BONUS: Beyond Frameworks, A Provocative Guide to Real Agility | Erwin Verweij

BONUS: Beyond Frameworks, A Provocative Guide to Real Agility | Erwin Verweij

BONUS: Beyond Frameworks, A Provocative Guide to Real Agility With Erwin Verweij

In this BONUS episode, we dive into the provocative world of Erwin Verweij's latest book: 'How the f*ck to be Agile?' Erwin shares his journey from frustration to clarity as he witnesses organizations adopting Agile frameworks without understanding their purpose. With candid stories from his coaching experiences, Erwin reveals what happens when teams wake up to real agility beyond dogmatic practices and how organizations can find their own path to meaningful change.

The Wake-Up Call for Agile Adoption

"What the f*ck dude! Do you even know what it means? Do you really know what it means?"

Erwin's journey to writing this book began with growing frustration at how companies approach agility. He frequently encountered teams proudly declaring "We're Agile!" or "Our department is Agile" without understanding what that truly meant.

This disconnect between label and understanding became the catalyst for his provocatively-titled wake-up call. Erwin describes his exasperation with organizations adopting frameworks halfheartedly, following mindsets that were completely off track, and ultimately "doing stuff without knowing what they're doing and why they're doing it." The F-word in his book title serves dual purposes - expressing his frustration while also functioning as a power word to wake people up from their complacency.

Breaking Free from Framework Dogma

"We're not gonna do Agile. Forget it. And we're not gonna do Scrum, even though you're doing Scrum. Let's look at what really works for you people."

Rather than imposing rigid frameworks, Erwin advocates for teams to discover what actually works in their specific context. He shares a memorable story of tearing down Scrum posters that management had installed, shocking team members who couldn't believe he would challenge the prescribed approach.

In another example, Erwin creatively used a manager's "quarantine" language by posting contamination warnings at a department's entrance with the message: "If you enter this room, you might get contaminated with a new way of working." These disruptive approaches are designed to shake people from blindly following orders and encourage them to think critically about their processes.

Finding Your Own Path to Agility

"Any coach who goes into a company with a strict plan and a set approach - don't hire them. They don't have a clue what to do."

After the wake-up call, Erwin focuses on helping teams discover their own effective ways of working. He believes that the key is to observe what's already working well, emphasize those elements, and discard what doesn't serve the team. This approach stands in stark contrast to consultants who arrive with predetermined solutions regardless of context.

Erwin emphasizes that real transformation happens when teams take ownership of their processes, adapt them to their unique needs, and make them their own. He cautions against hiring coaches who come with rigid, predetermined plans, as they often lack the flexibility to address a team's specific challenges.

The Never-Ending Journey of Adaptation

"We need to help teams to stay open for the change that is coming."

Erwin stresses that agility is not a destination but a continuous journey of adaptation. The world never stops changing, so teams must remain flexible and open to evolving their approaches. He encourages a mindset of experimentation with phrases like "let's try" and "what could we try" to keep teams responsive to new challenges.

According to Erwin, one of the most powerful ways to foster this adaptive culture is to model the behaviors you want to see in the teams you support. By demonstrating openness to change yourself, you help others embrace the continuous nature of improvement.

Scaling Without Bureaucracy

"Work with the system, learn what is needed, iterate."

When discussing scaling Agile across an organization, Erwin questions why companies feel the need to scale in the first place. He uses cities as a metaphor for how complex systems can organize beyond small groups without excessive bureaucracy.

In one organization where he currently coaches, teams have found a pragmatic approach by adopting elements from various frameworks that work for them. They use quarterly planning sessions from SAFe primarily as a networking opportunity that connects everybody and focuses their efforts, even though the planning itself might be "basically bullshit." This practical, results-oriented approach emphasizes what works rather than dogmatic adherence to frameworks.

Software as a Creative Process

"Software development is basically figuring out how stuff works. It's a creative process that mostly is being dealt with within the brain of people."

