The Hardest Part of Tech Leadership

John Fiedler, SVP of Engineering and CISO at Ironclad, joins the show to unpack the real challenges of technology leadership. From managing nonstop context switching to measuring success when you’re no longer shipping code, John shares hard-earned lessons on how leaders can protect their time, set priorities, and thrive in the chaos. Whether you’re moving from IC to manager or scaling as an executive, this conversation offers a candid look at what it truly takes to lead.

Key Takeaways

• Success in leadership isn’t about features shipped—it’s about execution, people, and culture.

• Context switching is constant, but leaders can design their calendars to minimize the chaos.

• Organizational size reshapes the challenge: startups reward speed, enterprises demand process.

• Protecting your time isn’t optional—leaders who don’t own their calendars quickly burn out.

• The leap from IC to manager requires starting fresh and mastering a new craft.

Timestamped Highlights

02:13 The hidden tax of context switching

06:53 How John measures success as a leader without code

10:45 What really slows executives down inside organizations

15:51 How John protects his calendar and finds focus time

24:47 The lessons every first-time manager needs to hear

A Line That Sticks

“If you don’t control your calendar, your calendar will control you.”

Call to Action

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