The CTO Playbook

• 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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• 62: Tech Debt Is Killing Your Team — Here’s What to Do About It

  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 biggest reason your team feels stuck isn’t money, but the weight of your own code?In this episode, I sit down with Lou Franco, author of Swimming in Tech Debt and a veteran software engineer who’s been a founding engineer at three successful startups, a principal engineer at Trello through its Atlassian acquisition, and now an advisor to software teams.We trace his journey from early lessons in fintech and startup acquisitions to the moments that exposed just how costly ignored tech debt can be. Lou shares what he learned from engineers on the ground, how small fixes can deliver outsized productivity gains, and why culture and process matter just as much as code when tackling debt.You’ll Learn:The reason most engineering teams carry hidden tech debt without clear solutionsWhat happens when day-to-day friction drags down delivery speed and moraleThe ROI of small, focused fixes that start paying back almost immediatelyThe damage that builds when debt is ignored until it hits a breaking pointThe link between a product’s lifecycle stage and the right level of debt reductionWhy dedicated engineering-led time creates accountability and better outcomesHow visible progress metrics help leadership see the value of paying down debtThe risk of jumping too fast into shiny new tech that stalls out in productionThe role of culture, style guides, and clear values in preventing runaway debtTimestamps:[00:00] Introduction[05:01] Early lessons on tech debt in fintech and startups[07:02] The exit interview that exposed ignored debt[08:59] Small fixes that delivered immediate productivity gains[11:00] When debt grows into brick walls and forced rewrites[14:01] Building team culture and values to tackle debt[16:59] Splitting engineering-led time from product-led work[23:00] Measuring debt payoff with metrics and visibility[29:01] Leading indicators of productivity and developer experience[36:59] High-risk systems, regressions, and measured approachesResources Mentioned:Swimming in Tech Debt by Lou Franco | BookCrossing the Chasm by Geoffrey Moore | Book or AudiobookYou can connect with Lou on LinkedIn and find his book here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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• 61: Why I Coach CTOs: Lessons from Avalanches, Startups, and Rebuilding Teams

  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 only difference between freezing in chaos and staying calm is how much practice you’ve done before the storm hits?In this episode, I trace the moments that shaped why I coach. From digging strangers out of an avalanche in Switzerland to carrying the weight of a teammate down Mont Blanc on one ski, survival and leadership kept pointing to the same truth: preparation creates calm. I talk about teaching kung fu to kids and bankers, seeing culture hold Palantir together at breakneck speed, and stumbling through my own startup without a coach. Later, I describe rebuilding both technology and trust at Realforce when fear was running high. All of it comes back to this: even the strongest leaders need someone in their corner, and that’s why I built The CTO Playbook.You’ll Learn:The reason practice beats panic when pressure hitsThe link between small wins and the breakthrough confidence they createThe damage of trying to figure everything out alone without guidanceWhat it feels like to rebuild trust and safety in a fearful teamWhy culture becomes the glue when growth outpaces structureThe moment persistence matters more than raw talent in leadership and coachingHow scaling without culture can tip a company into chaosTimestamps:[00:00] Introduction[06:00] Avalanche rescue and the calm that comes from practice[08:59] Skiing Mont Blanc and carrying the load so the team could get home[10:48] Kung fu teaching and the breakthrough power of persistence[13:00] Coaching adults and the hidden gaps even senior leaders face[13:52] Lessons from Palantir and why culture holds during chaos[14:55] Startup founder struggles and the cost of going it alone[15:46] Rebuilding trust and technology at Realforce[18:00] Why I coach and how Simon Sinek’s Golden Circle frames it[21:00] The five CTO archetypes every tech leader falls into[26:00] Basecamp, Elevate, and Ascent explained as the CTO Playbook journeyResources Mentioned:Start with Why by Simon Sinek | BookFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

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