From IC to Leader (and Back Again): Owning Your Career Path with Craig Bensemann

About this episode

Craig Bensemann discusses career growth and effective retrospectives in tech.

What makes a retro actually useful—and why do so many senior devs stall out? Craig Bensemann brings sharp insights and real-world fixes. Too many teams are “doing agile” without improving. And too many senior devs are stuck, unsure what’s next. Craig Bensemann—senior developer, mentor, and author of Retros Don’t Suck —joins Jakob to unpack both. With two decades in tech, Craig has led teams, mentored developers, and experienced firsthand what happens when retros become venting sessions and careers lose momentum. In this conversation, he explains why rigid scrum can be today’s waterfall, how to shorten feedback loops in real ways, and how to bring intentionality to career growth. They dig into practical ways to fix retrospectives (hint: fewer action items, more ownership), signs a senior dev might be coasting, and how to lead without a formal title. Craig shares why he stepped back into an IC role—and why that was exactly the right move for him. Whether you’re a team lead trying to reboot agile or a senior engineer feeling stuck, this episode offers both insight and next steps. Key topics: agile theatre, retrospective anti-patterns, career plateaus, developer mentoring, modern…

People in this episode

Host: Jakob

Guest: Craig Bensemann

Topics covered

• agile theatre
• retrospective anti-patterns
• career plateaus
• developer mentoring
• modern leadership without the title

Keywords

• agile
• retrospectives
• senior developers
• career growth
• mentoring

Sponsors

Wires Uncrossed

Mentioned in this episode

Products: Retros Don’t Suck

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