Business headshots are an art of their own.
On the one hand, it is supposed to look confident, serious and authentic. . . and on the other hand it also needs to look spotless, inviting and friendly. No one wants his staff to look tired or unhappy in photos.
To find the middle is not always easy but here's how I do it.
Step 1, BE READY !
Now, be ready doesn't mean much more than that you need to know your shit!
Have everything set up, do test shots and have a backup plan.
Unless you are 100% confident and good to go, don't involve the customers or others.
Because, those people are running a business on the the side and need to focus on their jobs. You don't want to take up their valued time unless you are good to do YOUR JOB!
Step 2, WHERE AM I?
Often the most important thing, what kind of environment am I in and who are the people around me. Dress appropriately, smell nice, don't talk to much and know what you talking about. Be yourself and if you feel like it, crack a joke. Be authentic, you are who you are don't change to make a "better" impression.
Get to know the people you are shooting with and have a chat with them. Ask them a few questions and make them feel welcome and in good hands. Don't talk about yourself, you are hired to do a photoshoot and not to read bedtime stories.
Step 3, THE LOCATION!
Where are you guys shooting ? The headquarters, a studio, or right at the workplace...?
Find out before and have all the necessary equipment with you. Best case szenario, visit before the actual shooting day, get to know the people and the location and take a few pictures of the location (so you can see the colors and possibilities again). This will also leave a good impression with your customer cause... you care ;)!
Step 4, EQUIPMENT!
Have ALL of your gear charged and ready to go.. TRIPLE check your memory cards, batteries and lights. Nothing is more embarrassing and unprofessional then "not having" something that you forgot in the office.
Step 5, EXTRAS!
Every customer and job is different and all of them value different things.
For some it's a important to select pictures themselves, others might like a little more retouching. Offer different packages, suited for each individual customer.
In the end, everything works with recommendations and knowing the right people. So if you leave a great impression and deliver professional work FAST, you are very likely to get hired again and make yourself a very good name. Communication and listening to what your customer wants are the key elements! Deliver your work as soon as possible and give your customers different options and styles (for example a b/w option, it's literally one button) to choose from.
Last but not least, don't be a bitch about criticism!!! This might be the most important thing in here. Taste is different and some people like white chocolate some don't. It doesn't matter because you get paid to do a job. If your customer is unhappy or wants changes, you don't have to argue about lights and focus points. . . Take your time and LISTEN to what exactly they are looking for and what you can do better.
Change it, double check it and communicate in the process to make sure you don't have to do it three times.