Carmela Then: When Remote Teams Stop Listening—The Silent Killer of Agile Collaboration 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. "Two minutes into it, my mind's starting to wander and I started to do my own thing." - Carmela Then Carmela paints a vivid picture of a distributed team stretched across Sydney, New Zealand, India, and beyond—a team where communication had quietly become the enemy of progress. The warning signs were subtle at first: in meetings with 20 people on the call, only two or three would speak for the entire hour or two, with no visual aids, no PowerPoints, no drawings. The result? Within minutes, attention drifted, and everyone assumed someone else understood the message. The speakers believed their ideas had landed; the listeners had already tuned out. This miscommunication compounded sprint after sprint until, just two months before go-live, the team was still discussing proof of concept. Trust eroded completely, and the Product Owner resorted to micromanagement—tracking developers by the hour, turning what was supposed to be an Agile team into a waterfall nightmare. Carmela points to a critical missing element: the Scrum Master had been assigned delivery management duties, leaving no one to address the communication dysfunction. The lesson is clear—in remote, cross-cultural teams, you cannot simply talk your way through complex ideas; you need visual anchors, shared artifacts, and constant verification that understanding has truly been achieved. In this segment, we talk about the importance of visual communication in remote teams and psychological safety. Self-reflection Question: How do you verify that your message has truly landed with every team member, especially when working across time zones and cultures? Featured Book of the Week: How to Win Friends and Influence People by Dale Carnegie Carmela recommends How to Win Friends and Influence People by Dale Carnegie, a timeless classic that remains essential reading for every Scrum Master. As Carmela explains, "We work with people—customers are people, and our team, they are human beings as well. Whether we want it or not, we are leaders, we are coaches, and sometimes we could even be mentors." Written during the Great Depression and predating software entirely, this book emphasizes that relationships and understanding people are the foundation of personal and professional success. Carmela was first introduced to the book by a successful person outside of work who advised her not just to read it once, but to revisit it every year. For Scrum Masters navigating team dynamics, stakeholder relationships, and the human side of Agile, Carnegie's principles remain as relevant today as they were nearly a century ago. [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 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. You can link with Carmela Then on LinkedIn.
Carmela Then: The Scrum Master Who Learned That Perfect Boards Don't Build Perfect 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 failure part is, instead of leading the team to work toward a common vision, I was probably one of the persons that helped the divide." - Carmela Then Carmela shares a vulnerable story from her first Scrum Master role at a bank. Armed with training, certifications, and the ability to build a beautiful physical Scrum board with perfectly straight lines, she believed she was ready to lead. But Carmela quickly discovered a crucial truth: mastering the mechanics of Scrum is vastly different from serving a team's real needs. Instead of showing up as a humble learner willing to grow alongside her team, she put on a facade of competence and confidence. When two Product Owners began fighting for dominance, rather than stepping back and focusing the teams on their shared purpose, Carmela found herself drawn into the political battle, supporting one PO over the other. The result was devastating—a toxic environment where one PO was demoted, and talented team members left the organization entirely. Looking back, Carmela recognizes that her failure wasn't about the Scrum board or ceremonies; it was about not putting the customer and common goals at the center. She learned that Scrum Masters must lead with humility, focus on outcomes rather than egos, and help teams unite rather than divide. In this episode, we refer to John C. Maxwell and Failing Forward by John C. Maxwell. Self-reflection Question: When was the last time you prioritized looking competent over truly serving your team's needs, and what did that cost you? [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 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. You can link with Carmela Then on LinkedIn.
Steve Martin: Coaching Product Owners to Be the Voice of the Customer In this episode, we refer to Henrik Kniberg's "Product Owner in a Nutshell" video and Product Ownership by Geoff Watts. The Great Product Owner: Rob Gard's Customer Obsession 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 role of the PO really is to help the team empathize with the user, the customer of the product, because that's how they can develop great solutions." - Steve Martin Rob Gard worked at a fintech firm and is now CPO of a major fintech company. Steve describes him as having a brilliant mind and being a real agileist—someone Steve learned a huge amount about Agile from. Rob's defining characteristic was his absolute obsession with the user. Everything focused on customer pain points. Working with engineering teams serving military customers, Rob held regular workshops with those customers to understand their pain firsthand. He was literally the voice of the customer, not theoretically but practically. Rob pushed and challenged teams to be more innovative, always looking for better ways of providing better software. His gift was communication—specifically, briefing the team on the problem rather than just reading out stories in refinement sessions. This is the anti-pattern many Product Owners fall into: going through the motions, reading requirements without context. Real product ownership, as Rob demonstrated, is telling a story that helps the team empathize and understand the pain. When teams can internalize customer problems, they develop better solutions. Rob's ability to communicate the problem into the minds of teams enabled them to serve customers more effectively. This is the essence of great Product Ownership: not being a proxy for management, not juggling multiple teams, but being deeply connected to customer pain and translating that pain into context the team can work with. Self-reflection Question: Do your refinement sessions tell stories that help the team empathize with customer pain, or do you just read out requirements? The Bad Product Owner: Proxies for Management Instead of Customer Advocates 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. "They weren't a team, they were a group of individuals working on multiple different projects." - Vasco Duarte Steve emphasizes that Product Owners often have great intentions but struggle due to lack of training and coaching. The anti-patterns are systemic: commercial managers "dressed up" as Product Owners without understanding the role. Project managers transitioning to PO roles—though Steve notes PMs can make really good POs with proper support. The most damaging pattern is Product Owners spread across multiple teams, having very little time to focus on any single team or their customers. These POs become proxies—representing the voice of senior management rather than the voice of the customer. They cascade requirements downward instead of bringing customer insights upward. The solution isn't to criticize these struggling Product Owners but to help them understand their role and see what good looks like. Steve recommends Henrik Kniberg's "Product Owner in a Nutshell" video—15 minutes, 15 years old, still profoundly relevant. He also points to Product Ownership by Geoff Watts and formal training like CSPO or IC Agile Product Ownership courses. The fundamental issue is meeting Product Owners where they are, providing coaching and support to transform them from management proxies into customer advocates. When POs understand their role as empathy builders between customers and teams, everything changes. Self-reflection Question: Is your Product Owner the voice of senior management or the voice of the customer? [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 Steve Martin You can link with Steve Martin on LinkedIn. Steve is an Agile Coach, mentor, and founder of The Agile Master Academy. After over 14 years leading Agile transformation programmes, he's on a mission to elevate Scrum Masters—building high-performing teams, measurable impact, and influence—and raising industry standards of Agile mastery through practical, evidence-led coaching. You can also find Steve's insights on his YouTube channel: Agile Mastery Show.
Steve Martin: Making Scrum Master Success Visible with OKRs That Actually Work 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. "It is not the retrospective that is the success of the retrospective. It is the ownership and accountability where you take improvements after the session." - Steve Martin The biggest problem for Scrum Masters isn't just defining success—it's being able to shout it from the rooftops with tangible evidence. Steve champions OKRs as an amazing way to define and measure success, but with a critical caveat: they've historically been poorly written and implemented in dark rooms by executives, then cascaded down to teams who never bought in. Steve's approach is radically different. Create OKRs collectively with the team, stakeholders, and end users. Start by focusing on the pain—what problems or pain points do customers, users, and stakeholders actually experience? Make the objective the goal to solve that problem, then define how to measure progress with key results. When everyone is bought in—Scrum Master, engineers, Product Owner, stakeholders, leaders—all pulling in the same direction, magic happens. Make progress visible on the wall like a speedometer, showing exactly where you are at any moment. For an e-commerce checkout, the problem might be too many steps. The objective: reduce pain for users checking out quickly. The baseline: 15 steps today. The target: 5 clicks in three months. Everyone can see the dial moving. Everything should focus on the customer as the endpoint. The challenge is distinguishing between targets imposed from above ("increase sales by 10%") and objectives created collaboratively based on factors the team can actually control. Find what you can control first, work with customers to understand their pain, and start from there. Self-reflection Question: Can you articulate your team's success with specific, measurable outcomes that everyone—from developers to executives—understands and owns? Featured Retrospective Format for the Week: Post-Retro Actions and Ownership The success of a retrospective isn't the retrospective itself—it's what happens after. Steve emphasizes that ownership and accountability matter more than the format of the session. Take improvements from the retrospective and bring them into the sprint as user stories with clear structure: this is the problem, how we'll solve it, and how we'll measure impact. Assign collective ownership—not just a single person, but the whole team owns the improvement. Then bring improvements into the demo so the team showcases what changed. This creates cultural transformation: the team themselves want to bring improvements, not just because the Scrum Master pushed them. For ongoing impediments, conduct root cause analysis. Create a system to escalate issues beyond the team's control—make these visible on another board or with the leadership team. Find peers in pain: teams with the same problems can work together collectively. The retrospective format matters less than this system of ownership, action, measurement, and visibility. Stop retrospective theatre—going through the motions without taking action. Make improvements real by treating them like any other work: visible, measured, owned, and demonstrated. [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 Steve Martin You can link with Steve Martin on LinkedIn. Steve is an Agile Coach, mentor, and founder of The Agile Master Academy. After over 14 years leading Agile transformation programmes, he's on a mission to elevate Scrum Masters—building high-performing teams, measurable impact, and influence—and raising industry standards of Agile mastery through practical, evidence-led coaching. You can also find Steve's insights on his YouTube channel: Agile Mastery Show.
