Want to take employee photos that don't suck

You got plenty of great advice already and I don't have much to add, but I'd summarize what I would do if I were in your shoes:
  • Set up in one place and keep it as simple as possible. Every image will look the same, which has some advantages when it's time to use them. The background can be a wall or some gray paper taped to the wall. Keep your subjects quite a few feet from the wall if you want the background darker, or close to the wall (2-3 ft) if you want the background to be lit by your flash. This assumes the flash will not reach the wall. If the flash fills the room with light, the background exposure can't be controlled so easily.
  • Bounce the flash off to the side, away from the subject, so that the reflected light comes from up above and from the side. If you make the flash point forward and up, the light reflected from the ceiling will not be flattering... better to have it come from the side if at all possible. This assumes you have white surfaces to reflect light... if they are colored this is not going to work well.
  • Set up your camera to manual to have a consistent exposure with every shot. Make sure you have enough batteries in case your flash runs out.
  • Put the camera on a tripod and have the subject point their chest towards the wall where you're bouncing the light off. This will give you "short lighting" which is probably more flattering for most people. It's best if they are seated so that they are not uncomfortable with their hands. You may want to engage them in small talk to elicit a natural expression, and make sure the focus is on the eyes.
  • The 105mm is probably the best choice, smaller and great image quality... you need to have the room to use it. I'd go with f/5.6, low iso and a steady tripod.
  • Make sure you practice until you get the exposure and composition right, and then get someone to line up the employees and take 3-5 frames of each.
You'll do fine! Share the images after you're done...
 
Use the 105mm lens, get an extra flash, or two, and put diffusers on all of them. These can be plastic flash head covers, or white 'box' like attachments, or you can put a white hanky over the flash head, and secure it there with a rubber band. Put your subject on a stool, facing the lens, and have them turn their bodies about 45 degrees to the left, or right, of the lens. With their body there, have them turn their head back towards the lens, perhaps 40 degrees...almost, but not quite, looking directly into the lens...so one eye is slightly nearer the lens than the other eye is. Place one flash 90 degrees away from the subject's face...aimed at an ear. Place another flash on the opposite side of the body, at about a 45 degree angle...aimed in line with the subject's knees. If you have still another flash, place it behind the subject, out of sight, aimed up at the ceiling. Focus on the subject's eye which is nearest the lens, and shoot. Use an aperture which is a bit down from maximum. If you use the 2.8 105mm lens, shoot at aperture 3.5, or 4. If that does not give you the Bokeh you want, re-organize everything so the camera is nearer the subject, and the subject is further away from the background. Using foliage-trees / bushes outdoors, potted plants indoors-as a background will be best. If you have extra money to spend, use a green screen system as a background, and make one subject seem to be on a beach in Hawaii, another seem to be atop a mountain, another seem to be standing beside a movie star, etc. Do not mix lighting by using a flash, and an overhead room light, and a desk lamp, etc, as the different lights will have different colors. Your eyes won't notice, but the camera sensor will. Done right, the setup mentioned here will give you photos which can be used on: company websites, billboard ads, company ID cards, online dating sites, greeting cards, business cards, etc.
 

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