The CTO Playbook

Adam Horner

Join Adam Horner, a CTO with over 30 years in the tech industry, on The CTO Playbook — the podcast dedicated to helping CTOs excel. Perfect for CTOs and tech leaders navigating the complexities of their roles, each episode offers clear insights, innovative strategies, and practical advice from top leaders in tech. With Adam’s extensive experience mentoring engineers and tech leaders, and over a decade as a CTO, you’ll gain the tools and knowledge to build and refine your own CTO playbook. Whether you're tackling complex projects, fostering innovation, leading teams, or shaping your company's tech strategy, this podcast is your go-to resource. Adam’s journey from engineer to strategic CTO was challenging. He learned through the school of hard knocks, making avoidable mistakes and facing countless challenges. Often out of his comfort zone and wishing for more guidance, he created this podcast to provide the support and advice he once lacked. Tune in for engaging interviews, leadership tips, and the latest in technology strategy. Each episode is designed to help you lead with confidence and level up as a CTO. Listen now to start your journey with The CTO Playbook and build your own playbook to excel in your role.

  1. 1d ago

    Ep 115: Impostor syndrome is a strategy you are running

    Most leaders treat impostor syndrome as something they need to overcome. But what if the belief that you're not good enough is actually serving a purpose? Adrian Koehler is a leadership coach at Take New Ground. He has spent 15 years coaching founders and technical leaders. He joins Adam Horner on The CTO Playbook to explore why leaders hold on to self-doubt, what they gain from it, and what it costs them. Adrian explains why feeling like a fraud can be good news. It often means you're stepping beyond what you've already proved you can do. But the belief can also offer a sense of safety, giving you reasons to hide, hold back ideas, or wait until you're certain before acting. Through his approach to "hugging the cactus," Adrian challenges leaders to face uncomfortable truths about themselves and compare how they see themselves with what their teams actually see. He also shares a practical eight-step process for working through impostor syndrome. In this episode, he explains: ■ 𝗥𝗲𝗳𝗿𝗮𝗺𝗶𝗻𝗴 𝗜𝗺𝗽𝗼𝘀𝘁𝗼𝗿 𝗦𝘆𝗻𝗱𝗿𝗼𝗺𝗲: Why feeling like a fraud can be a sign that you're stepping beyond what you've already proved, rather than evidence that you don't belong. ■ 𝗧𝗵𝗲 𝗛𝗶𝗱𝗱𝗲𝗻 𝗣𝗮𝘆𝗼𝗳𝗳𝘀 𝗼𝗳 𝗦𝗲𝗹𝗳-𝗗𝗼𝘂𝗯𝘁: How believing you're an impostor can give you permission to hide, hold back ideas, and avoid difficult situations. ■ 𝗧𝗵𝗲 𝗖𝗼𝘀𝘁 𝗼𝗳 𝗟𝗶𝗺𝗶𝘁𝗶𝗻𝗴 𝗕𝗲𝗹𝗶𝗲𝗳𝘀: Why the stories that help you feel safe can limit your confidence, relationships, and impact as a leader. ■ 𝗛𝘂𝗴𝗴𝗶𝗻𝗴 𝘁𝗵𝗲 𝗖𝗮𝗰𝘁𝘂𝘀: How facing the things you don't want to see about yourself can turn them from a threat into an early warning sign. ■ 𝗦𝗲𝗹𝗳-𝗣𝗲𝗿𝗰𝗲𝗽𝘁𝗶𝗼𝗻 𝘃𝘀. 𝗥𝗲𝗮𝗹𝗶𝘁𝘆: Why asking the people you work with what they actually see can challenge the assumptions you hold about yourself. ■ 𝗣𝘂𝗿𝗽𝗼𝘀𝗲𝗳𝘂𝗹 𝗜𝗺𝗽𝗲𝗿𝗳𝗲𝗰𝘁𝗶𝗼𝗻: Why sharing unfinished ideas and fully participating beats holding back until everything feels perfect. ■ 𝗧𝗵𝗲 𝗘𝗶𝗴𝗵𝘁-𝗦𝘁𝗲𝗽 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸: How owning the belief, listing its payoffs and prices, and checking it against reality can help you decide what to do differently. 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. You'll Learn: [0:00] Introduction [1:34] Adrian's Four Careers and His Heart for Engineers [7:46] Adam's Shadow on a London Bike Ride [9:35] Why People Love a Diagnosis [9:52] Why Impostor Syndrome Can Be Good News [11:16] How Certainty Becomes a Source of Loneliness [16:03] The Hidden Payoffs of Impostor Syndrome [18:53] Identifying the Complaints You Choose to Keep [20:14] Counting the Prices of the Belief [24:14] Asking What Was Missing From You as a Leader [28:51] What "Hugging the Cactus" Really Means [34:14] Being Purposefully Imperfect [35:32] Adrian's Eight Steps for Working Through Impostor Syndrome [40:48] Why It's Hard to Be a Human [43:25] Where to Connect With Adrian Follow Adrian Koehler: ■ Email: adrian@takenewground.com ■ LinkedIn: https://www.linkedin.com/in/adriankoehler/ ■ Instagram: https://www.instagram.com/adrian.k/ ■ Website: https://takenewground.com The CTO Playbook: ■ Build your own CTO Playbook at https://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. ■ Follow Adam: https://www.linkedin.com/in/adamhorner/ ■ YouTube: https://www.youtube.com/@TheCTOplaybook ■ Prefer listening? Catch the podcast: https://bit.ly/thectoplaybook

