The CTO Playbook

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.

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.

Join The CTO Playbook Slack Community to connect with other CTOs!Are you managing your individual contributors in a way that fuels growth, performance, and alignment?In this episode, I’m talking with Faris Aranki, founder of Shiageto Consulting, about leading individual contributors through regular one-on-one meetings. Faris brings a wealth of experience from his career in strategy consulting and leadership coaching. We dive into a proven system for structuring these meetings to keep performance management simple, effective, and human-centered.We explore how to align individual performance with company goals, why weekly check-ins are crucial, and how to integrate these meetings into your larger performance frameworks. Faris also shares how building rapport and listening actively can lead to stronger relationships with your team, ensuring that growth is both continuous and aligned with the broader mission.You’ll Learn:The real reason weekly one-on-ones are critical for individual contributor successWhy a rolling agenda document is your most powerful tool in building trust and accountabilityHow to use silence strategically in one-on-one meetings to encourage deeper conversationThe quiet damage of neglecting active listening in engineering teamsWhat it feels like to lead with empathy and get results without micromanagingHow to align individual performance with company goals through simple, structured conversationsThe surprising link between personal development plans and long-term organizational successWhy you should avoid status updates in one-on-ones and focus on personal growthHow asking the right questions based on learning styles can level up your coaching approachTimestamps:[00:00] Introduction[06:30] The impact of the rolling agenda document on trust and accountability[08:00] How to structure one-on-ones to focus on personal growth and alignment[10:15] The role of silence in encouraging deeper conversations[12:00] How active listening can strengthen team communication and trust[16:30] Using the VARK model to tailor coaching to individual learning styles[19:10] How to integrate weekly, quarterly, and annual meetings into a performance management system[22:50] The benefits of focusing on experience over output in one-on-one meetings[25:00] Handling performance improvement plans and documentation for legal clarity[28:30] How to use one-on-ones to build influence and promote personal development[32:00] The importance of aligning individual goals with company objectives[34:50] Best practices for conducting quarterly and annual performance reviewsResources Mentioned:The Five Dysfunctions of a Team by Patrick Lencioni | Book or AudiobookLeaders Eat Last by Simon Sinek | Book or AudiobookHanlon's Razor | PrincipleMovie: MoneyballYou can connect with Faris on LinkedIn or take the Shiageto effectiveness assessment here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Are you managing individual contributors the best way possible?In this episode, I sit down with Peter Wong, a seasoned CTO, to discuss how to lead individual contributors effectively with a structured and personalized approach. You’ll hear how weekly one-on-one meetings, a simple but powerful rolling agenda, and understanding how each person learns can take performance management from stressful to seamless.We dive into how this method helps you align your team with company goals, nurture personal growth, and create trust—ensuring the continuous development of your engineering team, one conversation at a time. This approach ensures clarity and consistency, allowing your team to thrive.You’ll Learn:Why weekly one-on-one meetings are more powerful than lengthier sessionsThe real reason a rolling agenda can transform your leadership approachHow to foster trust and build rapport by simply listening more than speakingWhat happens when you tailor your questions to how each person learnsThe surprising link between performance management and building personal connectionsWhy writing things down in meetings isn’t just a formality—it’s a trust-builderThe quiet damage of skipping regular check-ins with your teamWhat it feels like to have an annual review with zero surprisesThe key to making performance feedback feel like a natural progressionHow to use small actions like weekly meetings to drive big results over timeTimestamps:[00:00] Introduction[05:25] How to build trust through active listening in one-on-ones[06:45] Tailoring questions to different learning styles for better coaching[08:05] The value of writing things down in meetings[09:20] Structuring one-on-one meetings for maximum impact[11:15] Keeping feedback focused on personal growth[12:40] The power of regular check-ins for performance momentum[14:05] Linking weekly meetings to quarterly and annual reviews[15:35] Using the VARK model to understand how your team learns[17:10] Handling performance improvement plans effectively[21:00] Simplifying annual reviews with structured feedback[22:45] Making performance reviews a natural progression[28:05] The role of a structured approach in leadership[30:10] Why a rolling agenda document is a game-changerYou can connect with Peter and learn more about his work through his LinkedIn and website.