Erwin views software development fundamentally as a creative process rather than a production line. He explains that it's not about "typing as fast as you can" but about thinking, problem-solving, and creating. This perspective helps explain why iterative approaches with small steps work better than trying to plan everything upfront.

Erwin notes that when complex problems become routine, teams might not need the full framework structure, but they should retain the values that help them coordinate effectively. The essence of frameworks like Scrum, he suggests, is simply "start working, figure it out, and see what happens" - an approach that many organizations have become afraid to embrace.

Awakening Organizational Intelligence

"We raise children, which is basically programming another human being - it's really complex. And we just take it for granted. And then we go to work, and we don't know how to make decisions anymore."

One of Erwin's most powerful insights is how organizational structures can suppress the natural intelligence and decision-making abilities that people demonstrate in their personal lives. He points out the irony that we navigate incredibly complex systems like raising children or driving in traffic, yet when we arrive at work, we suddenly act as if we can't make decisions without higher approval. This disconnect creates frustration and wastes human potential. Erwin challenges organizations to wake up to this contradiction and create environments where people can bring their full capabilities to work, rather than checking their intelligence at the door.

In this section, we refer to Jurgen Appelo's Book Management 3.0.

About Erwin Verweij

Erwin is a seasoned Agile Coach, Certified Enterprise Coach, and author of Viking Law and How the f*ck to be Agile?. With 15+ years' experience driving meaningful change, he helps organizations embrace real agility through coaching, transformation, and workshops—cutting through complexity to spark courage, clarity, and action.

You can link with Erwin Verweij on LinkedIn and connect with Erwin Verweij on Twitter.

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Sustainable Value—Redefining Success Beyond Profit | Joel Bancroft-Connors

Sustainable Value—Redefining Success Beyond Profit | Joel Bancroft-Connors

Joel Bancroft-Connors: Sustainable Value—Redefining Success Beyond Profit 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. Joel has evolved his definition of Scrum Master success over time, moving beyond traditional metrics to focus on what truly matters: sustainable value delivery. While Agile principles clearly state the goal of delivering value continuously, Joel emphasizes that success isn't just about making profit - it's about creating sustainable profit through sustainable processes and people practices. He challenges Scrum Masters to consider their "people sustainability metric" and asks whether their approach supports long-term team health and organizational resilience. Joel's definition encompasses three pillars: delivering sustainable value, maintaining sustainable processes, and ensuring sustainability for people. This holistic view of success requires Scrum Masters to think beyond immediate outcomes and consider the long-term impact of their practices. In this segment, we refer to the book Turn the ship around! by David Marquet. Self-reflection Question: What is your people sustainability metric, and how are you measuring whether your Scrum practices support long-term team and organizational health? Featured Retrospective Format for the Week: Back to Basics Joel advocates for returning to the foundational retrospective format outlined in "Agile Retrospectives" by Derby and Larsen. Rather than getting caught up in complex or creative retrospective techniques, he emphasizes the power of following the basic steps: set the stage, gather data, generate insights, decide what to do, and close the retrospective. Joel stresses that there's an important arc to retrospectives that shouldn't be overlooked. By taking time to properly gather data and following the structured approach from the agile retrospectives book, teams can achieve more meaningful and actionable outcomes. Sometimes the most effective approach is simply executing the fundamentals exceptionally well. In this segment, we refer to the book Agile retrospectives, by Derby and Larsen. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Joel Bancroft-Connors Joel Bancroft-Connors is The Gorilla Coach — a Certified Scrum Trainer and Agile disruptor focused on sustainable value and effectiveness. With a background in product, project, and coaching, Joel blends sharp insights with practical tools to help teams thrive. He is a Miro power user and rocks curated classroom playlists. You can link with Joel Bancroft-Connors on LinkedIn.