  2. Oct 13

    114: Building the builder: how CTOs fix the AI code review bottleneck

    AI has made building software dramatically faster. The problem is that the rest of the engineering system hasn’t caught up.  AI agents can now produce code, tests, documentation, migrations, and pull requests at a pace most engineering organisations weren’t designed to handle. But when everything around code review accelerates, review becomes the bottleneck. Pull requests pile up, reviewers spend more time reconstructing intent, and experienced engineers can end up reduced to repeatedly saying yes or sending work back for fixes. Adam Horner explores why making code review faster isn’t enough. The deeper problem is that teams are often reviewing the output instead of the decisions that produced it. The episode looks back at the evolution of compilers, when engineers moved from inspecting machine code to trusting verified outcomes, and asks whether AI-assisted development is creating a similar shift in software engineering. The answer is a move upstream. Instead of relying on code review to recover intent, teams can review the goal, requirements, constraints, boundaries, invariants, architecture, and increasingly the agent definitions and context that guide how software gets built. Adam calls this “building the builder.” The idea is simple: when something goes wrong, don’t just fix the output. Improve the system that produced it so every future change benefits. 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. You’ll Learn: [0:00] Why AI-powered development is creating a new review bottleneck [4:07] What the history of compilers teaches us about AI engineering [8:26] Why faster code review doesn’t solve the real problem [12:10] Moving engineering review upstream to intent and design [16:22] Building the builder and improving the development system The CTO Playbook: ■ Build your own CTO Playbook at https://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. ■ Follow Adam: https://www.linkedin.com/in/adamhorner/ ■ YouTube: https://www.youtube.com/@TheCTOplaybook ■ Prefer listening? Catch the podcast: https://bit.ly/thectoplaybook