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Are you getting the most out of your individual contributors?In this episode, I sit down with Matan Kubovsky to dive into the art of managing individual contributors through weekly one-on-one meetings. Matan shares his experience and a proven system for leading teams with consistency, clarity, and alignment. This method isn’t just about project updates—it’s about shaping growth and connecting each person’s role to the broader organizational mission.We cover how to structure meetings, build trust, and set the right cadence to keep momentum going. Matan also discusses how to track progress with a rolling agenda and how to use the VARK learning model to tailor coaching to the team’s learning styles. Whether leading a small team or guiding team leads, this episode is packed with actionable insights to make performance management smoother and more effective.You’ll Learn:The real reason weekly one-on-ones are the most powerful tool for individual contributor growthWhat happens when you set the right cadence for meetings and stick to itThe surprising link between active listening and building trust with your teamWhy silence in meetings can be your secret weapon to get more from your teamHow to use the VARK model to tailor coaching and accelerate learningThe quiet damage of losing momentum by meeting less than once a weekWhat it feels like to lead with clarity by aligning individual performance with company goalsWhy recording your one-on-one meetings can build confidence and create valuable evidenceThe key difference between a mission statement and a personal development planHow to avoid the performance review “surprise” by keeping a rolling agenda documentTimestamps:[00:00] Introduction[06:30] Why many engineering teams lack performance management skills[08:05] The problem with annual performance reviews[09:35] How feedback frequency impacts team performance[11:10] The Start/Stop/Continue framework explained[13:25] The need for weekly one-on-one meetings with individual contributors[16:05] Why silence in meetings can drive more meaningful conversations[19:15] How to help engineers improve their listening and communication skills[21:40] The importance of shifting focus from output to experience in meetings[25:00] Why keeping a rolling agenda document is essential for tracking progress[30:20] How to structure quarterly reviews and set goals for the next quarterResources Mentioned:McKinsey Research | WebsiteYou can connect with Matan through his Linkedin or schedule a meeting to learn more here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Being busy isn’t your problem—being absent is.In this special episode, Adam dives into the hidden cost of not showing up—at work, at home, and especially as a leader. If you’ve ever coasted through a Zoom call, half-listened to a teammate, or checked your phone while spending time with your kids, this one will hit hard.Adam pulls back the curtain on what it really means to lead with presence—not perfection—and how that simple act can radically transform trust, engagement, and team performance. You’ll hear personal stories, hard-won lessons, and five tactical steps to build a leadership style grounded in consistency and connection. Whether you're burned out or just trying to level up, this episode delivers the wake-up call (and the playbook) you didn’t know you needed.You’ll Learn:How showing up with full presence activates trust, connection, and influenceWhy “being there” isn’t the same as actually being presentWhat distracted leadership signals to your team—and how it erodes performanceHow to create friction against distractions and train consistent focusWhy celebration is a strategic act—not a soft oneHow to structure 1:1s that deepen trust and engagementWhat a simple “thank you” does to long-term team motivationWhy consistency beats charisma in high-stakes leadershipHow to audit your calendar for high-impact presence opportunitiesWhat missed moments teach us about recommitment and integrityTimestamps:[00:00] Introduction[02:20] Why presence matters more than perfection[03:08] The real meaning of “showing up”[03:47] Story: daughter calls out her dad for not watching[04:29] Story: child notices when phone is put away[05:07] Why absence creates disconnection—even in the same room[05:35] What presence looks like in a professional setting[06:10] How presence builds or destroys trust[06:45] Story: transforming a demoralized team through consistency[07:56] The role of showing up in changing team culture[08:25] Why presence includes celebrating wins[08:58] Story: the 15-minute celebration that stuck[09:50] Why being noticed beats being rewarded[10:36] What makes consistency so difficult[11:05] The support systems that enable presence[12:02] Step 1: know where presence matters most[12:22] Step 2: create friction for distraction[12:45] Step 3: celebrate outcomes deliberately[13:04] Step 4: practice active presence in 1:1s[13:30] Step 5: acknowledge your misses and recommitResources Mentioned:The CTO Playbook Platform | WebsiteFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!You’re leading everyone else—but are you quietly abandoning yourself?This episode features executive coach and former engineer Natalya Tarasova, who brings a rare blend of technical credibility, Eastern philosophy, and mountaineering metaphors to the world of tech