Steve Martin: Why Agile Fatigue Means We Need to Change Our Approach 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. "We teach transformation, we support transformation, we help change, but we don't really understand what they're changing from." - Steve Martin Steve believes Agile as a whole is on the back foot, possibly regressing. There's palpable fatigue in the industry, and transformation in its current form hasn't been the success we hoped. Organizations still need to work in a state of agility—making rapid decisions, aligning teams, delivering value at pace—but they're exhausted by how we've implemented Agile. As Agile professionals, Steve argues, we have a responsibility to take stock and reflect on what's not working. The problem isn't that organizations don't need agility; it's that we've been force-feeding them frameworks without understanding their context. Steve invokes an ancient principle: "When the student is ready, the teacher will appear." But we haven't waited for readiness—we've barged in with Big Bang transformations, bringing 10, 15, or 20 Agile coaches to "save the world." The solution requires meeting people where they are, understanding what they're changing from, not just what they're changing to. Steve's coaching conversation centers on a radical idea: stop trying to help teams that don't want to be helped. Focus on teams already interested in incremental, adaptable delivery. Run small pilots, learn what works, then scale when ready. The age of prescriptive transformation is over. We need to adapt to the reality of the moment, experiment with what works, and have the courage to change the plan when our approach isn't working. Self-reflection Question: Are you forcing Agile on teams that aren't ready, or are you working with those who genuinely want to improve their delivery approach? [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 Steve Martin You can link with Steve Martin on LinkedIn. Steve is an Agile Coach, mentor, and founder of The Agile Master Academy. After over 14 years leading Agile transformation programmes, he's on a mission to elevate Scrum Masters—building high-performing teams, measurable impact, and influence—and raising industry standards of Agile mastery through practical, evidence-led coaching. You can also find Steve's insights on his YouTube channel: Agile Mastery Show.
Steve Martin: When a Distributed Team's Energy Vanishes into the Virtual Void 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. "They weren't a team, they were a group of individuals working on multiple different projects." - Vasco Duarte (describing Steve's team situation) The infrastructure team looked promising on paper: Product Owner in Italy, hardware engineers in Budapest, software engineers in Bucharest, designers in the UK. The team started with energy and enthusiasm, but within a month, something shifted. People stopped showing up for daily stand-ups. Cameras went dark during meetings. Engagement in retrospectives withered. This wasn't just about being distributed—plenty of teams work across time zones successfully. The problem ran deeper. The Scrum Master had a conflict of interest, serving dual roles as both facilitator and engineer. Team members were simultaneously juggling three or four other projects, treating this work as just another item on an impossibly long list. Steve spent a couple of months watching the deterioration before recognizing the root cause: there was no leadership sponsorship or buy-in. Stakeholders weren't invested. The team wasn't actually a team—they were individuals happening to work on the same project. Steve considers this a failure because he couldn't solve it. Sometimes, the absence of organizational support creates an unsolvable puzzle. Without leadership commitment, even the most skilled Scrum Master can't manufacture the conditions for team success. In this episode, we refer to The Phoenix Project by Gene Kim, a book about organizational culture disguised as a DevOps novel. Self-reflection Question: Is your team truly dedicated to one mission, or are they a collection of individuals spread across competing priorities? Featured Book of the Week: The Phoenix Project by Gene Kim "There's a lot of good lightning bulb moments that go off." - Steve Martin Steve describes The Phoenix Project as a book about culture, not just DevOps. Written like a novel following a mock company, it creates continuous light bulb moments for readers. The book resonated deeply with Steve because it exposed patterns he'd experienced firsthand—particularly the anti-pattern of single points of failure. Steve had worked with an engineer who would spend entire weekends doing releases, holding everything in his head, then burning out and taking three days off to recover. This engineer was the bottleneck, the single point of failure that put the entire system at risk. The Phoenix Project illuminates how knowledge hoarding and dependency on individuals creates organizational fragility. The solution isn't just technical—it's cultural. Teams need to share knowledge and understanding, deliberately de-risking the concentration of expertise in one person's mind. Steve recommends this book for anyone trying to understand why organizational transformation requires more than process changes—it demands a fundamental shift in how teams think about knowledge, risk, and collaboration. [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 Steve Martin You can link with Steve Martin on LinkedIn. Steve is an Agile Coach, mentor, and founder of The Agile Master Academy. After over 14 years leading Agile transformation programmes, he's on a mission to elevate Scrum Masters—building high-performing teams, measurable impact, and influence—and raising industry standards of Agile mastery through practical, evidence-led coaching. You can also find Steve's insights on his YouTube channel: Agile Mastery Show.
Steve Martin: When the Gospel of Agile Becomes a Barrier to 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. "It took me a while to realize that that's what I was doing. I felt the reason wasn't working was them, it wasn't me." - Steve Martin Steve carried the Scrum Guide like a Bible in his early days as an Agile coach. He was a purist—convinced he had an army of Agile practitioners behind him, ready to transform every team he encountered. When teams questioned his approach, he would shut down the conversation: "Don't challenge me on this, because this is how it's supposed to be." But pushing against the tide and spreading the gospel created something unexpected: resistance. The more Steve insisted on his purist view, the more teams pushed back. It took him a couple of years to recognize the pattern. The problem wasn't the teams refusing to change—it was his approach. Steve's breakthrough came when he started teaching and realized he needed to meet people where they are, not force them to come to him. Like understanding a customer's needs, he learned to build empathy with teams, Product Owners, and leaders. He discovered the power of creating personas for the people he was coaching, understanding their context before prescribing solutions. The hardest part wasn't learning this lesson—it was being honest about his failures and admitting that his righteous certainty had been the real impediment to transformation. Self-reflection Question: Are you meeting your teams where they are, or are you pushing them toward where you think they should be? [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 Steve Martin You can link with Steve Martin on LinkedIn. Steve is an Agile Coach, mentor, and founder of The Agile Master Academy. After over 14 years leading Agile transformation programmes, he's on a mission to elevate Scrum Masters—building high-performing teams, measurable impact, and influence—and raising industry standards of Agile mastery through practical, evidence-led coaching. You can also find Steve's insights on his YouTube channel: Agile Mastery Show.
