🦬 Over-measurement, Decision-making, Good Conflict, Healthy Teams, Security, LLM Fine-tuning, Receiving Feedback, Awkwardness: TMW #405

Hello again, welcome to the week!

We're getting very close to the end of Super Early Bird tickets for CTO Craft Con: London, which means your chance to grab a ticket at the discounted rate is getting smaller - don't miss out! Community members will have early access to the conference agenda this week, so keep your eyes peeled.

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

How effective is your Performance Review process? There have been many conversations about reviews in the community over the years, as well as posts about approaches and ways to improve it. Let us know how you're doing:

That's it, on with the links!

Andy @ CTO Craft

The challenges of setting up a near-shore team (and 6 things that can go badly wrong) | CTO Craft

Damilah Founder Iain Bishop reveals 6 traps to avoid when setting up your near-shore team.

CTO CraftIain Bishop

CTO Craft Events

CTO Craft Bytes: Scaling Pains: Navigating the Ups and Downs of Growth

The secret to scaling up and down seamlessly: A three-pronged strategy

CTO Craft

Psssst - we have lots of local Mixer events coming up, including ones in Edinburgh, Paris, Boston, Goteborg, Manchester and Bristol in November.. Would you like to run one in your city? Drop us a line

Reads of the Week

Solving staffing challenges with concentric circles - The Engineering Manager

If you lead a large organization, how do you solve teams that are asking for more people? Start inside out, rather than top down.

The Engineering ManagerJames Stanier

The Measurement Trap

The Hidden Costs of Over Reliance on Metrics

Fish Food for ThoughtMike Fisher

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Leadership, Strategy & Business

What layoffs teach us about technical leadership

In March I published a piece called How do we evaluate people for their technical leadership? It demonstrates (I hope) why production line metrics shouldn’t be copied and pasted onto knowledg…

Chelsea TroyView all posts by Chelsea

8 leadership principles and how to embody them - Work Life by Atlassian

Eight leadership principles that will help you inspire trust, build stronger teams, and lead with confidence – no matter your leadership style.

Work Life by AtlassianKat Boogaard

Seek the Decision, Not the Endless Options

People tend to fantasize about what they will do after the decision instead of pushing for a yes-or-no answer because they dread one simple…

Management MattersTom Vogel

Do Hard Things Carefully

Leaning in without falling over.

Depths of RepairPatrick Maguire

Culture, People & Teams

Eng org seniority-mix model.

One of the trademarks of private equity ownership is the expectation that either the company maintains their current margin and grows revenue at 25-30%, or they instead grow slower and increase their free cash flow year over year. In many organizations, engineering costs have a major impact on their free cash flow. There are many costs to reduce, cloud hosting and such, but inevitably part of the discussion is addressing engineering headcount costs directly.

Irrational Exuberance

Stop avoiding conflict on your teams

Avoiding conflict is the death knell of organizations that leads to a lack of progress and careers that implode.

Doug Turnbull's BlogDoug Turnbull

Go, teams: When teams get healthier, the whole organization benefits

Creating effective teams depends on multiple factors, including high levels of trust and communication, and understanding team context. A new approach helps elevate performance and create value.

McKinsey & CompanyAaron De Smet

To build a meritocracy

About a year ago, we at Affirm decided to add an OKR to our annual planning titled “High-Performance Culture”, to help shore up the necessary means (for the necessary means) of improving our…

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Technology, Operations & Delivery

How to get started with Cybersecurity

As Engineering Leaders we’re often in charge for establishing a culture of cybersecurity from the ground up. We’ll explore some ways you can get started and how to think about the next steps.

Sudo Make Me a CTOSergio Visinoni

Testing the Untestable

The four phases of automated evals for LLM-powered features.

Allen Pike

A brief summary of language model finetuning - Stack Overflow

Stack OverflowCameron R. Wolfe, PhD

Why Zero Tech Debt is a Myth (and Maybe a Red Flag)

A project boasting zero technical debt? That’s a flag you should definitely raise

Level Up CodingJonatan Kruszewski

Stress, Wellbeing & Growth

Enough on Giving Feedback—The Real Success Comes from Learning to Receive It

You own your growth. Instead of hoping your manager will give you quality feedback, focus on improving as a receiver of feedback.

Management Excellence by Art PettyArt Petty

Solving employee loneliness is the first step to better teams

ALSO: live careers event tickets on sale now

Make Work BetterBruce Daisley

Do It Your Way

The ultimate success metric is whether you get what you want out of life.

Morgan HouselMorgan Housel

The joy of awkwardness

why we should embrace it instead of avoid people in the audience who said that awkwardness held them back. (Photo: Emily Webber) Here’s something I talked about for 10 minutes at Agile on the…

Cara Bermingham

That’s it!

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Have an amazing week!

Andy