CTO Confessions: The Human Side of Tech Leadership
“If not you, then who? If not now, when?”
This ancient wisdom from Hillel the Elder emerged as a central theme during my recent conversation on the CTO Confessions podcast. It captures a fundamental lesson I’ve learned through years of leadership: the willingness to take action, knowing mistakes will happen, matters more than striving for perfection. And perhaps counterintuitively, the more senior your leadership role, the more valuable it becomes to show your human side—your low points, your mistakes, and yes, even your bad jokes.
Throughout the conversation, we explored what this means for leading engineering organizations. Here are the key insights that emerged:
- Intuition backed by systems thinking: Remember that gut feeling when something’s off, but you can’t quite put your finger on it? I’ve learned to embrace these moments. Rather than dismissing intuition as irrational, I use it as a signal to dive deeper with systematic analysis. We explored this through a story of how a nagging feeling about a contract led to discovering a crucial omission—a realization that would later save the company during COVID. The key isn’t just trusting your gut—it’s using that initial signal to find the logical inconsistencies that your intuition is picking up on.
- Connecting technology and business: You know that moment when you’re explaining a complex technical constraint and see glazed eyes across the room? That’s where the Spider-Man drawings come in. During our chat, I shared how this simple visual analogy helps executives instantly grasp project trade-offs better than any technical explanation could. But it’s more than just clever analogies—we explored how technical leaders can build genuine understanding by combining hard data with intuitive examples, always remembering that the person across the table brings valuable expertise from a different domain.
- Work and life integration: I used to think leadership meant maintaining a professional distance. I was wrong. In the podcast, we explored how authentic leadership requires thoughtful integration of personal and professional sides. When I’m exhausted after being sick, I tell people—not for sympathy, but because humans fill information voids with their own narratives. We discussed how this approach transforms team dynamics, while still maintaining healthy boundaries. It’s not about oversharing; it’s about creating space for genuine human connection.
- Culture of safe mistakes and real feedback: Want to hear about a half-million euro mistake I made? In the podcast, we dove deep into how leaders can transform mistakes from sources of fear into catalysts for growth. We explored how broadcasting mistakes—rather than hiding them—fundamentally changes organizational dynamics. When leaders show vulnerability first, it creates space for honest feedback to flow in both directions, building the foundation for genuine psychological safety.
- The role of humor in leadership: Those awkward three minutes before a big meeting starts? We discussed how these moments present unexpected leadership opportunities. It’s not about being funny—it’s about creating moments of human connection that make the serious conversations more impactful. The podcast dives into how this approach helps break down hierarchical barriers while actually strengthening leadership effectiveness.
We unpacked many other topics during our conversation—from concrete advice for aspiring engineering leaders to pondering about Europe’s unique position to lead the GreenTech revolution.
Want to hear the full conversation? You can find the episode on Spotify, Apple podcast, or CTO confessions website.
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