The CTO Playbook

Pasha Jam, CTO of Bumper who scaled engineering from a few people to 110 across countries, prioritizes people-first leadership. He discusses psychological safety, how culture beats tech for hiring and retention, practices that build camaraderie like blameless incident response and AMAs, and scaling culture across remote offices while avoiding micromanagement.

They unpack gut instinct as experience compressed into quick pattern-matching signals. Real coaching stories show roadmap dilemmas, staged modernization choices, and when fast instincts saved or failed leaders. A practical three-question tool and a six-step playbook teach how to name, test, and train instincts without killing their speed. The conversation focuses on spotting weak domains, using data to validate feelings, and learning from retrospectives.

Massimo Belloni, Head of Machine Learning and Data Science at Docplanner and author of The Imposter newsletter, shares key insights on effective leadership. He emphasizes that true leadership is about people, not just technical skills, and how curiosity fosters trust. Massimo discusses the importance of autonomy in engineering, the unseen work that supports leadership, and learning from past mistakes. He encourages leaders to visualize future goals and act with intention, prioritizing transparency and the assumption of good intentions for team dynamics.

Maximiliaan van Kuyk, an entrepreneur specializing in trust within payments and the founder of IOU Marker, dives deep into the pressing issue of late invoice payments. He reveals that trust and misaligned incentives, rather than just finances, are the root causes of payment delays. Discussing the emotional toll on small business owners, he emphasizes the importance of consistency over confrontation in collections. With insights on AI tools for accounts receivable and the role of social accountability, Maximiliaan offers valuable strategies for CTOs to enhance cash flow management.

Join James Webster, a former Amazon engineer and founder of SheepCRM, as he shares insights on scaling operational maturity. He introduces the Three Mountains model, a framework for assessing organizational readiness. Topics include the pitfalls of ignoring where teams actually are, how clarity beats speed during hypergrowth, and the importance of facing reality in leadership. James also discusses the challenges of transforming operations and the role of AI in amplifying capabilities while posing risks. Perfect for those leading through change!

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.What if the real blocker in your certification isn’t the rules at all, but how you’re playing the game?What really happens when you treat compliance like a fixed checklist and then get hit with yet another vague delay? I take you into the moment a CTO realized that being technically right still left him carrying months of uncertainty on his shoulders. That crack in his old mental model opened the door to seeing regulation as a human system shaped by people instead of boxes to tick.The same compliance posture can lead to totally different timelines depending on relationships, incentives, and how you show up in the room. Instead of obsessing over perfection, the focus shifts to mapping the people in the process and asking sharper questions that actually move things forward. By the end of this episode, you’ll see how small moves of influence can change a certification journey that once felt completely out of your hands.You’ll Learn:[00:00] Introduction[01:12] Why the real certification roadblock is rarely the checklist[03:56] What changes when you treat compliance as a human system instead of binary rules[05:22] The question that flips frustration into influence and momentum[07:18] How a single shift in communication makes leadership lean in[08:42] The reason two identical compliance postures get wildly different timelines[09:31] How mapping people instead of tasks reveals hidden bottlenecks and unstuck paths[11:54] What a high-stakes UK implementation showed about friction-free compliance[14:38] Why aligned incentives accelerate timelines faster than documentation ever will[17:42] Where influence replaces waiting and CTOs move from reactive to strategic[18:22] Five steps that turn regulatory uncertainty into predictable progressFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

In this discussion, Gerald Chablowski, a lead developer and engineering leader with a unique background in archaeology, highlights the vital role of clear systems and documentation in tech. He argues that teams often struggle due to unspoken rules, which lead to chaos instead of creativity. Gerald emphasizes the importance of human-centered practices and how small pull requests can enhance code quality. He also discusses the balance between firm guidelines and flexibility, advocating for trust-building over micromanagement as key to effective leadership.

In this chat with Rory Herriman, US CTO at Zip Co, he shares insights from his 30-year journey across military and fintech landscapes. Rory emphasizes that a CTO's true role is about creating a culture and people-centric environment rather than mere tech oversight. He introduces a five-part framework focusing on fundamentals, organizational fluidity, and the seamless integration of AI into teams. He stresses the importance of aligning decisions with business impact and the value of mentorship in evolving leadership styles.

In this engaging discussion, Caroline Elliott, an experienced mountain rescue professional and former avalanche dog handler, shares how to apply rescue mindsets to corporate leadership. She reveals the physical effects of crisis on decision-making and the importance of calm language to ground overwhelmed teams. Caroline introduces the concept of a three-second reset to regain situational clarity and highlights the need for effective non-verbal communication. Her insights bridge the gap between high-stakes rescue scenarios and the pressures faced by tech leaders.

Radhika Dutt, an engineer and product strategist known for her book 'Radical Product Thinking,' dives into the pitfalls of traditional goal-setting and OKRs. She shares how focusing on targets can distract teams from genuine learning and problem-solving. Radhika advocates for a 'puzzle-setting' approach to motivate creativity and collaboration, encouraging leaders to embrace uncertainty. With real-world examples, she illustrates how reframing objectives can lead to smarter decisions and a culture of exploration, ultimately driving better product outcomes.