What I Learned From Taking 200 Headshots in Just a Few Days

I enjoy taking headshots for people, and I shy away from the commercial, copy-paste, white background styles where the deliverable image is straight out of the camera. However, last month, I combined my preferred style of headshot with the number of subjects you'd typically see with a large corporate, straight-out-of-the-camera shoot. Here's what I learned.

I have nothing against headshots where the final image is the one on the back of the camera, the background is perfectly white, and the subject is in focus front to back. I just don't want to take them. I prefer the editorial, cinematic style you're more likely to see in magazines, even if they have to be on a white backdrop. Think more like Peter Hurley's brand of headshot or Martin Schoeller. Well, a couple of months ago, I was approached by one of the world's best hedge funds regarding headshots and how they would like to update theirs. I met with them and explained that I like to do things a little different to the purist corporate style headshot, and showed them my natural light headshot series which was created to demonstrate consistency, something I discussed last month. Well, that's what they wanted, just with a white background. The tricky part was, I needed to take just under 200 of these headshots in just a few days.

I have shot portraits for companies before, even hedge funds, but I can usually get everything done in two days maximum. This was by far going to be the most demanding, and with a host of important (and very busy) subjects, the pressure to deliver was on too. The shoot was ultimately a success, but I learned a lot through not only what went well, but what I could have improved on.

Equipment and Preparation

This area is a double-edged sword of my personality. I am tirelessly anal about ensuring not only that everything is working, charged, and packed securely before each and every job, but that I have duplicates of everything to handle all unexpected eventualities that might occur. While prudent of me, it's stressful and time-consuming. However, I think it's fair to say my erring on the side of caution is the best approach. Every day, my cameras, two batteries for each, my lights, two batteries for each, my tablet, my laptop, and my phone were fully charged, as well as a plethora of different-sized batteries for remotes and receivers. Each night, I would return home late, but ensure that my assembly line of charging units was put back together, ready for the next day. I would then pack all of those chargers to take with me on the shoot in case a spare didn't work. Funnily enough, not once did I change the batteries on any device, something that I appreciate has improved vastly over the last decade.

I don't doubt this is a step too far for most, but for me, it gives me a sense of peace of mind. I've had things go wrong on a shoot before, and despite my body going dark and a red siren swirling in my mind, I remain outwardly calm and exchange the offending article for its understudy.

Schedule and Timings

This is something that could easily fall by the wayside, lost in the gray area of responsibility between you and the person who is arranging the job for the company. You need somebody running point at the company's end who can schedule everyone in and draft up an order of play for the time you're there. I had an amazingly organized, efficient, and frankly, invaluable person doing it for me on this job, and without that, I'm almost certain it would have been somewhere between "worse" and "disastrous." Ensure that everyone knows when to visit you, where, and any instructions they need beforehand with regards to dress etc.

Timings are the next tricky part, and you could certainly argue I got this wrong, but I believe I got it right. For each person I was shooting, I'd allocate a five-minute window. I would say less than one percent used those full five minutes, and often — particularly after the first batch of shots, when everyone was firing on all cylinders — the shots would take less than 30 seconds to get the shot, and then, the next person would come in. On occasion, I shot four or five in one fiv-minute window. However, allocating a generous time slot has several benefits. Firstly, it puts the subject more at ease, as they know they aren't being rushed. Secondly, the subject doesn't feel like it's a school picture where you're plonked in front of a photographer, snapped, and then booted out the door; everything about how I work I would like to be completely different to those mass production style shoots. Thirdly, if the subject doesn't like something about how they look in an image, they have time to make adjustments, and we can experiment with lots of tweaks. Fourthly, if anything goes wrong my side — a battery runs out, a piece of equipment malfunctions, or something similar — I can fix it without a queue of busy people forming at my door. So, again, err on the side of caution with timings as you should with equipment.