  3. Oct 6

    113: Anyone with an API key can copy your AI strategy, with Ritavan

    AI adoption is getting easier for everyone. The harder question is whether you're using it to optimise the game you're already in, or to build a position that changes the game. Ritavan, author of The System Gambit and Data Impact, returns to The CTO Playbook after his first appearance on episode 30. A System Gambit is a deliberate sacrifice that builds a structural advantage that compounds. Rather than optimising within the system you're already in, it changes the system so competitors can't simply buy or copy their way to your position. Ritavan explains the difference between a System Gambit and a System Anti-Gambit, using Nokia and Amazon as examples. He also explains why adding AI to the data your business already generates tends to keep you inside your existing paradigm. Adam then puts his own move from fractional CTO work to coaching through Ritavan's three tests: self-improving loops, path dependence, and management logic antagonism. In this episode, he explains: ■ 𝗪𝗵𝗮𝘁 𝗮 𝗦𝘆𝘀𝘁𝗲𝗺 𝗚𝗮𝗺𝗯𝗶𝘁 𝗜𝘀: Why a deliberate sacrifice now can unlock a structural advantage that compounds. ■ 𝗧𝗵𝗲 𝗦𝘆𝘀𝘁𝗲𝗺 𝗔𝗻𝘁𝗶-𝗚𝗮𝗺𝗯𝗶𝘁: Why optimising inside your current system is rational, and why it leaves you exposed when a rival changes the game. ■ 𝗔𝗴𝗶𝗹𝗶𝘁𝘆 𝗪𝗶𝘁𝗵𝗼𝘂𝘁 𝗮 𝗧𝗵𝗲𝘀𝗶𝘀: What Nokia shows about reaching peak agility and still losing badly in a market. ■ 𝗔𝗜 𝗮𝗻𝗱 𝘁𝗵𝗲 𝗘𝘅𝗶𝘀𝘁𝗶𝗻𝗴 𝗣𝗮𝗿𝗮𝗱𝗶𝗴𝗺: Why adding AI to your own business data may bring incremental gains without moving you into a new system. ■ 𝗧𝗵𝗲 𝗧𝗵𝗿𝗲𝗲 𝗧𝗲𝘀𝘁𝘀: Self-improving loops, path dependence and management logic antagonism, applied to Adam's own CTO coaching journey. ■ 𝗪𝗵𝗲𝗻 𝗡𝗼𝘁 𝘁𝗼 𝗠𝗮𝗸𝗲 𝗮 𝗚𝗮𝗺𝗯𝗶𝘁: Why a short runway, or a lack of real control over the system, makes it the wrong move. 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. You'll Learn: [0:00] Introduction [3:07] Why Strategic Advantage Requires a Sacrifice [5:34] Why a System Gambit Isn't a Gamble [8:37] The System Gambit vs the System Anti-Gambit [9:38] What Nokia Shows About Incremental Optimisation [13:41] What Actually Qualifies as a Paradigm Shift [23:12] Why AI Alone May Reinforce the Existing Paradigm [26:25] How Amazon Built Structural Advantage [29:37] Testing Adam's Own System Gambit [33:05] Applying the Tests Live [38:18] How Cross-Coupled Loops Create Compounding Advantage [40:29] Why Path Dependence Makes a Strategy Hard to Copy [46:42] When the System Anti-Gambit Is the Right Move [50:45] When You Actually Need a System Gambit [53:03] The Three Tests: Self-Improving Loops, Path Dependence and Management Logic Antagonism [55:39] Where to Find Ritavan Follow Ritavan: ■ Book: https://www.amazon.com/dp/B0GY8J23SK ■ Substack: https://systemgambit.substack.com ■ Website: https://ritavan.com ■ LinkedIn: https://www.linkedin.com/in/rritavan/?isSelfProfile=false ■ YouTube: http://www.youtube.com/@UCKf6F9wfQH56mCphHdbnCYg  The CTO Playbook: ■ Build your own CTO Playbook at https://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. ■ Follow Adam: https://www.linkedin.com/in/adamhorner/ ■ YouTube: https://www.youtube.com/@TheCTOplaybook ■ Prefer listening? Catch the podcast: https://bit.ly/thectoplaybook

  4. Sep 29

    112: Your best managers are the most replaceable, with Prof. Charles Wood

    AI isn't just changing how engineers work. It's forcing technology leaders to rethink what makes management valuable. Prof. Charles Wood is Senior Manager, Data Science & AI at Comcast, where he has spent nearly a decade leading enterprise AI strategy, and the author of Artificial Intelligence Management. Most of the AI and jobs conversation focuses on developers. Charles looks at the layer above them. His argument is that the qualities that make a manager good, like consistency, fairness and a repeatable process, are exactly what a language model can reproduce. He explains why the more predictable management work becomes, the easier it is to automate. He also covers why implementing AI means nothing until you prove the impact, and why the managers who stay valuable will be the ones creating outcomes that can't be reduced to an average. In this episode, he explains: ■ Why Middle Management Is Exposed: Why predictable, repeatable, standardized management work is easier to automate than engineering itself. ■ AI Is Arriving Top-Down: Why adoption is coming from the executive level, and why it has to start with business value. ■ Precision, Personalization and Scale: What AI makes possible, and where hallucinations, testing and human oversight still matter. ■ Stop Asking "Did We Implement AI?": Why every AI initiative needs measurable outcomes, and why the real question is "So what?" ■ Are You Average?: How managers can use AI to expand their scope, take on more complexity, and deliver results no model can replicate. ■ The New AI Playbook: Charles' principles for rebuilding your leadership playbook, starting with continuous learning and the willingness to nuke your old one. 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. You'll Learn: [0:00] Introduction [5:10] Why AI Could Disrupt Middle Management More Than Engineering [9:42] Why Predictable Management Work Is Easier to Automate [14:18] What LLMs Can and Cannot Replace in Technical Teams [19:06] Why AI Adoption Has to Start With Business Value [24:15] Hyper Precision, Personalization and Scale [29:37] Hallucinations, Testing and Human Oversight [34:21] Why Every AI Initiative Needs Measurable Outcomes [39:04] Using AI to Expand Your Scope and Stay Relevant [44:12] Continuous Learning as a Leadership Requirement [49:06] The Five Principles of the New AI Playbook [54:18] From "Did We Implement AI?" to "So What?" Follow Prof. Charles Wood: ■ Book: Artificial Intelligence Management ■ Convergent Lens: https://convergentlens.com ■ LinkedIn: https://www.linkedin.com/in/profwood/ The CTO Playbook: ■ Build your own CTO Playbook at https://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. ■ Follow Adam: https://www.linkedin.com/in/adamhorner/ ■ YouTube: https://www.youtube.com/@TheCTOplaybook ■ Prefer listening? Catch the podcast: https://bit.ly/thectoplaybook

