I believe it was Tom Robbins who observed that there are two kinds of people: those who believe there are only two kinds of people and those who know better.
That said, I face precisely two types of headshot shooting situations. On rare occasions, I photograph people who want to have their picture taken and patiently participate in the process. Most of the time, however, I need to rattle off headshots of several people who need to be doing something else at the time and stand in front of my camera only because their director or producer or organization head requires that they do so. In these situations, I need to create a lighting set-up and background that will work for people regardless of their height, skin and hair color, etc. And then I need to shuttle them through the process as quickly as possible, snapping three or four images and, quite frankly, hoping for the best.
The Ojai Film Festival wanted pictures of its board for the website, and the nine members agreed to arrive 30 minutes before their regular board meeting for the shoot. A little over three minutes per person does not allow much opportunity to reset lights, try different angles, and chat people into a relaxed state. To keep things interesting, the thirty minutes included dusk, so the ambient light shifted as we shot.
I chose to cross-light with a shoot-through umbrella above right, and a direct flash positioned lower left. My intent was to use this set-up for the gentlemen and then reset with butterfly lighting for the women, but time was so tight, we had to shoot as people arrived, without moving the lights. The tallest member of the group was not treated well by the sidelight, but overall, I think these suited their purpose. Since they appear very small on a website, the hard sidelight gives the images some punch a softly lit portrait would lack.