leadership. With a background in physics, machine learning, and organizational coaching, Natalya doesn’t just talk about change—she’s lived it through multiple career pivots and international moves. Her perspective is especially powerful for high-performing CTOs who’ve built their careers on delivering results but feel disconnected from their own needs.In this conversation, Adam and Natalya break down why so many senior tech leaders are brilliant at leading others but terrible at leading themselves. You’ll learn how to recognize when you’ve put yourself last for too long, how to approach inner transformation with the same strategy you’d use for scaling a system, and why burnout often hides behind high output. Expect unconventional insights on emotional regulation, breathing as a leadership tool, the myth of waiting until you’re “ready,” and how to rewire your mental architecture for sustainable impact. This episode is a must-listen if you’re ready to stop sprinting and start leading from stillness.You’ll Learn:How high performers unknowingly sabotage themselves by avoiding stillnessWhy “putting yourself first” is essential—not selfish—for sustainable leadershipHow to use mountaineering metaphors to map out complex personal growthWhat breathing techniques reveal about nervous system regulation under stressHow to shift from reactive change to intentional transformationWhy visualizing your “inner mountain” creates clarity in career transitionsHow to identify the emotional weight you're carrying that’s slowing your progressWhat Eastern philosophy teaches about integrating body, mind, and identityHow to coach others more effectively by first learning to coach yourselfWhy most CTOs delay change until they feel “ready”—and why that’s a trapTimestamps:[00:00] Introduction[04:58] What constant career change reveals about personal adaptability[06:36] The hidden cost of being too externally focused[09:08] Are you a victim of change or a driver of it[10:18] How to take control of your state and response[12:30] Why CTOs say they don’t know how to put themselves first[14:56] Using a mountain metaphor to visualize growth[17:05] Why high achievers struggle to slow down[18:16] The role of stillness in understanding motion[20:12] Why breathwork is the fastest reset for high performers[23:12] How to prepare for the next phase of your leadership[25:11] How to know when it’s time to move[27:09] What leaders need to leave behind to grow[28:12] Change is not linear—it’s a spiral[30:01] What most high performers miss when working on themselves[31:07] Why change starts with rewiring your identity[33:00] Giving yourself permission to fail and learn[35:03] Why emotional empathy can’t be intellectualized[37:06] How embodied wisdom changes your leadership presence[39:04] The hidden power of integrating personal and professional growth[41:05] How self-leadership creates ripple effects across teams[42:12] The 4-step change framework for CTOs[44:05] Why timing your next change is a skill, not luckYou can connect with Natalya on LinkedIn and learn more about her company, Tarasova Coaching on its website.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Your KPIs aren’t just underperforming—some of them are actively lying to you.In this episode, Adam sits down with Lior Gerson, co-founder and CEO of Target Board, a company that's redefining how tech leaders track and prove their impact. With two decades of experience leading both e-commerce and SaaS companies, and advising giants like Macy’s and Sephora, Lior brings a brutally honest take on why most CTOs are flying blind when it comes to metrics—and how to fix it.This conversation is a no-BS breakdown of the most overlooked lever in engineering leadership: meaningful, actionable KPIs. You’ll learn how to turn your data into a defensive shield, why most dashboards are vanity theater, and what it actually takes to align your metrics with strategic business outcomes. If you’re a CTO tired of being reactive—or worse, irrelevant—this is your wake-up call. Expect a tactical playbook for building real visibility, accountability, and leverage inside your org.You’ll Learn:How bad KPIs create blind spots—and how to replace them with metrics that drive resultsWhy most dashboards fail to align with business outcomes (and what to do instead)How to use KPIs as a defensive shield to prove your value as a CTOWhat engineering leaders can learn from consumer companies about data disciplineWhy many CTOs unconsciously resist accountability—and how that holds teams backHow to build a metric system that connects engineering output to revenueWhy founder-led companies often ignore metrics—and what fractional CTOs must do differentlyHow to identify whether your team is measuring for impact or just checking boxesWhat makes a KPI actually meaningful (hint: it’s not speed or story points)How to avoid the DORA trap and surface the metrics your exec team actually cares aboutTimestamps:[00:00] Introduction[00:52] Why KPIs are critical infrastructure, not just reports[01:28] Common CTO struggles with metrics and alignment[03:54] The shock of entering a $100M SaaS company with no metrics[05:32] The impact of analytical leadership on performance[06:18] Why understanding other C-level roles gives CTOs an edge[07:12] How fractional CTOs prove impact fast[08:48] Why engineering teams resist accountability and