Engineering Leadership

Engineering Leadership

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Engineering Leadership
Engineering Leadership
First time in a leading position? This is what to do
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First time in a leading position? This is what to do

You are a lot better leader than you may think, this is why!

Gregor Ojstersek's avatar
Gregor Ojstersek
Jun 11, 2025
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Engineering Leadership
Engineering Leadership
First time in a leading position? This is what to do
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Intro

You have been a Software Engineer for a while now and you are really good at coding and solving problems.

But now, you get assigned to lead a project and you freeze. You think that leading a project is not for you.

The first instinct you may have is to decline the opportunity. But, is that really the best thing to do? It may certainly be the most comfortable thing to do 🤷‍♂️

Well, let me tell you that if you decline it → you rob yourself of an opportunity to learn and increase your set of skills → very important set of skills that will help you immensely throughout your whole career.

If you believe that being a leader is not for you, this is a must-read article for you.

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

- “Leadership is not for me”
- Some of the best leaders that I worked with were introverts
- You are a lot better leader than you may think
- You just need to start trusting yourself
- To help you with this, here are my top tips that will help you to be successful as a first-time leader
🔒 Notion Template: List of questions to ask before making a technical decision
🔒 How to become a leader everyone wants to work with
🔒 Last words

If you already know that you want to progress as a leader and break into the engineering leadership roles, you can find a full roadmap here:

Full Roadmap to Break Into Engineering Leadership in 2025

Full Roadmap to Break Into Engineering Leadership in 2025

Gregor Ojstersek
·
Apr 23
Read full story

Let’s first start with breaking some of the false beliefs.

“Leadership is not for me”

I’ve heard this a lot of times before especially from fellow engineers and I know many other people think the same way (especially introverts) that being a leader "is not for them".

I’ve had such thoughts early in my career as well. But then the more I grew and the more projects I finished → I understood that a lot of what I am already doing is being a leader.

It’s important to understand that everyone can be a leader. No matter whether you are extroverted or introverted.

Here are 3 facts:

  • Everyone leads in a different way. There is no “one way of leading”.

  • The stigma that you need to be a “born leader” to be a great leader is simply not true.

  • Leadership needs to be learned. You are not born with these skills.

Leadership is not about the title or position, it's a mindset. We all can be leaders and lead in our own way.

Let’s get a bit more into being an introverted leader.

Some of the best leaders that I worked with were introverts

I had the pleasure of working with some really great people in our industry and they were introverts. So it’s definitely not true that you need to be an extrovert in order to be a leader.

They weren’t the loudest or the most talkative, but they:

  • were really great technically,

  • enjoyed being in fine details,

  • enjoyed helping and supporting others with coaching and mentoring.

They were leaders, just in their own way and it’s totally fine to be like that. They brought SO much value to the organization by being like that.

They were making great technical decisions and being great engineers/managers to work with → with the right attitude and mindset. They were a great example for others and also inspired others to be like them.

They were not just doing great work, but they also greatly contributed to making others around them better.

People who are like that contribute enormous value to the organization.

You are a lot better leader than you may think

When I started my career as an engineer, I quickly started doing freelance work. And one of my first “real” clients (outside of my friends or family) asked to have a meeting in person.

A meeting to let them know my thoughts on how they can improve their website.

Well, the most comfortable thing to do here would be to decline it, but I knew that I’d have more such meeting requests in the future and that I need to do them if I wish to keep doing freelance projects.

So, I agreed to do it.

I was shaking before the meeting started and it felt uncomfortable, but I was well prepared to let them know what changes should they make to the website and that I’d be more than happy to do them.

What happened next? I kind of took the lead in the meeting and started sharing all the improvements that could be made. The whole meeting went a lot better than I thought!

The client liked the proposed adjustments and we agreed that I would do them. If I declined the meeting, I wouldn’t get the project and I would miss out on the important learning. The learning that I am better than I thought I was.

A lot is in our heads and we come up with worse-case scenarios when in reality we are a lot more capable than we thought.

You just need to start trusting yourself

That small win gave me confidence in myself and I’ve thought to myself: If I can overcome this, what else can I do?

This small win led to many other wins, like:

  • taking on more complex projects,

  • leading meetings with many people attending them,

  • becoming a Senior Software Engineer and leading important projects in my full-time roles,

  • agreeing to be a team lead, even though I had zero management experience,

  • all the way to becoming a CTO and now writing to more than 140k engineering leaders and teaching more than 200 students on my course Senior Engineer to Lead: Grow and thrive in the role.

Of course, I also made a LOT of mistakes along the way, but I didn’t let them stop me to keep getting better and better.

So, this is my exact message to everyone thinking that leading is not for them: Try it out, do your absolute best as you can and then you’ll see if it’s really not for you.

The worst-case scenario? You’ve learned something new and you’ve expanded your horizon. If you look at it that way, you turn any of the negative thoughts into positive ones.

To help you with this, make sure to read on, as I’ll be sharing many of the tips for you to make it a lot easier to say yes to opportunities, instead of hiding from them.

To help you with this, here are my top tips that will help you to be successful as a first-time leader

As I mentioned above, saying yes to the opportunity is the first step, now let’s get into how you can actually thrive as a leader.

The mindset shift is very important. You become a multiplier for the team and helping others around you becomes one of the main priorities.

You are not judged by your individual contribution anymore. The overall success of the team and the projects is what becomes important.

Let’s say that you have been assigned a project to lead as a Tech Lead and there are going to be 4 other engineers as part of the team building it.

The first thing you need to do is to ask all the right questions, especially important are the business/product-related questions.

Notion Template: List of questions to ask before making a technical decision

Use this list of 35+ product/business-oriented and technical questions to really understand WHY something is needed.

Paid subscribers, you can get the list of questions here: 🎁 Products for paid subscribers

After you understand the needs more in detail, you continue by creating a technical specification.

That is already the time to get everyone involved and start gathering ideas, brainstorming and making it a team effort. You can find a great example of how

Anna J McDougall
involved everyone and made it a team effort here.

Now, we get to the hard part, how to actually be a leader? Let’s get into that next.

How to become a leader everyone wants to work with

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