BONUS: The Operating System for Software-Native Organizations - The Five Core Principles In this BONUS episode, the final installment of our Special Xmas 2025 reflection on Software-native businesses, we explore the five fundamental principles that form the operating system for software-native organizations. Building on the previous four episodes, this conversation provides the blueprint for building organizations that can adapt at the speed of modern business demands, where the average company lifespan on the S&P 500 has dropped from 33 years in the 1960s to a projected 12 years by 2027. The Challenge of Adaptation "What we're observing in Ukraine is adaptation happening at a speed that would have been unthinkable in traditional military contexts - new drone capabilities emerge, countermeasures appear within days, and those get countered within weeks." The opening draws a powerful parallel between the rapid adaptation we're witnessing in drone warfare and the existential threats facing modern businesses. While our businesses aren't facing literal warfare, they are confronting dramatic disruption. Clayton Christensen documented this in "The Innovator's Dilemma," but what he observed in the 1970s and 80s is happening exponentially faster now, with software as the accelerant. If we can improve businesses' chances of survival even by 10-15%, we're talking about thousands of companies that could thrive instead of fail, millions of jobs preserved, and enormous value created. The central question becomes: how do you build an organization that can adapt at this speed? Principle 1: Constant Experimentation with Tight Feedback Loops "Everything becomes an experiment. Not in the sense of being reckless or uncommitted, but in being clear about what we're testing and what we expect to learn. I call this: work like a scientist: learning is the goal." Software developers have practiced this for decades through Test-Driven Development, but now this TDD mindset is becoming the ruling metaphor for managing products and entire businesses. The practice involves framing every initiative with three clear elements: the goal (what are we trying to achieve?), the action (what specific thing will we do?), and the learning (what will we measure to know if it worked?). When a client says "we need to improve our retrospectives," software-native organizations don't just implement a new format. Instead, they connect it to business value - improving the NPS score for users of a specific feature by running focused retrospectives that explicitly target user pain points and tracking both the improvements implemented and the actual NPS impact. After two weeks, you know whether it worked. The experiment mindset means you're always learning, never stuck. This is TDD applied to organizational change, and it's powerful because every process change connects directly to customer outcomes. Principle 2: Clear Connection to Business Value "Software-native organizations don't measure success by tasks completed, story points delivered, or features shipped. Or even cycle time or throughput. They measure success by business outcomes achieved." While this seems obvious, most organizations still optimize for output, not outcomes. The practice uses Impact Mapping or similar outcome-focused frameworks where every initiative answers three questions: What business behavior are we trying to change? How will we measure that change? What's the minimum software needed to create that change? A financial services client wanted to "modernize their reporting system" - a 12-month initiative with dozens of features in project terms. Reframed through a business value lens, the goal became reducing time analysts spend preparing monthly reports from 80 hours to 20 hours, measured by tracking actual analyst time, starting with automating just the three most time-consuming report components. The first delivery reduced time to 50 hours - not perfect, but 30 hours saved, with clear learning about which parts of reporting actually mattered. The organization wasn't trying to fulfill requirements; they were laser focused on the business value that actually mattered. When you're connected to business value, you can adapt. When you're committed to a feature list, you're stuck. Principle 3: Software as Value Amplifier "Software isn't just 'something we do' or a support function. Software is an amplifier of your business model. If your business model generates $X of value per customer through manual processes, software should help you generate $10X or more." Before investing in software, ask whether this can amplify your business model by 10x or more - not 10% improvement, but 10x. That's the threshold where software's unique properties (zero marginal cost, infinite scale, instant distribution) actually matter, and where the cost/value curve starts to invert. Remember: software is still the slowest and most expensive way to check if a feature would deliver value, so you better have a 10x or more expectation of return. Stripe exemplifies this principle perfectly. Before Stripe, accepting payments online required a merchant account (weeks to set up), integration with payment gateways (months of development), and PCI compliance (expensive and complex). Stripe reduced that to adding seven lines of code - not 10% easier, but 100x easier. This enabled an entire generation of internet businesses that couldn't have existed otherwise: subscription services, marketplaces, on-demand platforms. That's software as amplifier. It didn't optimize the old model; it made new models possible. If your software initiatives are about 5-10% improvements, ask yourself: is software the right medium for this problem, or should you focus where software can create genuine amplification? Principle 4: Software as Strategic Advantage "Software-native organizations use software for strategic advantage and competitive differentiation, not just optimization, automation, or cost reduction. This means treating software development as part of your very strategy, not a way to implement a strategy that is separate from the software." This concept, discussed with Tom Gilb and Simon Holzapfel on the podcast as "continuous strategy," means that instead of creating a strategy every few years and deploying it like a project, strategy and execution are continuously intertwined when it comes to software delivery. The practice involves organizing around competitive capabilities that software uniquely enables by asking: How can software 10x the value we generate right now? What can we do with software that competitors can't easily replicate? Where does software create a defensible advantage? How does our software create compounding value over time? Amazon Web Services didn't start as a product strategy but emerged from Amazon building internal capabilities to run their e-commerce platform at scale. They realized they'd built infrastructure that was extremely hard to replicate and asked: "What if we offered it to others?" AWS became Amazon's most profitable business - not because they optimized their existing retail business, but because they turned an internal capability into a strategic platform. The software wasn't supporting the strategy - the software became the strategy. Compare this to companies that use software just for cost reduction or process optimization - they're playing defense. Software-native companies use software to play offense, creating capabilities that change the competitive landscape. Continuous strategy means your software capabilities and your business strategy evolve together, in real-time, not in annual planning cycles. Principle 5: Real-Time Observability and Adaptive Systems "Software-native organizations use telemetry and real-time analytics not just to understand their software, but to understand their entire business and adapt dynamically. Observability practices from DevOps are actually ways of managing software delivery itself. We're bootstrapping our own operating system for software businesses." This principle connects back to Principle 1 but takes it to the organizational level. The practice involves building systems that constantly sense what's happening and can adapt in real-time: deploy with feature flags so you can turn capabilities on/off instantly, use A/B testing not just for UI tweaks but for business model experiments, instrument everything so you know how users actually behave, and build feedback loops that let the system respond automatically. Social media companies and algorithmic trading firms already operate this way. Instagram doesn't deploy a new feed algorithm and wait six months to see if it works - they're constantly testing variations, measuring engagement in real-time, adapting the algorithm continuously. The system is sensing and responding every second. High-frequency trading firms make thousands of micro-adjustments per day based on market signals. Imagine applying this to all businesses: a retail company that adjusts pricing, inventory, and promotions in real-time based on demand signals; a healthcare system that dynamically reallocates resources based on patient flow patterns; a logistics company whose routing algorithms adapt to traffic, weather, and delivery success rates continuously. This is the future of software-native organizations - not just fast decision-making, but systems that sense and adapt at software speed, with humans setting goals and constraints but software executing continuous optimization. We're moving from "make a decision, deploy it, wait to see results" to "deploy multiple variants, measure continuously, let the system learn." This closes the loop back to Principle 1 - everything is an experiment, but now the experiments run automatically at scale with near real-time signal collection and decision making. It's Experiments All The Way Down "We established that software has become societa
BONUS: Breaking Through The Organizational Immune System - Why Software-Native Organizations Are Still Rare With Vasco Duarte In this BONUS episode, we explore the organizational barriers that prevent companies from becoming truly software-native. Despite having proof that agile, iterative approaches work at scale—from Spotify to Amazon to Etsy—most organizations still struggle to adopt these practices. We reveal the root cause behind this resistance and expose four critical barriers that form what we call "The Organizational Immune System." This isn't about resistance to change; it's about embedded structures, incentives, and mental models that actively reject beneficial transformation. The Root Cause: Project Management as an Incompatible Mindset "Project management as a mental model is fundamentally incompatible with software development. And will continue to be, because 'project management' as an art needs to support industries that are not software-native." The fundamental problem isn't about tools or practices—it's about how we think about work itself. Project management operates on assumptions that simply don't hold true for software development. It assumes you can know the scope upfront, plan everything in advance, and execute according to that plan. But software is fundamentally different. A significant portion of the work only becomes visible once you start building. You discover that the "simple" feature requires refactoring three other systems. You learn that users actually need something different than what they asked for. This isn't poor planning—it's the nature of software. Project management treats discovery as failure ("we missed requirements"), while software-native thinking treats discovery as progress ("we learned something critical"). As Vasco points out in his NoEstimates work, what project management calls "scope creep" should really be labeled "value discovery" in software—because we're discovering more value to add. Discovery vs. Execution: Why Software Needs Different Success Metrics "Software hypotheses need to be tested in hours or days, not weeks, and certainly not months. You can't wait until the end of a 12-month project to find out your core assumption was wrong." The timing mismatch between project management and software development creates fundamental problems. Project management optimizes for plan execution with feedback loops that are months or years long, with clear distinctions between teams doing requirements, design, building, and testing. But software needs to probe and validate assumptions in hours or days. Questions like "Will users actually use this feature?" or "Does this architecture handle the load?" can't wait for the end of a 12-month project. When we finally discover our core assumption was wrong, we need to fully replan—not just "change the plan." Software-native organizations optimize for learning speed, while project management optimizes for plan adherence. These are opposing and mutually exclusive definitions of success. The Language Gap: Why Software Needs Its Own Vocabulary "When you force software into project management language, you lose the ability to manage what actually matters. You end up tracking task completion while missing that you're building the wrong thing." The vocabulary we use shapes how we think about problems and solutions. Project management talks about tasks, milestones, percent complete, resource allocation, and critical path. Software needs to talk about user value, technical debt, architectural runway, learning velocity, deployment frequency, and lead time. These aren't just different words—they represent fundamentally different ways of thinking about work. When organizations force software teams to speak in project management terms, they lose the ability to discuss and manage what actually