7 min read

🧀 OKRs for AI, Managing Sideways, Manager Scorecards, Agentic Team Topologies, Flattening, Trusting AI, Networking: TMW #488

CTO Craft Con: Europe - join us in Amsterdam this September!
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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!

If your calendar only has room for one in-person event this autumn, make it CTO Craft Con: Europe in Amsterdam, 29 - 30 September. Built specifically for CTOs, VPs of Engineering and Heads of Technology, this is where senior tech leaders come to think out loud with peers who genuinely get the role, not to sit through vendor pitches or passive keynotes.

Confirmed speakers include Randy Shoup (SVP Engineering, CircleCI), Raffi Krikorian (CTO, Mozilla) and Sarah Abrantes (VP Engineering, Adyen). Two days of your time is a real investment, and this event is designed to earn it:

  • Structured roundtables where you compare real decisions with peers at similar-stage companies
  • Themed Coffee Corner sessions on scaling teams, hiring headaches, leadership transitions and more
  • Candid, off-the-record conversations that no Slack thread or LinkedIn post can replicate
  • 16+ hours of content across AI adoption, org design and platform strategy, with recordings after the event

Prices will rise as September gets closer, so lock in your advance rate ticket now at conference.ctocraft.com/europe-2026. See you in Amsterdam!

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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AI-enabled engineering organizations need different KPIs 

Lines of code used to measure output. Now they measure how much code you'll have to maintain. When developers generate code in minutes, activity stops meaning anything, and AI amplifies activity faster than any org can validate impact. Dave lays out the five KPIs that actually matter now, including the quality tax: high output with growing instability isn't efficiency, it's deferred cost.

Read more about KPIs

CTO Craft Events Coming Up

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

Reads of the Week

Make AI Boring Again
On the ethics of engagement, the problem with purity politics, and a world worth fighting for
% How to write OKRs for an AI product
If your AI product delivers different outputs to each user and prompt, here is how you measure the success of that product with OKRs.

Leadership, Strategy & Business

Managing Sideways
Everyone Nodded, Then Nothing Happened
Paging Charity! How can engineering leaders avoid becoming Bond villains? - Stack Overflow
Thrive as a manager: build your own scoreboard
What I learned going from senior engineer to Head of Technology
What being “inspiring” actually means
You are not Viggo Mortensen rallying men to fight Sauron. You are a knowledge worker in tech. Here’s what it means to inspire in this context.

Culture, People & Teams

Key activities for sustainable engineering team
The signal loops that tell managers when to change altitude
Who Does What? Team Topologies for the Agentic Platform
The agentic platform defines what needs to be provided. Team Topologies defines who provides it, and how teams interact to make it happen. This second article applies Skelton and Pais’s model to a world where agents produce and humans orchestrate.
RDEL #149: Where is the flattening of engineering organizations actually happening?
Reorgs hit 67% of organizations while layoffs stayed flat, but management cuts at the top nearly doubled in two years, from 13% to 23%.
Holacracy disadvantages: honest criticism and challenges of frameworks
Holacracy disadvantages explored: a masterclass story, Marc-Peter Pijper’s expert view, and why the framework is dead without the mindset.

Technology, Operations & Delivery

How to safely build trust in AI generated code
You’re rolling out AI-assisted engineering wrong, and it’s going to slow you down! Learn to build trust safely and quickly.
Lost confidence
RICE and other confidence-based frameworks are mostly noise. Here’s how to make decisions without pretending to know the unknowable.
Why Problem Statements Aren’t Enough
A Staff+ engineering story about using technical, organizational, and business context to turn strong technical work into organizational value.
TBM 427: The Bottleneck Strike Again!
My goodness.

Stress, Wellbeing & Growth

The Network You Can’t See
Why the smartest leaders cultivate the connections they don’t manage
Not a Thicker Skin
What I’m learning about not letting things get to me, and teaching my kids the same.
What No One Tells You About Healing From Burnout
I thought rest would fix it.

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

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