The CTO Playbook

• 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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• 60: What Do You Do When No One’s Watching? The Truth About Proactive Leadership

  Build your own CTO Playbook at our website — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Proactivity isn’t an all-or-nothing game.In this episode, I break down the myth that leaders are either “proactive” or “reactive” and share why even small, flickering moments of foresight can put you ahead. I get into what happens when you’re forced into reactive mode and how to inject just a bit of proactivity into those moments so they don’t derail you. I talk about the “pressure off” test, those quiet weeks when your defaults show up, and how to use them to reset your habits. I wrap up with five practical steps you can start this week to shift from constant firefighting to being seen as a steady, strategic leader.You’ll Learn:The real reason proactivity isn’t a fixed leadership traitWhat a flickering light bulb can teach you about staying aheadWhy just 5% more foresight each week changes how your team sees youHow to inject proactive moves into high-pressure, reactive situationsThe quiet damage of coasting during “pressure off” weeksWhat the “pressure off” test reveals about your default leadership modePractical ways to prepare for outages and crises before they happenThe surprising link between military “go bags” and tech leadership readinessHow to turn firefighting moments into long-term strategic winsFive simple steps to build steady, visible proactivity into your weekTimestamps:[00:00] Introduction[05:00] Busting the myth of proactive vs reactive leadership[06:14] The flickering light bulb analogy for building proactivity[07:55] Injecting proactive actions into reactive situations[09:59] Building your leadership “go bag” for crises[11:42] The pressure off test and why quiet weeks matter[13:50] Using downtime to reset strategic habits[14:56] Five steps to increase consistent proactivity[18:45] Why small, steady choices outweigh perfectionFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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• 59: The Future of the CTO: Etienne de Bruin on Leadership, Liquid & Lasting Impact

  Build your own CTO Playbook at our website — 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 hardest part of being a CTO isn’t about the technology at all, but learning to lead without a map?In this episode, I’m joined by Etienne de Bruin, founder of Seven CTOs and CTO Levels, and co-author of the upcoming book Liquid. For more than a decade, Etienne has worked with CTOs navigating the shift from hands-on coding to executive leadership.We talk about the moment he realized his value wasn’t in the code anymore, how he built a peer network to fill the gaps he couldn’t see, and the pivotal lessons that shaped his approach to coaching. Etienne also shares the thinking behind Liquid, exploring how CTOs can find balance between chaos and rigidity while mastering the four “sentinels” every tech leader needs to succeed.You’ll Learn:What it feels like to be pushed or pulled out of the codebase as a CTOThe real reason Etienne founded Seven CTOs and why most early members walked awayHow ontological coaching changes the way CTOs solve problems and influence outcomesThe quiet damage of solving the wrong problem when your influence goes uncheckedThe four “sentinels” every CTO must master to earn trust at the executive tableWhy balancing “boiling” chaos and “frozen” rigidity can make or break a tech teamThe surprising link between financial fluency and a CTO’s long-term successHow the Levels framework reveals capability gaps that stall growthWhat happens when a CTO builds genuine alignment with sales and product leadersTimestamps:[00:00] Introduction[06:58] The challenge of stepping away from coding into leadership[14:00] Building a startup and the moment to stop coding[17:57] Creating Seven CTOs and the need for peer groups[27:15] How ontological coaching transforms CTO problem solving[37:14] The core role of a CTO and the importance of financial fluency[45:11] The concept of Liquid and navigating boiling vs frozen states[47:59] The four sentinels every CTO must manage[53:54] Using the Levels framework to diagnose capability gapsYou can connect with Etienne on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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