Interview with Gregor Ojstersek

For those who may not be familiar with you, could you give a brief introduction about yourself and your professional journey so far?

My name is Gregor and I have over 10 years of experience both as an engineer and engineering leader.

In my career, I grew from Engineer to Senior Engineer and later to Lead roles (Team Lead to Engineering Manager to Head of Engineering to VP of Engineering and to CTO)

So currently, I am the CTO at Zorion. We are a fintech startup offering exclusive investments in pre-IPO companies.

I also write a weekly newsletter called Engineering Leadership and I teach a cohort-based course called Senior Engineer to Lead: Grow and thrive in the role.

You've held various engineering and leadership roles throughout your career. What motivated you to transition into leadership positions?

When I grew to the Senior Software Engineer position, I got kind of stuck in not knowing what would be the next step for me.

I was always good at communicating and collaborating + making sure that we were building the right things. And my track record of successfully finishing different projects got me the offer to try myself as a Team Lead.

In my first few months, I made a lot of mistakes, but after a while, I got a hang of it and especially when I grew to become an Engineering Manager, I knew that this was the right path for me.

Let's talk about your current role as a CTO. What are your key responsibilities, and how does your day-to-day look like?

We at Zorion are building a mobile application and we are a company of around 15 people. If I would pick my top 3 responsibilities, that would be:

• Making sure that the tech is aligned with the business.
• Making sure that we have a great process in place that we consistently deliver new increments.
• Making sure that we are building a stable, usable app that our users love to use.

My daily responsibilities are heavily aligned with making sure we are achieving these things.

I consider myself a good generalist that can if needed go into details of a certain part. Being a generalist, I am automatically looking to have experts on my team.

So what I currently do: I am doing a mix of being a manager and an engineer. I am aligning everything that we are doing with the business, simplifying and aligning goals for us and managing expectations, facilitating and leading the meetings, have 1:1 meetings with my team.

At the same time, I am working on different projects, like building the administration application that our operational team uses, improving the SEO of the website, doing technical specifications, doing performance optimizations, code reviews, building proof of concepts, etc.

You've managed fully remote teams across different time zones. What strategies have you found effective for ensuring smooth collaboration and communication within your teams?

This is a great question and a lot of it is connected with how well organized we are + how responsible and accountable we are not only with ourselves but to others as well. Here are some key things that I always keep in mind:

• Assumptions are the worst in a remote environment and over-communication is the way to go.
• Good process is important, giving regular feedback and keeping people/teams accountable is very important as well.
• Take some time to just talk and have some fun as well, not go strictly straight to work-related things all the time. That ensures that we have a great atmosphere in the team.

In your experience, what are the common challenges engineers face when transitioning into leadership roles, and how can they overcome them?

When moving to a leadership role, the mindset shift is very much needed. You are not judged based on your own contribution anymore, but the contribution of the whole team.

Here are the main challenges (which I also faced) when moving to the first leadership role:

• Managing time and priorities

You find yourself in a position where you need to juggle a lot of different responsibilities like projects, helping your team, communicating with stakeholders, attending various of different meetings, code reviews, etc. The success of your team depends heavily on how well you manage your time.

So what to do? Learning to say no to things is very important and I also highly recommend separating your time to manager and maker time to ensure that you have time to focus.

• Control what you can control

You can control the changes or responsibilities of your team, but for teams outside of your area, you are not able to make decisions for them.

So the best thing you can do is to focus on building good relationships with other leaders of teams and collaborate well.

• Stay technical, but avoid going into too many details

To help the team the most, you need to understand as well as have strong opinions about particular technical decisions or directions. But don’t go into too many details - rather delegate the details to the team.

You need to be involved in important decisions that are crucial for the business, but delegate the small details which are not so important.

You can get overwhelmed by too much information very quickly if you have too many things on your mind.

You've worked with a diverse range of technologies. How do you stay updated with the constantly evolving tech landscape?

Continuous learning is a must in our industry and I like to believe that if you are not learning new things, you are not just stagnating, but you are actually getting worse (since tech is evolving very fast).