tracking[10:51] How internal pressure forces KPI adoption[11:23] Using metrics as a defensive shield in leadership[12:42] How lazy KPI systems fail ambitious CTOs[14:11] Why every team needs different metrics to improve[15:28] Why most BI teams can’t deliver what CTOs need[16:42] How Target Board replaces data teams in days[17:52] Why DORA metrics don’t move the business needle[19:07] Connecting metrics to revenue and business outcomes[20:26] Why paychecks depend on the metrics people ignore[22:13] What causes misalignment between execs and data[23:31] How OKRs can sabotage team performance[25:01] Why full metric visibility empowers better decisions[27:01] Automating metric modeling across platforms[28:13] The hardest part of using KPIs effectively[29:58] The mindset shift needed to use metrics well[31:09] What data can’t fix when politics blocks accountability[32:28] A step-by-step playbook for KPI-driven executionYou can connect with Lior and his company on Linkedin.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!"Compliance doesn’t make you good—so how do you really know if your tech team is any good at all?"In this episode, Adam sits down with Andy Graham, former CTO with 30 years of M&A and enterprise tech leadership, and Dane Eldridge, serial entrepreneur and CEO of Stackup. Together, they’ve built a deceptively simple tool that’s flipping the script on how tech leaders assess their teams—and uncover hidden risks before they explode.You’ll learn why most CTOs are unknowingly flying blind, how to detect the silent killers of innovation (like misaligned architecture or fuzzy definitions of "automation"), and how a single 30-minute assessment can surface the unknown unknowns holding your business back. Whether you're a scaleup CTO, a board member trying to evaluate tech health, or a founder wondering if your dev team is as strong as they say—they break down the real reason so many companies move slow, and how to fix it. You'll walk away with a new lens on language, leadership, and the hidden liabilities inside most tech functions.You’ll Learn:How benchmarking reveals hidden risks and weak spots in your tech functionWhy compliance frameworks can create a false sense of confidenceHow to detect misalignment between your tech strategy and business goalsWhat most CTOs miss about the real cost of technical debt during scale-upWhy “automation” means different things to different teams—and why that’s dangerousHow to use Stackup’s 30-minute assessment to surface unknown unknownsWhat poor communication habits are silently sabotaging CTO credibilityHow to use objective scoring to drive strategic investment and track improvement over timeTimestamps:[00:00] Introduction[04:41] Common pitfalls in developer-turned-CTOs[06:33] Triggers for assessing your tech function[08:00] How Stackup surfaces unknown unknowns[09:23] Real-world horror stories that drive urgency[10:07] Why misaligned language leads to costly misunderstandings[11:56] When tech due diligence reveals million-dollar mistakes[13:35] What technical debt really costs in scaleups[14:20] Why early architecture choices are critical[16:14] Planning upgrades with trigger points[17:45] How Stackup supports smarter, faster decisions[20:39] Why slowness doesn’t show up on the P&L[26:15] Using storytelling to align leadership around tech[28:01] What Stackup assesses in just 30 minutes[29:47] Simple questions that reveal massive security flaws[31:08] Why shiny tools like AI won’t fix misalignment[33:22] How to counter hype with strategy and expectations[35:31] When to use Stackup as a new or evolving CTO[37:59] Proving your tech value with objective results[39:13] Why Stackup delivers reports in video and podcast formats[41:19] Running the assessment quarterly to track growth[43:12] Focusing on just four priorities for maximum ROI[45:10] How the scoring system ensures objectivity[47:31] Why most leaders want to improve—transparently[49:12] Upcoming AI-powered CTO assistant and benchmarking[52:06] Using Stackup data to shape strategy and performanceYou can follow Andy and Dane on LinkedIn and learn more about their work here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!"Most CTOs spend all their time chasing rabbits—and miss the real future right in front of them."In this sharp, no-fluff episode, Adam cuts through the chaos CTOs face daily and reveals the underrated superpower every tech leader must develop: strategic foresight. Forget firefighting and sprint planning—this is about learning to think deeply and see the horizon others can’t. Adam shares why boredom (yes, boredom) might be your secret weapon for unlocking creativity and how slowing down can give you the attitude needed to lead confidently instead of just managing crises. You’ll get a clear three-step playbook to zoom out beyond the immediate, create deliberate mental space, and build a network that challenges your perspective. If you’re ready to escape the cycle of reactive firefighting and step into real leadership, this episode will push you to rethink what it means to lead technology—and how to spot the future before it’s obvious to anyone else.You’ll Learn:How strategic foresight shifts CTO leadership from reactive to visionaryWhy boredom can unlock breakthrough creativity and clear thinkingHow to create mental space for insight in a nonstop, distraction-heavy worldWhat the