Company portrait projects go wrong at the briefing stage, not the production stage.
Count who already has a usable photograph
Frequently half, and many of those are decent images cropped wrongly. Five minutes each, no cost, and it turns a forty-person job into a twenty-person one.
A pre-rollout checklist covers the rest, and this is the highest-value item on it because it is free and nobody does it.
Write down three lines
Background colour, crop ratio, whether people look at the camera. Most companies never write these down, and that omission — not budget, not vendor choice — is why the page drifts back into four styles within two years.
Look at examples rather than specifications
Whether a set coheres is hard to specify and obvious to see. Worked examples are more useful here than any rule list, and the pattern in the ones that work is unexciting: identical crop, identical background, identical colour temperature, variation only in the faces.
Decide what a photographer is actually for
What a corporate photographer provides is not equipment — it is a person watching who tells you your chin is slightly too high, plus the ability to run forty people through one setup in a day.
The first is irreplaceable. The second is the part that breaks, because the day never contains everyone.
Test the "just do it yourselves" option honestly
Doing it at home works better than expected with three things right: two metres of distance rather than arm's length, a window rather than the ceiling light, and a wall contrasting with the person's hair.
What it cannot deliver is uniformity. Forty people each doing their reasonable best produces forty different backgrounds.
Establish what happens in fourteen months
If adding one new person requires organising anything, it will not happen. The generated route exists mainly because of that question, and the general company approach covers both paths.
The number that changes everything
How many people already have something usable. Establish it before the first conversation with any vendor, because it changes what you are buying.
Disclosure: I work on a 4K AI headshot generator.