5 Juni 17min

The 90-Day Rule—Building Trust Before Disrupting the Status Quo | Joel Bancroft-Connors

The 90-Day Rule—Building Trust Before Disrupting the Status Quo | Joel Bancroft-Connors

Joel Bancroft-Connors: The 90-Day Rule—Building Trust Before Disrupting the Status Quo 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. Joel shares his first experience as a CSM at a traditional hard drive manufacturing company, where he learned the art of patient change management. Tasked with bridging the gap between a rigid mothership company and their agile startup division, Joel discovered the power of focusing on principles rather than processes. For six months, he concentrated on creating transparency and shifting focus from status reporting to "getting to done" without ever mentioning Scrum or Agile. His approach followed what he calls the 90-day rule: "In the first 90 days - do no harm, but then have a plan to do something." By listening first and building trust, Joel helped the team deliver a product in just three months. He emphasizes the importance of making people feel valued and using "future perfect thinking" to envision desired outcomes before introducing change. In this episode we refer to Luke Hohmann's Innovation Games, the website and resource Manager-Tools.com, and Daniel Pink's book Drive. Self-reflection Question: Are you rushing to implement changes, or are you taking time to build trust and understand the current state before introducing new practices? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Joel Bancroft-Connors Joel Bancroft-Connors is The Gorilla Coach — a Certified Scrum Trainer and Agile disruptor focused on sustainable value and effectiveness. With a background in product, project, and coaching, Joel blends sharp insights with practical tools to help teams thrive. He is a Miro power user and rocks curated classroom playlists. You can link with Joel Bancroft-Connors on LinkedIn.

4 Juni 14min

How Performance Reviews Killed a Great Agile Team | Joel Bancroft-Connors

How Performance Reviews Killed a Great Agile Team | Joel Bancroft-Connors

Joel Bancroft-Connors: How Performance Reviews Killed a Great Agile Team 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. Joel tells the story of a team caught in the crossfire of a poorly executed large-scale agile transformation. While the CTO championed going agile, they quickly checked out, leaving the organization without clear direction or understanding of why they were adopting agile practices. The company measured success through output metrics like "number of teams trained" rather than meaningful outcomes. Joel worked with an exceptional team that had built their own collaborative workspace and was performing well, but external forces kept pulling them out of flow. Performance reviews created internal conflict, leading team members to focus on individual success rather than collective achievement. The team ultimately fell into their own traps, with everyone "focusing on themselves and throwing others under the bus." Joel recommends balancing performance evaluations with 50% team-based and 50% individual metrics to prevent this destructive pattern. Self-reflection Question: Does your team truly understand why they are using Scrum, or are they just going through the motions of the framework? Featured Book of the Week: Start with Why by Simon Sinek Joel credits Simon Sinek's "Start with Why" as a transformational influence on his coaching approach. The book's central principle that "people don't buy what you do, they buy why you do it" fundamentally changed how Joel teaches Scrum. He realized he had been teaching Scrum incorrectly by focusing on the mechanics rather than the purpose. Now Joel listens to this book annually and has shifted his focus to helping teams and organizations understand why Scrum matters and why it's important. This shift from teaching the "what" to emphasizing the "why" has made his coaching significantly more effective and meaningful. Joel also mentions the book Coaching Agile Teams by Lyssa Adkins. [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Joel Bancroft-Connors Joel Bancroft-Connors is The Gorilla Coach — a Certified Scrum Trainer and Agile disruptor focused on sustainable value and effectiveness. With a background in product, project, and coaching, Joel blends sharp insights with practical tools to help teams thrive. He is a Miro power user and rocks curated classroom playlists. You can link with Joel Bancroft-Connors on LinkedIn.

3 Juni 12min

When Great Scrum Masters Fail—The Hidden Cost of Poor Value Communication | Joel Bancroft-Connors

When Great Scrum Masters Fail—The Hidden Cost of Poor Value Communication | Joel Bancroft-Connors

