BONUS: When AI Knows Your Emotional Triggers Better Than You Do — Navigating Mindfulness in the AI Age | Mo Edjlali

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 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.

27 Maj 42min

BONUS: Solution-Focused Coaching: The Game-Changing Method Every Scrum Master Needs With Ralph Miarka and Veronika Jugwirth In this BONUS episode, we dive deep into solution-focused coaching with Ralph and Veronika, co-authors of "Solution Focused Coaching For Agile Teams." This conversation explores how to shift from problem-solving to solution-building, helping Agile teams thrive through a forward-looking approach that empowers teams to find their own path to success. Understanding Solution-Focused Coaching "Solution focus, focuses on the goal itself. We are not talking about 'how', but first start with 'what we want to achieve'." Solution-focused coaching represents a fundamental shift from traditional problem-solving approaches. Rather than diving into root cause analysis and retrospectives focused on what went wrong, this methodology centers on the future and desired outcomes. It operates as a communication system that recognizes the complexity of modern work environments where simple cause-effect relationships don't always apply. In engineering, root causes make sense when dealing with predictable systems, but in complex organizational dynamics, solution-focused coaching acknowledges that we often can't identify clear root causes and instead focuses on creating a "preferred future." In this segment we refer to Solution-focused brief therapy and the Cynefin model. The Power of Not-Knowing "Instead of suggesting solutions, we should start by asking questions. The "Not-knowing position" is about accepting this." The "not-knowing position" challenges coaches and leaders to resist the urge to immediately diagnose problems and offer solutions. When someone shares their story, they're not sharing the version we think we know. This approach transforms coaching conversations by starting with questions like "What difference would it make for you to solve this problem?" This shift toward asking questions about a positive future can even help identify advocates among those who initially resist change, creating unexpected allies in transformation efforts. Everyone as an Expert "When we help teams change by themselves, they change much faster." The principle that "everyone is an expert in their situation" fundamentally changes how coaches approach team dynamics, especially during periods of pressure or conflict. Instead of imposing external solutions, this approach involves asking teams what they already like about their current practices. For example, when observing daily standups with their natural diversity of approaches, focusing on what teams appreciate about their existing practices creates a foundation for sustainable change. Teams that discover their own path to improvement implement changes more rapidly and with greater commitment than those following prescribed solutions. The Miracle Question Technique "What would be a very small first sign that tells you that there was a small miracle during the night?" The Miracle Question emerges from real coaching conversations where clients express that "only a miracle can help." Rather than dismissing this statement, solution-focused coaches embrace the client's language to create powerful exploration opportunities. The technique involves asking teams to imagine their situation after a small miracle has occurred overnight, then identifying the first small signs they would notice. This approach helps teams explore possibilities and envision concrete steps toward their preferred future, making abstract goals tangible and achievable. Unlearning the Fix-It Mentality "Don't work by yourself in the problems of others, let them work." For Agile practitioners trained to identify and fix problems, solution-focused coaching requires a significant mindset shift. Instead of jumping into problem-solving mode, coaches must learn to hold space for solutions to emerge naturally from the team. This involves trusting that team members are experts in their own situations and developing strong questioning skills. Coaches and Scrum Masters need to clarify their own goals and resist the urge to solve problems for others, instead creating conditions where teams can work through challenges themselves. Practical Questions for Immediate Implementation "What do we want to achieve? What is our goal, and why?" Teams can immediately begin incorporating solution-focused approaches by bringing specific questions into their regular ceremonies. Key questions include exploring what the team wants to achieve and understanding the underlying purpose behind their goals. Additionally, asking "What works already?" helps teams build on existing strengths rather than focusing solely on problems. Confidence-building questions like "How confident are we?" and "What would make you more confident?" create opportunities for teams to identify specific actions that would increase their likelihood of success. About Ralph and Veronika Ralph Miarka is an Agile coach, trainer, and co-author of the book that is our topic for today's episode: Solution Focused Coaching For Agile Teams. Ralph helps teams thrive through solution-focused coaching. With a background in engineering and leadership, he bridges structure and empathy to spark real change. You can link with Ralph Miarka on LinkedIn. Veronika Jungwrith is a coach, consultant, and facilitator, Veronika blends solution-focused coaching with leadership development. Her work empowers individuals and teams to navigate complexity with clarity, meaning, and lasting impact. You can link with Veronika Jungwrith on LinkedIn.

26 Maj 44min

Deniz Ari: Why Great Product Owners Listen—Communication Lessons from Product Ownership Extremes The Great Product Owner: The Power of Clear Communication Deniz describes a truly exemplary Product Owner who excelled through outstanding communication skills. This PO was an exceptional listener who maintained openness throughout all interactions. They ensured the team thoroughly understood requirements and priorities, always clearly articulating the rationale behind decisions. With a well-defined product vision and transparent prioritization process, this PO successfully bridged the gap between the development team and clients. Deniz emphasizes how this clear communication style naturally fostered team motivation, as everyone understood not just what they were building, but why it mattered. The Bad Product Owner: The Tyrant PO Deniz shares a challenging experience with a problematic Product Owner during what initially appeared to be a straightforward public sector migration project with adequate budget and timeline. Despite these favorable conditions, the situation deteriorated when the PO began pushing the team to work overtime, overstepping boundaries by questioning architectural decisions, and inappropriately assuming Scrum Master responsibilities. Described as a "tyrant" or "despot," this PO exhibited extremely poor communication skills and preferred dictating rather than collaborating. When Deniz attempted to address these issues, the situation became so toxic that it affected Deniz's health, ultimately leading to their decision to leave the project. The PO subsequently claimed no Scrum Master was needed. Deniz reflects that sometimes the best option is to recognize when a situation cannot be changed and to move on. Self-reflection Question: What boundaries would you establish with a dominant Product Owner, and at what point would you decide that the situation cannot be improved? [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 Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

