Chapter 13. Working with Your CEO, Peers, and Engineering

There are so many stories about hiring a new executive who comes in and wreaks havoc. I’ve seen Engineering leaders who start with a giant, doomed migration, marketing leaders who accelerate expenses until they necessitate a round of layoffs, and a number of executives who are fired in their first month. When people tell these stories, they’re almost always framed as the failure of the individual executives, but these scenarios happen so frequently that I believe there’s an underlying structural challenge in addition to individual missteps. Fortunately, the structural trap that snags many executives can be avoided by acknowledging the built-in difficulties and navigating them with a deliberate approach.

When a new Engineering executive is hired, they are usually brought in by a CEO who believes that the Engineering function is underperforming. When you talk to members of Engineering, they will likely have a different perspective, potentially that the CEO keeps changing direction too frequently. When you talk to peer executives and the board of directors, you will hear a third and a fourth narrative about what’s happening. Where new executives fail is that they think of these as opposing perspectives, when in reality they are all incomplete but valid slices of a complex situation. Successful executives debug these mismatched concerns until they merge into a single cohesive perspective. Ineffective executives anchor to one ...

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