Joel Bancroft-Connors: When Great Scrum Masters Fail—The Hidden Cost of Poor Value Communication 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. Joel shares a powerful lesson about the critical importance of communicating value beyond team performance. Despite achieving remarkable success with multiple teams as an agile coach, Joel and his colleagues ultimately failed because they couldn't effectively demonstrate their value to leadership. The teams were thriving, but when budget cuts came, the coaching support was eliminated first. Without ongoing support, these successful teams began to deteriorate. Joel emphasizes that as Scrum Masters and agile coaches, we must actively communicate our impact and connect team success to business outcomes. Simply assuming that good team performance speaks for itself is not enough - we need to interact more with stakeholders and clearly articulate the value we create. In this episode, we refer to the TV series Ted Lasso, and the books Start with Why by Simon Sinek, and Coaching Agile Teams by Lyssa Adkins. Self-reflection Question: How effectively are you communicating the business value of your Scrum Master activities to leadership, and what specific metrics or stories could better demonstrate your impact? [Scrum Master Toolbox Podcast Recommends] 🚀 Global Agile Summit 2025 Join us in Tallinn, Estonia, from May 18th – 20th, 2025, for an event that will inspire, challenge, and equip you with real-world Agile success stories. 🌍 Connect with global Agile leaders. 💡 Learn practical strategies for impact. 🔥 Break free from Agile fatigue and become a Pragmatic Innovator Check Full Program [Scrum Master Toolbox Podcast Recommends] About Joel Bancroft-Connors Joel Bancroft-Connors is The Gorilla Coach — a Certified Scrum Trainer and Agile disruptor focused on sustainable value and effectiveness. With a background in product, project, and coaching, Joel blends sharp insights with practical tools to help teams thrive. He is a Miro power user and rocks curated classroom playlists. You can link with Joel Bancroft-Connors on LinkedIn.

2 Juni 15min

BONUS Martti Kuldma: How to Transform Century-Old Organizations Through Product-Driven Agile Transformation

BONUS Martti Kuldma: How to Transform Century-Old Organizations Through Product-Driven Agile Transformation

