Preparing a portrait for contexts you will not control
BetterPicSenior people do not choose where their headshot appears, and that single fact changes the specification.
Where it ends up
Conference programmes. News articles. Other people's slides. Industry roundups nobody asked you about.
Each crops it differently, places it against a different background, and reproduces it at a different size.
What to prepare in advance
Two crops — one tight, one wider. And a version that holds against both light and dark layouts.
Both cost nothing at the time and are impossible to retrofit, because the old portrait keeps resurfacing in places you did not put it.
The variable that decides survival
Contrast. Anything relying on a subtle tonal relationship fails somewhere: in print, on a dark slide, at fifteen millimetres in a programme.
The test
Place the headshot on a white background and then on a black one. If it works on both, it will survive whatever anyone does with it.