The CTO Playbook

• 67: People, Process, Technology: The Leadership Formula Every CTO Needs

  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.

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• 66: CTO Playbook: Leading Change Without Chaos — Giorgia Prestento

  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.

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• 65: Unrealistic Planning, Broken Collaboration — and How to Fix Both

  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.

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• 64: What Got You Here Won’t Get You There — CTO Leadership with Catherine Stagg-Macey

  Build your own CTO Playbook here, 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 playbook that built your career suddenly stopped working and nobody told you?In this episode, I sit down with Catherine Stagg-Macey, an executive coach who works with technical experts turned leaders. She knows firsthand what it’s like to move from coding and spreadsheets into managing people, and the struggle that comes with it.We get into what happens when being the smartest person in the room is no longer enough, the patterns that keep leaders trapped in the systems they built, and the hard pivot it takes to step into a new kind of leadership.You’ll Learn:The reason smart technical leaders hit a wall when old habits stop workingWhat happens when you try to manage people with the same mindset you used to write codeThe link between control, trust issues, and being stuck in endless meetingsThe damage of wearing the “superhero cape” and building a culture of firefightingWhy skepticism is common when leaders are first asked to work with a coachThe pivotal moment that led Catherine from consulting success to a coaching careerHow childhood patterns and early work experiences quietly shape leadership behaviorsThe role of feedback, or the lack of it, in pushing leaders toward breaking pointsWhy creating distance from your triggers opens space for better choicesTimestamps:[00:00] Introduction[06:15] Breaking patterns of overwork and constant meetings[08:55] The lure and cost of playing the workplace superhero[10:20] Catherine’s pivot from consulting success to coaching[16:05] When rock bottom moments force change[20:15] Early warning signs leaders ignore before burnout[26:45] Identity shifts required to let go of old leadership habits[30:10] Recognizing triggers and unconscious behavior patterns[41:20] How upbringing and culture shape leadership reactions[53:00] Building range as a leader in times of uncertaintyResources Mentioned:Conversations at the Edge | WebsiteYou Didn’t Chase Leadership. Leadership CHASED You. Join Catherine’s Inner Circle.Unlock your leadership superpower, discover what your leadership style is with Catherine’s Leadership Style Quiz.You can connect with Catherine on LinkedIn and listen to her podcast here. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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• 63: How Corey Hart Scaled a Crisis Team Fast — Without Losing Trust

  Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!Would you say yes to leading through chaos with no plan, little information, and no guarantee of success?In this episode, I sit down with Corey Hart, a crisis operator who’s built a career on scaling massive humanitarian and operations projects under extreme pressure. He’s said yes to projects most people would run from, from helping New York City respond to a sudden influx of asylum seekers to standing up global call centers and navigating cruise ship operations post-lockdown.We get into how he prepares for the unknown, what it takes to build trust in the middle of a storm, and why surrounding yourself with the right people makes the difference between collapse and momentum.You’ll Learn:The reason Corey says yes to high-stakes projects others avoidWhat happens when you’re asked to launch a humanitarian response overnightThe link between early onboarding and a culture of openness and candorThe damage of overcomplicating operations when speed is criticalWhat it feels like to land in a crisis with little info and no certaintyWhy bringing compliance and tech in early turns them into strategistsThe role of trust in holding teams together under extreme pressureHow living autopsies fix problems in real time, not after the factThe mindset shift that turns specialists into early-stage leadersWhy tracking from day one helps you see around corners in chaosTimestamps:[00:00] Introduction[05:58] Saying yes to unpredictable challenges[07:02] Scaling New York’s asylum seeker response[11:58] Handling moments when operations nearly collapse[14:02] Filtering signal from noise in crisis decision-making[17:56] Building openness and candor into team culture[20:06] Creating trust and making failure safe[22:01] Why saying yes builds momentum and possibility[27:00] Unlikely outcomes from saying yes[31:00] Keeping operations simple and avoiding scope creep[33:02] Tracking data early to guide decisions under pressure[35:00] Bringing compliance and tech in early to shape solutions[37:56] Knowing when and how to step out of a crisis projectResources Mentioned:Podcast Episode The CEO’s Playbook for Hiring the Right CTO with Warren Beasley | YouTubeYou can connect with Corey on LinkedIn and his website.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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