Choosing the Best Headshots

During the headshot or portrait session, your photographer should be working with you to produce a variety of poses and “looks” that will yield a variety of images. People’s faces are typically asymmetrical, and one of the first things I do in a session is determine with my client which side of their face looks better. For example, for many people one eye is slightly larger than the other – you often want to have that eye angled closer to the camera, making it appear larger than it actually is, resulting in it looking similar in size to the eye that is actually larger. Insure that your photographer has the ability to shoot in “tethered mode”, which allows both you and the photographer to look at each image on a large screen (vs. the small screen in the rear of the camera).

A typical individual headshot or portrait session will yield anywhere from 20-50+ images worth considering – here are some tips on how to go about selecting the best images to use.

First, your photographer should make the images (aka, a “gallery”) available to you online so you can view them and share them with others if needed – there’s no need to email files at this point. You may want to view the images on a computer monitor, smartphone/tablet as well just to insure they look good to you on multiple platforms/screen sizes.

I recommend planning on making 2-3 passes through the gallery, narrowing down the selections with each pass. The first pass should be all of the ones you initially like; during the 2nd and third passes, you’ll compare images to start to rank them in order of preference. I’d recommend asking for another opinion only after you’ve narrowed down your choice to no more than a handful.

So, what are you looking for? First, let’s talk about what NOT to look for – your selections should not be based on things such as lighting, a few stray hairs, etc. that are easily fixed in post-production by your photographer (be sure that your photographer offers this prior to booking your session). Your photographer should also be able to remove minor blemishes, razor-burn (for guys), whiten teeth, etc.

While some of this is subjective, DO look for the following:

1)      The overall look/feeling of the image – does it convey the message/impression you’d like to convey (e.g., confidence, friendliness, professionalism, warmth, etc.).

2)      Your smile – does it look genuine? Too much or too little? Some people’s smiles look better with teeth showing vs. not.

3)      Your eyes – should be open and also “smiling” (vs. glaring), and each one should be as close to similar in size as possible. And unless you’re going for a more artistic look, the eyes should be looking directly at you, the viewer.

4)      Head orientation/position – the position of your head can also significantly affect how you look – you’ll want to pay attention to

5)      How well the lighting gives definition to your face (this is different than exposure) – is it pleasing to look at?

6)      If you’ve tried different clothing options, how does the outfit enhance (or detract) from your face and the overall look of the image? If you’re using the image for your LinkedIn profile, how well does the image go with the description of your strengths, focus, accomplishments (your brand)?

Assuming you’ve got a number of great potential final selections, be careful not to overthink your choices. Focus on the most obvious things, and things that will really matter to the viewer. But if you do get stuck, take a break, come back to your selections and seek input from a spouse, significant other, trusted friend, etc.. We’re often overly critical of how we look (when was the last time you heard someone say they think they look great?).