Direction and People

This is the area I'm most conflicted about. I certainly did a lot right, which I can see by the number of people thrilled with their new headshot, but I made mistakes here. Between 30 seconds and 5 minutes is such a small sliver of time to build rapport with your subject. I like to believe I'm quite personable, but getting people to drop their guard to have their picture taken — which most human beings loathe at the best of times — is a tall order. I had developed my posing advice over a good few years, and I had that part down to a fine art. My instructions on how to stand are specific, and they make people feel silly, which has the unintended benefit of creating genuine smiles more often than not, which adds a lot of warmth to images that can easily seem quite cold and clinical without due care when shooting on this scale. However, shooting this many people, I noticed a flaw in my approach.

It has been observed by people close to me that I treat everybody the same. The first time someone said this to me directly, I immediately wore it like a badge of honor. I hadn't realized it was the case, but recognized straight away that it's exactly how I want to be. I maintain that's a great approach to life, but this shoot might have had some exceptions. I was photographing everyone from the part-time cleaning staff through to board of directors, several of which have been knighted and are titans in their fields. I spoke to and directed both of these examples and everyone in-between in the exact same way. While ethically admirable, it didn't serve my interests on this occasion as well as it might have. With the most important and revered members of this incredible company, I ought to have taken more time to explain my methods and give meaningful direction, with caveats about how it might make them feel uncomfortable. Instead, I expected them to listen to me and heed my advice with a misplaced confidence. It's not that anybody reacted poorly to me; nobody refused to do as I asked, and as far as I know, no one came away despising me, but with a few of the most important people in that company, I could have done better. They are extremely busy, and with the knowledge that I was pressed for time, I dove in too quickly and didn't do enough exposition to get their guards to drop. It was a misstep by me, and although not terminal, it's something I will take on board going forward.

Quick Fire Lessons

To avoid this article becoming too verbose, I will now offer some of the briefer but equally as important lessons. If you want any of these unpacked further, just ask me in the comments:

• Sometimes seemingly minor alterations with the angle of the subject's face can have a profound impact. If you can't immediately identify the best angle, experiment.
• Having someone from the company with you who will be honest with the subject in a way that's above your station can be helpful.
• Learning how to properly photograph people with glasses without getting a reflection ought to be figured out completely ahead of time. I had already done this, but there were a number of trickier subjects that had I not been as experienced, could have thrown me completely.
• Do a test shoot beforehand, not only to experiment with your lighting setup and get a feel for the process, but also to show your client exactly what their images will look like.
• Back up everything in multiple places as often as is feasible.
• If someone asks for something specific to be retouched, take a photo on your phone of the back of the camera with that subject's image, and write on it what they want done. You won't remember; don't lie to yourself.
• Don't be afraid to say "I think we can do better" if you're not completely happy with the image. Then, experiment with methods that will coax out different micro-expressions.
• If someone could not care less about their photo, don't try to win them over; your job is relatively unimportant, so swallow that though pill and move on.
• Have business cards and prints (or in my case, a tablet on a stand displaying a slideshow of my work) near the waiting area.
• Go the extra mile. I've written on this topic a lot, but it matters. If someone is having a bad hair day or is hungover, in a foul mood, or whatever else, invite them to come back another day and put in the overtime to accommodate them, no matter who they are. I did this 10 or more times, and I would have done it more. While as the tip above states, some might not care for their photo, some really will. If they forget it's their day for photos and are in a rush, they might be self-conscious and rescheduling them can make the world of difference.

Conclusion

I honestly don't believe I've covered everything I learned from this shoot, simply because it was a rich experience. It was rich in many ways, but primarily because it was high pressure, long, and unchartered for me with regards to concentration of images. I hadn't worked on a shoot of this magnitude before, because my style of headshots, while not fantastically unique, aren't typically what larger companies opt for, as it's more time-consuming to conduct and thus, more expensive. If there's one piece of advice I would want readers to leave with it would be this: when planning a large shoot, err on the side of caution with everything. It's far better to be overprepared than caught out by a lack of forethought and risk aversion.

If you have any specific questions or I can offer any useful insight for large shoots you have coming up, leave a comment below or message me privately.

All images used in the article are my own and are not from the shoot this article is about due to confidentiality agreements with the client company, but are of the same style. Lead image of Ben "Doc Brown" Bailey Smith.