The CTO Playbook

Most CTOs already know what to do about their time. The hard part is doing it, week after week.

Joel Chippindale, CTO coach and founder of Monkey's Thumb Coaching, joins Adam Horner on The CTO Playbook to talk about why senior leaders slide back into reactive busyness, and what really holds them there.

Joel joined FutureLearn as CTO before it had a single employee, and later became its COO as the company grew to around 130 people. He spent the early months of that role in almost constant overwhelm, and found that working with a coach helped him step back, make a plan and lean on the people around him.

He walks through Immunity to Change, the framework from Robert Kegan and Lisa Laskow Lahey, and shows how to surface the hidden commitments and assumptions behind our habits, then test them with small, safe experiments.

For any CTO who knows the change they need to make and is still waiting for it to stick.

In this episode, he explains:

■ 𝗧𝗵𝗲 𝗘𝘅𝗲𝗰𝘂𝘁𝗶𝗼𝗻 𝗧𝗿𝗮𝗽: Why overwhelm pushes capable leaders to work harder and longer instead of stepping back to think.

■ 𝗜𝘁 𝗜𝘀𝗻'𝘁 𝗔𝗹𝗹 𝗼𝗻 𝗬𝗼𝘂: How a clear plan, and leaning on the people around him, helped Joel regain a sense of control.

■ 𝗛𝗶𝗱𝗱𝗲𝗻 𝗖𝗼𝗺𝗺𝗶𝘁𝗺𝗲𝗻𝘁𝘀: How a habit like accepting every meeting can protect commitments we've never made explicit, such as being helpful, being heard or keeping relationships intact.

■ 𝗪𝗿𝗶𝘁𝗲 𝗗𝗼𝘄𝗻 𝘁𝗵𝗲 𝗔𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻𝘀: Why you don't have to be right about the assumptions behind those commitments to get value from writing them down.

■ 𝗦𝗺𝗮𝗹𝗹 𝗘𝘅𝗽𝗲𝗿𝗶𝗺𝗲𝗻𝘁𝘀 𝗮𝗻𝗱 𝗙𝗲𝗲𝗱𝗯𝗮𝗰𝗸 𝗟𝗼𝗼𝗽𝘀: How to test one assumption with one or two people, then decide whether the new behaviour sticks or what to try next.

■ 𝗪𝗼𝗿𝗸𝗶𝗻𝗴 𝗜𝘁 𝗧𝗵𝗿𝗼𝘂𝗴𝗵 𝘄𝗶𝘁𝗵 𝗢𝘁𝗵𝗲𝗿𝘀: Why talking it through with someone else, in coaching, workshops or peer circles, helps you see what you can't easily see yourself.

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

[1:20] Welcome, and the Mood at CTO CraftCon

[4:21] From Software Engineer to Manager, the Expensive Way

[8:09] Building FutureLearn From Day One

[10:50] The COO Role and Constant Overwhelm

[14:11] What Coaching Gave Him: A Plan, and Shared Weight

[17:02] Your Output Is Your Teams' Output

[17:51] Why Overwhelm Keeps Coming Back

[20:09] The Gap Between Knowing and Doing

[22:44] The Immunity to Change Framework

[24:54] Why CTOs Accept Every Meeting Invite

[26:24] The Hidden Commitments Behind Saying Yes

[27:52] Writing Down the Assumptions Underneath

[30:07] Small Experiments to Test Your Beliefs

[31:52] Feedback Loops: Is It Enough?

[35:04] You Can't Read the Label from Inside the Jar

[36:14] The Playbook

[38:11] Step Zero: When to Use It

[39:16] Peer Groups and CTO Craft Circles

[40:44] Where to Find Joel

Follow Joel Chippindale:

■ LinkedIn: https://www.linkedin.com/in/joelchippindale/

■ Monkey's Thumb Coaching: https://monkeysthumb.co.uk/coaching-for-engineering-leaders/

■ Immunity to Change, by Robert Kegan and Lisa Laskow Lahey: (link to add)

■ High Output Management, by Andy Grove: https://www.penguinrandomhouse.com/books/72467/high-output-management-by-andrew-s-grove/9780679762881

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

A solid technical case rarely wins the decision if the CFO, the CEO and the board can't follow it.

Jens Heitland, founder of Heitland Media Group and former Global Head of Innovation at IKEA Centres, joins Adam Horner on The CTO Playbook to explore how technology leaders can build authority beyond their job titles, adapt their communication to different audiences, and turn complex technical ideas into clear business outcomes.