  5. Sep 22

    111: Every technology decision you make now is a post-quantum decision

    Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives. 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. My guest this week is Conor Deegan, a security engineer, cryptographer, and co-founder of Project 11, focused on helping organizations prepare for the transition from classical cryptography to post-quantum cryptography. The quantum threat goes far beyond Bitcoin and digital assets. Conor explains how quantum computing could eventually affect the cryptography behind banking, communications, cloud infrastructure, authentication, health records, and everyday internet security. He breaks down what "Q Day" means, why organizations cannot simply wait until a powerful quantum computer exists, and how "harvest now, decrypt later" could put sensitive information collected today at risk in the future. The transition also comes with real engineering challenges. Post-quantum cryptography can require more computing resources, memory, storage, and bandwidth, while legacy systems and constrained devices such as IoT hardware can make migration even more difficult. Conor then shares a practical framework for CTOs: understand the threat, put someone in charge, identify critical systems and data, take the easy wins, put pressure on vendors, and stop creating migration debt. You'll Learn: [0:25] The Quantum Threat and Why It Matters [3:54] Understanding Q Day [7:52] How Quantum Computing Impacts Security [11:22] The Mission Behind Project 11 [18:58] Harvest Now, Decrypt Later [21:30] The Challenges of Post-Quantum Cryptography [27:29] From Engineer to CTO [30:20] A Practical Quantum Security Plan for CTOs [36:56] Identifying Critical Systems and Data [41:03] Taking the Easy Wins [43:12] Preparing Vendors for the Quantum Transition [43:57] Avoiding Migration Debt [45:59] Building Crypto Agility [48:35] The Quantum Challenge for IoT [54:50] Preparing for Q Day Find more from Conor Deegan and learn more about Project 11 through his professional channels: projecteleven.com, X, and LinkedIn. Conor welcomes direct contact on post-quantum migration questions. Find more from Adam on https://www.linkedin.com/in/adamhorner/ and https://www.youtube.com/@TheCTOplaybook, and explore coaching, cohorts, and how you can stay up to date at the https://www.thectoplaybook.com/, helping you build your own playbook for your path at your pace. If you prefer listening, check out the podcast at https://bit.ly/thectoplaybook.

  6. Sep 14

    110: AI Compressed the Work That Built Your Judgment

    Twenty years at one company should have made my guest predictable, and that is exactly the trap he built a method to escape. 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. Krystian Kolondra runs the browser portfolio at Opera, a set of products used by more than 300 million people, and he has spent two decades watching what happens to technical judgment when the work that built it starts to disappear. His argument is uncomfortable. Your judgment was earned through execution, and AI compresses execution. So what is training your judgment now? His answer starts somewhere I did not expect: an audit of the questions you stop asking. He calls it the shape of your curiosity, and he thinks most leaders have never looked at theirs. We get into why he refuses to check AI's output and flips the task back on the model instead. There is a sniper analogy that reframes what "learning from failure" actually requires. There is a story about Opera GX where the first questions his team asked turned out to be the wrong ones, and the right ones only appeared once they went somewhere uncomfortable. If you lead engineers, and you have felt the ground shift under what "senior judgment" means, this conversation gives you something concrete to practice tomorrow morning, before your first coffee. You'll Learn: [0:00] Introduction [5:46] Twenty years at Opera and the business behind free browsers [7:18] Why leading five hundred people is a different job entirely [9:39] The temptation to stick with what already worked [12:39] Curiosity as a counterweight to accumulated experience [17:44] How the gamer browser came from asking the wrong questions [23:26] Learning from failure means planning the shot before firing [29:06] How AI compresses execution but never the judgment [36:14] Auditing the questions you never ask to find blind spots Resources Mentioned: A Beautiful Constraint by Adam Morgan and Mark Barden | Book Theory of Constraints by Eliyahu M. Goldratt | Book Really Achieving Your Childhood Dreams (aka The Last Lecture) with Randy Pausch | TED Talk Eric Ries, Validated Learning | Wikipedia Igor Grossmann | Website A route to well-being: intelligence versus wise reasoning by Grossmann, I. et al. | Article Unlock more ways to make your browser yours with deeper personalization and an expanded modding universe with the Opera GX Gaming Browser here. Find more from Krystian Kolondra on LinkedIn. Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

