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.

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Building Self-Awareness in Overly-Technical Product Owners | Anamaria Ungureanu

Building Self-Awareness in Overly-Technical Product Owners | Anamaria Ungureanu

Anamaria Ungureanu: Building Self-Awareness in Overly-Technical Product Owners Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: The Master Storyteller Anamaria highlights a Product Owner who excelled at storytelling and vision communication, making every team member feel aligned with project goals. This exceptional PO consistently explained the "why" behind requirements and painted compelling pictures of how the team's current work would create future value. Their storytelling ability kept the team engaged and motivated, demonstrating how great Product Owners apply agile mindset principles to create shared understanding and purpose. The Bad Product Owner: The Monologue Specialist Anamaria describes a technically-skilled Product Owner who transitioned from a tech lead role but fell into the anti-pattern of excessive monologuing during sprint planning sessions. This PO, despite good intentions, overwhelmed the team with lengthy technical details, causing developers to withdraw from interactions and leaving them confused about project purposes. Through one-on-one coaching focused on building self-awareness and establishing working agreements, Anamaria helped this PO learn to communicate more effectively and engage collaboratively with the team. Self-reflection Question: How do you help Product Owners transition from technical expertise to effective team communication, and what signs indicate when detailed explanations become counterproductive monologues? [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 Anamaria Ungureanu Anamaria Ungureanu is an Agile evangelist driving transformations across IT, airlines, and automotive. She delivers projects with firms like IBM and Airbus, coaches from executives to teams in SAFe and Scrum, leads assessments, customizes workshops, and supports tool adoption, like Jira, and digital whiteboards like MIRO. You can link with Anamaria Ungureanu on LinkedIn.

1 Aug 14min

Measuring Success Through Team Evolution | Anamaria Ungureanu

Measuring Success Through Team Evolution | Anamaria Ungureanu

Anamaria Ungureanu: Tracking Scrum Team Behavioral Evolution Over Time Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Anamaria defines Scrum Master success by focusing on team behavioral trends and performance evolution over time. She monitors how teams increase trust with stakeholders, demonstrate commitment, and apply agile behaviors consistently. Her approach emphasizes seeking regular feedback from stakeholders and conducting honest self-assessments to ensure the Scrum Master role is truly maximizing team performance. Success isn't measured by a single moment but by sustained positive change in team dynamics and delivery capabilities. Featured Retrospective Format for the Week: Stop/Start/Continue with Enhanced Focus Anamaria recommends the classic Stop/Start/Continue format but emphasizes the importance of varying the questions and bringing both quantitative and qualitative data to drive meaningful conversations. She suggests picking specific themes for each retrospective (like testing) and ensuring that discussions lead to concrete, actionable outcomes rather than just surface-level feedback. Self-reflection Question: How do you currently measure your effectiveness as a Scrum Master, and what trends in your teams indicate genuine progress versus superficial compliance? [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 Anamaria Ungureanu Anamaria Ungureanu is an Agile evangelist driving transformations across IT, airlines, and automotive. She delivers projects with firms like IBM and Airbus, coaches from executives to teams in SAFe and Scrum, leads assessments, customizes workshops, and supports tool adoption, like Jira, and digital whiteboards like MIRO. You can link with Anamaria Ungureanu on LinkedIn.

31 Juli 15min

Practical Strategies for Organizational Tool Rollouts | Anamaria Ungureanu

Practical Strategies for Organizational Tool Rollouts | Anamaria Ungureanu

Anamaria Ungureanu: Practical Strategies for Organizational Tool Rollouts 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. Anamaria shares her approach to successfully implementing JIRA across an organization by focusing on practical value rather than forcing adoption. Her strategy involved identifying early believers within teams, conducting open discussions to gather feedback, and demonstrating concrete benefits like improved dependency management. Rather than trying to convince resisters, she concentrated on working with willing teams to showcase the tool's value, providing real-time support during implementation, and ensuring team members felt supported throughout the transition. Her method emphasizes being present to answer questions immediately and building momentum through successful early adopters. Self-reflection Question: When leading organizational change, how do you balance addressing resistance with amplifying the voices of those ready to embrace new approaches? [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 Anamaria Ungureanu Anamaria Ungureanu is an Agile evangelist driving transformations across IT, airlines, and automotive. She delivers projects with firms like IBM and Airbus, coaches from executives to teams in SAFe and Scrum, leads assessments, customizes workshops, and supports tool adoption, like Jira, and digital whiteboards like MIRO. You can link with Anamaria Ungureanu on LinkedIn.

