Chapter 24. Leaving the Job

If two friendly executives meet for dinner, it’s likely they start by exchanging just how messed up things are at work. Initiatives are behind, layoffs are happening everywhere, the team is in disarray. Then they’ll laugh and switch topics. Sometimes one of the executives can’t navigate the switch and will keep ranting throughout their meal. Having problems is part of being an executive, but when you’re that second executive who can’t turn off the frustration, it’s time to start thinking about leaving.

Departing an executive job is much messier than leaving an individual contributor role and will significantly impact the team and company around you. It’s also potentially impactful to your resume; I frequently talk with executives who hate their job but don’t want to leave because they’re worried it looks bad. “If I just make it to two years, it’ll look great.”

The optics are real and I understand why people get caught up in them. I’ve certainly gotten caught up in my own optics at times. That said, the deeper I get into my own career, the more convinced I become that we should think about departing roles in the context of managing our own energy.

In this chapter, we’ll walk through:

  • Succession planning before a transition

  • Making the decision to leave

  • How to think about short executive stints

  • Whether to line up another role before leaving

  • Telling the CEO

  • Negotiating the exit package

  • Transitioning out and actually leaving

Finally, we’ll end with a discussion ...

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