8 min read

🥨 Return on Tokens, Reliable Teams, Culture vs Innovation, Reorgs, Runbooks vs Checklists, Clean Code: TMW #486

Two AI-focused CTO events for your diary!
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This week's TMW is sponsored by Pensero - giving leaders objective visibility into delivery, quality, and AI impact across the organization.

Hello, hello, hello, welcome to the week!

We have two excellent AI-focused online events coming up in the next few weeks where I'll be interviewing two experts about how teams are bridging the gap between the old paradigms and the new. These will be absolutely unmissable, and there'll be time for Q&A for the audience, so please do join us!

On June 18th (this Thursday!) I'll be chatting with Johann Beukes from Svitla about what he and his teams have learned about control and its importance in team-wide AI adoption:

CTO Craft Bytes: AI is Already Inside Your Engineering Org. The Question is Not Adoption, it’s Control · Luma
Most conversations about AI in engineering circle the same territory: productivity claims, tool demos, adoption metrics. This session starts somewhere…

And then on July 8th, Carol Palombini and I will sit down for a chat about what happens when you face AI skepticism in your teams, and how to sell the transformation to them:

CTO Craft Bytes: From AI Resistance to Readiness · Luma
AI is changing how product and engineering teams work, but the bigger challenge is often human: trust, mindset, and leadership. In this intimate fireside chat,…

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

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 Craft Con - Dates for Your Diary

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: Fintech
Join CTO Craft Con: Fintech in London - 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 | Conversations Roadshow
Each gathering follows the same small-group, peer-led format, but every event is shaped by its local context. Attendees, facilitators, and discussion topics differ from city to city, reflecting the challenges and opportunities CTOs are experiencing in that region.
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Pensero - the AI-era engineering performance platform

You're told the team is shipping fast or running slow, but rarely shown why. Pensero gives leaders objective visibility into delivery, quality, and AI impact across the organization. It connects to your existing engineering and delivery tools, turning real activity into evidence: actual delivery, code quality, where work gets blocked, the true impact of AI on output and cost.

Trusted by finance and the board, because it's based on what your team actually shipped, not guesswork.

Learn more about Pensero

CTO Craft Events Coming Up

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

Reads of the Week

AI is the New OS | CTO Craft
Why the next decade of work will not run on the application stack you grew up with, and what technology leaders should do about it this quarter.
Return on Tokens (ROT)
Markie Wagner Co-Writes A Poetic Essay
AI demands more engineering discipline. Not less
If you lived through the shift from handcrafted server pets to immutable infrastructure, you should sense something oddly familiar about what’s happening now.

Leadership, Strategy & Business

The Reliable Team Trap
Why delivering well can quietly cap your career, and what to do about it
Paging Charity? How do I get my leaders to stop running teams Into the ground? - Stack Overflow
Your Culture Is Killing Your Innovation Capability — And The Data Proves It - Cris Beswick
What Emtrain’s 2026 Workplace Culture Report — drawing on 48 million employee responses — reveals about the hidden threat to your organisation’s ability to grow, adapt, and compete. Emtrain’s 2026 Workplace Culture Report is being framed by many as a people risk story. A compliance challenge, and a HR problem to be managed. The four […]
Becoming a manager means grieving the engineer you were.
As a manager, the hardest thing for me to measure was my own contribution.
Leading by example, even through uncertainty | Thoughtworks
Leading by example, even through uncertainty

Culture, People & Teams

The people aspect of building high-performing teams
A handful of people-centered principles that will consistently help you build high-performing teams and raise the bar on performance irrespective of geography, borders, and cultures.
Why AI hasn’t replaced software engineers, and won’t
Coding agents as normal technology
Reorgs happen | Ben Balter
In thirteen years at GitHub I was part of 25 reorgs—almost one every six months. Reorgs are a constant in tech, not a crisis. Here’s how to navigate them.
Your company needs agency, not agents.
So maybe try actually trusting your employees a bit?
Doing nothing at work

Technology, Operations & Delivery

Runbooks are not checklists
They are how teams turn operational knowledge into repeatable judgment
The Typing Was the Safety Harness — Leadership Garden
Typing code was doing load-bearing QA work nobody invoiced for. Agents removed the slowness, and now the work has to live somewhere on purpose.
Does clean code matter anymore?
We won’t ask whether it ever mattered…
How to Get Tech Debt Prioritized
Dev Leader Weekly 144

Stress, Wellbeing & Growth

How to Overcome Confirmation Bias
Stop Cognitive Bias from Ruining Your Decisions
High-Functioning Burnout at Work
You are still performing. Still showing up. Still getting it done. And you are running on empty in a way nobody around you can see.
Don’t Let Work Become the Whole Sky
Work is important, but it was never meant to become your whole life.

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!

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Have an amazing week!

Andy