Shaping Culture | Karim Harbott

You Can't Make a Flower Grow Faster—The Oblique Approach to Shaping Culture | Karim Harbott

Karim Harbott: You Can't Make a Flower Grow Faster—The Oblique Approach to Shaping Culture 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.   "How can I make a flower grow faster? Culture is a product of the behaviors of people in the system." - Karim Harbott   For Karim, one of the biggest challenges—and enablers—in his current work is creating a supporting culture. After years of learning what doesn't work, he's come to understand that culture isn't something you can force or mandate. Like trying to make a flower grow faster by pulling on it, direct approaches to culture change often backfire.  Instead, Karim uses what he calls the "oblique approach"—changing culture indirectly by adjusting the five levers: leadership behaviors, organizational structure, incentives, metrics, and systems. Leadership behaviors are particularly crucial.  When leaders step back and encourage ownership rather than micromanaging, teams transform. Incentives have a huge impact on how teams work—align them poorly, and you'll get exactly the wrong behaviors.  Karim references Team of Teams by General Stanley McChrystal, which demonstrates how changing organizational structure and leadership philosophy can unlock extraordinary performance. He also uses the Competing Values Framework to help leaders understand different cultural orientations and their tradeoffs. But the most important lesson? There are always unexpected consequences. Culture change requires patience, experimentation, and a willingness to observe how the system responds. You can't force a flower to grow, but you can create the conditions where it thrives.   Self-reflection Question: Are you trying to change your organization's culture directly, or are you adjusting the conditions that shape behavior?   [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.   Buy Now on Amazon   [The Scrum Master Toolbox Podcast Recommends]   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.   You can link with Karim Harbott on LinkedIn.

5 Nov 17min

Why System Design Beats Individual Coaching Every Time | Karim Harbott

Why System Design Beats Individual Coaching Every Time | Karim Harbott

Karim Harbott: Why System Design Beats Individual Coaching Every Time 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.   "You can't change people, but you can change the system. Change the environment, not the people." - Karim Harbott   Karim was coaching a distributed team that was struggling with defects appearing constantly during sprints. The developers and testers were at different sites, and communication seemed fractured. But Karim knew from experience that when teams are underperforming, the problem usually isn't the people—it's the system they're working in. He stepped back to examine the broader context, implementing behavior-driven development(BDD) and specification by example to improve clarity through BDD scenarios.  But the defects persisted.  Then, almost by accident, Karim discovered the root cause: the developers and testers were employed by different companies. They had competing interests, different incentives, and fundamentally misaligned goals. No amount of coaching the individuals would fix a structural problem like that.  It took months, but eventually the system changed—developers and testers were reorganized into unified teams from the same organization. Suddenly, the defects dropped dramatically. As Jocko Willink writes in Extreme Ownership, when something isn't working, look at the system first. Karim's experience proves that sometimes the most compassionate thing you can do is stop trying to fix people and start fixing the environment they work in.   Self-reflection Question: When your team struggles, do you look at the people or at the system they're embedded in? Featured Book of the Week: Scaling Lean and Agile Development by Craig Larman and Bas Vodde "This book was absolute gold. The way it is written, and the tools they talk about went beyond what I was talking about back then. They introduced many concepts that I now use." - Karim Harbott   Karim discovered Scaling Lean and Agile Development by accident, but it resonated with him immediately. The concepts Craig Larman and Bas Vodde introduced—particularly around LeSS (Large-Scale Scrum)—went far beyond the basics Karim had been working with. The book opened his eyes to system-level thinking at scale, showing how to maintain agility even as organizations grow.  It's packed with practical tools and frameworks that Karim still uses today. For anyone working beyond a single team, this book provides the depth and nuance that most scaling frameworks gloss over. Also worth reading: User Stories Applied by Mike Cohn, another foundational text that shaped Karim's approach to working with teams.   [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.   Buy Now on Amazon   [The Scrum Master Toolbox Podcast Recommends]   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.   You can link with Karim Harbott on LinkedIn.