Jens and his team help CEOs and management teams position themselves as thought leaders in their industries.

Jens shares how leaving his corporate role taught him the importance of building influence of his own, rather than relying on the reputation of the company he represented. He also recounts a meeting with a CFO that sent him home to prepare again, and why explaining innovation in terms of customer excitement wasn't enough without showing its financial value.

Through practical examples, including using a car to explain a complex project, Jens shows how CTOs can simplify their message without losing its meaning, connect technical decisions to business priorities, and build shared understanding with stakeholders. He also shares a practical approach to improving communication through testing, feedback and a 30-day video challenge.

In this episode, he explains:

■ 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗜𝗻𝗳𝗹𝘂𝗲𝗻𝗰𝗲 𝗕𝗲𝘆𝗼𝗻𝗱 𝗬𝗼𝘂𝗿 𝗝𝗼𝗯 𝗧𝗶𝘁𝗹𝗲: Why executives need to develop their own authority, share their perspectives, and build thought leadership beyond the company they represent.

■ 𝗥𝗲𝗮𝗱𝗶𝗻𝗴 𝘁𝗵𝗲 𝗥𝗼𝗼𝗺: How understanding people's intentions, priorities and communication styles helps leaders adapt without losing their authenticity.

■ 𝗧𝗿𝗮𝗻𝘀𝗹𝗮𝘁𝗶𝗻𝗴 𝗧𝗲𝗰𝗵𝗻𝗼𝗹𝗼𝗴𝘆 𝗶𝗻𝘁𝗼 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗩𝗮𝗹𝘂𝗲: Why CTOs need to connect technical projects to financial outcomes, return on investment, and the priorities of executive stakeholders.

■ 𝗦𝗶𝗺𝗽𝗹𝗶𝗳𝘆, 𝗭𝗼𝗼𝗺 𝗢𝘂𝘁, 𝗭𝗼𝗼𝗺 𝗜𝗻 𝗮𝗻𝗱 𝗟𝗼𝗼𝗽 𝗕𝗮𝗰𝗸: How a familiar analogy like a car, and moving between the bigger picture and the detail, helps stakeholders understand a complex project and why it matters to them.

■ 𝗧𝗲𝘀𝘁𝗶𝗻𝗴 𝗬𝗼𝘂𝗿 𝗠𝗲𝘀𝘀𝗮𝗴𝗲: Why CTOs should practise their messaging with their own teams first, and how recording yourself on your phone, as in Jens's 30-day challenge, builds the skill through repetition.

■ 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗬𝗼𝘂𝗿 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗠𝗮𝗻𝗱𝗮𝘁𝗲: Why new CTOs should clarify what they were hired to accomplish, communicate that purpose from day one, and reinforce it throughout their first 100 days.

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

[2:15] From Electrical Engineer to Global Head of Innovation at IKEA Centres

[4:50] Why Influence Must Extend Beyond Your Job Title

[6:00] Learning to Read the Room and Understand People

[7:35] How Communication Shapes Executive Influence

[10:28] Understanding Your Superpowers, Values, and Leadership Identity

[13:22] Why CTOs Need to Adapt Their Message to Different Audiences

[14:00] The CFO Meeting That Changed Jens's Approach to Communication

[16:40] Translating Technical Language into Financial Value

[17:29] Using Simple Analogies to Explain Complex Projects

[19:28] Why Simplifying Communication Creates Shared Understanding

[21:19] Zooming Out, Zooming In, and Looping Back to Business Goals

[24:03] How to Position Technology Leadership Around Business Strategy

[25:57] Testing Your Ideas and Building Influence Within Your Team

[27:30] Applying the Engineering Testing Mindset to Communication

[29:18] A Practical Step-by-Step Approach to Better Executive Communication

[30:01] The 30-Day Video Challenge for Improving Communication Skills

[32:46] Why Great Communicators Build Their Skills Through Repetition

[34:08] Learning by Doing, Experimenting, and Putting Yourself Out There

[35:23] Jens's Advice for CTOs Starting Their Leadership Journey

Follow Jens Heitland:

■ LinkedIn: https://linkedin.com/in/jensheitland

■ Free Authority Audit: Jens and his team at Heitland Media Group offer a free Authority Audit that shows you how outside parties see you. It's open to CTOs as well as CEOs. Book at https://calendly.com/jens-heitlandmediagroup/ceo-authority-audit- and mention The CTO Playbook in the booking comment.

■ Running challenge: Jens is starting a new personal challenge for a good cause, running every day for another year and 100 km every week.

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

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