loneliness of leadership really means—and how to handle itHow to spot hidden risks and opportunities before they become urgent problemsWhy zooming out beyond the quarter accelerates better decision-makingHow to build a support network that challenges your perspective and expands your thinkingWhat deliberate stillness in your schedule does for creative problem-solvingHow small early mitigations prepare you for future challenges without wasting resourcesWhy acting with conviction on unseen signals separates leaders from managersTimestamps:[00:00] Introduction[00:20] Why CTOs need to prioritize strategic thinking[01:30] The loneliness of seeing the future before others[03:00] Overview of the CTO playbook coaching programs[04:10] Analogy of terriers chasing rabbits to explain reactive behavior[05:10] Why CTOs get stuck solving immediate problems instead of leading[06:00] The value of seeing what others don’t yet see[07:00] Example of cascading impacts from a tech stack decision[08:00] How thinking several steps ahead expands perspective[09:00] Why being ahead of the curve can feel isolating[10:00] Personal story about early career risks and mitigations[11:00] Importance of finding a thinking partner or mentor[12:00] How natural abstraction helps in leadership altitude[13:00] The power of stillness and boredom for creative insight[14:00] Example of deliberate boredom sparking creativity in kids[15:00] How adults avoid boredom and lose creative moments[16:00] Using walks and notebooks to capture ideas without distractions[17:00] Integrating stillness into calendars as a priorityFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!What if the most complex part of your backend system... just vanished?In this episode, Adam sits down with Maxim Fateev, CTO and co-founder of Temporal, a platform quietly revolutionizing how distributed systems are built at companies like Stripe, Snap, and Netflix. With a career spanning Amazon, Google, Microsoft, and Uber, Maxim brings a rare, battle-tested perspective to the chaos of modern infrastructure.This conversation unpacks why the old way of building event-driven systems is fundamentally broken—and how Temporal’s concept of durable execution makes reliability and scale feel effortless. You’ll learn why your devs are wasting thousands of hours on boilerplate, how workflows are being redefined by AI, and why most “modern” architectures are really just legacy spaghetti in disguise. If you care about developer velocity, rock-solid uptime, or building tech that doesn’t implode at scale, this one’s a must-listen.You’ll Learn:How durable execution eliminates retries, race conditions, and orchestration chaosWhy event-driven systems create hidden coupling—and how to break itHow Amazon’s early monolith shaped a new paradigm for backend scaleWhat makes step functions a step backwards in modern architectureHow to write workflows that survive failures, restarts, and region-wide outagesWhy most business logic doesn’t need YAML, queues, or 12 microservicesHow to scale from prototype to production without rewriting core systemsWhat AI agents reveal about the future of workflow orchestrationHow Temporal boosts developer productivity by 5–10x in real-world teamsWhy durable execution is becoming the backbone of enterprise AI systemsTimestamps:[00:00] Introduction[00:37] Why durable execution matters in distributed systems[03:36] The pain of monoliths and the shift to microservices[05:19] Why events create tight coupling in architecture[07:00] Amazon’s early attempt at workflow orchestration[07:50] Why AWS step functions fall short[09:08] How durable execution actually works[10:44] Open-source vs cloud-hosted Temporal[12:48] Multi-region replication and total uptime[13:58] Write workflows in code, not configs[15:50] Is Temporal just for big companies?[16:37] 5–10x productivity gains with durable execution[18:26] Durable execution as a new middleware layer[20:03] Replacing bloated cloud architecture with one function[21:10] When not to use Temporal[23:03] Netflix’s switch from Spinnaker to Temporal[24:15] Language support and runtime challenges[25:03] New features: priority queues and fairness[26:36] Nexus: long-running RPC calls with full durability[28:34] Getting started with Temporal[30:19] Why Max stepped down as CEO[32:14] Durable execution powering AI workloads[35:18] Why AI agents need orchestration[37:03] Saving state between agent calls[39:34] Durable execution vs traditional AI workflowsResources Mentioned:Amazon Simple Workflow Service | WebsiteAWS Step Functions | WebsiteTemporal (Open Source) | WebsiteTemporal Documentation and Courses | WebsiteAzure Durable Functions | WebsiteTemporal Slack Community | WebsiteIf you want to learn more about Max’s work, follow him on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Most CEOs hire the wrong CTO—not because of a talent shortage, but because they don't know what they're actually looking for.In this episode, Adam sits down with returning guest Warren Beazley—known across the UK tech scene as The CTO Recruiter. With nearly 30 years in the industry and a track record of 96%+ retention rates, Warren specializes in helping founder-led and investor-backed companies make one of the most pivotal hires in their org: a world-class CTO.You’ll learn why most CTO searches fail before they begin, how top CEOs are quietly mapping their talent