Archive - Engineering Leadership

Lessons From Coaching 300+ Engineers and Engineering Leaders

What coaching hundreds of engineers and engineering leaders taught me about why people get stuck, and how they move forward.

21 mins ago • Gregor Ojstersek

How Technical Should an Engineering Manager Be?

Is being a highly technical engineering manager the best way to go these days? I am answering this question in this article.

Jul 13 • Gregor Ojstersek

How OpenAI Builds Infrastructure Teams

Insights from my conversation with Venkat Venkataramani, VP of Applied Infrastructure, OpenAI, and Emma Tang, who is leading Data Infrastructure at…

Jul 10 • Gregor Ojstersek

A Lot of Software Engineering Is Becoming Engineering Leadership

The important shift in software engineering work from 2 years ago to today.

Jul 6 • Gregor Ojstersek

How Anthropic Builds AI-Native Engineering Teams

Insights from my conversation with Katelyn Lesse, Head of Platform Engineering, Anthropic.

Jul 1 • Gregor Ojstersek

June 2026

5 Learnings Building Canva for AI Agents

Full recording and insights from the talk from Anwar Haneef, GM & Head of Ecosystem, Canva, at the Engineering Leadership LIVE event in San Francisco.

Jun 29 • Gregor Ojstersek

Building Trust and Credibility is the New Moat for Engineering Leaders

It's more important than ever to be considered trustworthy, especially to the leadership team and stakeholders. This is how to do it!

Jun 25 • Gregor Ojstersek

AI Transformation Journey: 3 Myths and Learnings

Full recording and insights from the talk from Vinay Perneti, VP of Engineering, Augment Code, at the Engineering Leadership LIVE event in San…

Jun 22 • Gregor Ojstersek

How to Do Performance Reviews

Full guide on how to set up successful performance reviews based on my personal experience and what has worked best for me and my teams.

Jun 18 • Gregor Ojstersek

What the Top 1% of Engineering Teams Do Differently with AI

Full recording and insights from the talk at the Engineering Leadership LIVE event in San Francisco.

Jun 15 • Gregor Ojstersek

Should You Go From Engineering Manager Back to Being an IC?

Engineering managers are more desired than ever to become ICs. Should you make the jump?

Jun 10 • Gregor Ojstersek

How to Grow From Senior to Staff Engineer in the AI Era

Case study from The Multiplier Mindset: How to Move from Senior Engineer to Tech Leader in the AI Era

Jun 7 • Gregor Ojstersek and Jordan Cutler

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