The CTO Playbook

• 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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• 58: You’re Not Leading If You’re Not Listening – Wesley Eugene on Empathy and Influence

  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.

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• 57: Why Leaders Fail to Grow — Even When They’re Doing Everything ‘Right’

  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.

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• 56: 14 Things Great CTOs Stop Doing (And You Should Too)

  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.Stop Doing These 14 Things If You Want to Be a Great CTOI’m not adding to your to-do list—I’m flipping it. These are the habits that keep you reactive, overwhelmed, or straight-up invisible to the rest of the exec team. I walk through the traps that I see CTOs fall into again and again, from packing your calendar like a bad game of Tetris to leading every decision and chasing every shiny trend. These aren’t theories. They’re mistakes I’ve coached dozens of tech leaders through—and screwed up myself too.You’ll Learn:The real reason packing your calendar wall-to-wall kills strategic thinkingWhat happens when you delegate tasks but not decisionsThe quiet damage of assuming your team understands the company visionWhy translating tech into business outcomes changes your exec team influenceThe simple phrase that makes hard feedback easier to hear and act onWhat it feels like to stop chasing trends and start trusting fundamentalsThe surprising link between avoiding trade-offs and leadership gridlockHow overusing jargon weakens your clarity and authorityWhat most CTOs get wrong about culture—and how to fix itWhy punishing mistakes kills innovation faster than any bad processTimestamps:[00:00] Introduction[03:06] Why filling every hour kills your ability to lead[04:15] The problem with working without strategic alignment[05:01] Delegating tasks vs delegating decisions[06:41] What happens when people don’t understand the vision[07:50] How to translate engineering into business language[08:55] Why leading with opinion weakens your credibility[10:00] The cost of chasing every shiny trend[11:00] You can’t scale if you lead everything alone[12:58] How to have hard conversations and handle feedback[13:54] Why jargon destroys clarity and influence[14:50] What culture is actually made of[15:36] Stop punishing mistakes if you want innovation[16:31] The danger of forcing rigid frameworks[17:29] How indecision leads to gridlock[18:49] Quick-fire recap of the 14 habits to stopFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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