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🦆 Tripwires, One-way Decisions, Psychological Costs of AI, Hiring Juniors, Brain Tabs: TMW #499

Only 15 tickets left for CTO Craft Con: Europe!
💾
This week's TMW is sponsored by Nortal - a trusted strategic partner for governments, healthcare institutions, leading businesses, and Fortune 500 companies.

Hello, hello, hello, welcome to the week!

There are just two weeks to go until CTO Craft Con: Europe lands in Amsterdam on 29–30 September - and there are only 15 tickets remaining. Join CTOs and senior technology leaders at Capital C for two packed days of practical insights, candid conversations and the kind of peer connections that are difficult to replicate anywhere else. With AI adoption, organisational change, scaling and engineering leadership on the agenda, this is your chance to step away from the day-to-day and spend focused time with people tackling the same challenges.

If Amsterdam has been on your list, now is the moment to make it happen. The closer we get, the fewer tickets will be available, and you don’t want to be hearing about the best conversations, ideas and introductions after the event instead of being part of them. Secure your place at CTO Craft Con: Europe now, and join us for an energising two days with one of Europe’s most engaged technology leadership communities.

CTO Craft Con: Europe 2026
Join CTO Craft Con Europe 2026 in Amsterdam - an intimate, community-centered gathering for engineering leaders to connect, learn through insightful sessions, and build real peer relationships in a supportive environment.
CTO Craft Con: Europe 2026

That's it, let's look at some links! See you next week

Andy @ CTO Craft

Ps. If you're in an engineering leadership role, you absolutely need to be on top of the latest data on compensation and long-term incentives - have a look at our recent Compensation Report for all the latest insights.

Compensation Survey Report 2026 | CTO Craft
Welcome to the 2026 CTO Compensation Report, presented by CTO Craft and Albany.
CTO CraftMatt Hunt

CTO Craft Con - Dates for Your Diary

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CTO Craft Bytes: Your AI Strategy Is Only as Good as Your Data

AI ambitions are growing quickly, but for many organisations, the data foundations needed to deliver them are struggling to keep pace.

​In this CTO Craft Bytes session, Edward Fowler, Global Chief Technology & Delivery Officer at Nortal, and Richard Wiles from News UK will explore what it really takes to move AI beyond isolated experiments and into reliable, scalable production.

They’ll discuss:

  • ​How to tell whether your data is genuinely ready for AI
  • ​Why so many organisations struggle to move from experimentation to production
  • ​The balance between data quality and data availability
  • ​The role governance plays in enabling - rather than slowing - AI adoption
  • ​How to overcome fragmented data estates and disconnected systems
  • ​What a data platform capable of supporting AI for the next 5–10 years should look like
  • ​How much of their existing data infrastructure CTOs really need to rebuild​
Register for the free event 👉

CTO Craft Mixers Coming Up

See the whole calendar here - not in your city yet? Drop us a line!

Reads of the Week

AI doesn’t create leadership problems - it exposes them — Kate Leto
I’ve been talking with senior leaders about what AI is doing to the human side of their organisations - not adoption rates or tooling decisions, but what is happening to trust, psychological safety, status, identity, expertise and the way work gets done. Five patterns are beginning to emerge from th
Kate LetoKate Leto
Tripwires
Everyone is making the same argument: code is no longer the bottleneck, and the bottleneck has shifted to the phases before and after coding. But describing this as a moving bottleneck understates the …
Writing is clarifying

Leadership, Strategy & Business

Ten things nobody tells you when you become a manager.
Congratulations on the promotion. The reward is a job you have never done, no training, and a team reading your face for clues. Ten things to know.
Technically FeasibleLouise Deason
The Mistakes You Can’t Take Back
Why do one-way door decisions feel so easy to walk through?
A Life EngineeredSteve Huynh
The Rain Comes In The Fall
Bring an umbrella, not a forecast: What engineering managers learn about uncertainty.
Thriving In EngineeringAlex Ponomarev
What is Leadership Really For?
The overaching philosophy that led to the creation of the Connected Technology Leadership
LinkedInLee Clayton

Culture, People & Teams

RDEL #160: What psychological costs does AI adoption create for engineers?
New research finds the psychological cost of AI adoption scales with how much of a role’s generative work the tool takes over.
Research-Driven Engineering LeadershipResearch-Driven Engineering Leadership
A Product Builder’s Path: The EM & PM Coalition
PMs are choosing to build. EMs are being pushed into the same room. What works and what you should refuse.
The Socratic LeadershipPetros Bountis
Navigating the Realities of Engineering Promotions
Why Climbing the Tech Ladder Feels Complex
Sev’s SubstackSev
Is hiring juniors a bad idea in 2026?
It might be the opposite
High-Impact EngineeringRoman Nikolaev

Technology, Operations & Delivery

James Shore: Are You Getting Your Money’s Worth from AI?
The Cost of an Objection Went to Zero — Leadership Garden
AI lets you produce work you can’t evaluate. Worse, it lets everyone else critique yours. What engineering leaders should actually do about it.
Leadership GardenCsaba Okrona
Inside a Software Factory
Go from vibe coding to generating clean, maintainable code
O'Reilly MediaPaul Iusztin
How to write a definition of done for an AI feature
Evals are quickly becoming the new PRD but to know you are truly done they lack one key customer-facing element: outcomes.
Jeff GothelfJeff Gothelf

Stress, Wellbeing & Growth

Your brain has 500 tabs open. Here’s how to close them.
The six-step system for clearing mental clutter, closing open loops, and finally feeling like you can breathe
Ambition Without BurnoutAngelica Councilman
Do You Ever Feel Imposter Syndrome?
It may be something on your glasses.
Drawn to LeadKacy Maxwell
What Is Holding Us Back as Leaders?
There have been days when I looked at my calendar at the end of the day and wondered where my time had gone.
People In SoftwareGeorge Dedes

That’s it!

If you’d like to be considered for the free CTO Craft Community, fill in your details here, and we’ll be in touch!

Campus by CTO Craft: The Go-to Resource for Senior Technology Leaders
Created for CTOs, by CTOs: A transformative learning community for senior technology leaders in startups and scale-ups
CTO Craft Campus

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Have an amazing week!

Andy

Published by:

Andy Skipper