I had convinced my wife (who is not of the tech world) to switch to a password manager a couple years ago, and while she didn't love it, she's now totally on board.
My mother runs a fairly successful small online business and kept getting BS charges on her business cards along with other various occurrences. She and her employees were sharing a couple passwords for everything the company used. They weren't _bad_ passwords, but it wasn't a great set-up.
Finally, my wife and I convinced her to try out a password manager. After quite a few excuses why it would never work for her over a couple weeks, she got a another bogus charge and begrudgingly accepted. My wife went and spent a day to help her move _everything_ over, generate strong passwords, and showed her how to set up accounts for her team and share them so her team could do the same.
I'd since forgotten about all of that, as it's been well over a year since all that happened, and I assumed she went back to her old ways. Then last weekend I heard her bragging to a colleague about using a PW manager and how it's changed her life significantly - recommending they do the same.
She said excitedly "I don't even know my passwords! It's great!"