creates value in software development. The Scholarship Crisis: An Industry-Wide Knowledge Gap "Agile software development represents the first worldwide trend in scholarship around software delivery. But most organizational investment still goes into project management scholarship and training." There's extensive scholarship in IT, but almost none about delivery processes until recently. The agile movement represents the first major wave of people studying what actually works for building software, rather than adapting thinking from manufacturing or construction. Yet most organizational investment continues to flow into project management certifications like PMI and Prince2, and traditional MBA programs—all teaching an approach with fundamental problems when applied to software. This creates an industry-wide challenge: when CFOs, executives, and business partners all think in project management terms, they literally cannot understand why software needs to work differently. The mental model mismatch isn't just a team problem—it's affecting everyone in the organization and the broader industry. Budget Cycles: The Project Funding Trap "You commit to a scope at the start, when you know the least about what you need to build. The budget runs out exactly when you're starting to understand what users actually need." Project thinking drives project funding: organizations approve a fixed budget (say $2M over 9 months) to deliver specific features. This seems rational and gives finance predictability, but it's completely misaligned with how software creates value. Teams commit to scope when they know the least about what needs building. The budget expires just when they're starting to understand what users actually need. When the "project" ends, the team disbands, taking all their accumulated knowledge with them. Next year, the cycle starts over with a new project, new team, and zero retained context. Meanwhile, the software itself needs continuous evolution, but the funding structure treats it as a series of temporary initiatives with hard stops. The Alternative: Incremental Funding and Real-Time Signals "Instead of approving $2M for 9 months, approve smaller increments—maybe $200K for 6 weeks. Then decide whether to continue based on what you've learned." Software-native organizations fund teams working on products, not projects. This means incremental funding decisions based on learning rather than upfront commitments. Instead of detailed estimates that pretend to predict the future, they use lightweight signals from the NoEstimates approach to detect problems early: Are we delivering value regularly? Are we learning? Are users responding positively? These signals provide more useful information than any Gantt chart. Portfolio managers shift from being "task police" asking "are you on schedule?" to investment curators asking "are we seeing the value we expected? Should we invest more, pivot, or stop?" This mirrors how venture capital works—and software is inherently more like VC than construction. Amazon exemplifies this approach, giving teams continuous funding as long as they're delivering value and learning, with no arbitrary end date to the investment. The Business/IT Separation: A Structural Disaster "'The business' doesn't understand software—and often doesn't want to. They think in terms of features and deadlines, not capabilities and evolution." Project thinking reinforces organizational separation: "the business" defines requirements, "IT" implements them, and project managers coordinate the handoff. This seems logical with clear specialization and defined responsibilities. But it creates a disaster. The business writes requirements documents without understanding what's technically possible or what users actually need. IT receives them, estimates, and builds—but the requirements are usually wrong. By the time IT delivers, the business need has changed, or the software works but doesn't solve the real problem. Sometimes worst of all, it works exactly as specified but nobody wants it. This isn't a communication problem—it's a structural problem created by project thinking. Product Thinking: Starting with Behavior Change "Instead of 'build a new reporting dashboard,' the goal is 'reduce time finance team spends preparing monthly reports from 40 hours to 4 hours.'" Software-native organizations eliminate the business/IT separation by creating product teams focused on outcomes. Using approaches like Impact Mapping, they start with behavior change instead of features. The goal becomes a measurable change in business behavior or performance, not a list of requirements. Teams measure business outcomes, not task completion—tracking whether finance actually spends less time on reports. If the first version doesn't achieve that outcome, they iterate. The "requirement" isn't sacred; the outcome is. "Business" and "IT" collaborate on goals rather than handing off requirements. They're on the same team, working toward the same measurable outcome with no walls to throw things over. Spotify's squad model popularized this approach, with each squad including product managers, designers, and engineers all focused on the same part of the product, all owning the outcome together. Risk Management Theater: The Appearance of Control "Here's the real risk in software: delivering software that nobody wants, and having to maintain it forever." Project thinking creates elaborate risk management processes—steering committees, gate reviews, sign-offs, extensive documentation, and governance frameworks. These create the appearance of managing risk and make everyone feel professional and in control. But paradoxically, the very practices meant to manage risk end up increasing the risk of catastrophic failure. This mirrors Chesterton's Fence paradox. The real risk in software isn't about following the plan—it's delivering software nobody wants and having to maintain it forever. Every line of code becomes a maintenance burden. If it's not delivering value, you're paying the cost forever or paying additional cost to re
Xmas Special: Recovering the Essence of Agile - What's Already Working in Software-Native Organizations 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. References for Further Reading A book on the shift from "projects" to "products": "Project to Product" by Mik Kersten About Vasco Duarte 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. You can link with Vasco Duarte on LinkedIn.
Xmas Special: Why project management tools fail software development - and what works instead! In this BONUS episode, we dive deep into The Project Management Trap, continuing our exploration from Episode 1 where we established that software is societal infrastructure being managed with tools from the 1800s. We examine why project management frameworks - designed for building railroads and ships - are fundamentally misaligned with software development, and what happens when we treat living capabilities like construction projects with defined endpoints. The Origin Story - Where Project Management Came From "The problem isn't that project management is bad. The problem is that software isn't building a railroad or a building, or setting up a process that will run forever (like a factory)." Project management emerged from industries with hard physical constraints - building the Transcontinental Railroad in the 1860s, coordinating factory machinery, managing finite and expensive materials. The Gantt chart, invented in the 1910s for factory scheduling, worked brilliantly for coordinating massive undertakings with calculable physics, irreversible decisions, and clear completion points. When the rails met, you were done. When the bridge was built, the project ended. These tools gave us remarkable precision for building ships, bridges, factories, and highways. But software operates in a completely different reality - one where the raw materials are time and brainpower, not minerals and hardware, and where the transformation happens in unique creative moments rather than repeated mechanical movements. The Seductive Clarity Of Project Management Artifacts "In software, we almost never know either of those things with certainty." Project management is tempting for software leaders because it offers comforting certainty. Gantt charts show every task laid out, milestones mark clear progress, "percent complete" gives us a number, and a defined "done" promises relief. The typical software project kickoff breaks down into neat phases: requirements gathering (6 weeks), design (4 weeks), development (16 weeks), testing (4 weeks), deployment (2 weeks) - total 32 weeks, done by Q3. Leadership loves this. Finance can budget it. Everyone can plan around it. But this is false precision. Software isn't pouring concrete where you measure twice and pour once. Every line of code is a hypothesis about what users need and how the system should behave. That 32-week plan assumes we know exactly what to build and exactly how long each piece takes - assumptions that are almost never true in software development. The Completion Illusion "Software products succeed by evolving. Projects end; products adapt." "Done" is the wrong goal for living software. We expand on the Slack story from Episode 1 to illustrate this point. If Slack's team had thought in project terms in 2013, they might have built a functional tool with channels, direct messages, file sharing, and search - shipped on time and on budget by Q2 2014, project complete. But that wasn't the end; it was the beginning. Through continuous user feedback and evolution, Slack added threaded conversations (2017), audio/video calls (2016), workflow automation (2019), and Canvas for knowledge management (2023). Each wasn't maintenance or bug fixing - these were fundamental enhancements. Glass's research shows that 60% of maintenance costs are enhancements, not fixes. By 2021, when Salesforce acquired Slack for $27.7 billion, it bore little resemblance to the 2014 version. The value wasn't in that initial "project" - it was in the continuous evolution. If they'd thought "build it, ship it, done," Slack would have died competing against HipChat and Campfire. When Projects Succeed (Well, Some Do, Anyway) But Software Fails "They tried to succeed at project management. They ended up failing at both software delivery AND project management!" Vasco references his article "The Software Crisis is Real," examining five distinct cases from five different countries that represent what's wrong with project thinking for software. These projects tried hard to do everything right by project management standards: detailed requirements (thousands of pages), milestone tracking, contractor coordination, hitting fixed deadlines, and proper auditing. What they didn't have was iterative delivery to test with real users early, feedback loops to discover problems incrementally, adaptability to change based on learning, or a "living capability" mindset. Project thinking demanded: get all requirements right upfront (otherwise no funding), build it all, test at the end, launch on deadline. Software thinking demands: launch something minimal early, get real user feedback, iterate rapidly, evolve the capability. These projects succeeded at following project management rules but failed at delivering valuable software. What Software-Native Delivery Management Looks Like "Software is unpredictable not because we're bad at planning - it's unpredictable because we're creating novel solutions to complex problems, and in a completely different economic system." If not projects, then what? Vasco has been exploring this question for years, since publishing the NoEstimates book. The answer starts with thinking in products and capabilities, not projects - recognizing that products have ongoing evolution, capabilities are cultivated and improved rather than "delivered" and done, and value is measured in outcomes rather than task completion. Instead of comprehensive planning, we need iteration and constant decision-making based on validated hypotheses: start with "We believe users need X," run experiments by building small and testing with real users, then learn and adapt. Instead of fixed scope, define the problem (not the solution), allow the solution to evolve as you learn, and optimize for learning speed rather than task completion. The contrast is clear: project thinking says "We will build features A, B, C, D, and E by Q3, then we're done." Software-native thinking says "We're solving problem X for users. We'll start with the riskiest hypothesis, build a minimal version, ship it to 100 users next week, and learn whether we're on the right track." The appropriate response to software's inherent unpredictability isn't better planning - it's faster learning. References for Further Reading Vasco Duarte's article on the Software Leadership Workshop newsletter: "The Software Crisis is Real" Glass, Robert L. "Facts and Fallacies of Software Engineering" - Fact 42: "Enhancement is responsible for roughly 60 percent of software maintenance costs. Error correction is roughly 17 percent. Therefore, software maintenance is largely about adding new capability to old software, not fixing it." NoEstimates Book: How To Measure Project Progress Without Estimating Slack evolution timeline: Company history and feature releases The unexpected design challenge behind Slack's new threaded conversations Slack voice and video chat Slack launches admin workflow automation and announcement channels Meet Slack Canvas - Slack's answer to the knowledge management problem. About Vasco Duarte 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. You can link with Vasco Duarte on LinkedIn.
