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