The IT guy at my old job told me my password was 'cute' and I still think about it
This happened at a small insurance office in Boise about two years ago. We had one IT guy for the whole company, and he came around every few months to check on our machines. One day he sat down at my desk, pulled up my password settings, and just laughed. Then he said, out loud, in front of two coworkers, that my password was cute and that he could guess it in about ten seconds. He was right, by the way, it was my dog's name plus my birth year. The thing that got me was that he never told me to change it. He just made fun of it and walked off. Two months later our whole email system got hit with a phishing scam that locked everyone out for a full day. I still don't know if it was related to weak passwords, but that moment stuck with me way more than any security training video ever did. The guy made me feel dumb instead of safe, and that is backwards. How do you get people to actually care about this stuff without making them feel stupid?
Cute. Yeah, real cute until the whole office gets locked out for a day.
That line about him making you feel dumb instead of safe is the whole thing right there. If you tell someone their password is weak and then just walk off, you taught them shame, not security. Shame makes people hide their bad habits, not fix them. The better move is to sit down, show them how fast a program cracks a pet name plus a year, then help them build a passphrase they can actually remember. Five minutes of that beats an hour of training videos, every time.