pipelines long before they’re hiring, and the exact behavioral tools Warren uses to identify true leadership fit—not just technical skill. Whether you’re a CEO hiring your first tech exec or a CTO positioning yourself for your next role, this episode reveals how high-stakes technical hiring actually works behind the scenes. Expect sharp insights on filtering through noise, diagnosing culture clashes before they happen, and why gut instinct is no longer enough.You’ll Learn:How elite CEOs reverse-engineer their CTO hires for long-term fitWhy mapping your talent market beats relying on inbound candidatesHow Warren’s “12-month success review” technique clarifies role expectationsWhat most CEOs get wrong about job specs—and how to fix itHow behavioral surveys predict executive compatibility before it’s too lateHow to test for strategic thinking without asking cliché interview questionsWhat to do when you’re not the candidate’s first choice—and how to tellHow to spot red flags in resumes that even experienced recruiters missWhy most hiring failures aren’t about skills—they’re about culture mismatchesTimestamps:[00:00] Introduction[00:37] Why the CTO hiring market is still tough in 2025[05:07] What makes hiring CTOs more like poker than chess[07:15] The difference between founder-led vs investor-led hiring[10:18] Why great CEOs pivot and redefine their own role[12:16] Why most companies don’t know who their top candidates are[14:03] Employed vs. unemployed CTO hiring strategy[15:00] How to pitch your company to elite CTOs[16:13] Why money isn’t the main motivator for great candidates[17:41] The “12-month success review” for defining your ideal hire[20:00] Why job ads fail and how to create story-driven ones[22:03] Mapping the market to uncover passive candidates[25:00] The challenge of filtering hundreds of resumes[27:00] How structured interviews speed up good hiring[29:16] What your resume should reveal—but probably doesn’t[31:14] Culture and compatibility: the real reasons hires fail[33:00] How behavioral surveys predict long-term fit[36:03] Using personality data to shape interview questions[38:06] Why a 3-day decision window makes or breaks offers[40:01] Setting salary expectations early to avoid breakdowns[42:15] Open feedback channels that improve CTO retention[45:03] What really happens when a great hire walks awayYou can learn more about Warren's work on his website. or you can book a FREE 10 Minute call to understand if his hiring blueprint would work for you.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!What if the part of you causing burnout is the same one that got you where you are?In this episode, Adam sits down with Rob Kalwarowsky—executive coach, TEDx speaker, and author of Capitalizing on Chaos—to explore how high performers can stop white-knuckling their leadership journey and start transforming from within. Rob has helped tech execs and founders all over the world how to fast-track deep change through his FIRE method, a unique four-step framework that rewires how we lead, scale, and relate to chaos itself.If you’ve ever looked “successful” on the outside while feeling stuck, burned out, or quietly miserable on the inside, this conversation will hit home. You’ll hear Rob’s deeply personal journey from MIT engineer to global coach, how internal family systems reshaped his leadership philosophy, and why chaos might be the exact catalyst you need. Expect mindset rewiring, counterintuitive truth bombs, and tools to break through the next ceiling in your growth.This one’s not just about business. It’s about the human behind the title.You’ll Learn:How Rob’s FIRE method rewires leadership by turning inner chaos into strategic clarityWhy imposter syndrome signals deeper misalignment, not personal failureWhat Internal Family Systems reveals about the voices that shape executive behaviorHow high achievers unknowingly sabotage themselves by clinging to “productive” masksWhy logical self-talk fails—and what actually works to shift emotional patternsWhat guilt and overachievement often hide in leadership dynamicsHow emotional check-ins create trust and coherence in your inner teamWhy leaning into chaos can unlock innovation, not just survivalHow to evolve your leadership identity without losing your edgeTimestamps:[00:00] Introduction[06:13] The cost of a “perfect” life[08:42] The role of coaching and therapy in real growth[11:41] What Internal Family Systems therapy reveals[13:21] Why mindset hacks don’t solve deep issues[15:11] Even destructive inner voices have a purpose[16:27] Rob’s 6-minute self-leadership exercise[16:53] Step 1 of the FIRE method: find your reason[17:32] Step 2: ignite the masks and uncover inner blocks[21:56] Step 3: rapidly transform your identity[25:04] Step 4: expand and evolve your leadership[26:17] Why fear shuts down innovation[28:00] How to lead teams through disruption[30:10] Chaos opens new possibilities for growth[31:33] Summary of the FIRE method[32:57] The importance of guided transformation[35:55] Why leadership growth is deeply personalResources Mentioned:How to Handle a Bad Boss | TEDx TalkSaboteur Assessment | WebsiteInternal Family Systems by Dr. Richard Schwartz | WebsiteMovie: Inside OutIf you want the first 2 chapters of Capitalizing on Chaos for FREE, sign up for Robs newsletter!Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Ever wondered what it really takes to produce a high-quality tech podcast from scratch—while wrangling kids, late nights, and a studio in your basement?In this rare behind-the-scenes solo episode of The CTO Playbook, Adam pulls back the curtain on the exact gear, workflows, and production team that bring each episode to life. You’ll get a candid tour of his setup—from boom mics and soundproofing hacks to lighting rigs, software automation, and the husband-and-wife editing duo who shape the final sound. Whether you're a tech leader curious about content creation, or just a gear nerd wondering how to level up your own audio-video presence, this episode delivers a crisp, tactical walkthrough of what goes into building a professional podcast from the ground up.You’ll Learn:How low-tech soundproofing methods can dramatically boost audio qualityWhy lighting—not camera quality—is the secret weapon for pro-looking videoWhat Adam’s minimalist mic and soundboard setup reveals about smart gear investmentHow in-ear monitors solve a hidden distraction problem in podcastingHow to repurpose MIDI buttons and OBS for seamless video scene controlWhat behind-the-scenes editing reveals about capturing a guest’s true voiceHow a modular, portable gear setup enables studio-quality content on the roadWhy recording late at night might be your best move for consistency and clarityHow to transform a standing desk into a high-performance media stationWhat working with a small production team unlocks in creativity and output qualityTimestamps:[00:00] Introduction[00:25] Purpose of this behind-the-scenes episode[01:27] Who produces the podcast[02:19] Why episodes are recorded at night[03:00] Microphone and audio gear overview[04:00] How the audio is routed and optimized[05:05] Acoustic treatment in the room[06:00] Webcam, monitor, and lighting overview[07:15] Lighting gear and why it's travel-friendly[08:25] Background lighting setup[09:25] Software used to control lighting[10:22] OBS setup and live scene switching[11:45] Using Riverside and production handoff[13:08] Desk setup and standing comfort[14:10] Music used and its personal connection[15:00] Using the setup for coaching callsWant to start a podcast like this one? Book your free podcast planning call here.Resources Mentioned:Shure SM7B Microphone | WebsiteElgato Low Profile Wave Mic Arm | WebsiteSennheiser IE 200 In-Ear Monitors | WebsiteRØDECaster Duo | WebsiteAmaran 100X S | WebsiteAputure Light Dome Mini III | WebsiteKeep It by Justin J. Moore and Mortiz Houwen | Spotify or AppleFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Victor Nicollet is an expert in mechanical sympathy for software, focusing on how software design can better align with the hardware it runs on for smarter, faster systems.In this episode, you're going to learn what mechanical sympathy is and why understanding your hardware can massively improve software performance, how to predict when software should be optimized instead of waiting for users to feel pain, why abstraction layers can hurt performance and how to navigate escape hatches when needed, the importance of building broad but shallow systems to keep software fast and manageable, and when it makes sense to build your own tools instead of buying or using existing ones.Timestamps:[00:00] Introduction[02:00] What mechanical sympathy means for software[07:00] Building a custom language for supply chain optimization[09:00] Real-time analysis and scaling big data[11:00] When to optimize before pain shows up[13:00] Diagnosing hidden performance issues[15:00] How hardware understanding drives smarter software[17:00] Fighting abstraction layers to regain speed[20:00] Data size matters more than you think[23:00] Using smaller memory layouts for faster performance[26:00] Lossy compression vs real-time performance needs[29:00] Structuring broad but shallow systems[31:00] Using optimized black boxes the right way[34:00] Where glue code bottlenecks appear[37:00] Build vs buy decisions based on real needs[39:00] Why Lokad had to create its own data format[41:00] Storing petabytes for supply chain forecasting[44:00] Summarizing the 7-step optimization strategyResources Mentioned:Lokad | WebsiteIf you want to learn more from Victor, follow him on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!In this episode, you'll learn how the rise of citizen builders is reshaping software creation, why leadership now demands alignment over control, how to measure real impact across teams, and what it takes to scale safely in a world of AI-assisted development.Timestamps:[00:00] Introduction[02:00] Overview of the 4-part structure in this episode[02:54] Principle one: everyone can build — but can they build right?