30 Juli 12min

Knowledge Hoarding and Team Dependencies | Anamaria Ungureanu

Knowledge Hoarding and Team Dependencies | Anamaria Ungureanu

Anamaria Ungureanu: The Tech Lead Who Nearly Destroyed the 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. Anamaria describes a seven-member software team that initially seemed engaged but began self-destructing when a senior tech lead refused to embrace transparency and knowledge sharing principles.  The situation escalated when this key team member's four-day absence completely blocked the team's ability to deliver, creating a dangerous single point of failure. Through careful retrospective facilitation and strategic motivation techniques, including offering the specialist new learning opportunities while gradually transferring their legacy knowledge to teammates, Anamaria helped the team overcome knowledge silos and establish sustainable collaboration patterns. Featured Book of the Week: Never Split the Difference by Chris Voss Anamaria recommends “Never Split the Difference” by Chris Voss, a negotiation masterpiece because it taught her essential communication strategies for establishing trust and navigating tense situations. She emphasizes that negotiation is a critical Scrum Master skill, and Voss's techniques help build rapport with stakeholders while managing difficult conversations that arise during team transformations and organizational change initiatives. Self-reflection Question: What knowledge silos exist in your teams, and how might you motivate specialists to share their expertise while providing them with new growth opportunities? [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 Anamaria Ungureanu Anamaria Ungureanu is an Agile evangelist driving transformations across IT, airlines, and automotive. She delivers projects with firms like IBM and Airbus, coaches from executives to teams in SAFe and Scrum, leads assessments, customizes workshops, and supports tool adoption, like Jira, and digital whiteboards like MIRO. You can link with Anamaria Ungureanu on LinkedIn.

29 Juli 18min

Goal Clarity—The Missing Piece in Agile Team Performance | Anamaria Ungureanu

Goal Clarity—The Missing Piece in Agile Team Performance | Anamaria Ungureanu

Anamaria Ungureanu: Goal Clarity—The Missing Piece in Agile Team Performance 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. Anamaria shares her experience working with a platform implementation team that appeared engaged but was actually struggling in silence. Despite initial assumptions that everything was fine, the team's quiet demeanor masked their lack of understanding about project goals and deliverables.  Through strategic intervention including goal clarification with the Product Owner, confidence level assessments, and story mapping sessions, Anamaria helped transform a disengaged team into one capable of successful delivery. Her approach emphasized the importance of fostering constructive conflict, asking open questions during sprint planning about demo expectations, and facilitating better PO-team interactions to create transparency and shared understanding. In this episode, we refer to User Story Mapping and the concept of Gemba, or Gemba Walk Self-reflection Question: How might your teams be silently struggling, and what signs should you watch for to identify when apparent engagement actually masks confusion or disengagement? [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 Anamaria Ungureanu Anamaria Ungureanu is an Agile evangelist driving transformations across IT, airlines, and automotive. She delivers projects with firms like IBM and Airbus, coaches from executives to teams in SAFe and Scrum, leads assessments, customizes workshops, and supports tool adoption, like Jira, and digital whiteboards like MIRO. You can link with Anamaria Ungureanu on LinkedIn.

28 Juli 13min

The Hidden Cost of Decision-Making Delays in Product Development | Anh Vu

The Hidden Cost of Decision-Making Delays in Product Development | Anh Vu

Anh Vu: The Hidden Cost of Decision-Making Delays in Product Development Read the full Show Notes and search through the world's largest audio library on Agile and Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: The Strategic Connector Anh describes an exceptional Product Owner who went far beyond managing the backlog to become a strategic connector between customer needs, business requirements, technical constraints, and overall strategy. What made this PO remarkable was their background - they came from a developer background rather than business, yet quickly mastered the Product Owner role through dedicated learning. Despite being new to the PO role, they rapidly developed the ability to connect backlog items directly to customer pain points, often using techniques like user story mapping. This PO brought both clarity and purpose to the team, significantly boosting team motivation by helping developers understand how their work directly impacted customers and business outcomes. The Bad Product Owner: The Proxy Problem The worst Product Owner situation Anh encountered involved a Proxy PO who lacked the authority to make decisions independently. This created significant challenges for both the team and the PO, as every new problem or decision required seeking permission from external stakeholders. This pattern lengthened feedback cycles and demotivated both the PO and the development team, who couldn't move forward efficiently when blocked by decisions. Anh's approach to addressing this involved coaching the PO on engaging with external stakeholders, setting up regular touchpoints (2-3 times per week) to shorten feedback cycles, and focusing on improving the decision-making process to unblock the team. He also emphasized creating a strong network of connections for the PO to navigate the organization effectively and always having a Plan B when certain decisions couldn't be made quickly. Self-reflection Question: Does your Product Owner have true decision-making authority, or are they frequently forced to seek permission from others, and how is this affecting your team's velocity and motivation? [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 Anh Vu Anh Vu is a seasoned Project Manager with 10+ years in software delivery, Agile, DevOps, and PM. As a PMP trainer, he has empowered 200+ professionals. Passionate about continuous learning, Anh explores practical tools and methodologies to help PMs and teams succeed in fast-paced, tech-driven environments. You can link with Anh Vu on LinkedIn.

