The CTO Playbook

Build your own CTO Playbook at www.theCTOplaybook.com — 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 future of startups isn’t decided by who builds the flashiest AI, but by who solves the right problems?In this episode, I’m joined again by my friend Thorgeir Einarsson, almost a year since we last spoke, to unpack how AI funding and investor expectations have shifted from hype cycles to hard realities. Thor runs PGO, a service that helps founders get truly investment-ready with real pre-diligence instead of lipstick on a pig.Pre-seed and seed are brutal right now, and traction beats vibes. Investors are placing smaller, option-like bets at the AI application layer while steering clear of generic models. Hardware is back where it matters, from defense tech to medical devices, when firmware and software meet close to the metal. We trace the PE-ification of VC: rolling up vertical SaaS, “AI-firing” them, and rebuilding moats from customer bases and domain data. Thor flags a blind spot worth building for: AI safety and guardrails for agentic workflows. Then we get practical: preparation beats performative decks, checklist-driven pre-diligence forces the hard questions, and the playbook is simple… know yourself, know your co-founders, keep investors updated, and track the numbers.You’ll Learn:The reason many VCs focus on the AI application layerWhat happens when nobody knows what a great AI company looks like yetThe link between defense and medical devices and hardware-plus-software productsThe damage of skipping investor updates and simple monthly KPIsWhat it feels like to raise when only one to three percent get a checkThe reason pre-diligence and checklists come before the pitchWhat happens when agentic workflows scale without safety guardrailsTimestamps:[00:00] Introduction[05:42] Why AI investment has shifted from hype to hard reality[12:18] The brutal truth about pre-seed and seed fundraising in 2025[18:33] Why investors are betting smaller at the AI application layer[25:47] How defense tech and medical devices are bringing hardware back[32:11] The rise of “AI-firing” old SaaS companies and the PE-ification of VC[40:26] The missed opportunity in AI safety and agentic workflow guardrails[48:59] How founders can prepare for due diligence the right way[56:22] Why investor updates and clear KPIs determine long-term trustConnect more with Thorgeir on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook at www.theCTOplaybook.com — 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 real lever isn’t the tech at all?In this episode, I sit down with Matthew Carr, who does interim work and often comes in as the firefighter when a company has taken a wrong turn. He lays out why people come first, processes second, and technology follows.He started in classic ASP and built a loyalty program for the heating and engineering sector. Real-time results beat long compile cycles and changed how he delivered. A private-equity buyout couldn’t get the startup’s tech delivered, so he sat one-to-one with everyone to map the problems. Turns out, fixing broken delivery isn’t about new tools. It’s about people, trust, and having the guts to act fast.You’ll Learn:The reason putting people first makes process work and technology followWhat happens when you plan three sprints ahead and tie outcomes to business valueThe link between quick wins and winning trust in the first 30 daysThe damage of being six to twelve months off on deliverables after a PE acquisitionWhat it feels like to inherit a program that hasn’t shipped in 18 monthsThe link between weekly iterations, monthly demos, and a product becoming a bedrock of the businessThe reason trust, leadership, and alignment are the core enablers of the people pillarWhat happens when you play their game first by showing a six-week plan the board can approveThe reason “believe in yourself” is the sharpest one-line tip for new CTOsTimestamps:[00:00] Introduction[05:12] Why people come first before process and technology[10:46] Lessons from early development work in classic ASP and loyalty programs[15:58] How a private equity acquisition exposed major delivery delays[21:37] Running a massive retrospective and uncovering 110 problems[28:04] The importance of quick wins and building trust in the first 30 days[33:41] Planning three sprints ahead and reporting outcomes instead of outputs[38:22] Turning around a project that hadn’t shipped in 18 months[45:09] How weekly iterations and monthly demos rebuilt momentum[51:28] The one-line advice Matthew gives every new CTOLearn more from Matthew on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Logic alone won’t land; people react to change emotionally.In this episode, I sit down with Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s here to show why change so often derails and how CTOs can lead through it with clarity and confidence.We break down why rational explanations fall flat, the different speeds leaders and teams move at, and how losing control sparks uncertainty and anxiety. A call center story shows how rewarding quick answers without customer outcomes skews behavior. A Hong Kong example proves that “ask your line manager” messaging failed culturally, so we rewrote it to a nominated peer contact. A pre-mortem setup surfaces blind spots by declaring the project failed and collecting reasons before execution. We run through an eight-step playbook from purpose and alignment to blind spots, impacts, resistance, indicators, validation, and finally execution.You’ll Learn:The reason logic-only change pitches backfireWhat happens when leaders move faster than teamsThe link between the metric you reward and the behavior you getWhat it feels like to run layoffs twiceThe reason pre-mortems workWhat