[04:53] Principle two: redefining junior vs senior in a cross-functional world[05:38] What growth actually looks like beyond technical skill[06:20] Principle three: abstraction saves time, understanding prevents disaster[07:08] AI tools vs foundational knowledge[07:47] Why elite builders accelerate others[08:39] Principle four: direction beats control[09:23] Teaching others how to make decisions[09:57] Broadcasting context until it feels repetitive[10:18] Principle five: organizational design is system design[11:03] Avoiding the productivity dip during scaling[11:36] Conway’s Law and communication-driven design[12:34] Principle six: measure velocity, not busyness[14:00] The power of aligned data visibility[14:44] Dashboards that trigger strategic pivots[15:20] Principle seven: developer experience is now your product[16:00] Builders outside engineering — even the CEO[16:36] The danger of unchecked shadow IT[17:10] What guardrails are you offering citizen builders[18:01] Principle eight: outcomes are the new OKRs[18:49] Why measuring customer activation changed everything[19:26] Shifting priorities when you focus on real outcomes[20:00] Principle nine: solve across the organization[20:43] Rethinking engineering as a business-wide competency[21:08] Empowering non-engineers to solve with softwareFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!Zacharias Beckman is a technology leader and creator of the Customer Obsessed Delivery Playbook.In this episode, you're going to learn what the Customer Obsessed Delivery Playbook is and why having a checklist is critical for complex software projects, how event storming and steel threads can help prevent costly surprises in software delivery, how Zac used lessons from government projects, cruise lines, and iPhone launches to shape a better approach to technical delivery, why a visual “subway map” model can make software development easier to navigate, and how to keep customer needs front and center throughout an entire project.Timestamps:[00:00] Introduction[01:57] Why software projects need a checklist approach[03:04] Mistakes early in Zac’s career that led to building a playbook[05:08] The role of structure and guardrails in complex delivery[06:04] Creativity versus consistency in engineering playbooks[07:45] Giving teams flexibility to experiment[09:55] Evolution of the playbook from large companies to startups[11:03] How startups and big companies use the playbook differently[12:58] How the playbook can uncover process gaps in existing teams[16:30] Inspiration behind using a subway map for software delivery[18:01] Problems Zac saw in government projects that sparked change[19:12] Miscommunication between customers and tech teams[20:55] How R&D uncertainty compares to building cars or bridges[22:05] How to structure checkpoints and quality gates in delivery[23:04] Why event storming is a crucial early exercise[24:09] Zac’s first experience with event storming on cruise ships[25:40] Why cruise ships are a major software engineering challenge[26:40] How event storming reveals hidden complexity[27:35] Importance of having business and tech teams in event storming[28:01] What a steel thread is and why it matters[29:12] Differences between a steel thread and an MVP[30:02] Building end-to-end scaffolding before scaling[31:05] Real-world example of a steel thread fixing a telco iPhone launch[32:33] How Lightbend proved their solution in six weeks[33:30] Why building the full system first is a mistake[34:02] What a target state architecture is[35:10] Why you need an incremental path to a target state[36:05] Risks of pulling future features into early development[36:58] Why customer needs often change during projects[37:40] How to avoid failed big bang product launches[38:00] How to keep the customer visible throughout delivery[39:05] How event storms connect to engineering artifacts[40:20] Avoiding translation errors from customer to code[41:00] Testing outputs based on original customer events[42:45] The importance of empirically measuring project outcomes[43:50] Why teams must create their own processes[44:30] How to tie product features to measurable business outcomesThe best way to connect with Zac is by subscribing to his Substack and reading his Blog.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!In this episode, you'll learn how to win support for a tough proposal, avoid getting blindsided in meetings, use informal conversations to map your allies and blockers, and turn neutral teammates into advocates.Timestamps:  [00:00] Introduction [01:04] A failed pitch story and key lesson [02:18] The importance of having a playbook [02:55] Why great ideas get shot down [03:12] Stage 1: Test the waters [04:40] How early insights shape your pitch [05:30] Stage 2: Understand the numbers [06:00] Identify veto players and the majority needed [06:45] Plan around timing and meetings [07:30] The power of loud voices in group settings [08:10] Stage 3: Strengthen your supporters [08:50] Ask for feedback, not support [09:30] Involve people by including their suggestions [09:50] Win over key skeptics [10:20] Turning opponents into advocates [10:50] Leverage respected voices in the group [11:15] Why being heard matters more than being right [11:35] Coaching for executive communication [12:10] Why logic often loses to emotion [12:50] How storytelling wins the room [13:20] Stage 4: Engage the neutrals [13:50] Connect your idea to their priorities [14:15] Use win-win framing for middle-ground people [14:40] Avoid turning neutrals into opponents [15:00] Use social proof to tip the balance [15:30] Stage 5: Presentation and decision [16:20] Call out contributors by name [16:45] Make it feel like the next logical step [17:00] Keep the decision meeting short and smooth [17:45] How to avoid meeting debates and delays [18:00] Creating watercooler moments in remote work [18:30] How to test ideas before remote meetings [19:25] Follow-up strategy after remote conversationsFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.