At our recent Leadership Lessons webinar, we sat down with Gregor Ojstersek, CTO and author of the Engineering Leadership Newsletter. We unpacked his journey from engineer to leader, the mindset shifts that shaped his path, how he manages challenging situations, and his views on AI’s impact on tech leadership and teams.
🎥 Watch the full conversation below
What shaped your transition from engineer to leader, and how do you think about it today?
When I was a senior software engineer, I felt stuck. I didn’t know which path to take: becoming an architect, staff engineer, or manager. My manager asked me where I saw myself in one or two years, and I wasn’t confident. Luckily, the company restructured, and I was offered a team lead role. I said yes, which was one of the best decisions I’ve made.
The hardest mindset shift was realising that as a leader, success isn’t measured by your individual contributions but by how well your team performs. I had to learn to say no, delegate, and trust my team because trying to do everything myself would have led to burnout.
I also learned that making too many cross-team changes without responsibility can backfire, so focusing on what you can control and delegating effectively is critical.
What advice do you have for engineers ready to step into leadership roles?
Leadership isn’t about having the title. Start leading now by owning projects aligned to where you want to grow, whether that’s becoming a staff engineer, team lead, or architect. Show the behaviours expected at the next level.
Managers want to de-risk promotion decisions, so demonstrating these behaviours early makes you a low-risk candidate. Also, build strong relationships with your manager and communicate your goals clearly. Managers aren’t mind readers, so keeping the dialogue open is essential to progress.
How do you manage difficult situations or failures as a leader?
Leadership isn’t just about good times. I remember launching a project that wasn’t well-received. I made sure the team knew that it was an experiment and an opportunity to learn. It’s important to keep morale high and stay composed, your confidence sets the tone for your team.
You have to embrace failure as a natural part of growth.
Imposter syndrome is common among engineers and leaders, how do you recommend dealing with it?
Everyone has imposter syndrome, even me, especially when trying something new. It’s a sign you’re growing. Nobody is ever 100% ready for the next step. You can prepare for years and still make mistakes; that’s part of the journey. Embrace the discomfort, because after a few months, you’ll look back and wonder why it felt so intimidating.
How do you navigate the identity shift from individual contributor to leader?
When you become a lead, you must shift your identity from being the most technically skilled person to someone who uplifts others. That’s the hardest shift.
Start by sharing knowledge openly and helping others improve. Hoarding knowledge is an anti-pattern and not senior behavior. The more you share, the more you demonstrate leadership readiness.
How do you build trust and alignment while leading change?
When joining a new team or project, I focus on understanding the context deeply and don’t rush to change everything. I seek buy-in from leadership first and then share clearly with the team why we’re making changes — what the business value and benefits are.
I involve the team in decision-making and assign ownership so people feel part of the journey. Facilitating change rather than dictating it helps build engagement and alignment.
What skills are most important for tech leaders today, especially in an AI-driven world?
Communication and people skills have become even more important than technical skills. Leaders need to build strong relationships, clearly articulate goals and context, and foster alignment.
Coding solves problems one way, but culture, clarity, and empathy solve many others.
How is AI impacting tech leadership and engineering teams?
AI isn’t magic; it’s a tool to enhance workflows and automate where sensible. Leaders must manage expectations confidently, especially from CEOs who might have hype-driven ideas.
Don’t wait to be told what to do, own your AI strategy proactively. Engineers know better than most what building AI products entails, and leveraging this insight avoids wasted effort.
Importantly, never blindly merge AI-generated code without checking it, because you’re still accountable for quality.
If you want to dive deeper into these topics and hear more from Gregor Ojstersek’s experience, watch the full Leadership Lessons AMA video on demand here.