The CTO Playbook

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.

Michael Louis Schank, an author and consultant specializing in digital transformation, shares insights from his extensive background at major firms like Accenture and Bank of America. He reveals that the real bottlenecks in transformations are not technology or people, but rather the complexity that breeds chaos. Michael emphasizes the importance of mapping business processes and assigning ownership to clarify change and prevent drift. He discusses bridging the communication gap between tech and business, and how simple process inventories can enable better outcomes and innovation.

Ever struggled to explain tech concepts to non-techies? Discover how one CTO transformed his message using a floating city metaphor to secure buy-in from co-founders. Learn why traditional analogies like buildings fall short and how to reframe your platform as a living, modular system. Hear how mapping platform components to an oil rig can clarify complex ideas. Get insights on powerful storytelling that enhances leadership without oversimplifying the truth. Practical steps included for anyone looking to communicate effectively!

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.When your CTO dies and no one can read the code, you realize the real problem was never the software.In this episode, I sit down with Matteo Di Battista and Marcello Modica, two Italian innovators who’ve spent decades helping companies escape the grip of outdated ERP systems. From IBM mainframes to cloud-native development, they’ve seen how technical debt and siloed knowledge can quietly strangle growth.We get into what happens when your tech stack outlives your people, why monoliths breed fragility, and how breaking systems into small, pluggable services changes everything. It’s not just about new tools—it’s about a new kind of teamwork that keeps knowledge alive even when key players leave.Because modernization isn’t just a tech upgrade—it’s a survival strategy.You’ll Learn:[00:00] Introduction[05:32] Why monolithic ERP systems quietly trap companies in technical debt[09:47] What happens when a CTO’s death exposes a company’s hidden knowledge silos[12:18] The moment you know it’s time to modernize your software before it collapses[15:44] How low-code and visual tools can close the gap between design and delivery[18:56] Why developers are becoming replaceable, and what that means for software teams[23:51] How building a shared development community protects both companies and clients[26:28] The real reason developers resist change even when innovation would make life easier[33:42] What the new network API standard means for identity, payments, and fraud prevention[45:37] How converting old databases into REST APIs transforms legacy systems into living platformsYou can connect on LinkedIn with both Matteo and Marcello, and their work though wavemaker.com and oneclickapp.it.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

In this discussion, Thorgeir Einarsson, founder of Pitchago, delves into the shifting landscape of startup funding and AI. He highlights that traction is now more crucial than ever as investors prefer application-layer AI over generic models. Hardware is seeing a resurgence, especially in defense and medical sectors. Thorgeir emphasizes the importance of pre-diligence to prepare founders for real investor scrutiny and warns about the overlooked area of AI safety. He offers valuable insights on maintaining strong co-founder relationships and the need for startups to truly understand their customers.