BONUS: Martti Kuldma shares how to transform century-old organizations through product-driven agile transformation In this BONUS episode we explore the remarkable transformation journey at Omniva with CEO Martti Kuldma. From traditional postal services to innovative logistics solutions, we explore how a 100+ year old company embraced product thinking, DevOps practices, and agile transformation to become a competitive force in modern logistics. Omniva's Digital Evolution—IT as a Revenue Center "We innovated the parcel machine business for a few years, and software has been an area of investment for us - software as a separate vertical in our business." Omniva represents a fascinating case study in organizational transformation. While many know it as Estonia's post office, the company has evolved into an international logistics powerhouse with significant revenue streams beyond traditional postal services. Under Martti's leadership, the organization has reimagined software not as a support function but as a core revenue driver, positioning itself for the dramatic shifts expected in logistics delivery over the next five years. The Vision: Physical Mailing as the Next IP Network "The Vision: physical mailing as the next IP network - this will give us a lot more freedom to adapt to changes in delivery demand." Martti's strategic vision extends far beyond conventional logistics thinking. By conceptualizing physical delivery networks similar to internet protocols, Omniva is preparing for a future where logistics companies leverage their physical infrastructure advantages. This approach addresses the fundamental challenge of fluctuating demand in e-commerce and traditional logistics, creating opportunities for crowd delivery solutions and gig economy integration that capitalize on existing network effects. Breaking Down Waterfall Barriers "When I came we had waterfall processes - annual budgeting, procurement for software development. It took a couple of weeks to do the first rounds, and understand what could be improved." The transformation from traditional procurement-based software development to agile product teams required dismantling entrenched processes. Martti discovered that the contractor model, while seemingly cost-effective, created expensive knowledge transfer cycles and left the organization vulnerable when external teams departed. His engineering background enabled him to recruit talent and build sustainable development capabilities that keep critical knowledge within the organization. Creating Cross-Functional Product Teams "We started to create cross-functional product area teams. We are not going to tell you what you need to build. You are accountable for the logistics efficiency." The shift from eleven distinct roles in software development to autonomous product teams represents more than organizational restructuring. By empowering teams with accountability for business outcomes rather than just deliverables, Omniva transformed how work gets planned and executed. This approach eliminates traditional handoffs and role silos, creating teams that own both the problem and the solution. The Product Manager Evolution "For me, the PM is directly accountable for the business results. The final step of the transformation started when I took the CEO role." Martti identifies a critical challenge in agile transformations: the misunderstanding of Product Manager responsibilities. Rather than falling into delivery or project management patterns, effective PMs at Omniva own business results directly. This shift required company-wide transformation because technical changes alone cannot sustain organizational evolution without corresponding changes in mindset and accountability structures. Leadership Through Storytelling "My main tool is just talking. All I do is story-telling internally and externally. I needed to become the best salesman in the company." The transition from technical leadership to CEO revealed that transformation leadership requires different skills than technical management. Martti discovered that his primary value comes through narrative construction and communication rather than direct technical contribution. This realization highlights how senior leaders must evolve their impact methods as organizations scale and transform. Real-Time Feedback Philosophy "The feedback needs to be given immediately. 'Last year, in May your performance was not the best' - this is completely useless feedback." Martti's rejection of annual reviews stems from practical experience with feedback effectiveness. Immediate, personal feedback creates learning opportunities and course corrections that annual cycles cannot provide. Anonymous 360 feedback systems often dilute accountability and actionability, whereas direct, timely conversations enable meaningful professional development and relationship building. Essential Transformation Practices "You need to tell the story - and convince people that this transformation is essential and needed. You need to trust and let them make their own decisions." Drawing from experiences at both Pipedrive and Omniva, Martti identifies three critical elements for leading complex organizational change: Compelling narrative: People need to understand why transformation is necessary and how it benefits both the organization and their individual growth Distributed decision-making: Trust enables teams to solve problems creatively rather than waiting for hierarchical approval Business accountability for engineers: When technical teams understand and own business outcomes, they innovate more effectively toward meaningful goals The dynamic team formation model used at Pipedrive, where engineers and PMs pitched ideas and assembled mission-focused teams, demonstrates how organizational structure can enable rather than constrain innovation. About Martti Kuldma Martti Kuldma is CEO of Omniva, leading its transformation into a product-driven logistics company. A former engineering leader at Pipedrive and CTO at Omniva, he brings deep expertise in scaling teams, agile transformation, and digital innovation. Martti is also a startup founder and passionate advocate for high-impact product organizations. You can link with Martti Kuldma on LinkedIn.

31 Maj 44min

BONUS Entertainment That Makes Change: Lessons in Product Thinking from Believe Ltd. With Patrick James Lynch

BONUS Entertainment That Makes Change: Lessons in Product Thinking from Believe Ltd. With Patrick James Lynch

