The CTO Playbook

• 54: CTO Secrets to Scaling Fast: Lessons from COVID, Culture & Code with Peter Wong

  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.

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• 53: Why Most Tech Managers Fail at Feedback (and How Top CTOs Fix It)

  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.

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• 52: How to lead with presence: 5 habits every technology leader needs

  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.

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• 51: Leadership, Change & Stillness: What Tech Leaders Can Learn from Hiking

  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.

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• 50: From Chaos to Clarity: Using KPIs to Protect, Persuade, and Prioritize as CTO

  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.

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