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🍦 Brownfield Agentic, Hierarchy, Human Routers, Group Performance, Silo Tax, Budgeting for Nothing, Refinement: TMW #500

Happy 500th TMW!
🐋
This week's TMW is sponsored by Skiller Whale - built by tech leaders, for tech teams, to mimic the feeling of learning engineering topics from experience.

Hello, hello, hello, welcome to the week!

Well, we made it - this is the 500th issue of Tech Manager Weekly. A huge thanks to all the amazing writers who've created a never-ending supply of brain food, frameworks and thought experiments for us all, and thank you to you, our dear readers, for the constant positive feedback and support.

Happy 500th from the CTO Craft team!

That's it, let's look at some links! See you next week

Andy @ CTO Craft

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Reads of the Week

The broken windows theory of coding agents
When my most experienced engineer got tired of our shitty code
Manager.devAnton Zaides
Brownfield Agentic Engineering
What it takes to run agents in a codebase older than the team
ElevateAddy Osmani

Leadership, Strategy & Business

Hierarchy Exists
Veteran CTO who built successful companies through empathic leadership and mastery of software delivery - from sustainable code to stakeholder trust. Now exploring the future of empathic and sustainable tech.
Nobody needs a human router
We should do more than push information around.
The Engineering ManagerJames Stanier
Leading Without a Clean Cause
The market is either lying or right. Either way your job is the same.
The Socratic LeadershipPetros Bountis
Maximizing Return-on-Feedback — Aviv Ben-Yosef
When I asked, the VPE said it’s been a while since he got feedback. When I asked how he handled the last few times it happened, I understood why. When you…
Aviv Ben-YosefAviv Ben-Yosef · 5 min read

Culture, People & Teams

Same People
What changes when you stop treating performance as an individual problem
Fish Food for ThoughtMike Fisher
The Silo Tax: What absorbs your AI return before it reaches the organisation - Zen Ex Machina
Most organisations have deployed AI but few capture returns. The Silo Tax — coordination overhead at functional boundaries — explains why.
Zen Ex MachinaMatthew Hodgson
When an Engineering Team’s Execution Becomes Unhealthy
Getting a team’s execution back on track when execution becomes unhealthy
Effective Engineering LeadersJames Samuel
How to Give Feedback to Someone You Don’t Manage?
Learn how to give feedback to someone you don’t manage by focusing on shared work, specific observations and a credible reason for speaking up.
Andi Roberts - Executive Coach | Leadership Trainer | FacilitatorAndi Roberts

Technology, Operations & Delivery

Paying for Nothing to Happen
Budgeting for Security, Compliance, and Reliability
It Depends: Lessons in Technology LeadershipKevin Goldsmith
Mastering the Four Abstraction Levels of Refinement
Refinement Sucks: Here’s How To Fix It
Maarten’s NewsletterMaarten Dalmijn
The Cost of Near
Recently, I spoke to a principal engineer who reviewed a team’s solution that took just a few days to build but where something didn’t seem quite right.
Jamie Smith WebbJamie Smith Webb
Agents of Change
Last week, one of our teams noticed broadband conversion had softened. That’s a relatively normal thing: conversion moves every day for all…
RVU TechPaul Ingles

Stress, Wellbeing & Growth

Research: Work Stress Isn’t Always About Workload
When employees seem stressed, leaders typically blame workload and respond with the usual remedies: task redistribution, time off, time management training. But a meta-analysis of 515 studies reveals a costly blind spot. Work overload is only one stressor—and not necessarily the most damaging one. The research identifies three distinct culprits, each with different consequences: role ambiguity (unclear expectations) most erodes job satisfaction and performance; role conflict (incompatible demands) drives burnout and turnover; and role overload (overwork) produces emotional and physical symptoms. Leaders who address stress without diagnosing which stressor dominates at their organization waste resources and miss the real problem. Lasting solutions require targeted interventions: clarifying expectations, resolving conflicting priorities at the leadership level, and making deliberate choices about what work actually gets done.
Harvard Business ReviewGargi Sawhney and Mallory McCord
Why I Still Believe in Mentorship | Matthias Endler
One of the best tips I ever got was from my tab…
Matthias EndlerMatthias Endler
TBM 440: The Problem With Putting People in Boxes
Personality and “strength” tests at work have never sat right with me.
The Beautiful MessJohn Cutler
A different way of overcoming conflict in culturally diverse teams
When a team is stuck in a cycle of tension and misunderstanding, jumping straight into conflict resolution often backfires. By shifting the focus from conflict to high-context vs low-context …
Cara Bermingham

That’s it!

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Have an amazing week!

Andy

Published by:

Andy Skipper