BONUS: Patrick James Lynch on Entertainment That Makes Change - Lessons in Product Thinking from Believe Ltd. In this BONUS episode we explore how Patrick James Lynch, filmmaker, media executive, and rare disease advocate, has built Believe Limited around a powerful mission: entertainment that effects change. Patrick shares his journey from personal experience with his brother's hemophilia to creating award-winning content that empowers rare and chronic disease communities, offering valuable lessons for product managers on human-centered design, stakeholder alignment, and building emotionally viable products. The Genesis of Entertainment That Effects Change "This is more than a product." Patrick's journey began with a deeply personal question about his brother who had hemophilia. As an entrepreneur, he set out to respond to an identified need with one product to meet that need, but quickly realized the scope was much larger. His curiosity about what was different between him and his brother led him to understand that he needed to help people like his brother. This realization drove him to create valuable online videos to engage their audience, marking the beginning of Believe Ltd.'s mission of entertainment that effects change. Essential Product Lessons: Listen, Learn, and Do No Harm "The fact that I am my audience, does not mean that I'm an expert." Patrick emphasizes the critical importance of conducting thorough needs assessments and truly understanding your community before building products. Key insights include: Embed yourself in the community you're serving rather than making assumptions Follow the principle of "listen, learn and do no harm" as your starting point Involve community engagement as a dedicated role - Believe Ltd. has a VP of community engagement Define clear phrases that explain the value you deliver to your audience Use your personal story to establish credibility and relate experiences to your audience The goal is to get as familiar with your community as possible, then conduct your own research and development based on those deep insights. Navigating Multi-Stakeholder Complexity "Collaboration only succeeds when all points of view are respected." Working with patients, funders, healthcare professionals, and pharmaceutical companies requires careful orchestration. Patrick's approach centers on prioritizing the end game and identifying the north star goal that aligns all parties. He emphasizes focusing on combined skills and networks rather than trying to accomplish everything at the start. The key is ensuring that aligning stakeholders becomes a central part of the process, with everyone being accounted for throughout the journey. Human-Centered Storytelling as Product Strategy "What's the story that shows the value add of your product?" Patrick advocates for human-centered storytelling as a fundamental product approach. Rather than leading with features or specifications, he suggests crafting stories that demonstrate real value - like how a thermos saved someone's life while hiking. Stories have been humanity's primary communication tool since the beginning of time, and they remain the most effective way to show product value and connect with audiences on a meaningful level. Being a Value Fundamentalist "At any given moment, if anyone takes a screen grab, and set it against our five core values as a company - you see it's playing out." Patrick describes himself as a value fundamentalist, meaning that their company's core values are always present in everything they do. This requires courage, including the willingness to say "no" when opportunities don't align with their values. As CEO, he believes in embodying these values consistently, even when it's challenging, because who they are must always be visible in their work. Balancing Vision with Community Feedback "When you ask the audience for a solution, there's no innovation." Patrick warns against sacrificing vision simply because you're working closely with your audience. While being in the sandbox with your community is essential, maintaining your original vision for entertainment that changes minds is equally important. He recommends having someone you can bounce ideas off to help maintain this balance, and remembers that all great things start small and are inherently iterative. Creating Emotionally Viable Products "We can't develop emotional connection by going through a list of features." Beyond minimum viable products, Patrick focuses on emotional viability - the hook that makes people truly care. Emotional connection cannot be built through feature lists but rather through compelling stories that capture people's imagination. When audiences engage with products outside of direct supervision, storytelling becomes the bridge that helps them discover new uses and applications. This creates a dance between product creators and their audience, leading to better product design. The Currency of Attention "Attention is the only currency - there's great wisdom in that." Patrick recognizes that in today's landscape, capturing and maintaining attention is the fundamental challenge. Since everyone is an audience member at different times, this perspective helps inform both strategy and tactics. Products must compete not just on functionality but on their ability to engage and maintain audience interest over time. As a recommended reading, Patrick suggests that we should read "Save The Cat! The Last Book on Screenwriting You'll Ever Need" to understand how to better tell stories about our products. About Patrick James Lynch Patrick James Lynch is a filmmaker, media executive, and rare disease advocate. CEO of Believe Limited and founder of BloodStream Media, he uses his experience with hemophilia to drive award-winning storytelling, health advocacy, and mission-driven content that inspires and empowers rare and chronic disease communities worldwide. You can link with Patrick James Lynch on LinkedIn and follow Patrick James Lynch's work on his website.

