🐡 Bad Metrics, The Duck-Rabbit, Wardley Mapping, Sync-Ups, Version Control, AI Coding Tools, Luck Surface Area: TMW #413

Hello there, welcome to 2025!

As we step into the new year here at CTO Craft, the free Slack community sits at just a few under 7,000 members - 8 years down the line, it's become one of the most powerful communities of engineering leaders in the world. Every day, members call out for support with managerial, technical, personal and strategic challenges and situations, and get help from the collective experience of thousands. If you're leading a team of engineers, there's no reason not to join - come and take part!

Don't forget, as a TMW subscriber you have access to the Member Pricing for upcoming CTO Craft Con events.  You can unlock membership pricing by using the following access codes in the checkout when purchasing tickets:

CTO Craft Con: London 2025 - Community-Spring-25
CTO Craft Con: Toronto 2025 - Community-Toronto-25

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

Andy @ CTO Craft

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CTO Craft Events

CTO Craft Con: London 2025

CTO Craft Con will bring together over 500 Chief Technology Officers and other senior technology leaders from the most exciting start-ups, scale-ups, unicorns, and big tech companies to elevate their engineering culture in London, March 2025.

CTO Craft Con London 2025

CTO Craft Con: Toronto 2025

CTO Craft Con will bring together over 200 Chief Technology Officers and other senior technology leaders from the most exciting start-ups, scale-ups, unicorns, and big tech companies to elevate their engineering culture in Toronto, 2025.

CTO Craft Con: Toronto 2025

Reads of the Week

Unintended Consequences

The perils of poorly designed metrics and incentives

Fish Food for ThoughtMike Fisher

Twenty Tiny Leadership Lessons

Most leadership learning is experiential. We observe, learn, and emulate from others, often subconsciously. Yet, the core of such learning starts shallow, leading to behavioral and decision-making mistakes, learned and uncorrected bad behaviors, and dysfunction. Some get better with experience and scope, but more often than not, we wing it, frequently repeating the same behaviors and mistakes for years. Recognizing this challenge, two years ago, I enrolled in a Master’s program in the Psychology of Leadership at Penn State University. It turned out to be an excellent investment of time and money. In this article, I share the top twenty things I learned from those studies.

because writing is clarifying

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Leadership, Strategy & Business

The Duck-Rabbit & the Polarities of Leadership

We experience polarities in leadership all the time, often without even realising. How can you navigate competing tensions harmoniously?

Richard Hughes-JonesRichard Hughes-Jones

6 reasons why the senior leadership doesn’t take you seriously

Simple changes that will unblock your career

Leading DevelopersAnton Zaides

TBM 331: Strategy & Decisiveness

However, my basic observation is that while strategy involves making decisions, not all strategic decisions look decisive. A strategy might involve being indecisive about many things!

The Beautiful MessJohn Cutler

Refining strategy with Wardley Mapping.

The first time I heard about Wardley Mapping was from Charity Majors discussing it on Twitter. Of the three core strategy refinement techniques, this is the technique that I’ve personally used the least. Despite that, I decided to include it in this book because it highlights how many different techniques can be used for refining strategy, and also because it’s particularly effective at looking at the broadest ecosystems your organization exists in.

Irrational Exuberance

Culture, People & Teams

Engineering Growth — From Charmander to Charizard

Over the past 15 years, I’ve been privileged to lead engineering teams at startups and established companies. During this time, I’ve…

Level Up CodingDennis Nerush

Mastering the Art of Effective Sync-Ups

A Guide to Productive Meetings

Management MattersKrzysztof Jamroz

Managers Believe Downsizing Is Effective. Research Says: Nope. - Blog

According to research, downsizing is not the silver bullet for saving a company. It’s more like shooting yourself in the foot. Let’s explore.

Corporate Rebels

How To Fix Broken Teams

Most teams break in very similar ways. And, even more luckily, most teams can be fixed in similar ways. So, let’s talk about diagnosing and fixing the most broken of teams.

Stay SaaSy

Technology, Operations & Delivery

Version Control in Agile: Best Practices for Teams

Some version control practices for Agile teams to improve collaboration, streamline workflows, and prevent conflicts, ensuring efficient software delivery.

DZoneDeepika Gupta

How developers (really) used AI coding tools in 2024 - Stack Overflow

Stack OverflowEira May

Building effective agents

A post for developers with advice and workflows for building effective AI agents

The Canva outage: another tale of saturation and resilience

Today’s public incident writeup comes courtesy of Brendan Humphries, the CTO of Canva. Like so many other incidents that came before, this is another tale of saturation, where the failure mod…

Surfing ComplexityLorin Hochstein

Stress, Wellbeing & Growth

How to Increase Your Luck Surface Area (Ultimate Guide)

While there are many things in life that we don’t have much control over—including luck—there are strategies we can use to increase our potential for good luck and good opportunities. Practical…

Sam MatlaSam Matla

Feeling Stuck? Revisit Drucker’s “Managing Oneself” and ask and answer these questions

Peter Drucker’s classic article, “Managing Oneself” is something I read annually. The gold in this article is in his five powerful questions we all need to ask and answer to create alignment between ourselves and our work and lives. I share these and offer six additional questions worth considering.

Management Excellence by Art PettyArt Petty

Ratchet effects determine engineer reputation at large companies

Why you can’t skip to the top (but you can skip to the bottom)

sean goedecke

It’s Perfect Time for a Self-Audit

The office was quiet, the kind of silence that settles only after everyone else had left.

Management MattersThat Crazy Moment

That’s it!

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Have an amazing week!

Andy