  7. Sep 7

    109: Your Agents Are Held to a Lower Standard Than Your Engineers

    Most CTOs think adopting AI means picking the right tools, but Sumeet argues the real work is closing the accountability gap between agents and engineers. 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. My guest this week is Sumeet Vaidya, co-founder and CEO of Crafting, who spent years at Facebook, Uber, and Discord before building the infrastructure enterprise engineering teams now use to put agents to work safely. His perspective matters because he sees what CTOs say publicly, and what their teams are actually doing internally, and the gap is bigger than most leaders want to admit. Roughly 80% of enterprise engineering orgs, he estimates, are doing close to nothing meaningful with AI. The rest are either reacting to hype or trying to build something durable, and the difference is not the tools they pick. One partner running 3,000 agents against 250 engineers changed how he thinks about capacity entirely. That number is where his six diagnostic questions come from and where the cracks appear first: brittle CI/CD, accountability gaps for agents, and a hiring pattern that's storing up debt for the next downturn. If you're under pressure to show AI gains while cutting token spend, this one is aimed at you. You'll Learn: [0:00] Introduction [2:25] The disconnect between what companies say and what teams do [4:38] Why 80% of enterprises watch and wait on agents [9:31] Chasing the latest model as a vanity metric [14:14] Resilient cultures survive shocks that short-term thinking cannot [15:46] The engineering cultures that shaped Sumeet's career [28:51] Silicon Valley is not the whole world [33:02] What breaks if you 10X the team today [42:31] Hiring only senior engineers stores up hidden debt [47:11] Turning engineers from code writers into builders Find more from Sumeet Vaidya on LinkedIn, X, or explore the Crafting Website. Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

  8. Aug 31

    108: Your Most Valuable Executive Relationship Is the CFO

    Ask a CTO which executive relationship matters most, and they'll name the CEO, but my guest today would send you to the CFO instead. 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. Anoop Tripathi is 32 years into a career that spans from writing firmware for telephone exchanges to sitting as CTO at Sauce Labs, and he's unusually direct about what decides whether your technical work gets funded. Most of us step into this role believing the job is to be the strongest technologist in the building. Anoop thinks that's the fastest way to build an organisation of people waiting for commandments from the top. The conversation gets sharper when he talks about scaling an engineering team from zero to over 100, then having to bring it back down to 70 in a tough market. His lessons from that period are not the ones I expected. There's also a serious defence of laziness as an engineering virtue, a story about resellers walking out of a Citrix demo because the product was too good, and a framework he calls SHAPE that he uses to run his own career. Fear is the dominant feeling across my coaching practice right now. Anoop's take on what that fear is costing tech leaders is worth contemplating. You'll Learn: [0:00] Introduction [2:51] The double-edged sword of laziness as an engineering trait [7:18] Reframing tech debt as a business outcome your CEO hears [10:24] How investor pressure and a faster POC upended the Citrix integration story [18:01] What he learned cutting a team from 100 to 70 [26:19] Spotting an inflection point before hindsight makes it obvious [29:50] Fear you plant in your head tends to come true [32:52] The SHAPE framework for tech leadership [47:44] One piece of advice for a first-time CTO Resources Mentioned: Sauce Labs | Website Find more from Anoop Tripathi on LinkedIn. Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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About

Join Adam Horner, a CTO with over 30 years in the tech industry, on The CTO Playbook — the podcast dedicated to helping CTOs excel. Perfect for CTOs and tech leaders navigating the complexities of their roles, each episode offers clear insights, innovative strategies, and practical advice from top leaders in tech. With Adam’s extensive experience mentoring engineers and tech leaders, and over a decade as a CTO, you’ll gain the tools and knowledge to build and refine your own CTO playbook. Whether you're tackling complex projects, fostering innovation, leading teams, or shaping your company's tech strategy, this podcast is your go-to resource. Adam’s journey from engineer to strategic CTO was challenging. He learned through the school of hard knocks, making avoidable mistakes and facing countless challenges. Often out of his comfort zone and wishing for more guidance, he created this podcast to provide the support and advice he once lacked. Tune in for engaging interviews, leadership tips, and the latest in technology strategy. Each episode is designed to help you lead with confidence and level up as a CTO. Listen now to start your journey with The CTO Playbook and build your own playbook to excel in your role.

Information

  • Creator
    Adam Horner
  • Years Active
    2024 - 2026
  • Episodes
    115
  • Rating
    Clean
  • Copyright
    © Copyright Synova Technology 2024-2026
  • Show Website
    The CTO Playbook

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