23 Maj 19min

Deniz Ari: Stakeholder Management Rhythms for Successful Scrum Masters 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. For Deniz, successful Scrum Masters create environments with positive team dynamics, easy communication, and a focus on continuous improvement that leads to valuable deliverables. The key indicators include whether team members can speak freely, whether there's trust between team members, and if the team feels like "a safe place to fail." Deniz recommends admitting your own mistakes in front of the team to model vulnerability, continuously observing team interactions, and noticing whether teams openly discuss obstacles. For stakeholder management, Deniz suggests establishing regular catch-up calls with leaders to keep team messages in the conversation and setting up routine discussions with stakeholders to maintain alignment. Featured Retrospective Format for the Week: The Worst Retro Deniz shares a playful yet effective retrospective format called "The Worst Retro," conducted using a MURAL board. The session begins with an energy/mood check to establish the team's current state. Then it moves into three key sections: what team members remember from the sprint, how they could make the next sprint worse, and finally deciding what actions to take next. Deniz explains that the power of this approach lies in using humor to discuss serious problems—by asking how to make things worse, team members can indirectly highlight what's already not working. This format creates an informal, relaxed environment where people feel comfortable addressing challenging topics that might otherwise remain unspoken. Self-reflection Question: How might introducing an element of humor or "reverse thinking" help your team discuss problems they've been avoiding in traditional retrospective formats? [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 Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

22 Maj 14min

Deniz Ari: Why Your Process Changes Are Failing—The Stakeholder Alignment Problem 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. Deniz explores the challenges of implementing change in organizations, emphasizing that change is always a long and difficult process requiring patience and trust. Drawing on the Change Curve concept, Deniz shares a personal experience trying to improve project visibility by cleaning up backlogs in JIRA for 10 in-flight projects. Despite good intentions, Deniz found themselves as the only person using the tool, with team members and Product Owners using different systems that better suited their specific needs—POs wanting only high-level items while the development team needed to split items into smaller tasks. Through this experience, Deniz learned the crucial importance of having all stakeholders (Product Owners, development teams, and managers) aligned on using the same tool, and understanding the unique perspectives of each group before implementing process changes. In this episode, we refer to the Change Curve. Self-reflection Question: What changes have you attempted to implement that failed because you didn't fully understand the different needs and perspectives of all stakeholders involved? [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 Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

21 Maj 16min

Deniz Ari: Security Team Breakdown—The Devastating Impact of Poor Product Ownership 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. Deniz shares the story of a security project with a team of eight experienced, senior engineers working on mission-critical systems. Despite initial motivation and clear architectural solutions, the team soon exhibited signs of negative behavior including complaints and criticism. The root cause traced back to frequent Product Owner changes—several within less than a year—and poor client management. Instead of shielding the team, the PO directly transferred stress from clients to the team, demanded overtime, and created unnecessary tension by bringing unfiltered conflicts to the team and requesting excessive details. Deniz emphasizes the importance of avoiding unnecessary tensions, being more political when necessary to protect the team, and being mindful of tone in written communications. Self-reflection Question: In what ways might you be failing to set proper boundaries in your role, and how could establishing clearer limits improve both your effectiveness and your team's performance? Featured Book of the Week: Boundaries by Henrik Cloud Deniz recommends "Boundaries" by Henrik Cloud, a book about human relationships and personal limitations. The book addresses crucial questions: Does your life feel out of control? Do you keep saying yes to everyone? Are you taking responsibility for others' feelings and problems? Have you forgotten your own limitations? Deniz explains how this book helped them learn to say "no" while still considering others' realities and feelings, and understanding why we often struggle with setting boundaries. Deniz highlights that being a Scrum Master involves much more than just processes and methods—it requires healthy personal boundaries. [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 Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

20 Maj 17min

Deniz Ari: How Intense Delivery Pressure Destroyed Team Trust, Culture, and Brought Burnout 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. Working in the public sector, Deniz faced a challenging situation during a particularly busy winter period when the client wanted to combine multiple major initiatives simultaneously: migration, new features, and security improvements. This led to an oversized team of 25 engineers, which ultimately caused significant problems. The pressure to continuously deliver became overwhelming, breaking team trust and leaving members feeling abandoned. Several team members left, the team culture disintegrated, and cases of burnout emerged. After this difficult experience, Deniz conducted a comprehensive retrospective to process what happened and provide feedback to management about the dangers of excessive pressure in Scrum environments. Self-reflection Question: How might you recognize the early warning signs of team burnout before it reaches a critical point, and what boundaries would you establish to protect your team? [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 Deniz Ari Deniz is an innovative, driven professional with expertise in Agile coaching, delivery management, data science, and technology transformation. As a Scrum Master and Agile Coach, Deniz builds high-performing teams, drives strategic execution, and fosters collaboration. Passionate about continuous improvement, they lead cultural shifts, optimize processes, and deliver scalable, high-quality outcomes. You can link with Deniz Ari on LinkedIn.

19 Maj 18min