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8 min read

🐝 Curious Proxies, Control-Lovers, Absorbing Complexity, Nice Cultures, Delegation, Human Judgment, AI ROI, XP in 2026: TMW #496

The best engineering leadership reads from the last week
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This week's TMW is sponsored by Re:cinq - a hands-on consultancy helping business become AI Native around the world

Hello, hello, hello, welcome to the week!

Goodbye to Hosted Git?

This week's most active thread in the CTO Craft community started with a GitHub-outage gripe and spiralled into an existential debate about whether hosted git is still necessary at all: after venting about downtime and comparing GitHub, GitLab, and Bitbucket, one member argued that with AI agents now writing and reviewing most PRs, hosted git has become "just a habit, not a necessity," sparking nostalgic (and slightly horrified) detours through Visual SourceSafe, Mercurial's file-locking days, and self-hosted Forgejo as a real alternative some are already running.

It's a great snapshot of a community rethinking its tooling assumptions in real time. The "we've always used GitHub" reflex is exactly the kind of load-bearing habit worth pressure-testing once AI changes who's actually doing the reviewing, though the "just email zipped code" jokes are a useful reminder that centralised history, CI, and security scanning didn't become optional just because the workflow got faster...

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

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CTO Craft Con: Europe 2026
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The AI Adoption Ladder: From First Licences to the Dark Factory

AI coding tools can make individual developers dramatically more productive, yet many engineering organisations see little improvement in overall software delivery. Why? The AI Adoption Ladder introduces a practical framework that explains where productivity gains stall, the bottlenecks that emerge at each stage of AI adoption, and how leading engineering teams overcome them.

Drawing on real-world enterprise engagements, industry research, and lessons from organisations adopting agentic development, this whitepaper outlines nine stages of AI maturity - from first licences to the software factory - and provides a practical roadmap for scaling AI adoption into measurable business outcomes.

Read the Whitepaper 👉

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Reads of the Week

TBM 437: Tokens, Hours, Points, and Other Curious Proxies
Everyone is talking about “return on tokens.” Vendors love it (as long as the news is good).
The Beautiful MessJohn Cutler

Leadership, Strategy & Business

Build vs Buy When Building Just Got Cheap
Ask Who Patches It in Year Three
It Depends: Lessons in Technology LeadershipKevin Goldsmith
“Just run it past me first”
A reader asks: how do you get a control-lover who has become a bottleneck for the whole team to let go? On the vicious circle of micro-supervision and how to break a loop that keeps proving itself.
Technically FeasibleLouise Deason
How to “Tell It Like It Is” more effectively
Why staying direct isn’t the problem, and being certain is.
Mark Grebler’s SubstackMark Grebler
Tesler’s Law of Communication
Why Leaders Must Absorb Complexity
Practical Engineering ManagementMirek Stanek

Culture, People & Teams

Is Your Organizational Culture Too Nice?
Organizations with a culture of “niceness” can undermine performance when leaders prioritize harmony and comfort over candor, accountability, and results. Shifting toward a more rigorous culture requires senior leaders to model and reward candid feedback, create measurable successes that demonstrate that tougher choices improve performance, and redesign operating processes like review meetings and governance routines so that they encourage substantive debate rather than polite approval.
Harvard Business ReviewRon Ashkenas and Gali Cooks
The Problem With Asking Employees to “Take Ownership”
And then punishing initiative
SeattleDataGuy’s NewsletterSeattleDataGuy
3 rules of delegation I learned the hard way
I thought I could just assign tasks and watch them happen
Diary of an Engineering ManagerSuresh Choudhary
Coaching Questions that Work - Leadership Freak
Some questions focus on situations. What happened? What’s wrong? What do you want? Begin with situations, but don’t park there. Coaching questions turn attention to the person. Problems are mirrors that help us see ourselves. Don’t rush to solutions. Make space for people to notice themselves. Click for more insight.
Leadership FreakDan Rockwell

Technology, Operations & Delivery

How juniors learn the trade when an agent writes the code
In my last post I described how we structure delivery so that human judgement is spent where it matters, and I left one problem open: that model assumes seasoned judgement at the gates, and I could not say how a junior grows it inside a system that shields them from the grind that used to build it. I still would not call it solved. AI-native is a young way of working, and, as far as I know, nobody has grown a whole cohort of engineers inside it yet. But I am confident in the approach, because most of it was already there in how juniors learnt the craft before any of this existed. This is where my thinking stands today.
Jean-François Moy
Human judgment doesn’t leave the software factory. It relocates.
A field guide to building a software factory that still has an owner.
ElevateAddy Osmani
RDEL #157: How should engineering leaders measure the ROI of AI?
98% of CIOs face rising board pressure to prove AI ROI. A methodology converts complexity-weighted throughput into dollars, then holds the result against speed, quality, and developer experience.
Research-Driven Engineering LeadershipResearch-Driven Engineering Leadership
Extreme Programming 1999->2026
A method created 30 years ago is still your best guide for building software
Manager.dev

Stress, Wellbeing & Growth

The Elephant in the Brownfield
In recent weeks, I met several talented, driven, experienced engineers and leaders working hard to bootstrap their ideas into startups. I call them brownfield refugees — people who left or were …
Writing is clarifying
AI, Burnout, and the Death of “Good Enough”
We were promised time. That was always the pitch: automate the tedious parts of work, and humans get to reclaim their hours for rest…
MediumHashaam
Emotional Diversification — Devin Martin Lifestyle Integrity
Why do success and anxiety seem to go hand in hand? What do these three, real people have in common (besides panic attacks): The CEO of a global brand walks into my office for a consultation and tells me he has suddenly started having panic attacks every time he has to speak in front of a group.
Devin Martin Lifestyle IntegrityDevin Martin
Emotional Inquiry • Ness Labs
The Ness Letters are a weekly newsletter by Ness Labs, exploring how we can think better, work smarter, and live happier.
Ness Labs

That’s it!

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Have an amazing week!

Andy

Published by:

Andy Skipper