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 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.

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.

In this engaging discussion, Natalya Tarasova, an executive coach and former engineer with a rich background in physics and machine learning, shares her unique insights on leadership. She emphasizes the crucial need for tech leaders to prioritize self-care and the power of stillness for personal growth. The conversation explores how adaptability, self-reflection, and mindful goal-setting are essential for effective leadership. Natalya also offers practical strategies for managing change and highlights the importance of empathy and support systems in navigating complex transformations.

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.