29 Maj 41min

BONUS The Startup CTO's Handbook With Zach Goldberg

BONUS The Startup CTO's Handbook With Zach Goldberg

BONUS: Zach Goldberg shares how to build high-performing engineering teams and master the startup CTO role In this BONUS episode, we dive deep into the world of startup leadership with Zach Goldberg, author of The Startup CTO's Handbook. We explore the critical transition from engineering to leadership, the art of balancing technical debt with startup urgency, and the communication skills that separate great CTOs from the rest. The Genesis of The Startup CTO's Handbook "My original training in software engineering was not enough for being a leader. All the people and leadership skills, I had to learn on my own." Zach's journey to writing The Startup CTO's Handbook began with a stark realization about the gap between technical training and leadership reality. Despite his classical software engineering background, he discovered that the people and leadership skills required for CTO success had to be self-taught. The book emerged from a growing Google Doc of topics and frameworks addressing the leadership and management challenges that CTOs consistently face - from hiring and performance management to making strategic decisions under pressure. Today, we can either buy the digital/print book on Amazon, or read the book on GitHub. In this segment, we also refer to the book The Great CEO Within. Learning to Truly Learn: The Max Mintz Story "Max only cared about my ability to learn - to get curious about something hard. He wanted to help me deal with complexity." Zach opens his book with a deeply personal story about his mentor, Max Mintz, who fundamentally changed his approach to learning during what he calls "the most impactful single coffee" of his life. Over 1.5 years of conversations, Max taught him that true learning isn't about accumulating facts, but about developing curiosity for hard problems and building the capacity to handle complexity. This lesson forms the foundation of effective CTO leadership - the ability to continuously learn and adapt in an ever-changing technical landscape. The Three Critical CTO Mistakes "As a CTO, the most important 3 things: people, people, people. Do the people have the right energy, the right passion? Assemble the right team." Zach identifies consistent patterns in startup CTO failures across his experience. The first and most critical mistake is undervaluing people decisions - failing to prioritize team energy, passion, and the right assembly of talent. The second category involves investment mistakes, particularly the challenge of balancing short-term survival needs with long-term technical goals. In startups, the ROI timespan is exceptionally short, requiring optimization for immediate objectives rather than hypothetical scale. The third mistake is treating technology as religion rather than tools, losing sight of what the business actually needs. Optimizing for Velocity and Developer Experience "You are optimizing for velocity! What are you doing to help developers get their work done? Look at developer experience as a metric." Successful startup CTOs understand that velocity - the time from idea to valuable market delivery - is paramount. This requires a fundamental shift in thinking about technology decisions, focusing on features that deliver real customer value rather than technical elegance. Zach emphasizes measuring developer experience as a key metric, recognizing that anything that helps developers work more effectively directly impacts the company's ability to survive and thrive in competitive markets. The Professional Skill Tree Concept "It's like a character progression in an RPG. When we learn one type of skills, we don't learn other types of skills. We make investments every day and we have a choice on where we learn." Drawing from gaming metaphors, Zach explains how technical professionals often reach Level 100 in engineering skills while remaining Level 1 in management. The skill tree concept highlights that every learning investment is a choice - time spent developing one skill area means less time available for others. For engineers transitioning to leadership, the key is recognizing opportunities to serve as tech leads, where they can begin setting culture and quality standards while still leveraging their technical expertise. Balancing Kaizen with Startup Urgency "Pick the high-impact debt, and pay that down. This is not always easy, especially because we also need to pick what debt we don't invest on." The tension between continuous improvement and startup speed requires sophisticated thinking about technical debt. Using financial analogies, Zach explains that technical debt has both principal and interest components. The key is identifying which debt carries the highest interest rates and can be paid down most quickly, while consciously choosing which debt to carry forward. This approach maintains the healthy tension between quality and speed that defines successful startup engineering. The Power of Audience Empathy "The single hardest skill, especially for very tech leaders is that of 'audience empathy.' When you explain ideas to people, you usually assume a lot - but they might not." According to Zach, the most undervalued communication habit for startup tech leaders is developing audience empathy. Technical leaders often suffer from the curse of knowledge, assuming their audience shares their context and understanding. The solution requires deliberately considering what the audience already knows before crafting any communication, whether it's explaining technical concepts to non-technical stakeholders or providing clear direction to team members. In this segment we refer to the concept of "the curse of knowledge", a cognitive bias that occurs when a person who has specialized knowledge assumes that others share in that knowledge. About Zach Goldberg Zach Goldberg is a seasoned technical entrepreneur, executive coach, and author of The Startup CTO's Handbook. With a founder's mentality and a passion for systems thinking, Zach helps engineering leaders build high-performing teams. He also founded Advance The World, a nonprofit inspiring youth in STEM through immersive experiences. You can link with Zach Goldberg on LinkedIn, and visit Zach's website at CTOHB.com.

