09/03/2026
I spent 90 days being the most organized person in the room. Then AI replaced me
In my first 90 days as a Chief of Staff, I made the mistake almost everyone makes.
I tried to be useful.
I said yes to everything. Took the notes. Chased the actions. Cleaned up the decks. I was extremely busy, my principal was pleased, and I was completely replaceable.
Useful is not the job. Useful is what an excellent coordinator does, and coordinators are hired at a different level for a reason.
The job is judgment.
Deciding what reaches your executive and what does not. Saying "I don't think this deserves the leadership meeting." Writing the memo in their voice and watching them send it without changing a word.
The move from useful to trusted is the entire role. Nobody tells you it is a move. You assume you are being rewarded for doing more, but doing more is why you get kept. Deciding well is why you get trusted.
That took me about a year to understand.
You can get there faster than I did.
What did your first 90 days teach you that nobody warned you about?
