Engineering Leadership

Engineering Leadership

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Engineering Leadership
Engineering Leadership
My learnings from teaching 200+ engineers and leads
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My learnings from teaching 200+ engineers and leads

Teaching has been one of the most fulfilling things that I am doing, here are my learnings!

Gregor Ojstersek's avatar
Gregor Ojstersek
Mar 12, 2025
โˆ™ Paid
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Engineering Leadership
Engineering Leadership
My learnings from teaching 200+ engineers and leads
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Intro

I have taught over 200 engineers and leads in the last 9 months.

And a cool thing? I learned a lot from doing this.

I've gotten to know all the different challenges and problems that all of my students are facing and we talked through them in our sessions!

Today, I am sharing my top learnings in this newsletter article.

This is an article for paid subscribers, and here is the full index:

- I have taught 8 engineers and leads by hosting a roundtable at the Plato Elevate Conference
- I have taught 50+ engineers and leads hosting a workshop on C3 Conference
- I have taught 150+ engineers and leads in the course Senior Engineer to Lead: Grow and thrive in the role
๐Ÿ”’ My personal 3 learnings from teaching 200+ engineers and leads
๐Ÿ”’ 1. If you can teach it, you understand it
๐Ÿ”’ 2. Sharing personal experience resonates with people
๐Ÿ”’ 3. Teaching is very rewarding
๐Ÿ”’ 3 main learnings from teaching 200+ engineers and leads
๐Ÿ”’ 1. Fear that becoming a manager would mean being less technical
๐Ÿ”’ 2. Students really enjoy the career path discussions and planning their next steps
๐Ÿ”’ 3. The networking effect of cohort-based learning is underrated
๐Ÿ”’ Last words

Resources mentioned in the article:

  • Senior Engineer to Lead: Who to promote and how to train them (paid article)

  • My secret for growing from engineer to CTO (paid article)

  • Become a great engineering leader in 2025 (paid article)

Letโ€™s get straight into it!

I have taught 8 engineers and leads by hosting a roundtable at the Plato Elevate Conference

This was in June 2024 in San Francisco, CA. The topic of the roundtable was: โ€œSenior Engineer to Lead: Who to promote and how to train themโ€.

We had a great mix of Senior Engineers and Managers from various companies like Meta, Bloomberg, Google, Lyft to name a few. Which made the discussion very fruitful and there were a LOT of insightful questions asked.

Also had the pleasure of meeting friends

Jordan Cutler
and
Hemant Pandey
there!

You can read the overview of the whole discussion we had on the roundtable here: Senior Engineer to Lead: Who to promote and how to train them (paid article).

I have taught 50+ engineers and leads hosting a workshop on C3 Conference

This was also in June 2024 and in Amsterdam, NL. It was a 2-hour workshop titled โ€œFrom Senior to Lead: Grow and thrive in the roleโ€. We covered:

  • Differences between engineering lead roles.

  • How to grow toward a lead role.

  • How to thrive in the role.

I remember how engaged everyone was in the workshop, there were a LOT of interesting questions being asked and everyone seemed eager to learn.

Also had the pleasure of meeting my friend Richard Donovan.

I have taught 150+ engineers and leads in the course Senior Engineer to Lead: Grow and thrive in the role

If you are a regular reader, you have probably seen the course being mentioned in previous articles, but for everyone who doesnโ€™t know โ†’ I teach a course that is helping (Senior) Software Engineers to become high-performers and grow to lead roles.

Also with the course, I help leads to thrive in lead roles or provide actionable steps that they can use to help their reports to become high-performers and grow to lead roles.

Itโ€™s a cohort-based course which means that sessions are live and recorded. I hosted 4 cohorts so far:

  • Cohort 1 โ†’ July 2024

  • Cohort 2 โ†’ September 2024

  • Cohort 3 โ†’ November 2024

  • Cohort 4 โ†’ January 2025

  • Cohort 5 โ†’ March 2025 (currently in progress, we had the first session yesterday)

  • Cohort 6 โ†’ will be in June 2025

We have 4 different sessions across 4 days. So, for 2 weeks every Tuesday and Thursday, we meet for 1.5 hours on a Zoom call and go through prepared topics.

After each session, there is also a special time of 30 minutes dedicated just to Q&A.

The sessions are highly interactive and I encourage everyone to ask questions or share their insights. I believe half of the time in every session we go through the questions and specific cases from the students.

For every cohort, we also have a special dedicated Slack workspace, where we all get to know each other better and I use it for faster feedback loops.

To ensure that the newly acquired knowledge can be applied immediately, we have 10 different optional exercises across the course.

My personal 3 learnings from teaching 200+ engineers and leads

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