🐉 Tech Debt, Supply Chain Risk, Permission to Hibernate, Leader Blindspots, Trust vs Competence, OWASP and Agentic AI: TMW #461

Hello, hello, hello! Welcome to the week

We haven't run our regular Community Bytes sessions in a couple of years, but it's something we've really missed here at CTO Craft. So, they're coming back!

The first Community Bytes session of 2026 will happen on Jan 14th, and the topic for the panel will be the Journey from CTO to Founder. On the panel will be three members who have made the leap from leading the technology function of their organisations to building a new organisation from the ground up and what they learned and un-learned along the way. If you're considering building your own thing, you won't want to miss it.

CTO Craft Bytes: The CTO to Founder Path | CTO Craft

Every founder’s story begins with a simple question — what if I built something of my own? For many CTOs, the leap from leading technology to leading a company feels both thrilling and uncertain. This session invites you to explore that turning point: when years of technical leadership, product intuition, and team-building experience merge into the drive to create something from scratch.

CTO Craft

We'll be releasing details of the next few fortnightly Bytes over the next couple of weeks, so keep your eyes peeled.

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

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Reads of the Week

Tech Debt Is a Signal, Not a Sin

What tech debt actually tells you about your team and your system

It Depends: Lessons in Technology LeadershipKevin Goldsmith

When Rules Override Results: Breaking Free from Bureaucracy - Organizational Physics

Summary Insight: Bureaucracy happens when rules override results. Break the pattern by changing structure first—behavior follows. Key Takeaways: Structure naturally calcifies over time, turning execution into motion without progress. You can’t change behavior without changing structure—the system always wins. Move authority to information, not information to authority. I read this description of bureaucracy last week […]

Organizational PhysicsLex Sisney

Leadership, Strategy & Business

The Management Pendulum: Are We Unknowingly Back to 1910 Taylorism? - Yaniv Preiss

But lately, I’ve been asking myself whether we’re actually sliding back to Taylorism, in a swing back of the management pendulum.

Yaniv PreissYaniv Preiss

The 10 Biggest Leadership Blindspots Based on 10 Years of Research

How to identify these blindspots for yourself, and most importantly, how to avoid them

The HeartbeatClaire Lew

Useful engineering management artifacts

When managing a growing organization, it can be useful to have certain document templates on hand. Here’s a collection of documents I find useful.

BjorgBjorn Roche

Why Leaders Don’t Seek Feedback - Leadership Freak

You don’t seek feedback because you care. It feels personal. Besides, you already beat yourself down.

Leadership FreakDan Rockwell

Culture, People & Teams

The Slipstream Model of Competence

Why a High-Trust Environment Is More Important Than Working With Smart People

Maarten’s NewsletterMaarten Dalmijn

How Organisational Dynamics Break Collaboration

The unseen forces that shape prioritisation, estimation, and cross-team collaboration

Szymon's SubstackSzymon Baranowski

The High Performing Teams (HPT) Framework

A proven framework that enables you to grow high performing teams. We’ve developed a framework to help teams unlock their full potential by balancing purpose, trust, safety, ownership, growth, and …

Evolving Leadership

RDEL #122: How do daily stand-ups boost team performance?

Stand-ups don’t directly improve satisfaction or performance—but they foster psychological safety, which drives both outcomes with high effect sizes.

Research-Driven Engineering LeadershipResearch-Driven Engineering Leadership

Technology, Operations & Delivery

OWASP Top 10 for Agentic Applications

As I’ve written about extensively 2025 has been dubbed the year of AI Agents, although many now suspect it is more accurate to say we’re entering the decade of Agentic AI.

Resilient CyberChris Hughes

Product engineering teams must own supply chain risk

Product teams must own software supply chain risk as third-party dependencies become the primary attack surface. Learn how provenance, attestations, and SLSA make trust explicit, enforceable, and verifiable.

Hyperact LogoJacob Clark

AI for the Enterprise: The Playbook for Developing and Scaling Your AI Strategy

It’s time to move beyond the hype. Get the playbook for building an intentional, secure, and people-first AI strategy that delivers measurable ROI and long-term success.

The New StackFrederic Lardinois

2 years with Shape-Up, and why we switched back

Lessons learned from applying shape-up for 2 years, and why it was no longer as good a fit for us.

Scale XAlex Wauters

Stress, Wellbeing & Growth

Ness Letters: Permission to Hibernate

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

Ness Labs

The hidden burnout devs face even when they love the work

A story about hitting the wall no one talks about the one that shows up even when you’re doing the…

DEV Community<devtips/>

Calendar rules I learned from an EA | Jade Rubick - Engineering Leadership

Calendar rules I learned from an executive assistant and colleagues

Jade RubickJade Rubick

Why the “boring” tasks you are automating were actually the only thing keeping your workforce sane.

Hello H.A.

LinkedInMartyn Redstone

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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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