The CTO Playbook

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 your biggest advantage as a CTO has almost nothing to do with technology at all?In this episode, I sit down with Rory Herriman, US CTO at Zip Co, whose thirty year career runs from the military through large enterprises to high growth fintech. Rory brings a playbook forged in real world pressure, from learning to stay calm under fire to realizing that the job is as much about business impact as it is about systems and code. That journey taught him to care less about flashy problems and more about culture, fundamentals and the people he is working with every day.We get honest about what it feels like when you're the one carrying the unspoken weight of every decision while everyone else assumes you've got it handled. It is very easy to slip into chasing hype or focusing on the wrong signals when the real leverage is in resilient fundamentals and a clear link between decisions and business impact. We explore what it actually looks like to stand on that bedrock, keep things fluid around your people, and lean into a near-term future where humans and AI are working side by side. And you'll see why leading this way makes the CTO journey feel a lot less lonely and a lot more sustainable.You’ll Learn:[00:00] Introduction[04:14] How military calm under pressure becomes one of a CTO’s most transferable advantages[08:02] Why the real job isn’t technology but understanding business impact at a deep level[13:03] What shifts when you stop being the smartest technologist and start leading through people[17:06] The humbling moment that proved one org chart can’t fix cultural differences[19:48] Why a strong bedrock of fundamentals makes everything else faster and easier[24:58] How treating people and systems as symbiotic unlocks execution instead of friction[28:54] The power of fluid teams that move to the work rather than waiting for work to come to them[33:04] What changes when a CTO stops chasing the future and starts shaping it[46:12] The reason AI isn’t cost-cutting, but a resource multiplier that expands what humans can do[50:28] What hybrid human + AI teams look like inside an organization right now[55:02] Why excellence, velocity and integrity aren’t trade-offs but a three-part operating balanceYou can connect with Rory and his work on his LinkedIn and his website.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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.

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 lever isn’t the tech at all?In this episode, I sit down with Matthew Carr, who does interim work and often comes in as the firefighter when a company has taken a wrong turn. He lays out why people come first, processes second, and technology follows.He started in classic ASP and built a loyalty program for the heating and engineering sector. Real-time results beat long compile cycles and changed how he delivered. A private-equity buyout couldn’t get the startup’s tech delivered, so he sat one-to-one with everyone to map the problems. Turns out, fixing broken delivery isn’t about new tools. It’s about people, trust, and having the guts to act fast.You’ll Learn:The reason putting people first makes process work and technology followWhat happens when you plan three sprints ahead and tie outcomes to business valueThe link between quick wins and winning trust in the first 30 daysThe damage of being six to twelve months off on deliverables after a PE acquisitionWhat it feels like to inherit a program that hasn’t shipped in 18 monthsThe link between weekly iterations, monthly demos, and a product becoming a bedrock of the businessThe reason trust, leadership, and alignment are the core enablers of the people pillarWhat happens when you play their game first by showing a six-week plan the board can approveThe reason “believe in yourself” is the sharpest one-line tip for new CTOsTimestamps:[00:00] Introduction[05:12] Why people come first before process and technology[10:46] Lessons from early development work in classic ASP and loyalty programs[15:58] How a private equity acquisition exposed major delivery delays[21:37] Running a massive retrospective and uncovering 110 problems[28:04] The importance of quick wins and building trust in the first 30 days[33:41] Planning three sprints ahead and reporting outcomes instead of outputs[38:22] Turning around a project that hadn’t shipped in 18 months[45:09] How weekly iterations and monthly demos rebuilt momentum[51:28] The one-line advice Matthew gives every new CTOLearn more from Matthew on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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.Logic alone won’t land; people react to change emotionally.In this episode, I sit down with Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s here to show why change so often derails and how CTOs can lead through it with clarity and confidence.We break down why rational explanations fall flat, the different speeds leaders and teams move at, and how losing control sparks uncertainty and anxiety. A call center story shows how rewarding quick answers without customer outcomes skews behavior. A Hong Kong example proves that “ask your line manager” messaging failed culturally, so we rewrote it to a nominated peer contact. A pre-mortem setup surfaces blind spots by declaring the project failed and collecting reasons before execution. We run through an eight-step playbook from purpose and alignment to blind spots, impacts, resistance, indicators, validation, and finally execution.You’ll Learn:The reason logic-only change pitches backfireWhat happens when leaders move faster than teamsThe link between the metric you reward and the behavior you getWhat it feels like to run layoffs twiceThe reason pre-mortems workWhat happens when you don’t set indicators earlyThe link between purpose, alignment, and smoother executionWhat happens when a key trainer is missingThe damage of losing clarity at the topTimestamps:[00:00] Introduction[05:18] Why logic fails when leading change[10:42] The emotional side of resistance and uncertainty[15:56] How leaders move faster than their teams[20:11] The blind spot that halted a global SAP rollout[26:27] Why bad metrics destroy good behavior[31:03] Cultural barriers that derail transformation[36:49] The pre-mortem method for spotting hidden risks[42:08] The eight-step change playbookResources Mentioned:Master the Change Maze by Giorgia Prestento | BookGiorgia offers a short assessment 'Leaders: Are You Change Ready?' You will gain valuable insights across the categories of Leadership Style, Change Expertise and the Readiness of your organisation. It takes less than 3 minutes. You get readiness scores in a personalised report. Plus a digital copy of her book, Master the Change Maze. Click here to get started.You can connect more with Giorgia on LinkedIn. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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.Are you optimizing for starting work instead of finishing?In this episode, I’m joined by Joakim von Prónay, an engineer and psychologist by education and a coach by passion.We break down how fake roadmaps and a “Global Roadmap Owner” role turn planning into a Gantt chart exercise. We make planning useful with a simple rule: it’s better to be roughly right than precisely wrong. Predictability becomes the lever for real accountability, measured by “did we do the things we said we were gonna do.” Escalation culture gives way to real collaboration, not the default “ask the boss” reflex.You’ll Learn:The reason long-term planning works when it’s roughly right instead of precisely wrongWhat happens when teams are incentivized to start work instead of finish itThe link between delivery predictability and real prioritization and accountabilityThe damage of treating roadmaps like a Gantt chart exerciseWhat it feels like when every question defaults to “ask the boss” instead of talking directlyThe reason fragmented steering creates conflicting directionsThe link between a single “central rule” and measurable goalsTimestamps:[00:00] Introduction[06:14] Why high-performing teams are so rare[09:27] The danger of planning for perfection[15:46] Why teams start work instead of finishing it[19:32] The power of predictability and real accountability[25:40] When collaboration breaks down into escalation[31:58] What fragmented steering really looks like[38:45] The rule that defines true strategy[46:23] A Spotify story and the engineer’s warning[51:17] How alignment turns insight into actionConnect more with Joakim on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.