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March 25, 2026

Am I comfortable letting them know that I used AI?

Hi,

I attended CTO Craft Con London a few weeks ago. It was great to have the opportunity to chat to a number of you in person.

🎑 CTO Craft Con in London

Much of the the energy, excitement and anxiety being shared by leaders at the conference was around AI. Two talks on AI and leadership particularly stood out to me:

The first was James Stanier's keynote, AI as a Thinking Partner: Leading with Clarity and Confidence, where he shared how he was building a personal "AI Executive Assistant" based on Claude Code to support him in his work as a CTO. It made me keen to experiment.

Are you experimenting with anything similar? If so, I'd love to hear about it.

The second was Hywel Carver's talk, Unautomatable You: Your Value in the Age of AI, about the value of empathy and what we could not automate. In the talk he suggested we ask the question, "Am I comfortable telling them that I used AI?", when thinking about whether to automate something that we do.

It's a deceptively simple test. Where does it make you pause?

🍳 CTO Breakfast Club

This is an opportunity to meet, discuss and make connections with CTOs and other senior engineering leaders over a lovely breakfast.

Our next breakfast will be at Grind, London Bridge on Wednesday 15th April.

β†’ Register here β€” places are limited.

πŸ”— Links

  • 10 Things I Learned From CTO Craft Con 2026: Andi Smith shares his reflections on CTO Craft Con
  • Comprehension Debt - the hidden cost of AI generated code: What happens when your team relies on AI tools to the extent that they no longer understand the codebase. Addy Osmani shares his view on how this scenario plays out.
  • How not to measure the ROI from AI in your software organization: Cat Hicks outlines the pitfalls of measuring the return part of your investment in AI in developing software, and some valuable mitigations.
  • Harness engineering: Birgitta BΓΆckeler on the rise of importance of constraining your development environment
  • The five types of network connections you need at work: Jill Wetzler's categorisation is a useful lens to consider when reflecting on your current network and how you might evolve it
  • Proceed until apprehended: Harriet Minter on the power of not waiting for explicit permission
  • My engineering leadership job search in numbers: Anna J McDougall shares their experience of looking for an engineering leadership role in 2025/26

Take care,

J.

β†’ monkeysthumb.co.uk

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