The CTO Playbook

Catherine Stagg-Macey, an executive coach for technical experts transitioning into leadership, shares her insights on the struggles of moving from individual contributor to team leader. She highlights why being the smartest person in the room can become a hindrance and explores the damaging 'hero' culture that leads to burnout. Catherine discusses the importance of recognizing triggers, testing new leadership behaviors, and how upbringing influences leadership styles. The conversation also touches on the potential role of AI in coaching.

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.

Lou Franco, a veteran software engineer and author of "Swimming in Tech Debt," joins to discuss the often-overlooked burden of tech debt on engineering teams. He shares insights from his career, including critical lessons learned during fintech projects and startup acquisitions. Lou explains how small, focused fixes can drastically improve productivity and morale while highlighting the risks of ignoring tech debt. He emphasizes the importance of creating a culture that acknowledges and manages debt effectively, linking it to a product's lifecycle for optimal tech management.

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.

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.

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.

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 your most important leadership skill had nothing to do with technology, and everything to do with how people feel?In this episode, I’m joined by Wesley Eugene, SVP at HIT Global and former CIO at IDEO. Wesley’s career has taken him from building computers in college to leading technology and transformation for some of the world’s most innovative companies. At HIT Global, he’s helping usher in a new way of thinking about tech leadership with a framework built entirely around human-first principles.We talk about the moments in his career that drove home the power of trust, relationships, and empathy in technology. Wesley shares how human-centered design, storytelling, and a focus on real-world experiences can transform how leaders guide their teams and serve their customers. This is a conversation about leading people, not just managing processes.You’ll Learn:The leadership shift that happens when you treat experience as your North StarWhy telling better stories with data wins more than just argumentsThe surprising power of empathy as a competitive edge in tech leadershipHow radical candor transforms the way feedback is given and receivedThe quiet damage of outsourcing critical customer experiencesWhat it feels like to lead through a global crisis with trust as your main currencyThe link between human-centered design and faster, smoother transformationsWhy going analog can unlock your most creative and strategic thinkingHow to anchor digital transformation in moments that truly matter to peopleTimestamps:[00:00] Introduction[05:58] Starting in tech through service desk work and early career moves[08:56] Driving digital transformation and workforce reskilling at Aflac[09:58] Leading secure remote transitions during the pandemic through trust and relationships[12:57] Frameworks that shaped leadership including TBM and radical candor[17:49] Immersion in human-centered design at Aflac and IDEO[21:01] Realizing the importance of designing for real-world user experiences[25:02] Breaking down the Human First playbook principles[34:09] The role of unplugging and analog thinking in creativity and leadershipResources Mentioned:Technology Business Management Council | WebsiteRadical Candor by Kim Scott | Book or AudiobookRadical Respect by Kim Scott | Book or AudiobookWant to learn how to lead with empathy, design, and story at the core? You can connect with Wesley on LinkedIn, where he is building the Humanising IT™ movement; training, certifying, and coaching the next generation of human-first tech leaders.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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 very habits that once made you successful are now holding you back?In this episode, I talk with Dr. Ravi Iyer, a physician, scientist, and leader with over four decades of experience in medicine, research, and hospital leadership. His work has taken him from studying molecular immunology at Harvard to serving as Chairman of a Department of Medicine, and his career has been driven by one relentless question: how do you make life work when it doesn’t?We dig into why our brains cling to patterns, how those patterns can trap even the smartest leaders, and what it really takes to see beyond the “menu” of our past playbooks so we can actually taste the meal of life. This is a conversation about awareness, choice, and breaking free from default thinking, both in leadership and in life.You’ll Learn:The real reason even accomplished leaders cling to outdated playbooksWhat happens when life stops matching the patterns you’ve always relied onThe link between an amoeba’s behavior and human decision-makingWhy subconscious “choices” are actually compulsions in disguiseHow success can lock you into strategies that block future growthThe two forces powerful enough to break a leader’s mental resistanceWhy chasing novelty can become just another limiting patternThe quiet damage of confusing the “menu” for the actual “meal” of lifeHow to use sensory deprivation to break stale relational or leadership habitsWhat it feels like to lead from the space that contains all your optionsTimestamps:[00:00] Introduction[03:02] The lifelong question that shaped a career in science and medicine[06:46] How pattern matching drives human behavior and decision-making[11:41] Lessons from a grandfather on reframing problems and breaking patterns[17:08] Why subconscious choices limit freedom and success[24:54] How successful playbooks create plateaus in leadership growth[28:01] The “menu vs meal” analogy and the search for real experience[33:42] Using sensory deprivation to reset relationships and leadership habits[39:24] Applying new data collection methods to break organizational patterns[42:51] Why personal experience should guide your ultimate playbookGet a FREE copy of Dr. Ravi Iyer’s digital books here.If you want to connect more with Dr. Ravi, follow him on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Great CTOs are made by unlearning bad habits. Learn why overstuffing your calendar stifles strategic thinking. Find out the importance of delegating decisions, not just tasks. Discover how clear communication of company vision boosts team alignment. Hear why chasing every new trend can hinder innovation and how overusing jargon can dilute your authority. Explore the surprising connection between avoiding trade-offs and leadership gridlock, and get tips on embracing mistakes as part of the innovation process.

Faris Aranki, founder of Shiageto Consulting and former strategy consultant, shares his insights on effective leadership and team dynamics. He emphasizes the criticality of weekly one-on-ones for individual success and aligning performance with company goals. Aranki discusses the integration of IQ, EQ, and FQ for fostering collaboration, particularly in high-stakes environments. Through active listening, he shows how building trust can enhance productivity while addressing the impacts of marginalization in tech teams. The conversation is rich with practical strategies for leaders.