Xmas Special: Software Industry Transformation - Why Software Development Must Mature Welcome to the 2025 Xmas special - a five-episode deep dive into how software as an industry needs to transform. In this opening episode, we explore the fundamental disconnect between how we manage software and what software actually is. From small businesses to global infrastructure, software has become the backbone of modern society, yet we continue to manage it with tools designed for building ships in the 1800s. This episode sets the stage for understanding why software development must evolve into a mature discipline. Software Runs Everything Now "Without any single piece, I couldn't operate - and I'm tiny. Scale this reality up: software isn't just in tech companies anymore." Even the smallest businesses today run entirely on software infrastructure. A small consulting and media business depends on WordPress for websites, Kajabi for courses, Stripe for payments, Quaderno for accounting, plus email, calendar, CRM systems, and AI assistants for content creation. The challenge? We're managing this critical infrastructure with tools designed for building physical structures with fixed requirements - an approach that fundamentally misunderstands what software is and how it evolves. This disconnect has to change. The Oscillation Between Technology and Process "AI amplifies our ability to create software, but doesn't solve the fundamental process problems of maintaining, evolving, and enhancing that software over its lifetime." Software improvement follows a predictable pattern: technology leaps forward, then processes must adapt to manage the new complexity. In the 1960s-70s, we moved from machine code to COBOL and Fortran, which was revolutionary but led to the "software crisis" when we couldn't manage the resulting complexity. This eventually drove us toward structured programming and object-oriented programming as process responses, which, in turn, resulted in technology changes! Today, AI tools like GitHub Copilot, ChatGPT, and Claude make writing code absurdly easy - but writing code was never the hard part. Robert Glass documents in "Facts and Fallacies of Software Engineering" that maintenance typically consumes between 40 and 80 percent of software costs, making "maintenance" probably the most important life cycle phase. We're overdue for a process evolution that addresses the real challenge: maintaining, evolving, and enhancing software over its lifetime. Software Creates An Expanding Possibility Space "If they'd treated it like a construction project ('ship v1.0 and we're done'), it would never have reached that value." Traditional project management assumes fixed scope, known solutions, and a definable "done" state. The Sydney Opera House exemplifies this: designed in 1957, completed in 1973, ten times over budget, with the architect resigning - but once built, it stands with "minimal" (compared to initial cost) maintenance. Software operates fundamentally differently. Slack started as an internal tool for a failed gaming company called Glitch in 2013. When the game failed, they noticed their communication tool was special and pivoted entirely. After launching in 2014, Slack continuously evolved based on user feedback: adding threads in 2017, calls in 2016, workflow builder in 2019, and Canvas in 2023. Each addition changed what was possible in organizational communication. In 2021, Salesforce acquired Slack for $27.7 billion precisely because it kept evolving with user needs. The key difference is that software creates possibility space that didn't exist before, and that space keeps expanding through continuous evolution. Software Is Societal Infrastructure "This wasn't a cyber attack - it was a software update gone wrong." Software has become essential societal infrastructure, not optional and not just for tech companies. In July 2024, a faulty software update from cybersecurity firm CrowdStrike crashed 8.5 million Windows computers globally. Airlines grounded flights, hospitals canceled surgeries, banks couldn't process transactions, and 911 services went down. The global cost exceeded $10 billion. This wasn't an attack - it was a routine update that failed catastrophically. AWS outages in 2021 and 2023 took down major portions of the internet, stopping Netflix, Disney+, Robinhood, and Ring doorbells from working. CloudFlare outages similarly cascaded across daily-use services. When software fails, society fails. We cannot keep managing something this critical with tools designed for building physical things with fixed requirements. Project management was brilliant for its era, but that era isn't this one. The Path Ahead: Four Critical Challenges "The software industry doesn't just need better tools - it needs to become a mature discipline." This five-episode series will address how we mature as an industry by facing four critical challenges: Episode 2: The Project Management Trap - Why we think in terms of projects, dates, scope, and "done" when software is never done, and how this mindset prevents us from treating software as a living capability Episode 3: What's Already Working - The better approaches we've already discovered, including iterative delivery, feedback loops, and continuous improvement, with real examples of companies doing this well Episode 4: The Organizational Immune System - Why better approaches aren't universal, how organizations unconsciously resist what would help them, and the hidden forces preventing adoption Episode 5: Software-Native Organizations - What it means to truly be a software-native organization, transforming how the business thinks, not just using agile on teams Software is too important to our society to keep getting it wrong. We have much of the knowledge we need - the challenge is adoption and evolution. Over the next four episodes, we'll build this case together, starting with understanding why we keep falling into the same trap. References For Further Reading Glass, Robert L. "Facts and Fallacies of Software Engineering" - Fact 41, page 115 CrowdStrike incident: https://en.wikipedia.org/wiki/2024_CrowdStrike_incident AWS outages: 2021 (Dec 7), 2023 (June 13), and November 2025 incidents CloudFlare outages: 2022 (June 21), and November 2025 major incident Slack history and Salesforce acquisition: https://en.wikipedia.org/wiki/Slack_(software) Sydney Opera House: https://en.wikipedia.org/wiki/Sydney_Opera_House About Vasco Duarte 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. You can link with Vasco Duarte on LinkedIn.
Natalia Curusi: From Spreadsheets to Discovery—Helping POs Make the Transition The Great Product Owner: Taking Ownership and Coaching the Team Forward 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. "That person was not just a great product owner, but a great coach—he had excellent communication and stakeholder management skills, and he coached myself as a Scrum Master, showing me how product ownership should look like." - Natalia Curusi Natalia worked with a Product Owner who embodied everything the role should be. He didn't come from a technical background, but he possessed exceptional domain knowledge, outstanding communication skills, and stakeholder management expertise you rarely find in one person. What made him truly remarkable was that he coached everyone around him, including Natalia as the Scrum Master. He demonstrated full empowerment and ownership—making decisions himself rather than constantly escalating to higher management. When risks needed to be taken, he took them with courage and conviction. The team trusted him completely because he balanced business needs with team capacity, always understanding what they could realistically achieve. Over the past five years, this person has been promoted multiple times and now serves as a global director of product, still with the same company. When Natalia thinks about what great product ownership looks like, she thinks of him—someone who combined technical understanding with coaching ability, took genuine ownership of outcomes, and empowered the team through clear vision and decisive leadership. These are exactly the skills that are hardest to find in the market, yet when you find them, the impact is transformative for the entire organization. Self-reflection Question: Does your Product Owner take ownership and make decisions, or do they constantly escalate to higher management, preventing the team from moving forward with confidence? The Bad Product Owner: Assigned Without Training, Support, or Willingness "She was a great subject matter expert with deep domain knowledge, but the organization assigned her the product owner role without her willingness, without training, and while she was already 80% loaded with other responsibilities." - Natalia Curusi Natalia encountered a Product Owner anti-pattern that reveals a systemic organizational failure. The person was an exceptional subject matter expert with incredible domain knowledge, but when the organization decided to adopt Agile, they assigned her the PO role like sticking a label on a box—no training, no consent, no preparation. She was already working at 80% capacity on other responsibilities and had no understanding of what product ownership meant. Frustrated and overwhelmed, she approached the role from a command-and-control mindset. At the project start, she brought a massive spreadsheet of requirements, expecting the team to implement them sequentially. The team tried a different approach, wanting to understand problems before discussing solutions, but the PO surprised everyone by re-introducing the spreadsheet in a later meeting—a clear sign of misalignment and broken trust. Natalia, recognizing this was a battle she couldn't win without organizational support, chose to manage the relationship rather than create open conflict. She worked to mediate between the PO's spreadsheet approach and the team's need for discovery and iterative development. The real anti-pattern wasn't the individual—it was the organization assigning critical roles without providing training, time, or psychological safety. This situation illustrates why product ownership fails: not from bad people, but from bad systems that set people up to fail. Self-reflection Question: When you see a struggling Product Owner, are you addressing the individual's behavior or the systemic conditions that set them up to fail in the first place? [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 Natalia Curusi With over 20 years in software delivery, Natalia Curusi is an expert in Agile Transformations, Delivery Optimisation, and Systems Thinking. As an Agile Coach at Endava, she leads Asia Pacific initiatives, driving business agility and continuous improvement while mentoring teams to build customer-centric, high-performing, and collaborative cultures. You can link with Natalia Curusi on LinkedIn. You can also follow Natalia on Twitter.
