When the portrait becomes a specification rather than a preference

Companies with brand guidelines discover that headshots are subject to them, usually late.

What gets specified

A background value rather than "neutral". A crop ratio rather than "head and shoulders". An aspect that has to match existing assets, and sometimes a colour temperature.

Those are tolerances. Hitting them across forty different faces is harder than making any single portrait look good, and it is a different skill.

The conflict that arises

A specified background will not separate equally from every person's hair. Very dark hair against a specified charcoal produces, at small sizes, a silhouette with no face in it.

The correct resolution is to choose the value that works across the widest range and accept it is nobody's individual optimum. A coherent set beats forty individually flattering images.

What to do first

Test the specification on the two hardest faces in the company, not the most photogenic.