The CEO at my last place used to forget his passwords at least once a week, would write them on Post-It notes on his desk (and lose them by day's end).

We had a dashboard that showed failed security and he was many, many times worse than the rest of the business combined. That man cost the business more in IT time than anyone.

This was a bank. Granted, a small lending-only bank but still, I would never get a mortgage or loan with these people.

They should have just put a Yubikey on his keys. He never lost those.