I recently read a blog post about Gregor Ojstersek’s journey from software engineer to CTO. It was well written, and what struck me most wasn’t the milestones or titles—it was the internal shift that comes with each step. You start by solving problems yourself, then learn to help others solve them, and eventually, you’re guiding systems, teams, and decisions that affect people far beyond what you directly touch. It made me reflect: I’ve seen that path in others. And, in hindsight, I think parts of it mirror my own experience too—not always neatly, not always intentionally, but in ways that shaped how I think and lead today.
This post isn’t meant to be a “how-to,” and definitely not a highlight reel. It’s more like a set of field notes: things I noticed, patterns I’ve come to appreciate, and a few turning points I only recognized much later.
1. It Starts with the Work
I’ve always been drawn to fixing things—not just improving efficiency, but helping businesses do what they do, better. In the early days, that meant working directly on process problems. I remember my first independent project at a rural bank, where the goal was to disburse credit within two hours from a complete request submission.
This was my first solo project, and also my first experience with financial institutions. I had to quickly learn the technical aspects of rural banking operations, understand their unique constraints, and grasp why these institutions existed and what made them successful. All while trying to appear knowledgeable and credible enough for the bank staff to take me seriously.
I wasn’t trying to lead yet. I was just trying to solve a problem that mattered while navigating a steep learning curve. But looking back, that pressure to quickly build expertise in an unfamiliar domain was the beginning of learning how to align myself with new contexts and challenges—a skill that would become crucial for leadership later.
2. Mentoring Is Where Leadership Quietly Begins
Having been mentored myself previously, I thought I understood what mentoring entailed when I was asked to guide a new colleague. What caught me off guard was the burden of consistency—the realization that I needed to embody every standard I set.
If I expected my mentee to arrive prepared with research and documentation, I had to demonstrate that same level of preparation. If punctuality mattered, I needed to be early for every meeting. The challenge wasn’t just explaining why I did things, but consistently modeling those behaviors myself. That’s when I started converting intuition into clarity, not just for someone else’s benefit, but for my own accountability. This discipline of leading by example, rather than just instruction, became a foundational part of how I approach leadership today.
3. Influence Comes Before Authority
Later, I began coaching Lean Six Sigma teams for our clients, where no one reported to me. This was very different—people didn’t have to listen, and that forced me to get better at influence, not instruction. What I found most challenging was working with seasoned professionals who had been in their roles for years. They had valid reasons for their current processes and often saw me as an outsider who couldn’t possibly understand their day-to-day realities. Building credibility meant I had to first acknowledge their expertise before suggesting any changes.
I remember one manufacturing team that initially rejected every suggestion. What turned things around wasn’t my process knowledge—it was taking the time to observe their workflow for three full days, asking thoughtful questions, and admitting when I didn’t understand something. It surprised me.Only after they saw I was genuinely trying to learn their context did they begin to engage with my ideas.
The most powerful moment came when I stopped presenting solutions and instead started asking carefully framed questions: “What if we tried…?” or “I’m curious what would happen if…” This subtle shift allowed them to maintain ownership of the process while still considering new approaches. That was when I really began to understand leadership—not as authority, but as alignment and behavior change. Influence, I realized, is something you earn—not something you’re given. And it’s built on a foundation of genuine respect and curiosity.
4. From Solving to Scaling
Eventually, my focus shifted from leading individual projects to building a team that could tackle multiple challenges simultaneously. This wasn’t a planned move into entrepreneurship—it emerged from realizing that impact at scale required more than just my own effort.
The transition was humbling. I’d grown comfortable with directly influencing outcomes, seeing problems and fixing them myself. Now I needed to create an environment where others could develop that same ability. It wasn’t about doing the work—it was about creating the conditions for good work to happen without me.
Building the team meant learning new skills: identifying talent with growth potential, creating systems that reinforced our values, and balancing autonomy with accountability. I shifted from being evaluated on my output to the collective impact of people I supported.
What surprised me most was how this changed my relationship with failure. When doing the work myself, failures felt personal. As a team builder, I began to see failures as data points and opportunities. The question changed from “How do I fix this?” to “How do we ensure we learn from this?“
5. Real Growth Looks More Like a Spiral than a Ladder
None of these transitions felt dramatic at the time. There was no single promotion that suddenly made me a “leader.” Instead, it felt more like spiraling forward—returning to familiar challenges, but with a new perspective and broader context.
I’m reminded of this every time I find myself back in the trenches, working directly on a problem rather than guiding others. Early in my career, I might have seen this as a step backward. Now I see these moments as essential calibration points—opportunities to test my assumptions and reconnect with the ground truth.
Nowadays I’m drawn into AI projects, working to understand adoption problems firsthand. I try the tools myself, talk to more people on the ground, and commit to learning more about both the technology and its human impact. The formal metrics might show implementation progress, but it’s these direct conversations that reveal whether people are truly embracing the change or just going through the motions.
By immersing myself in the practical realities, I discover friction points that aren’t visible in status reports. More importantly, I gain new language for explaining why these innovations matter—language rooted in day-to-day work experiences, not abstract technological promises.
And even now, I don’t think of myself as having “arrived” anywhere. I still dive deep into details when needed. I still revisit old lessons with new eyes. Leadership, I’ve come to believe, isn’t about letting go of the work—it’s about knowing which part of the work only you can do now, and recognizing that sometimes that means getting your hands dirty again.