4 Nov 15min

The Day I Discovered I Was a Scrum Project Manager, Not a Scrum Master | Karim Harbott

The Day I Discovered I Was a Scrum Project Manager, Not a Scrum Master | Karim Harbott

Karim Harbott: The Day I Discovered I Was a Scrum Project Manager, Not a Scrum Master 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.   "I was telling the team what to do, instead of helping the team to be better on their own. There's a lot more to being a Scrum Master than Agile—working with people is such a different skillset." - Karim Harbott   Karim thought he had mastered Scrum. He had read the books, understood the framework, and was getting things done. His team seemed to be moving forward smoothly—until he stepped away for a few weeks.  But, when he returned, everything had fallen apart. The team couldn't function without him constantly directing their work. That's when Karim realized he had fallen into one of the most common anti-patterns in Agile: the Scrum Project Manager.  Instead of enabling his team to be more effective, he had become their bottleneck. Every decision flowed through him, every task needed his approval, and the team had learned to wait for his direction rather than taking ownership themselves. The wake-up call was brutal but necessary.  Karim discovered that pushing project management responsibilities to the people doing the work—as David Marquet advocates—was far more powerful than being the hero who solves all problems. The real skill wasn't in telling people what to do; it was in creating an environment where they could figure it out themselves. Geoff Watts calls this servant leadership, and Karim learned it the hard way: a great Scrum Master makes themselves progressively less necessary, not more indispensable.   Self-reflection Question: Are you enabling your team to be more effective, or have you become the person they can't function without?   [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.   Buy Now on Amazon   [The Scrum Master Toolbox Podcast Recommends]   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.   You can link with Karim Harbott on LinkedIn.

3 Nov 16min

Organizations as Ecosystems — Understanding Complexity, Innovation, and the Three-Body Problem at Work With Simon Holzapfel

Organizations as Ecosystems — Understanding Complexity, Innovation, and the Three-Body Problem at Work With Simon Holzapfel

BONUS: Organizations as Ecosystems — Understanding Complexity, Innovation, and the Three-Body Problem at Work 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. In this segment, we refer to the Stella systems modeling application. The Journey from Planning to Emergence "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. In this segment, we refer to the Systems Innovation YouTube channel. The Three-Body Problem: A Metaphor for Teams "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:  The Origin of Wealth, by Eric Beinhocker The Systems Innovation YouTube channel   About Simon Holzapfel   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.   You can link with Simon Holzapfel on LinkedIn.

1 Nov 40min

From Missing in Action to Present and Collaborative—The Product Owner Spectrum | Darryl Wright

From Missing in Action to Present and Collaborative—The Product Owner Spectrum | Darryl Wright