happens when you don’t set indicators earlyThe link between purpose, alignment, and smoother executionWhat happens when a key trainer is missingThe damage of losing clarity at the topTimestamps:[00:00] Introduction[05:18] Why logic fails when leading change[10:42] The emotional side of resistance and uncertainty[15:56] How leaders move faster than their teams[20:11] The blind spot that halted a global SAP rollout[26:27] Why bad metrics destroy good behavior[31:03] Cultural barriers that derail transformation[36:49] The pre-mortem method for spotting hidden risks[42:08] The eight-step change playbookResources Mentioned:Master the Change Maze by Giorgia Prestento | BookGiorgia offers a short assessment 'Leaders: Are You Change Ready?' You will gain valuable insights across the categories of Leadership Style, Change Expertise and the Readiness of your organisation. It takes less than 3 minutes. You get readiness scores in a personalised report. Plus a digital copy of her book, Master the Change Maze. Click here to get started.You can connect more with Giorgia on LinkedIn. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Are you optimizing for starting work instead of finishing?In this episode, I’m joined by Joakim von Prónay, an engineer and psychologist by education and a coach by passion.We break down how fake roadmaps and a “Global Roadmap Owner” role turn planning into a Gantt chart exercise. We make planning useful with a simple rule: it’s better to be roughly right than precisely wrong. Predictability becomes the lever for real accountability, measured by “did we do the things we said we were gonna do.” Escalation culture gives way to real collaboration, not the default “ask the boss” reflex.You’ll Learn:The reason long-term planning works when it’s roughly right instead of precisely wrongWhat happens when teams are incentivized to start work instead of finish itThe link between delivery predictability and real prioritization and accountabilityThe damage of treating roadmaps like a Gantt chart exerciseWhat it feels like when every question defaults to “ask the boss” instead of talking directlyThe reason fragmented steering creates conflicting directionsThe link between a single “central rule” and measurable goalsTimestamps:[00:00] Introduction[06:14] Why high-performing teams are so rare[09:27] The danger of planning for perfection[15:46] Why teams start work instead of finishing it[19:32] The power of predictability and real accountability[25:40] When collaboration breaks down into escalation[31:58] What fragmented steering really looks like[38:45] The rule that defines true strategy[46:23] A Spotify story and the engineer’s warning[51:17] How alignment turns insight into actionConnect more with Joakim on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!What if the playbook that built your career suddenly stopped working and nobody told you?In this episode, I sit down with Catherine Stagg-Macey, an executive coach who works with technical experts turned leaders. She knows firsthand what it’s like to move from coding and spreadsheets into managing people, and the struggle that comes with it.We get into what happens when being the smartest person in the room is no longer enough, the patterns that keep leaders trapped in the systems they built, and the hard pivot it takes to step into a new kind of leadership.You’ll Learn:The reason smart technical leaders hit a wall when old habits stop workingWhat happens when you try to manage people with the same mindset you used to write codeThe link between control, trust issues, and being stuck in endless meetingsThe damage of wearing the “superhero cape” and building a culture of firefightingWhy skepticism is common when leaders are first asked to work with a coachThe pivotal moment that led Catherine from consulting success to a coaching careerHow childhood patterns and early work experiences quietly shape leadership behaviorsThe role of feedback, or the lack of it, in pushing leaders toward breaking pointsWhy creating distance from your triggers opens space for better choicesTimestamps:[00:00] Introduction[06:15] Breaking patterns of overwork and constant meetings[08:55] The lure and cost of playing the workplace superhero[10:20] Catherine’s pivot from consulting success to coaching[16:05] When rock bottom moments force change[20:15] Early warning signs leaders ignore before burnout[26:45] Identity shifts required to let go of old leadership habits[30:10] Recognizing triggers and unconscious behavior patterns[41:20] How upbringing and culture shape leadership reactions[53:00] Building range as a leader in times of uncertaintyResources Mentioned:Conversations at the Edge | WebsiteYou Didn’t Chase Leadership. Leadership CHASED You. Join Catherine’s Inner Circle.Unlock your leadership superpower, discover what your leadership style is with Catherine’s Leadership Style Quiz.You can connect with Catherine on LinkedIn and listen to her podcast here. Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!Would you say yes to leading through chaos with no plan, little information, and no guarantee of success?In this episode, I sit down with Corey Hart, a crisis operator who’s built a career on scaling massive humanitarian and operations projects under extreme pressure. He’s said yes to projects most people would run from, from helping New York City respond to a sudden influx of asylum seekers to standing up global call centers and navigating cruise ship operations post-lockdown.We get into how he prepares for the unknown, what it takes to build trust in the middle of a storm, and why surrounding yourself with the right people makes the difference between collapse and momentum.You’ll Learn:The reason Corey says yes to high-stakes projects others avoidWhat happens when you’re asked to launch a humanitarian response overnightThe link between early onboarding and a culture of openness and candorThe damage of overcomplicating operations when speed is criticalWhat it feels like to land in a crisis with little info and no certaintyWhy bringing compliance and tech in early turns them into strategistsThe role of trust in holding teams together under extreme pressureHow living autopsies fix problems in real time, not after the factThe mindset shift that turns specialists into early-stage leadersWhy tracking from day one helps you see around corners in chaosTimestamps:[00:00] Introduction[05:58] Saying yes to unpredictable challenges[07:02] Scaling New York’s asylum seeker response[11:58] Handling moments when operations nearly collapse[14:02] Filtering signal from noise in crisis decision-making[17:56] Building openness and candor into team culture[20:06] Creating trust and making failure safe[22:01] Why saying yes builds momentum and possibility[27:00] Unlikely outcomes from saying yes[31:00] Keeping operations simple and avoiding scope creep[33:02] Tracking data early to guide decisions under pressure[35:00] Bringing compliance and tech in early to shape solutions[37:56] Knowing when and how to step out of a crisis projectResources Mentioned:Podcast Episode The CEO’s Playbook for Hiring the Right CTO with Warren Beasley | YouTubeYou can connect with Corey on LinkedIn and his website.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!What if the biggest reason your team feels stuck isn’t money, but the weight of your own code?In this episode, I sit down with Lou Franco, author of Swimming in Tech Debt and a veteran software engineer who’s been a founding engineer at three successful startups, a principal engineer at Trello through its Atlassian acquisition, and now an advisor to software teams.We trace his journey from early lessons in fintech and startup acquisitions to the moments that exposed just how costly ignored tech debt can be. Lou shares what he learned from engineers on the ground, how small fixes can deliver outsized productivity gains, and why culture and process matter just as much as code when tackling debt.You’ll Learn:The reason most engineering teams carry hidden tech debt without clear solutionsWhat happens when day-to-day friction drags down delivery speed and moraleThe ROI of small, focused fixes that start paying back almost immediatelyThe damage that builds when debt is ignored until it hits a breaking pointThe link between a product’s lifecycle stage and the right level of debt reductionWhy dedicated engineering-led time creates accountability and better outcomesHow visible progress metrics help leadership see the value of paying down debtThe risk of jumping too fast into shiny new tech that stalls out in productionThe role of culture, style guides, and clear values in preventing runaway debtTimestamps:[00:00] Introduction[05:01] Early lessons on tech debt in fintech and startups[07:02] The exit interview that exposed ignored debt[08:59] Small fixes that delivered immediate productivity gains[11:00] When debt grows into brick walls and forced rewrites[14:01] Building team culture and values to tackle debt[16:59] Splitting engineering-led time from product-led work[23:00] Measuring debt payoff with metrics and visibility[29:01] Leading indicators of productivity and developer experience[36:59] High-risk systems, regressions, and measured approachesResources Mentioned:Swimming in Tech Debt by Lou Franco | BookCrossing the Chasm by Geoffrey Moore | Book or AudiobookYou can connect with Lou on LinkedIn and find his book here.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook here, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact!What if the only difference between freezing in chaos and staying calm is how much practice you’ve done before the storm hits?In this episode, I trace the moments that shaped why I coach. From digging strangers out of an avalanche in Switzerland to carrying the weight of a teammate down Mont Blanc on one ski, survival and leadership kept pointing to the same truth: preparation creates calm. I talk about teaching kung fu to kids and bankers, seeing culture hold Palantir together at breakneck speed, and stumbling through my own startup without a coach. Later, I describe rebuilding both technology and trust at Realforce when fear was running high. All of it comes back to this: even the strongest leaders need someone in their corner, and that’s why I built The CTO Playbook.You’ll Learn:The reason practice beats panic when pressure hitsThe link between small wins and the breakthrough confidence they createThe damage of trying to figure everything out alone without guidanceWhat it feels like to rebuild trust and safety in a fearful teamWhy culture becomes the glue when growth outpaces structureThe moment persistence matters more than raw talent in leadership and coachingHow scaling without culture can tip a company into chaosTimestamps:[00:00] Introduction[06:00] Avalanche rescue and the calm that comes from practice[08:59] Skiing Mont Blanc and carrying the load so the team could get home[10:48] Kung fu teaching and the breakthrough power of persistence[13:00] Coaching adults and the hidden gaps even senior leaders face[13:52] Lessons from Palantir and why culture holds during chaos[14:55] Startup founder struggles and the cost of going it alone[15:46] Rebuilding trust and technology at Realforce[18:00] Why I coach and how Simon Sinek’s Golden Circle frames it[21:00] The five CTO archetypes every tech leader falls into[26:00] Basecamp, Elevate, and Ascent explained as the CTO Playbook journeyResources Mentioned:Start with Why by Simon Sinek | BookFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.