28 Maj 41min

BONUS Tom Gilb: Building True Engineering Culture and Delivering Value Through Evolutionary Methods

BONUS Tom Gilb: Building True Engineering Culture and Delivering Value Through Evolutionary Methods

BONUS: Tom Gilb on Building True Engineering Culture and Delivering Value Through Evolutionary Methods In this BONUS episode, we dive deep into the world of true engineering discipline with Tom Gilb, a pioneer who was writing about Agile principles before Agile was even named. We explore his latest book "Success - Super Secrets & Strategies for Efficient Value Delivery in Projects and Programs, and Plans" and uncover the fundamental flaws in how organizations approach project delivery and stakeholder management. The Genesis of Success-Focused Engineering "People were failing at project deliveries - even when using Agile. I saw there was very little about setting clear goals and reaching them, it had nothing to do with being successful." Tom's motivation for writing his latest book stems from a critical observation: despite the widespread adoption of Agile methodologies, project failure rates remain unacceptably high. The core issue isn't methodology but rather the fundamental lack of clarity around what success actually means. Tom emphasizes that true success is about achieving the improvements you want at a price you can afford, yet most organizations fail to define this clearly from the outset. In this segment, we refer to the book How Big Things Get Done by Bent Flyvbjerg who published statistics on the poor performance of projects in general. Beyond OKRs: The Power of Quantified Multi-Dimensional Objectives "First you need to have a definition of what it means to succeed. And that needs to be multi-dimensional. And you need to clarify what they are." While many organizations believe they're already quantifying objectives through frameworks like OKRs, Tom reveals significant weaknesses in these approaches. True value isn't just profit—it encompasses multiple dimensions including security, usability, and other stakeholder-specific benefits. The key insight is learning to quantify what needs to be achieved across all critical dimensions, as you simply cannot design for high-quality attributes like security without first quantifying and designing for them explicitly. In this segment, we talk about Tom's paper on OKR's titled "OKR Objectives and Key Results: what's wrong and how to fix it". The Missing Engineering Discipline "Why is the failure rate of our projects so high?" Tom identifies a paradoxical problem: engineering organizations often lack true engineering discipline. This fundamental gap explains why project success rates remain low despite technological advances. Real engineering requires systematic approaches to design, stakeholder analysis, and incremental value delivery—disciplines that are often overlooked in favor of rushed implementations. Stakeholder Analysis: Beyond User Stories "Stakeholders have a requirement - even if we don't know it. They might be people, but also law, contract, policies, etc. They all have requirements for us." Traditional user-centered methods like user stories can lead to failure when critical stakeholders are overlooked. Tom advocates for comprehensive stakeholder analysis as the foundation of engineering discipline. Stakeholders aren't just people—they include laws, contracts, policies, and other constraints that have requirements for your system. The practical tip here is to use AI tools to help identify and list these stakeholders, then quantify their specific requirements using structured approaches like Planguage. The Gilb Cycle: True Incremental Value Delivery "Get things done every week, next week, until it's all done. We need to decompose any possible design into enough increments so that each increment delivers some value." What distinguishes Tom's evolutionary approach from popular Agile frameworks is the focus on choosing the most efficient design and then systematically improving existing systems through measured increments. Each increment must deliver tangible value, and the decomposition process should be aided by AI tools to ensure optimal value delivery. This isn't just about iteration—it's about strategic improvement with measurable outcomes. Building Engineering Culture: A Two-Leader Approach "There are two leaders: the tech leaders and the management leaders. For management leaders: demand a value stream of results starting next week. To the tech leaders: learn the engineering process." Creating a true engineering culture requires coordinated effort from both management and technical leadership. Management leaders should demand immediate value streams with weekly results, while technical leaders must master fundamental engineering processes including stakeholder analysis and requirement quantification. This dual approach ensures both accountability and capability development within the organization. Further Resources During this episode we refer to several of Tom's books and papers. You can see this list below Software Metrics by Tom Gilb Principles of software engineering management - Also available in PDF Evo book About Tom Gilb 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 that Tom used to describe his approach. You can link with Tom Gilb on LinkedIn.

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