🥝 Shadow Structures, OKRs as GPS, Culture and Uncertainty, Data Models, Delivery vs Architecture First, Charlie Munger's Inversion: TMW #458

Hello, hello, hello! Welcome to the week

What a great couple of days we had at the leafy and lovely Barbican Conservatory in London, with over 150 CTOs and senior technology leaders from the best fintech and financial services organisations from right across Europe. CTO Craft Con: the Finance Edition was our first industry-specific event for technology leaders, and it's safe to say we'll be doing it again in 2026. Keep your eyes peeled for announcements in the coming months.

All the talks from the Con will be available to attendees and also to Campus members in the next couple of weeks, so check in if you'd like to see what our experts had to say about Generative Finance, open source in fintech, security and compliance, green IT, architectures for fintech products and a whole lot more.

Coming next is our flagship CTO Craft Con: London, where we'll be back at the QEII Centre in London in March 2026. Tickets are already on sale, so secure a spot for you and your team. See you there!

That's it, on with the links! See you next Monday

Andy @ CTO Craft

CTO Craft Con - Dates for Your Diary

CTO Craft Con: London

Join CTO Craft Con: 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 Con: London 2026

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 | CTO Craft

CTO Craft Con: Europe 2026 Be the first to know CTO Craft Con: Europe arrives in Amsterdam, 29-30 September, 2026. Two days of real conversations, practical sessions, and peer connections designed for technology leaders across the continent. Register your interest today to get early updates, first access to tickets, and the latest speaker announcements. Register Your interest

CTO Craft

SPONSORED

Solving the Engineering Productivity Paradox

While some companies see AI generating over 30% of code, engineering velocity is up only 10%. This paradox reveals that AI-generated code is exposing other bottlenecks in the development process. To capture the real productivity gains of AI, these bottlenecks in review and deployment must be addressed. 

Find Out Why and Learn How to Fix It

Reads of the Week

Critical Thinking during the age of AI

Who, what, where, when, why, how

ElevateAddy Osmani

Leadership, Strategy & Business

Shadow Structures: The Unofficial Systems That Actually Run Your Organization | Lost Consultants

Every team wants freedom — until chaos hits. Every leader wants control — until bureaucracy kills speed. Here’s how to find the sweet spot where governance and flow work together, not against each other.

lostconsultants.comMaik Seyfert

KPIs Are Your Dashboard. OKRs Are Your GPS to Somewhere New.

I got asked again last week: “What’s the difference between KPIs and OKRs?”The person asking was a PM at a mid-sized company. Smart guy. Been in product for five years. His company had just rolled out OKRs and he was staring at a template, genuinely confused about what to write

Christina WodtkeChristina

Leading Through Inspiration

Why Wisdom Alone Isn’t Enough

Living CodeLiving Code

Alignment Without Accountability Is Theater

The third and final story in the AAA Triangle series — where clarity meets consequence. “Alignment gives purpose.

LinkedInJim Highsmith

Culture, People & Teams

5 Hacks to Build a World-Class Engineering Team

Why Mentoring > Micromanaging

Growth AlgorithmDaniil Shykhov

Uncertainty Tests Culture... How Do You Lead in Times of Uncertainty?

I always find it really interesting to observe and hear stories about how behaviour changes when there is a shift economically across the industry causing a little bit more fear in terms of job safety. Stories about protectionism, about a lack of collaboration, not sharing information or over-sharin

LinkedInDan Ashby

How to Assess Mindset and Attitude During the Interview

How to uncover how someone really thinks — before you hire them.

Sergey BolshchikovSergey Bolshchikov

A Human-Centred Feedback Model: How to Give Feedback That Grows People

With performance review season coming into play, feedback is suddenly a hot topic. Everyone’s talking about it, but not all feedback is created equal.

LinkedInDan Ashby

SPONSORED

Mind the Gap: Bridging from Sandbox to Scale

For senior tech leaders, the challenge isn’t proving AI’s potential; it’s scaling it responsibly. Mind the Gap: Bridging from Sandbox to Scale reveals the hidden organisational and governance barriers that keep promising projects stuck in pilot mode. Explore data-backed insights and proven strategies to help your teams turn experimentation into real, production-ready impact.

Learn how to take AI experiments into Production - Free Report

Technology, Operations & Delivery

Both Architecture-First and Delivery-First Suck

Complex Is More Dangerous Than Simple: YAGNI And Gall’s Law

Maarten’s NewsletterMaarten Dalmijn

RDEL #119: What process inefficiencies have the biggest impact on developer satisfaction?

A study of agile-based software engineers finds process inefficiencies account for 33.8% of job satisfaction variance

Research-Driven Engineering LeadershipResearch-Driven Engineering Leadership

Shadow work in engineering teams

And the price your team pays for it

Manager.devAnton Zaides

Your data model is your destiny

Your product’s core abstractions determine whether new features compound into a moat or just add to a feature list. Here’s how to get it right.

Matt Brown's NotesMatt Brown

How revenue decisions shape technical debt

A critical exploration of how short-term revenue decisions create and compound technical debt.

Hyperact LogoJacob Clark

Stress, Wellbeing & Growth

Invert, always invert - The Engineering Manager

By pulling on the sage advice of Charlie Munger, we can use pessimism to its full advantage, giving us safer planning, estimation and rollout.

The Engineering ManagerJames Stanier

Ness Letters: Loving to Learn

The Ness Letters are a weekly newsletter by Ness Labs, exploring how we can think better, work smarter, and live happier.

Ness Labs

Lead like you mean it: critical lessons in strength and staying human

From personal crises to the boardroom, discover how to build resilience in leadership, show up as your authentic self and leverage kindness and discipline for sustained influence.

Management-Issues.comNewmark Security plc

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!

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