Build your own CTO Playbook at our website — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Proactivity isn’t an all-or-nothing game.In this episode, I break down the myth that leaders are either “proactive” or “reactive” and share why even small, flickering moments of foresight can put you ahead. I get into what happens when you’re forced into reactive mode and how to inject just a bit of proactivity into those moments so they don’t derail you. I talk about the “pressure off” test, those quiet weeks when your defaults show up, and how to use them to reset your habits. I wrap up with five practical steps you can start this week to shift from constant firefighting to being seen as a steady, strategic leader.You’ll Learn:The real reason proactivity isn’t a fixed leadership traitWhat a flickering light bulb can teach you about staying aheadWhy just 5% more foresight each week changes how your team sees youHow to inject proactive moves into high-pressure, reactive situationsThe quiet damage of coasting during “pressure off” weeksWhat the “pressure off” test reveals about your default leadership modePractical ways to prepare for outages and crises before they happenThe surprising link between military “go bags” and tech leadership readinessHow to turn firefighting moments into long-term strategic winsFive simple steps to build steady, visible proactivity into your weekTimestamps:[00:00] Introduction[05:00] Busting the myth of proactive vs reactive leadership[06:14] The flickering light bulb analogy for building proactivity[07:55] Injecting proactive actions into reactive situations[09:59] Building your leadership “go bag” for crises[11:42] The pressure off test and why quiet weeks matter[13:50] Using downtime to reset strategic habits[14:56] Five steps to increase consistent proactivity[18:45] Why small, steady choices outweigh perfectionFind more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

Build your own CTO Playbook at our website — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.What if the hardest part of being a CTO isn’t about the technology at all, but learning to lead without a map?In this episode, I’m joined by Etienne de Bruin, founder of Seven CTOs and CTO Levels, and co-author of the upcoming book Liquid. For more than a decade, Etienne has worked with CTOs navigating the shift from hands-on coding to executive leadership.We talk about the moment he realized his value wasn’t in the code anymore, how he built a peer network to fill the gaps he couldn’t see, and the pivotal lessons that shaped his approach to coaching. Etienne also shares the thinking behind Liquid, exploring how CTOs can find balance between chaos and rigidity while mastering the four “sentinels” every tech leader needs to succeed.You’ll Learn:What it feels like to be pushed or pulled out of the codebase as a CTOThe real reason Etienne founded Seven CTOs and why most early members walked awayHow ontological coaching changes the way CTOs solve problems and influence outcomesThe quiet damage of solving the wrong problem when your influence goes uncheckedThe four “sentinels” every CTO must master to earn trust at the executive tableWhy balancing “boiling” chaos and “frozen” rigidity can make or break a tech teamThe surprising link between financial fluency and a CTO’s long-term successHow the Levels framework reveals capability gaps that stall growthWhat happens when a CTO builds genuine alignment with sales and product leadersTimestamps:[00:00] Introduction[06:58] The challenge of stepping away from coding into leadership[14:00] Building a startup and the moment to stop coding[17:57] Creating Seven CTOs and the need for peer groups[27:15] How ontological coaching transforms CTO problem solving[37:14] The core role of a CTO and the importance of financial fluency[45:11] The concept of Liquid and navigating boiling vs frozen states[47:59] The four sentinels every CTO must manage[53:54] Using the Levels framework to diagnose capability gapsYou can connect with Etienne on LinkedIn.Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.

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

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

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.