Natalia Curusi: Measuring What Matters Beyond Velocity and Story Points 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. "We as Scrum Masters need to put a scope for ourselves—we need to aim to leave the place where we work a little bit better than it was, and to make sure that this place could improve itself without us." - Natalia Curusi Natalia defines success for Scrum Masters with crystal clarity: leave the organization better than you found it, and ensure it can continue improving when you're gone. This means fostering independence and ownership in teams so they can perform whether you're on vacation, in another meeting, or have moved to coaching other teams. The opposite pattern—where everything falls apart when the Scrum Master isn't present—reveals someone who hasn't truly succeeded in the role. Natalia also emphasizes the importance of establishing metrics early, but not the traditional ones. Using velocity as a metric is an anti-pattern that focuses teams on the wrong outcomes. Instead, she recommends metrics like predictability, team morale, psychological safety measured through 360 feedback, and the quality of conversations both within teams and with stakeholders. But metrics alone don't tell the story. Natalia champions the concept of Gemba walks—going to see what's actually happening, talking to people, observing the reality rather than just reviewing dashboard numbers. Some metrics are easily gamed, others provide only narrow perspectives on reality. The most important practice is using metrics to trigger reflection and adaptation, not as fixed targets. Natalia believes strongly that the quality of conversations—how teams discuss options, make decisions together, and adapt when facing pressure—reveals more about a Scrum Master's success than any velocity chart ever could. The ultimate question: can your team succeed without you? Self-reflection Question: If you disappeared from your team tomorrow, would they continue improving, or would progress stop until someone replaced you? Featured Retrospective Format for the Week: Spotify Squad Health Check "This is a multidimensional retro that I run with teams every 2 to 3 months—you need around 30 minutes for it, and I often get insights and new ideas from this retrospective that help me as a Scrum Master." - Natalia Curusi The Spotify Squad Health Check is Natalia's favorite retrospective format because it provides a comprehensive view of team health across multiple dimensions. Unlike traditional retrospectives that might focus on a single sprint or specific issue, this format examines the team's overall state across areas like teamwork, support, mission clarity, and technical quality. Teams rate themselves on various health indicators, creating a visual representation that reveals patterns over time. What makes this particularly valuable is that it works whether you know the team well or are just starting with them—either way, you gain insights and "aha moments" about where the team truly stands. The multidimensional nature prevents teams from optimizing just one aspect while neglecting others, and the regular cadence (every 2-3 months) allows you to track trends and celebrate improvements. For Natalia, this format consistently surfaces the hidden challenges that teams might not raise in regular retrospectives, making it an essential tool in her Scrum Master toolkit. [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 Natalia Curusi With over 20 years in software delivery, Natalia Curusi is an expert in Agile Transformations, Delivery Optimisation, and Systems Thinking. As an Agile Coach at Endava, she leads Asia Pacific initiatives, driving business agility and continuous improvement while mentoring teams to build customer-centric, high-performing, and collaborative cultures. You can link with Natalia Curusi on LinkedIn.
Natalia Curusi: Demonstrating Your Value When the Market Questions Agile Roles 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 challenging topic is about the demand of agility in the market—how do we fit ourselves as scrum masters in that AI era? How can we demonstrate our competence and contribution when there's a perception that agile roles bring little value?" - Natalia Curusi Natalia faces the challenge every Scrum Master in 2025 grapples with: how to demonstrate value in an era when business perceives agile roles as optional overhead. The market has contracted, companies are optimizing budgets, and Scrum Masters often appear first on the chopping block. There's talk of "blended roles" where developers are expected to absorb Scrum Master responsibilities, and questions about how AI might replace the human facilitation work that coaches provide. But Natalia believes the answer lies in understanding something fundamental: the Scrum Master is a deeply situational and contextual role that adapts to what the team needs each day. Some teams need help with communication spaces, others need work structure like Kanban boards, still others need translation between technical realities and stakeholder expectations. The challenge is that this situational nature makes it incredibly hard to explain to business leaders who think in fixed job descriptions and measurable outputs. Natalia's approach involves bringing metrics—not velocity, which focuses on the wrong things, but metrics around team independence, continuous improvement, and organizational capability. She suggests concepts like Gemba walks—going to see what's actually happening rather than relying only on numbers. The real question Natalia poses is this: the biggest value we can bring to an organization is to leave it better than we found it, but how do we make that visible and tangible to business stakeholders who need justification for our roles? Self-reflection Question: If you had to demonstrate your value as a Scrum Master using only observable evidence from the past month, what would you show your leadership? [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 Natalia Curusi With over 20 years in software delivery, Natalia Curusi is an expert in Agile Transformations, Delivery Optimisation, and Systems Thinking. As an Agile Coach at Endava, she leads Asia Pacific initiatives, driving business agility and continuous improvement while mentoring teams to build customer-centric, high-performing, and collaborative cultures. You can link with Natalia Curusi on LinkedIn.
Natalia Curusi: The Dark Side of High-Performing Dream 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. "I was proud of this team—I helped form them from the start, we traveled to the client together, they were mature and independent, they even jelled outside the workplace. This was my dream team." - Natalia Curusi Natalia had built something special. The team was technically strong, emotionally connected, and highly productive. They socialized outside work, traveled together to client sites, and operated with remarkable independence. But when a new junior developer joined, everything started to unravel. The existing team members were like heroes—fast, skilled, confident. The newcomer couldn't keep pace, and slowly Natalia noticed something disturbing: the team started making fun of the new member during retrospectives and stand-ups. The person became an outlier, a black swan ignored by the group. Natalia conducted one-on-one meetings with both the new member and the team, but the situation only worsened. The new person insisted they were fine and didn't need help. The team members claimed they were just joking around. Meanwhile, the team structure and morale deteriorated. Natalia realized she was watching her dream team self-destruct through a form of bullying—something she hadn't even recognized at the time. Finally, she understood she couldn't handle this alone and escalated to the head of discipline and the organizational psychologist. Together, they decided to rotate the person to another team where they felt more comfortable. Natalia learned a painful lesson: as Scrum Masters, we don't need to solve everything ourselves, and sometimes the best solution is recognizing when to use the support structure around us rather than treating it as a personal failure. In this episode, we refer to Coaching Agile Teams by Lyssa Adkins and Training from the Back of the Room by Sharon Bowman. Self-reflection Question: When have you witnessed subtle forms of exclusion in your team, and did you recognize them early enough to intervene effectively? Featured Book of the Week: Coaching Agile Teams by Lyssa Adkins "This was the first book about agile coaching that I read, and it's how I understood that I was already playing the scrum master role without even knowing it—I understood that I was already acting like a glue for the team." - Natalia Curusi Natalia discovered Coaching Agile Teams at a pivotal moment in her career. The book revealed something profound: if you're irreplaceable, there's a problem. A great Scrum Master or coach makes themselves obsolete by growing team members who can replace them. The team should be able to perform independently when you're on vacation or move to another assignment. Lyssa Adkins showed Natalia that she needed to let go of over-control and over-responsibility, focusing instead on growing the team's capabilities. The book remains one of Natalia's top recommendations for every junior Scrum Master wanting to embrace the role, alongside Training from the Back of the Room, which teaches facilitators how to run interactive workshops where people learn from each other rather than just listening to slides. [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 Natalia Curusi With over 20 years in software delivery, Natalia Curusi is an expert in Agile Transformations, Delivery Optimisation, and Systems Thinking. As an Agile Coach at Endava, she leads Asia Pacific initiatives, driving business agility and continuous improvement while mentoring teams to build customer-centric, high-performing, and collaborative cultures. You can link with Natalia Curusi on LinkedIn.
