8 min read

🐟 Shadow AI, Learning Rotation, Decision Triangles, AI Brain Fog, Coding Assistants, Stoicism vs Burnout: TMW #420

Only a few tickets remaining for CTO Craft Con...
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Thanks to Gitpod for sponsoring this issue of TMW - an online IDE that allows developers to write, test, and deploy code in a cloud-based workspace.

Hello again! It's Monday..

Just two weeks until CTO Craft Con: London kicks off! A handful of tickets remain -  this is your last chance to join the biggest gathering of the CTO Craft community yet. You’ll be alongside fast-growing companies like Pleo, Planday, Talmix, and Gymshark, plus tech giants like Apple, Google, Amazon, JustEat, and the BBC, all tackling the challenges that keep tech leaders up at night.

Don’t forget - community members can unlock special pricing with the code Community-Spring-25 when registering here.

CTO Craft Con: London 2025
CTO Craft Con will bring together over 500 Chief Technology Officers and other senior technology leaders from the most exciting start-ups, scale-ups, unicorns, and big tech companies to elevate their engineering culture in London, March 2025.

Can’t wait? Join us in London this week for the CTO Craft Con Warm-Up - open to everyone, whether you're attending the main event or not. A great chance to meet your local tech leadership community.  Register for free here - see you there!

CTO Craft Mixer: London 2025
Join us for our pre-con Mixer and get to know our community of CTOs and senior tech leaders ahead of CTO Craft Con: London for a relaxed and insightful meet-up in London.

That's it, see you next week...

Andy @ CTO Craft

CTO Craft Events

Don't forget, as a TMW subscriber you have access to the Member Pricing for upcoming CTO Craft Con events.  You can unlock membership pricing by using the following access codes in the checkout when purchasing tickets:

CTO Craft Con: London 2025 - Community-Spring-25
CTO Craft Con: Toronto 2025 - Community-Toronto-25

CTO Craft Mixer: GdaƄsk
Join our community of CTOs and senior tech leaders for an informal meet-up in GdaƄsk.
CTO Craft Mixer: Manchester 2025
Join our community of CTOs and senior tech leaders for an informal meet-up in Manchester.

From our Sponsors

[From Gitpod] Don’t let "Shadow AI" put your data at risk

Your developers are already using AI coding assistants. How do you ensure responsible adoption? Our guide adapts the UK Government AI Playbook for engineering teams, providing practical steps for secure implementation, effective review processes, and proper tool selection.

Learn More

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If you're interested in sponsoring TMW or any of our events, drop us a line at partners@ctocraft.com.

Reads of the Week

The Rotation Program That Keeps This Startup’s Engineers Learning — and Not Leaving
Checkr VP of Engineering Krista Moroder opens up about the rotation program that’s helped keep her org’s non-regrettable attrition at near-zero.
How to develop capability in your team
Developing capabilities starts with being clear in the distinction between capable and capability - and building the right training from there.

Leadership, Strategy & Business

The Decision Triangle: a simple way to improve decision making - Peter Gillard-Moss
Improve the quality of your decisions by focussing on three key elements.
Attention To Details
Why the little things matter
5 mindset shifts needed to grow from engineer to leader
Become a leader that everyone appreciates, with these mindset shifts!
Diagnosis in engineering strategy.
Once you’ve written your strategy’s exploration, the next step is working on its diagnosis. Diagnosis is understanding the constraints and challenges your strategy needs to address. In particular, it’s about doing that understanding while slowing yourself down from deciding how to solve the problem at hand before you know the problem’s nuances and constraints. If you ever find yourself wanting to skip the diagnosis phase–let’s get to the solution already!–then maybe it’s worth acknowledging that every strategy that I’ve seen fail, did so due to a lazy or inaccurate diagnosis. It’s very challenging to fail with a proper diagnosis, and almost impossible to succeed without one.

Culture, People & Teams

đŸ€” Dear Lewis, my team has AI brain fog. How do I help them think for themselves again?
In today’s edition, a CEO grapples with the unintended consequences of introducing ChatGPT at work—leading to slower decisions, confusing deliverables, and a troubling case of AI brain fog.
Improving Team Morale is not an Objective
New managers often see making their team happy as their main objective. Here’s the problem with this approach.
Face The Productivity Phantom - The Force That Drains Your Team’s Potential
Every engineering team faces an invisible, destructive force: I’ve given it a nickname - the Productivity Phantom.
New Junior Developers Can’t Actually Code
Something’s been bugging me about how new devs and I need to talk about it. We’re at this weird inflection point in software development. Every junior dev I talk to has Copilot or Claude or GPT running 24/7. They’re shipping code faster than ever. But when I dig deeper into their understanding of what they’re shipping? That’s where things get concerning. Sure, the code works, but ask why it works that way instead of another way? Crickets. Ask about edge cases? Blank stares. The foundational knowledge that used to come from struggling through problems is just
 missing. We’re trading deep understanding for quick fixes, and while it feels great in the moment, we’re going to pay for this later.

Technology, Operations & Delivery

How much faster can coding assistants really make software delivery?
Can coding assistants like Copilot really speed up software delivery? The results of our tests might surprise you.
All Projects Are Business Projects
There are no technical projects: all tasks should be advancing business goals in one way or another.
Software development is

There is something puzzling about software development. It doesn’t work like many tasks, it doesn’t break down the same way. It feels strangely personal, like there’s a connection

Dedicated vs. Rotating Scrum Masters
Short personal thoughts, reflections, and ideas

Stress, Wellbeing & Growth

How Stoic Principles Can Help You Avoid Burnout
Burnout Isn’t About Working Too Hard—It’s About Chasing the Wrong Goal
“Comeback with a positive attitude: The Hidden Success in the Failure”
Many people look at failure or loss as the end of everything and consider themselves not good enough. But what if we see failure as the new

Why You’re More Qualified to Share Your Ideas Than You Think.
Ever typed out a LinkedIn post, read it back, and then
 deleted it? If you have, welcome to the club.

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!

https://ctocraft.com/community

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Have an amazing week!

Andy