Darryl Wright: The PONO—Product Owners in Name Only and How They Destroy Teams 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. The Great Product Owner: Collaborative, Present, and Clear in Vision "She was collaborative, and that meant that she was present—the opposite of the MIA product owner. She came, and she sat with the team, and she worked with them side by side. Even when she was working on something different, she'd be there, she'd be available." - Darryl Wright Darryl shares an unusual story about one of the best Product Owners he's ever encountered—someone who had never even heard of Agile before taking the role. Working for a large consulting company with 170,000 staff worldwide, they faced a difficult project that nobody wanted to do. Darryl suggested running it as an Agile project, but the entire team had zero Agile experience. The only person who'd heard of Agile was a new graduate who'd studied it for one week at university—he became the Scrum Master. The executive sponsor, with her business acumen and stakeholder management skills, became the Product Owner despite having no idea what that meant. The results were extraordinary: an 18-month project completed in just over 7 months, and when asked about the experience, the team's highest feedback was how much fun they had working on what was supposed to be an awful, difficult project. Darryl attributes this success to mindset—the team was open and willing to try something new. The Product Owner brought critical skills to the role even without technical Agile knowledge: She was collaborative and present, sitting with the team and remaining available. She was decisive, making prioritization calls clearly so nobody was ever confused about priorities. She had excellent communication skills, articulating the vision with clarity that inspired the team. Her stakeholder management capabilities kept external pressures managed appropriately. And her business acumen meant she instantly understood conversations about value, time to market, and customer impact. Without formal training, she became an amazing Product Owner simply by being open, willing, and committed. As Darryl reflects, going from never having heard of the role to being an inspiring Product Owner in 7 months was incredible—one of the most successful projects and teams he's ever worked with. Self-reflection Question: If you had to choose between a Product Owner with deep Agile certification and no business skills, or one with strong business acumen and willingness to learn—which would serve your team better? The Bad Product Owner: The PONO—Product Owner in Name Only "The team never saw the PO until the showcase. And so, the team would come along with work that they deemed was finished, and the product owner had not seen it before because he wasn't around. So he would be seeing it for the first time in the showcase, and he would then accept or reject the work in the showcase, in front of other stakeholders." - Darryl Wright The most destructive anti-pattern Darryl has witnessed was the MIA—Missing in Action—Product Owner, someone who was a Product Owner in Name Only (PONO). This senior business person was too busy to spend time with the team, only appearing at the sprint showcase. The damage this created was systematic and crushing. The team would build work without Product Owner engagement, then present it in the showcase looking to be proud of their accomplishment. The PO, seeing it for the first time, would accept or reject the work in front of stakeholders. When he rejected it, the team was crushed, deflated, demoralized, and made to look like fools in front of senior leaders—essentially thrown under the bus. This pattern violates multiple principles of Agile teamwork. First, there's no feedback loop during the sprint, so the team works blind, hoping they're building the right thing. Second, the showcase becomes a validation ceremony rather than a collaborative feedback session, creating a dynamic of subservience rather than curiosity. The team seeks approval instead of engaging as explorers discovering what delivers customer value together. Third, the PO positions themselves as judge rather than coach—extracting themselves from responsibility for what's delivered while placing all blame on the team. As Deming's quote reminds us, "A leader is a coach, not a judge." When the PO takes the judge role, they're betraying fundamental Agile values. The responsibility for what the team delivers belongs strictly to the Product Owner; the team owns how it's delivered. When Darryl encounters this situation as a Scrum Master, he lobbies intensely with the PO: "Even if you can't spare any other time for the entire sprint, give us just one hour the night before the showcase." That single hour lets the team preview what they'll present, getting early yes/no decisions so they never face public rejection. The basic building block of any Agile or Scrum way of working is an empowered team—and this anti-pattern strips all empowerment away. Self-reflection Question: Does your Product Owner show up as a coach who's building something together with the team, or as a judge who pronounces verdicts? How does that dynamic shape what your team is willing to try? [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. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] 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.