Natalia Curusi: When Your Technical Expertise Becomes Your Biggest Scrum Master Weakness 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 thought my technical background was my biggest strength, but I understood that this was my biggest weakness—I was coming into stand-ups saying 'I know how we need to fix that issue,' and I was a Scrum Master." - Natalia Curusi Natalia stepped into her first blended role as team leader and Scrum Master full of confidence. With years of programming experience behind her, she believed she could guide her team through any technical challenge. But during morning stand-ups, she found herself suggesting solutions, directing technical approaches, and sharing her expertise freely. The team listened—after all, she was their former leader. They implemented her suggestions, but when those solutions failed, the team didn't have the thinking process to adapt them to their context. Natalia realized she was preventing the team's learning and ownership by taking control away from them. The turning point came when she made a deliberate choice: she selected the most technical person on the team to become the technical authority and committed to never stepping on his feet again. From that moment forward, she focused purely on the Scrum Master role—asking questions, fostering collaboration, and shutting up to listen actively. Years later, that technical lead followed her to another job, and they remain friends to this day. Natalia learned that her contribution wasn't about giving solutions—it was about keeping the team from losing ownership of their work. Self-reflection Question: When you attend your team's daily stand-up, are you contributing to collaboration, or is your contribution keeping the team from owning their work? [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 Natalia Curusi With over 20 years in software delivery, Natalia Curusi is an expert in Agile Transformations, Delivery Optimisation, and Systems Thinking. As an Agile Coach at Endava, she leads Asia Pacific initiatives, driving business agility and continuous improvement while mentoring teams to build customer-centric, high-performing, and collaborative cultures. You can link with Natalia Curusi on LinkedIn.
BONUS: Swimming in Tech Debt — Practical Techniques to Keep Your Team from Drowning in Its Codebase In this fascinating conversation, veteran software engineer and author Lou Franco shares hard-won lessons from decades at startups, Trello, and Atlassian. We explore his book "Swimming in Tech Debt," diving deep into the 8 Questions framework for evaluating tech debt decisions, personal practices that compound over time, team-level strategies for systematic improvement, and leadership approaches that balance velocity with sustainability. Lou reveals why tech debt is often the result of success, how to navigate the spectrum between ignoring debt and rewriting too much, and practical techniques individuals, teams, and leaders can use starting today. The Exit Interview That Changed Everything "We didn't go slower by paying tech debt. We went actually faster, because we were constantly in that code, and now we didn't have to run into problems." — Lou Franco Lou's understanding of tech debt crystallized during an exit interview at Atalasoft, a small startup where he'd spent years. An engineer leaving the company confronted him: "You guys don't care about tech debt." Lou had been focused on shipping features, believing that paying tech debt would slow them down. But this engineer told a different story — when they finally fixed their terrible build and installation system, they actually sped up. They were constantly touching that code, and removing the friction made everything easier. This moment revealed a fundamental truth: tech debt isn't just about code quality or engineering pride. It's about velocity, momentum, and the ability to move fast sustainably. Lou carried this lesson through his career at Trello (where he learned the dangers of rewriting too much) and Atlassian (where he saw enterprise-scale tech debt management). These experiences became the foundation for "Swimming in Tech Debt." Tech Debt Is the Result of Success "Tech debt is often the result of success. Unsuccessful projects don't have tech debt." — Lou Franco This reframes the entire conversation about tech debt. Failed products don't accumulate debt — they disappear before it matters. Tech debt emerges when your code survives long enough to outlive its original assumptions, when your user base grows beyond initial expectations, when your team scales faster than your architecture anticipated. At Atalasoft, they built for 10 users and got 100. At Trello, mobile usage exploded beyond their web-first assumptions. Success creates tech debt by changing the context in which code operates. This means tech debt conversations should happen at different intensities depending on where you are in the product lifecycle. Early startups pursuing product-market fit should minimize tech debt investments — move fast, learn, potentially throw away the code. Growth-stage companies need balanced approaches. Mature products benefit significantly from tech debt investments because operational efficiency compounds over years. Understanding this lifecycle perspective helps teams make appropriate decisions rather than applying one-size-fits-all rules. The 8 Questions Framework for Tech Debt Decisions "Those 8 questions guide you to what you should do. If it's risky, has regressions, and you don't even know if it's gonna work, this is when you're gonna do a project spike." — Lou Franco Lou introduces a systematic framework for evaluating whether to pay tech debt, inspired by Bob Moesta's push-pull forces from product management. The 8 questions create a complete picture: Visibility — Will people outside the team understand what we're doing? Alignment — Does this match our engineering values and target architecture? Resistance — How hard is this code to work with right now? Volatility — How often do we touch this code? Regression Risk — What's the chance we'll introduce new problems? Project Size — How big is this to fix? Estimate Risk — How uncertain are we about the effort required? Outcome Uncertainty — How confident are we the fix will actually improve things? High volatility and high resistance with low regression risk? Pay the debt now. High regression risk with no tests? Write tests first, then reassess. Uncertain outcomes on a big project? Do a spike or proof of concept. The framework prevents both extremes — ignoring costly debt and undertaking risky rewrites without proper preparation. Personal Practices That Compound Daily "When I sit down at my desk, the first thing I do is I pay a little tech debt. I'm looking at code, I'm about to change it, do I even understand it? Am I having some kind of resistance to it? Put in a little helpful comment, maybe a little refactoring." — Lou Franco Lou shares personal habits that create compounding improvements over time. Start each coding session by paying a small amount of tech debt in the area you're about to work — add a clarifying comment, extract a confusing variable, improve a function name. This warms you up, reduces friction for your actual work, and leaves the code slightly better than you found it. The clean-as-you-go philosophy means tech debt never accumulates faster than you can manage it. But Lou's most powerful practice comes at the end of each session: mutation testing by hand. Before finishing for the day, deliberately break something — change a plus to minus, a less-than to less-than-or-equal. See if tests catch it. Often they don't, revealing gaps in test coverage. The key insight: don't fix it immediately. Leave that failing test as the bridge to tomorrow's coding session. It connects today's momentum to tomorrow's work, ensuring you always start with context and purpose rather than cold-starting each day. Mutation Testing: Breaking Things on Purpose "Before I'm done working on a coding session, I break something on purpose. I'll change a plus to a minus, a less than to a less than equals, and see if tests break. A lot of times tests don't break. Now you've found a problem in your test." — Lou Franco Manual mutation testing — deliberately breaking code to verify tests catch the break — reveals a critical gap in most test suites. You can have 100% code coverage and still have untested behavior. A line of code that's executed during tests isn't necessarily tested — the test might not actually verify what that line does. By changing operators, flipping booleans, or altering constants, you discover whether your tests protect against actual logic errors or just exercise code paths. Lou recommends doing this manually as part of your daily practice, but automated tools exist for systematic discovery: Stryker (for JavaScript, C#, Scala) and MutMut (for Python) can mutate your entire codebase and report which mutations survive uncaught. This isn't just about test quality — it's about understanding what your code actually does and building confidence that changes won't introduce subtle bugs. Team-Level Practices: Budgets, Backlogs, and Target Architecture "Create a target architecture document — where would we be if we started over today? Every PR is an opportunity to move slightly toward that target." — Lou Franco At the team level, Lou advocates for three interconnected practices. First, create a target architecture document that describes where you'd be if starting fresh today — not a detailed design, but architectural patterns, technology choices, and structural principles that represent current best practices. This isn't a rewrite plan; it's a North Star. Every pull request becomes an opportunity to move incrementally toward that target when touching relevant code. Second, establish a budget split between PM-led feature work and engineering-led tech debt work — perhaps 80/20 or whatever ratio fits your product lifecycle stage. This creates predictable capacity for tech debt without requiring constant negotiation. Third, hold quarterly tech debt backlog meetings separate from sprint planning. Treat this backlog like PMs treat product discovery — explore options, estimate