The best leadership articles of 2025

Happy New Year! 🥳

I hope you enjoyed a nice break. Based on the feedback I'm going to experiment with publishing the newsletter twice a week. Mondays and Thursdays. It'll be heaps of work but there's a lot of amazing content out there too that doesn't often make it into one issue. We'll see how it goes and maybe there'll be slightly different themes on each day.

And now, we'll kick this year off with 5 most popular articles from 2025.

Most outages don’t fail where you expect
sponsored by Upsun

Cloud outages rarely take systems down in obvious ways. They fail through hidden dependencies, brittle assumptions, and operational shortcuts that made sense… until they didn’t. This article looks at what really happens when the cloud goes dark — and what every engineering leader should have ready before the next outage.

1. Common problems managing senior engineers
6 minutes by Suresh Choudhary

The four hardest senior engineer archetypes to manage and how to coach them. Senior engineers are an asset. But they do need your help to overcome some of their blind spots to grow. They don’t need micromanaging, they need coaching. Remember that most of these gaps comes from their strengths.

2. Why engineers hate their managers
6 minutes by Matheus Lima

Here’s the uncomfortable truth: engineers often have good reasons to be frustrated with their managers. But understanding why this happens is the first step toward fixing (or just coping with?) it.

3. Agentic AI has changed my career
12 minutes by Elliot Graebert

Elliot went from never coding to becoming one of their top contributors using AI tools as a manager. He started with AI-assisted coding for simple bug fixes, then scaled up by running multiple AI agents simultaneously on different problems. By automating workflows with agentic AI tools that can work independently, he now submits up to 10 pull requests per hour while handling bigger tasks like complete code migrations.

4. Traits of a good tech lead
9 minutes by João Alves

Engineering managers handle people, projects, and processes. Tech leads focus on technical direction through architecture decisions, code quality, and mentoring developers. Good tech leads multiply team effectiveness by creating clear principles and reducing dependence on themselves. They use written documents for technical debates, negotiate scope carefully, and help teams make autonomous decisions.

5. The best product engineering org in the world
30 minutes by James Shore

“How are you measuring productivity?” It was September 2023, my CEO was asking me a question, my position was less than three months old, and I didn’t have an answer. So I told the truth.