25 Juli 12min

Situational Leadership for Scrum Masters - Knowing When to Step Back | Anh Vu

Situational Leadership for Scrum Masters - Knowing When to Step Back | Anh Vu

Anh Vu: Situational Leadership for Scrum Masters - Knowing When to Step Back 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. Anh defines success for Scrum Masters through a simple but powerful test: when you take vacation and return to find the team working exceptionally well without you. This ultimate measure of success focuses on building self-organization and enabling true team autonomy. He emphasizes that Scrum adoption should serve as a metaphor for autonomy and self-organization, with the Scrum Master's stance evolving alongside the team's growth. Drawing from Situational Leadership principles, Anh points out that a team can only become as autonomous as the Scrum Master can envision and facilitate. The key is recognizing when to step back and allow the team to demonstrate their independence while ensuring they have the foundation and confidence to succeed. Featured Retrospective Format for the Week: Free Form Retrospective Anh advocates for the free form retrospective format, which requires only a whiteboard, table, and people gathering for open reflection based on the previous sprint's goals. Rather than following structured formats, he invites team members to share their insights freely, considering the retrospective successful as long as the team leaves with 1-3 actionable insights. This approach works particularly well with teams he knows well, where trust and communication patterns have been established. He builds on this by incorporating silent thinking time to start conversations, a habit developed over time that makes teams more comfortable sharing in the free form format. Anh also recommends conducting retrospectives during in-office days when the team can eat together, investing heavily in these face-to-face interactions to strengthen team bonds. Self-reflection Question: What would happen if you took a week off from your current role - would your team continue to thrive, or would they struggle without your direct involvement? [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 Anh Vu Anh Vu is a seasoned Project Manager with 10+ years in software delivery, Agile, DevOps, and PM. As a PMP trainer, he has empowered 200+ professionals. Passionate about continuous learning, Anh explores practical tools and methodologies to help PMs and teams succeed in fast-paced, tech-driven environments. You can link with Anh Vu on LinkedIn.

24 Juli 14min

From Project Mindset to Product Thinking - Leading Client Transformation | Anh Vu

From Project Mindset to Product Thinking - Leading Client Transformation | Anh Vu

Anh Vu: From Project Mindset to Product Thinking - Leading Client Transformation 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. Anh describes a transformative collaboration experience while building multiple websites for a client. Over time, his team recognized significant commonalities between projects and saw the opportunity to create reusable components for future work. However, they faced resistance when trying to shift the client's mindset from short-term project delivery to long-term product thinking. The business stakeholders remained focused on immediate project completion rather than investing in sustainable, reusable solutions.  Anh's approach to leading this change involved presenting concrete evidence from previous projects to demonstrate the tangible benefits of component reusability. Rather than just proposing the idea theoretically, they suggested implementing reusable components immediately within the current project, showing rather than just telling. His strategy centered on providing clear evidence of benefits and demonstrating achievability, making the transition from project to product mindset more tangible and less risky for the client. In this episode, we refer to the book “From Project to Product” by Mik Kersten.  Self-reflection Question: How might you help your stakeholders see beyond immediate deliverables to recognize the long-term value of sustainable practices and reusable solutions? [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 Anh Vu Anh Vu is a seasoned Project Manager with 10+ years in software delivery, Agile, DevOps, and PM. As a PMP trainer, he has empowered 200+ professionals. Passionate about continuous learning, Anh explores practical tools and methodologies to help PMs and teams succeed in fast-paced, tech-driven environments. You can link with Anh Vu on LinkedIn.

23 Juli 12min

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