I collect a rogues gallery of really failed LinkedIn headshots. Yes, I am that type of LinkedIn geek.
A headshot should make it easy to recognize you, in a crowd, as you approach someone in a coffee shop, as someone speak to you on the phone so they can envision speaking to you in person (as you do the same), etc.
Not these; you will know why when you see them. If any is yours, sorry, but you need tough love:
The worst-absolute worst I ever saw was this:
Get a good headshot from a pro.
Get another one if yours no longer looks like you.
Don’t be generic–be a brand.
PS Shamed by this blog post, I am pleased to say the owner of the photo of the very pink-faced kid in the middle (probably taken at his Bar Mitzvah!) has updated his headshot to one from this century, a much improved version. Bravo (you know who you are)!