The Leadership Project Podcast · 2026-06-09 · 52 min
The leadership style that got you promoted can quietly become the thing that holds you back. When you move from building great work to leading people, the rules change fast, especially for technical founders and high-performing individual contributors who suddenly wake up running a business instead of writing code. We sit down with Mike Krupit , a serial entrepreneur and executive coach who has lived the journey from software engineer to CTO, COO, and CEO across eight startups. Together, we break down why humans are not deterministic, why “best performer” promotions often fail, and why not everyone should be pushed into people management. We also dig into smarter organizational design: building roles around real strengths and creating dual career ladders so experts can grow without becoming reluctant managers. Then we tackle the pressure cooker topic leaders cannot avoid: AI disruption. Mike shares how to lead through uncertainty when technology moves faster than people can grow, why overcommunication beats silence, and how to run real two-way dialogue that addresses fear without pretending you have perfect answers.
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