31 Okt 14min

Beyond Vanity Metrics—Defining Real Success for Scrum Masters | Darryl Wright

Beyond Vanity Metrics—Defining Real Success for Scrum Masters | Darryl Wright

Darryl Wright: The Retrospective Formats That Actually Generate Change 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. "My success is, how much have I helped the team achieve what they want? If what they want is to uplift quality, or to reduce their time to market, well then, my success is helping them achieve that." - Darryl Wright When Darryl enters a new organization, he's often told his success will be measured by percentage of Agile adoption or team maturity assessment scores. His response is direct: those are vanity metrics that show something for its own sake, not real success. True success requires multiple measures, carefully balanced to prevent gaming and to capture both the human and business dimensions of work. Darryl advocates balancing quantitative metrics like lead time and flow efficiency with qualitative measures like employee happiness and team self-assessment of productivity. He balances business outcomes like customer satisfaction and revenue with humanity metrics that track the team's journey toward high performance. Most importantly, Darryl believes his success metrics should be co-created with the team. If he's there to help the team, then success must be defined by how much he's helped them achieve what they want—not what he wants. When stakeholders fixate on output metrics like "more story points," Darryl uses a coaching approach to shift the conversation toward outcomes and value. "Would you be happy if your team checked off more boxes, but your customers were less happy?" he asks. This opens space for exploring what they really want to achieve and why it matters. The key is translating outputs into impacts, helping people articulate the business value or customer experience improvement they're actually seeking. As detailed in Better Value, Sooner, Safer, Happier by Jonathan Smart, comprehensive dashboards can track value across multiple domains simultaneously—balancing speed with quality, business success with humanity, quantitative data with qualitative experience. When done well, Agile teams can be highly productive, highly successful, and have high morale at the same time. We don't have to sacrifice one for the other—we can have both. Self-reflection Question: If your team could only track two metrics for the next sprint, what would they choose? What would you choose? And more importantly, whose choice should drive the selection? Featured Retrospective Format for the Week: The 4 L's and Three Little Pigs Darryl offers two favorites, tailored to different contexts. For learning environments, he loves the 4 L's retrospective: Liked, Learned, Lacked, and Longed For. This format creates space for teams to reflect on their learning journey, surfacing insights about what worked, what was missing, and what they aspire to moving forward. For operational environments, he recommends the Three Little Pigs retrospective, which brilliantly surfaces team strengths and weaknesses through a playful metaphor. The House of Straw represents things the team is weak at—nothing stands up, everything falls over. The House of Sticks is things they've put structure around, but it doesn't really work. The House of Bricks represents what they're solid on, what they can count on every time. Then comes the most important part: identifying the Big Bad Wolf—the scary thing, the elephant in the room that nobody wants to talk about but everyone knows is there. This format creates psychological safety to discuss the undiscussable. Darryl emphasizes two critical success factors for retrospectives: First, vary your formats. Teams that hear the same questions sprint after sprint will disengage, asking "why are you asking me again?" Different questions provide different lenses, generating fresh insights. Second, ensure actions come out of every retro. Nothing kills engagement faster than suggestions disappearing into the void. When people see their ideas lead to real changes, they'll eagerly return to the next retrospective. And don't forget to know your team—if they're sports fans, use sports retros; if they're scientists, use space exploration themes. Just don't make the mistake of running a "sailboat retro" with retiring mainframe engineers who'll ask if you think they're kindergarten children. For more retrospective formats, check out Retromat. [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. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] 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.

30 Okt 15min

Why AI Adoption Will Fail Just Like Agile Did—Unless We Change | Darryl Wright

Why AI Adoption Will Fail Just Like Agile Did—Unless We Change | Darryl Wright

Darryl Wright: Why AI Adoption Will Fail Just Like Agile Did—Unless We Change 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. "People are looking to AI to solve their problems, and they're doing it in the same way that they previously looked to Agile to solve their problems for them. The problem with that is, of course, that Agile doesn't solve problems for you. What it does is it shines a light on where your problems are." - Darryl Wright The world has gone AI crazy, and Darryl sees history repeating itself in troubling ways. Organizations are rushing to adopt AI with the same magical thinking they once applied to Agile—believing that simply implementing the tool will solve their fundamental problems. But just as Agile reveals problems rather than solving them, AI will do the same. Worse, AI threatens to accelerate existing problems: if you have too many things moving at once, AI won't fix that, it will amplify the chaos. If you automate a bad process, you've simply locked in badness at higher speed. As Darryl points out, when organizations don't understand that AI requires them to still do the hard work of problem-solving, they're setting themselves up for disillusionment, and in five or twenty years, we'll hear "AI is dead" just like we now hear "Agile is dead." The challenge for Scrum Masters and Agile coaches is profound: how do you help people with something they don't know they need? The answer lies in returning to first principles. Before adopting any tool—whether Agile or AI—organizations must clearly define the problem they're trying to solve. As Einstein reportedly said, "If I had an hour to solve a problem, I'd spend 55 minutes thinking about the problem and 5 minutes thinking about solutions." Value stream mapping becomes essential, allowing teams to visualize where humans and AI agents should operate, with clear handovers and explicit policies. The cognitive load on software teams will increase dramatically as AI generates more code, more options, and more complexity. Without clear thinking about problems and deliberate design of systems, AI adoption will follow the same disappointing trajectory as many Agile adoptions—lots of activity, little improvement, and eventually, blame directed at the tool rather than the system. Self-reflection Question: Are you adopting AI to solve a clearly defined problem, or because everyone else is doing it? If you automated your current process with AI, would you be locking in excellence or just accelerating dysfunction? [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. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] 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.

29 Okt 18min

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

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

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. [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. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] 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.

28 Okt 15min

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