The CTO Playbook

Women weren't pushed out of tech once. There were multiple waves, and the patterns are still showing up in how teams get built today.

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.

Most engineering leaders think their hiring process is neutral. Changing the job spec brought my guest three women applicants the following week, and her team hired two of them. Michelle McDaid spent two decades leading globally distributed engineering teams, became the first female director of engineering at her last company, and left it with 50% women in that role.

She then went back to university to put the evidence behind what she'd already seen on the ground. We sat with some of these ideas together at CTO Craft Con in London a couple of weeks ago, and the conversation was good enough that I wanted to bring it here. She's unusually calm about uncomfortable truths, and that's exactly why this matters. If you believe in diverse teams but keep ending up with more of the same, the gap isn't your intent. It's what you don't even know to look for. This one challenges the default assumptions most technical leaders never examine, and gives you something practical to do about it.

You'll Learn:

[00:00] Introduction
[02:29] What trust actually has to do with uncovering the real problem in any organization
[06:50] What Michelle's career across banking and tech revealed about leadership and self-worth
[15:56] Why the gender gap in tech is neither natural nor inevitable
[24:36] How the language in your job spec is quietly filtering out the people you want to hire
[28:36] The smallest changes that move teams from fearful to collaborative and how AI fits in
[33:47] A 10-point framework for intentionally broadening your talent pool
[44:20] What women lose in meetings every day and how anyone can change it

Resources Mentioned:

The Authority Gap by Mary Ann Sieghart | Book
Where Did the Women Go? by Michelle McDaid | Article
Textio | Website
Gender Decoder by Kat Matfield | Website

Learn more from Michelle on her LinkedIn and The Leading Place 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.

Most CTOs are promoted for technical judgment, then get stuck trying to lead people with the same playbook that got them there.

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.

Ric Hill has spent 14 years running Ghyston with his wife, CTO'd for startups and mid-corporates, and earned a spot on the CTO Craft 100. His central conviction is that there is no playbook worth following blindly.

Most CTOs are promoted on technical skill and then judged on leadership. The reflex is to import what worked last time. Ric argues that reflex is the problem.

What replaces the playbook is a sharper version of listening, knowing how long your "fresh eyes" window actually lasts, reading the difference between an unhealthy political culture and an unhealthy apathetic one, and noticing which person on your team has gone quiet.

This is a conversation about staying flexible without being indecisive, and delivering results without forcing a template onto a situation that doesn't fit it.

You’ll Learn:

[00:00] Introduction
[11:29] Why bespoke beats cookie-cutter software
[13:50] The first few weeks decide everything
[16:23] How long until you're part of the furniture
[18:19] Health versus outcomes in tech leadership
[20:21] The sticky note roadmap that changes everything
[25:38] Disagree and commit without losing trust
[28:40] When stubbornness becomes a liability
[30:35] Listen for the silences in your team
[32:59] Why engineering culture can stand apart
[40:20] The one tip every new CTO needs

Check out Ghyston for your software development needs.

Find more from Ric on LinkedIn.

Listen to Ric’s podcast, Giant Minds: From The Bristol Tech Community, on Spotify or Apple.

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.

What if the biggest impact you have as a leader isn’t the strategy you set, but the signals you leave behind in every interaction?

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.

In this episode, Paul Kinkaid, a former British Army officer, founder of Forensic Outcomes, and executive leadership coach, introduces a principle from forensic science: every contact leaves a trace.

Those small moments, the way you listen, the way you respond, the way you make decisions, shape how your leadership is experienced across an organization.

The focus is on the smallest behaviours that most leaders overlook, and how those behaviours shape trust, culture, and performance.

Leadership isn’t just about decisions or strategy. It’s about the signals you send every day.

You’ll Learn:

[00:00] Introduction
[00:06:02] What leadership presence is and why people listen before you speak
[00:09:10] Why pressure exposes the difference between real and performative leadership
[00:12:04] How small behaviours shape trust, clarity, and psychological safety
[00:21:36] What happens when leaders send the wrong signals without realizing
[00:34:12] Why the gap between intention and impact grows over time
[00:48:27] How communication patterns shape culture more than strategy
[01:02:14] What it takes to notice and shift the signals you send

Resources Mentioned:

Locard Exchange Principle by Saferstein, R., et al. | Article

Get Paul’s book, Forensic Leadership, in print or audiobook and start noticing the signals you’re sending every day.

Find more from Paul on LinkedIn, and visit his DactoApp landing page at Forensic Outcomes.

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.

What happens when execution matters more than strategy?

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.

Adam Spector is a four-time founder and investor in over 200 startups. He has seen firsthand how quickly expectations have shifted, and why what worked even a few years ago no longer holds up. The bar for startups has moved. Companies that once raised capital on early traction are now expected to show real revenue, working products, and meaningful growth almost immediately.

AI is beginning to change what teams can produce, even if it has not fully transformed day-to-day work yet. The pace is increasing, and the gap between what is possible and what most teams deliver is widening. Rigid strategy is becoming a liability. Founders who cannot adapt in real time are more likely to fail as conditions shift underneath them.

Efficiency is under a new lens. Metrics like revenue per employee are becoming signals of how well a company actually operates. The underlying question is harder to ignore: what is your role when code is no longer the constraint?

You’ll Learn:

[00:00] Introduction
[06:12] Why the bar for startups has changed faster than most founders realize
[10:47] What investors expect now and why early traction is no longer enough
[14:33] How AI is starting to affect workflows without fully replacing them
[18:05] Why time is becoming the only truly scarce resource
[22:41] What happens when startups grow fast but lack a real moat
[27:18] Why rigid strategy increases your risk of failure
[31:56] How revenue per employee is becoming a key efficiency signal
[36:22] What breaks when competitors move faster than you
[40:08] How to think about your role when code is no longer the constraint

Find more from Adam Spector on LinkedIn and the Chore Website.

Find more from Adam Horner 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.

A CTO hired a star engineer to push AI adoption forward, and within months, the team had lost its momentum, the new hire, and any sense of where they actually were.

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.

Almost every CTO Adam speaks to right now is carrying the same thing: exhaustion beneath loud pressure. The board wants speed. Investors want an AI strategy. The voice in their own head says everyone else has worked something out that they haven't.

The pressure to go faster with AI is usually the signal that the real work is somewhere else. Adam has watched organizations try to leap from pure experimentation to mature AI practice through a single hire, and watched what breaks when they do.

The fastest engineering teams aren't tuning the engine first. They're upgrading the brakes and tires, the testing automation, the review systems, and the people around the work, before they touch raw speed.

Tune in to learn about the three-stage pattern of AI adoption, two contrasting examples that show what acceleration actually costs, and the three postures that separate the CTOs making real progress from the ones spending money to look busy.

You’ll Learn:

[00:00] Introduction
[01:08] Why CTOs feel behind even when they’re moving fast
[02:48] The three stages of AI adoption and where most teams get stuck
[05:12] Why skipping stages creates friction that slows the whole team
[08:34] How lack of standards turns fast progress into team-wide frustration
[15:06] Why slowing down in the right way is what actually moves teams forward
[23:11] How to spot your team’s real stage and decide what to do next

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.