Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest

The CTO-to-CEO relationship is the highest leverage relationship in your career as a technology leader, and it's the one where getting the balance wrong has the biggest blast radius. You need to be close enough to influence, independent enough to be honest, and aligned enough to execute even when you disagree. Most people get at least one of those wrong.

This episode lays out a framework for building CEO trust around four foundations: competence, candor, commitment, and context. It also gets into the different types of CEOs you'll encounter, from founder-developers who still have strong technical opinions to operators who are completely hands-off on tech, and why your approach has to change depending on which one you're working with.

There's also an honest look at what happens when the relationship starts to erode, how to spot the warning signs on both sides, and when repairing it is worth the effort versus when it's time to go.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)
• "The Five Dysfunctions of a Team: A Leadership Fable" by Patrick M. Lencioni (Amazon Link)