The CTO Playbook

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

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

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

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

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.