It’s important to take some time for that and ensure you are up-to-date with what’s happening. What I like to do is:

• I like to speak to experts in a particular domain and ask them questions.
• I regularly read different newsletters, blogs, books + attend meetups and conferences.
• Just take some time to try out something new.

Your Engineering Leadership Newsletter has gained a significant following. How do you consistently create valuable content for your audience?

One of the key motivations for starting the newsletter was that I personally didn’t have such resources when I was growing as an engineer/engineering leader.

A lot of times I write my articles in a way that my past self would get a lot of value from it.

And whenever a certain idea comes to my mind, I make sure to store it in my Notion workspace.

I have over 1000 ideas currently stored and I don’t believe I will run out of them anytime soon :)

Ideas also come from feedback and requests from my readers, day-to-day challenges in my role, having conversations with various people or just reading different content online.

You've also created several practical guides and templates for engineering leaders through Gumroad. What feedback have you received on these products?

So far, people have enjoyed using the guides and templates, which really motivates me to create more and more resources like that. A lot of the resources that I create, I personally use on a daily basis.

And I believe that if I want to use them daily, some others might as well. Especially, been using the 1:1 template now for quite some time and it works really well for me.

As a leader, what are your thoughts on the importance of mentoring and coaching within engineering teams?

Mentoring and coaching is really important. I really believe that when people feel like they are growing in their role, they will be a lot more motivated/driven.

I consider 1:1 meetings to be exactly used for that. Too many managers are using this meeting to get info about the progress of projects.

But this meeting should be all about providing feedback for improvements and talking about your report’s career aspirations and goals.

What do you think are the essential skills a CTO or engineering leader needs to have to be successful in their role?

I’ve noted some of them above when I talked about my responsibilities, but I really believe it all comes down to:

• Understanding the business and making sure that the tech is aligned with it
• Being a good person, who is focused on growing and empowering your team
• It’s important to have a wide range of experience and skills. You become an expert in management, but it’s also very important that you are good in as many different fields as you can (but no need to be an expert in all of them - it’s also impossible to do that).

Can you share a memorable story or experience from your career that has significantly shaped your leadership style or approach?

When I grew from Senior Software Engineer to Team Lead, I saw that what made me a great engineer would not make me a great Team Lead.

I almost burned out trying to do so many things spanning from being the best engineer all the way to stakeholder communication and being a manager to my team.

I felt that I needed to empower and uplift others to be successful in the role and also that my team would be successful as well if I did that.

And after a lot of mistakes and a couple of wins, I got a hang of it and this kind of mentality sticks very firmly with me all of the time.

I always think about what is best for the team and how we can contribute the most value to the business as possible together as a team.

What specific challenges does your "Senior Engineer to Lead: grow and thrive in the role" course address?

As said above, my transition to a lead role didn’t go so smoothly. I made a LOT of mistakes and made a TON of learnings along the way.

With this course, I am sharing all of my learnings and mistakes with the students in order they can learn from them and have a lot easier time adjusting to the role.

We go quite into advanced topics as well, so it’s great for people who are already in lead roles as well. Plus, they get actionable items on how to help their reports (engineers) to level up in their roles.

Looking into the future, how do you see the engineering leadership landscape evolving in the next few years?

There is always going to be a need for great leadership in any organization. Without it, it’s impossible to have great results. So, I don’t see it going away anytime soon.

Though what I see and believe will happen in the future is that roles will get a lot more broad, as the tools to develop will become better and better. Therefore making sure to still stay technical as an engineering leader is the way to go.

The T-shape model works great for engineering leaders as well (be great in management and be good in many other things).

Finally, what advice would you give to engineers who aspire to transition into leadership roles and make a successful impact as leaders?

The #1 thing is to let know your manager about your goals and aspirations. The sooner you do this, the sooner your manager can put you in a position to showcase the needed skills in order to grow to a lead position.

#2 Make sure to focus on building up your credibility. By doing that, you’ll get a lot more opportunities.

#3 Prepare to make mistakes and be a fast learner when you start with your first lead role. Also, get a mentor or a coach.

And of course, my resources in the Engineering Leadership newsletter would help a lot with that. You can learn from 11 different learning tracks + my course would give you a huge jump start!