How do technical founders prove they can scale into executives?
How Technical Talent Grows Into Leadership
Deeply technical founders and engineers often struggle when their jobs shift from solving problems themselves to leading people who solve problems. In this episode, the VHTB team, Seyka Mejeur of AdAstra Talent Advisors, Matt Gjertsen of Better Every Day Studios, and Justus Kilian of Space Capital, break down why this transition is so challenging and what it takes to make it successful.
Technical leaders are used to tight feedback loops, direct control, and the satisfaction of “fixing the thing.” But executive roles demand something different: longer time horizons, ambiguous feedback, strategic focus, delegation, and trust. We go over the psychological friction behind this shift, the risks of staying in the weeds, and practical ways to build the leadership capacity needed at the founder and executive level.
From developing executive presence to building trust, and from knowing when to delegate to assessing whether founders can actually let go, we share a grounded look at one of the hardest transitions in the startup journey.
Episode Highlights:
00:00 Why the jump from technical expert to executive is so difficult
01:07 When strategic work feels like “not real work.”
03:22 The role of feedback loops and the loss of direct control
06:33 Turning long-term goals into clear quarterly targets
07:51 Communication, simplification, and learning to delegate
08:57 A three-part framework for understanding trust
12:24 How investors assess strategic thinking in technical founders
14:40 Red flags: under-leveling hires, decision bottlenecks, and weekend rescues
16:06 Why co-founders often outperform solo founders
17:29 “Who Not How”: hiring for leapfrog capability
21:22 The danger of being the constant bottleneck
Episode Takeaways
- Reframe the Work: Leadership problems aren’t “a distraction”—they are the job.
- Shorten the Loop: Break long-term goals into quarterly, measurable targets.
- Delegate Deliberately: Choose one decision a week to stop owning and hand to the team.
- Use the Trust Framework: Assess gaps in skill, judgment, or personal connection.
- Hire Above You: Don’t under-level—bring in people who elevate the company.
- Beware Bottleneck Syndrome: If all paths go through you, you’re slowing the company down.
- Let Strategy Win Over Muscle: What got you here won’t get you there.
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