impacts, prioritize based on the 8 Questions framework. Some items fit in sprints; others require dedicated engineers for a quarter or two. This systematic approach prevents tech debt from being perpetually deprioritized while avoiding the opposite extreme of engineers disappearing into six-month "improvement" projects with no visible progress. The Atlassian Five-Alarm Fire "The Atlassian CTO's 'five-alarm fire' — stopping all feature development to focus on reliability. I reduced sync errors by 75% during that initiative." — Lou Franco Lou shares a powerful example of leadership-driven tech debt management at scale. The Atlassian CTO called a "five-alarm fire" — halting all feature development across the company to focus exclusively on reliability and tech debt. This wasn't panic; it was strategic recognition that accumulated debt threatened the business. Lou worked on reducing sync errors, achieving a 75% reduction during this focused period. The initiative demonstrated several leadership principles: willingness to make hard calls that stop revenue-generating feature work, clear communication of why reliability matters strategically, trust that teams will use the time wisely, and commitment to see it through despite pressure to resume features. This level of intervention is rare and shouldn't be frequent, but it shows what's possible when leadership truly prioritizes tech debt. More commonly, leaders should express product lifecycle constraints (startup urgency vs. mature product stability), give teams autonomy to find appropriate projects within those constraints, and require accountability through visible metrics and dashboards that show progress. The Rewrite Trap: Why Big Rewrites Usually Fail "A system that took 10 years to write has implicit knowledge that can't be replicated in 6 months. I'm mostly gonna advocate for pie
BONUS: The Agile Organization as a Learning System Think Like a Farmer, Not a Factory Manager "Go slow to go fast. If you want to go somewhere, go together as a team. Take a farmer's mentality." Simon contrasts monoculture industrial thinking with the permaculture approach of Joel Salatin. Industrial approaches optimize for short-term efficiency but create fragile systems. Farmer thinking recognizes that healthy ecosystems require patience, diversity, and nurturing conditions for growth. The nervous system that's constantly stressed never builds much over time—think of the body, trust the body, let the body be a body. Value Masters, Not Scrum Masters "We need value masters, not Scrum Masters. Agile is a useful tool for delivering value, but value itself is primary. Everything else is secondary—Agile included." Tom makes his most provocative point: if you asked a top manager whether they'd prefer an agile person or value delivery, the answer is obvious. Agile is one tactic among many for delivering value—not even a necessary one. The shift required is from process mastery to value mastery, from Scrum Masters to people who understand and can deliver on critical stakeholder values. The DOVE Manifesto "I wrote a paper called DOVE—Deliver Optimum Values Efficiently. It's the manifesto focusing on delivering value, delivering value, delivering value." Tom offers his alternative to the Agile Manifesto: a set of principles laser-focused on value delivery. The document includes 10 principles on a single page that can guide any organization toward genuine impact. Everything else—processes, frameworks, methodologies—are secondary tools in service of this primary goal. Read Tom's DOVE manifesto here. Building the Glue Between Social and Physical Technology "Value is created in interactions. That's where the social and physical technology meet—that joyous boundary where stuff gets done." Simon describes seeing the world through two lenses: physical technology (visible tools and systems) and social technology (culture, relationships, the air we breathe). Eric Beinhoeker's insight is that progress happens at the intersection. The Gilbian learning loops provide the structure; trust and human connection provide the fuel. Together, they create organizations that can actually learn and adapt. Further Reading To Support Your Learning Journey Resources & Further Reading Explore these curated resources to deepen your understanding of strategic planning, value-based management, and transformative organizational change. 📚 Essential Reading Competitive Engineering Tom Gilb's seminal book on requirements engineering and value-based development approaches. What is Wrong with OKRs (Paper by Tom Gilb) A critical analysis of the popular OKR framework and its limitations in measuring real value. DOVE Manifesto by Tom Gilb Detailed exploration of the DOVE (Design Of Value Engineering) methodology for quantifying and optimizing stakeholder value. 🎓 Learning Materials Tom Gilb's Strategy Ringbook A comprehensive collection of strategic planning principles and practical frameworks. Tom Gilb's Video at the Strategy Meetup Watch Tom Gilb discuss key strategic concepts and answer questions from the community. Design Process Paper by Tom Gilb An in-depth look at value-driven design processes and their practical application. Esko Kilpi's Work on Conversations Exploring how organizational conversations shape thinking, decision-making, and change. 🧭 Frameworks & Models OODA Loop The Observe-Orient-Decide-Act decision cycle for rapid strategic thinking and adaptation. 🎯 Practical Tips Measurement of Increased Value Focus on tracking actual value delivery rather than activity completion. Establish baseline measurements and regularly assess improvements in stakeholder-defined value dimensions. Quantify Critical Values Identify the 3-5 most important value attributes for your stakeholders. Make these concrete and measurable, avoiding vague qualities in favor of specific, quantifiable metrics. Measurement vs Testing Process Understand the distinction: measurement tells you how much value exists, while testing validates whether something works. Use both strategically—test hypotheses early, then measure outcomes continuously. 🔗 Related Profiles Todd Covert - Montessori School of the Berkshires Educational leadership and innovative approaches to value-based learning environments. About Tom Gilb and Simon Holzapfel Tom Gilb, born in the US, lived in London, and then moved to Norway in 1958. An independent teacher, consultant, and writer, he has worked in software engineering, corporate top management, and large-scale systems engineering. As the saying goes, Tom was writing about Agile before Agile was named. In 1976, Tom introduced the term "evolutionary" in his book Software Metrics, advocating for development in small, measurable steps. Today, we talk about Evo, the name Tom uses to describe his approach. Tom has worked with Dr. Deming and holds a certificate personally signed by him. You can listen to Tom Gilb's previous episodes here. You can link with Tom Gilb on LinkedIn 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. And you can listen to Simon's previous episodes on the podcast here. You can link with Simon Holzapfel on LinkedIn.
BONUS: Quality 5.0—Quantifying the "Unmeasurable" With Tom Gilb and Simon Holzapfel Clarification Before Quantification "Quantification is not the main idea. The key idea is clarification—so that the executive team understands each other." Tom emphasizes that measurement is a means to an end. The real goal is shared understanding. But quantification is a powerful clarification tactic because it forces precision. When someone says they want a "very fast car," asking "can we define a scale of measure?" immediately surfaces the vagueness. Miles per hour? Acceleration time? Top speed? Each choice defines what you're actually optimizing for. The Scale-Meter-Target Framework "First, define a scale of measure. Second, define the meter—the device for measuring. Third, set numbers: where are we now, what's the minimum to survive, and what does success look like?" Tom's framework makes the abstract concrete: Scale of measure: What dimension are you measuring? (e.g., time to complete task) Meter: How will you measure it? (e.g., user testing with stopwatch) Past/Status: Where are you now? (e.g., currently takes 47 seconds) Tolerable: What's the minimum acceptable? (e.g., must be under 30 seconds to survive) Target/Goal: What does success look like? (e.g., 15 seconds or less) Many important concepts like "usability" decompose into 10+ different scales of measure—you're not looking for one magic number but a set of relevant metrics. Trust as the Organizational Hormone "Change moves at the speed of trust. Once there's trust, information flows. Once information flows, the system comes to life and can learn. Until there's trust, you have the Soviet problem." Simon introduces trust as the "human growth hormone" of organizational change—it's fast, doesn't require a user's manual, and enables everything else. Low-trust environments hoard information, guaranteeing poor outcomes. The practical advice? Make your work visible to your manager, alignment-check first, do something, show results. Living the learning cycle yourself builds trust incrementally. And as Tom adds: if you deliver increased critical value every week, you will build trust. About Tom Gilb and Simon Holzapfel Tom Gilb, born in the US, lived in London, and then moved to Norway in 1958. An independent teacher, consultant, and writer, he has worked in software engineering, corporate top management, and large-scale systems engineering. As the saying goes, Tom was writing about Agile before Agile was named. In 1976, Tom introduced the term "evolutionary" in his book Software Metrics, advocating for development in small, measurable steps. Today, we talk about Evo, the name Tom uses to describe his approach. Tom has worked with Dr. Deming and holds a certificate personally signed by him. You can listen to Tom Gilb's previous episodes here. You can link with Tom Gilb on LinkedIn 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. And you can listen to Simon's previous episodes on the podcast here. You can link with Simon Holzapfel on LinkedIn.
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