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7 min read

đŸ„š Losing Visibility, AI Strategies, Unreasonable Expectations, Sandboxing Teams, AI vs Agile, Introverts: TMW #477

In London this Thursday? Join us for the evening!
🏆
Thank you to Damilah for sponsoring this week's issue - a collaborative software design and engineering firm partnering with clients to build high-quality digital products through expert team extension, AI-accelerated workflows, and a strong, people-first culture.

Hello, hello, hello, welcome to the week!

This Thursday, we'll be getting the CTO Craft community in London together for an evening of chat, networking, tasty sustenance and swapping war stories at the Tessl AI HQ - Guy Podjarny, founder of Tessl and Snyk, will also be giving a quick talk on scaling AI use across larger teams of teams.

There are over 100 CTOs already signed up to join us on Thursday, and we've just opened up some more tickets - do come and say hello if you're free that evening!

CTO Craft Mixers: London · Luma
Join fellow CTOs and technology leaders in London for a relaxed evening of shared stories and experiences, networking and learning. Sponsors: Tessl AI and food

CTO Craft

Our recent survey with Damilah looked at how leaders in 2026 perceive how the role will change by 2028, what will be expected of us and our teams, and how to prepare for those changes. We'll be sitting down with the Damilah team in London on May 7th to dig into some of the findings - it's free to attend, so do come if you'd like to see what we discovered:

CTO Craft Bytes: Engineering 2028: A Leadership Masterclass | CTO Craft
Explore how leaders and teams can build psychological safety in remote work environments through practical strategies, real-world stories, and insights from experienced experts.
CTO Craft

That's it, let's look at some links....

Andy @ CTO Craft

CTO Craft Con - Dates for Your Diary

CTO Craft Con: Toronto
Join CTO Craft Con: Toronto- 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: Toronto 2026
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
Conversations Roadshow: Berlin
Join CTO Craft in Berlin for the Conversations Roadshow with peer led roundtables, senior facilitators, networking, and insights you’ll use straight away.
Conversations Roadshow
SPONSORED
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The Maturity Roadmap: From Early Adoption to AI-Enabled Leadership

Based on a recent report in collaboration with CTO Craft, "Engineering 2028: Leading Human + AI Teams Responsibly", Iain and Aleksandar from Damilah will dive into the messy middle between AI experiments and true transformation. Why do some teams scale while others stall? It’s not the tools, it’s governance, skills, and team design.

See what great looks like as human leaders orchestrate AI agents, reshape workflows, and redefine engineering teams. You’ll get a clear progress lens to understand where you are, a practical view of multi-agent teams, and the key investments to accelerate your journey.

If you’re already using AI but struggling to scale it, then this session is for you.

Free Online Session

CTO Craft Mixers Coming Up

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

Reads of the Week

The Alarm That Went Silent
Why losing visibility is more dangerous than losing control
Fish Food for ThoughtMike Fisher
The Human Cost of 10x AI Productivity
AI tools increased code review volume by 98% but your brain still runs at 10 bits per second. The physical toll on senior engineers is measurable.
From the TrenchesDenis Stetskov

Leadership, Strategy & Business

What 20+ Years Of Leadership Taught Me About Engineers, Business, And The Space Between
A candid reflection on two decades of building teams, bridging gaps, and learning what actually makes organizations work.
Thriving In EngineeringAlex Ponomarev
From World Model to Domain Intelligence
Jack Dorsey opened a door. This is an attempt to see further through it.
Boaz KatzBoaz Katz
Handling unreasonable expectations
A lot of unreasonable expectations are thrown around these days. In this article I offer concrete tips and examples that will help you manage them. Results are not guaranteed. At least I don’t lie.
Sudo Make Me a CTOSergio Visinoni
The messy truth of your AI strategies - Stack Overflow
Stack Overflow

Culture, People & Teams

Why Your Best Employee Becomes Your Worst Manager - Yaniv Preiss
It is sad and true: usually, people don’t leave companies, but they leave managers. Don’t let your best IC become your worst manager.
Yaniv PreissYaniv Preiss
Blessed With Constraints: Part II
Stop Railroading Your Teams and Start With Sandboxing
Maarten’s NewsletterMaarten Dalmijn
Your Offshore Team Is Probably as Frustrated as You Are
If your offshore team frustrates you, the feeling is mutual. Here’s how to fix a low-trust relationship across an ocean.
The protégé problem today
Issue 292: Knowledge flows downhill anymore
Proof of ConceptDavid Hoang

Technology, Operations & Delivery

No, AI Did Not Kill Agile
Why execution speed doesn’t solve a knowledge problem
Andrea’s SubstackAndrea Laforgia
Cheap Code means more Governance
(or at least I think it does)
JoTJeff
Rethinking Pair Programming in the Age of AI
Why “pairing with AI” is harmful to your team and what to do instead
Engineering StrategyAleix Morgadas
The new shift-left: Coding earlier! - The Quality Duck
Shift-left isn’t enough any more, you need to Shift-Coding-Left! Shrink feedback loops and empower your team to build at the speed of thought.
The Quality Duck - Technology Leadership founded on QualityStuart

Stress, Wellbeing & Growth

I’m an introvert. This is how I get myself to speak up.
Prepare go-to phrases to insert yourself in meetings, ask a colleague to keep you accountable, and other tactics I personally use to get myself to speak up.
Wes Kao's NewsletterWes Kao
Improve Your Influence (not clickbait, this truly did for me) — Ant Murphy
In this post, I explain why prioritization frameworks often fail, and what actually matters instead. Rather than relying on formulas like RICE or WSJF, I break down the four core mental models I use to prioritize work: impact, effort, urgency, and confidence.
Ant MurphyAnt Murphy
The hidden mental load of leading a product org
Nobody warns you about this part.
InsideProductOrgStephanie

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

Interested in sponsoring TMW or any of our events? Check out some stats here

Please do remember to share this link if you know of anyone who’d like to receive TMW: https://techmanagerweekly.com

Have an amazing week!

Andy

Published by:

Andy Skipper