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This is the last installment in this series. You’ve now heard from me four times in one week. Please don’t expect that on a regular basis. But you can expect it when I get fired up (which happens more frequently than you’d think). If I’ve got something to say, you can take great comfort in knowing that I’m absolutely going to say it. And you’ll get greater access to me than anyone else because you’ve generously contributed to this effort.
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POST 9: HOW TO KILL A CHIEF OF STAFF IN UNDER A WEEK
Ninth in a Series Responding to a16z’s “How to Hire a Chief of Staff”
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This post is for every CEO, founder, and executive who has ever hired a Chief of Staff and watched it fail.
I have news. It wasn’t them.
a16z spent 4,000 words telling you how to hire a Chief of Staff. Archetypes. Leveling frameworks. Assessment rubrics. A visual chart so detailed it looks like it was designed by someone who peaked in AP Art History.
What they never told you is how to avoid destroying the role in its first five days. Which is a bit like selling someone a Steinway grand piano and forgetting to mention you shouldn’t leave it in the rain.
This is the gap in the article that will cost you more than any bad archetype or wonky leveling framework. Because it doesn’t matter if you hire the perfect candidate from the perfect background with the perfect score on your precious MOC. If you botch the introduction, the role is dead before the business cards arrive.
Here are five ways you’re killing this role. I’ve seen every one of them. In some cases, I was the one getting killed.






