Balancing your CEO, peers, and Engineering.
There are so many stories of hiring a new executive who comes in and wreaks havoc. I’ve seen engineering leaders start with a giant, doomed migration, marketing leaders who accelerate expenses until they necessitate a round of layoffs, and a number of executives fired in their first month. When people tell these stories, it’s almost always framed as a failure of the individual executives, but they happen so frequently that I believe there’s an underlying structural challenge in addition to individual missteps.