DeMato Productions


NYC Branded Lifestyle Portrait Photographer | This is where I share with thought leaders and other high-level entrepreneurs how to present themselves powerfully, purposefully and authentically in their image content on their websites, social platforms and sales vehicles.

How I Helped My Client Select The Best Headshots For His Brand.

Thanks to digital SLR technology and compact flash cards with ridiculous amounts of storage capacity, I have the ability to shoot tons of ultra high-quality images per session.  On average, I shoot somewhere in the neighborhood of 200-400 images per 2-hour headshot session, depending upon the circumstances. 

Although it is a luxury to have this much material from which to choose, the chance that a client will become completely lost and overwhelmed by a sea of images is very high.  

In my experience, this is more the rule than the exception.  

Fortunately, I enjoy and also understand the importance of the image selection process, pointing out to my clients each headshot's strengths and weaknesses.  In fact, more time during the headshot session is spent in the office reviewing and analyzing the pictures than in the studio shooting the images.  

I always remark to clients that reviewing their images is where the bulk of the work happens; not only are the unusable images eliminated, but I also do a lot of coaching, pointing out what aspects of these images (body/head angles, posture, clothing, hair staging and positioning, etc.) is working and not working.  

Aside from offering technical direction, I also highlight the headshots that have truly authentic facial expressions and best represent the client's personality and brand. I set these images aside and point out to the client why she shots rock so we can plan to capture more images like it.

While the client might be overwhelmed by a large amount of useable headshots from which to choose, I love this problem - it means we had a very successful headshot session!

One of my most recent clients, Douglas, had this issue.


Douglas is a professional consultant who works in career development, transition and coaching for a variety of clients.  

He came to me to update his headshot for his marketing materials, including his website and LinkedIn page.  After a short chat to discuss the in's and out's of what he does for a living, while observing how he expresses his passion for it, I had a better sense of what types of images would work well in promoting the confident and approachable aspects of his personality.

When all was said and done, we ended up capturing 240 shots over the 2-hour session, with 4 different outfit looks.  Needless to say, there was a lot of headshots to look through and a bunch of tough choices to make, but I enjoy walking my client's through the process, one step at a time.

Between each outfit change, we would sit down to review every image on the big screen.  By the final round, we saved about 90 images, which was then cut in half by passing through the pile a couple times and cutting out the iffy images.  Our ultimate goal was to select 3 final headshots that each had it's own distinct vibe, yet managed to stay on message with his personality and brand.

Once we paired it down to under 20 images, that's when I group similar types of shots together on the screen so that it makes it easier for the client to see what's left and to find the best headshots. 

The first batch I wanted to review were the smiling expressions.


Fortunately, Douglas wasn't deathly afraid of the camera, so he presented himself quite naturally in his images.  It was also pretty easy to get a chuckle out of him, which really makes life easier behind the camera for me since I can't stand fake smiles in photo. 

Almost half the shots we captured were of him smiling or laughing, which is both a good and bad thing; the good thing is that he was able be loose and allow himself to be authentic in front of the camera.  The bad thing was that many of his laughing shots were a little too much to be used as a professional headshot.  We had to toe the line and find the image living in the sweet spot. 

Here are some of the finalists that we chose:





Although images 1 and 3 illustrate great personality, I pointed out that his laughing smile in both were a bit too gregarious to illustrate the authority figure stature tied to his brand. Although we wanted him to appear approachable and likable, we, simultaneously, don't want him to come off as guy who doesn't take himself - or his clients - too seriously.  Also of note, image 3 is a bit informal with the open-collared, plaid shirt.  

Although that look works for some professionals, it doesn't for him.  This would be a great image to post on his personal Facebook page, where there is more latitude for casual image posts.  

Though image 2 has a much more toned down laugh smile, I felt from the moment that we saw image 4 in the review session that it was the one.  We both agreed that image 4 was the most put together, on-brand image for his business.  Why?  Between the eye squint, the under control, yet lively, smile, the confident body language, the blue tie popping out and accentuating his blue eyes, we both fell in love with this image.  

Although each of these four headshots are wonderful in their own right, image 4 represents a man that a potential client can engage and trust with his or her business and be confident that the job will be done well.

2 more keepers to select.



For the next round, I wanted to stay away from teeth and find an image that had more a more complex expression to it; confident and approachable, yes. Pleasant guy to be around, yes.  Big, over-the-top smile, no.

We narrowed it down to these two:



Both images 5 and 6 stuck out to us when we initially came across them.  It was easy to find them since they were shot consecutively.  We both agreed how his nice guy nature shines through in both.  His jawline in both are solid, head angle is identical in both, and the tie/shirt combination compliments his eye color.  

There were a couple differences between the two, and that's what ultimately made the difference.  

With a solid eye squint and the addition of a subtle smile, we both concluded image 5 projected more warmth, while also presenting an authority figure quality necessary for a career coaches professional headshot. This headshot spoke to us in this way:

Though I clearly know what I'm talking about and have years of training and real-world experience, I come to you, humble and eager to assist, and will never judge or be condescending; I will meet you right where you are so we can work on you.  

He's reassuring, yet fully confident, knowledgable and a problem-solver.  We loved it, and he now had chosen his second headshot selected.

One more to go.


For his final headshot selection, I wanted to avoid a smile or smile-esque image by leaning him towards selecting a middle-of-the-road expression - not too much fun, not too serious - in order to inject that lets-get-down-to-business vibe into his headshot portfolio. 

These were the final two upon which we settled:



Douglas and I went back and forth on these, debating which one would work best to represent authentic aspects of his personality and brand.  He decided that they both do.


Obviously, he couldn't choose both, so we started to analyze the shots more intensely.  Both exhibit desirable qualities in a headshot.  Image 7 was a more straight-laced expression, yet confident and approachable, nonetheless.  His expression projected an authority figure presence.

Image 8, on the other hand, has a little more flavor sprinkled upon it.  Between the smirky mouth and the confidence projected through the eyes, this headshot possess a lively quality, and, it appeared that it was going to be the final selected headshot.  

But, then I started waffling again,  Although it's the more compelling shot of the two, was it the right choice as a professional headshot?  

After talking it over with Douglas for another couple minutes, I asked him that although we both feel image 8 is the more interesting expression of the two, and that he believes it accurately represents an aspect of his personality, was it a good fit for his brand?  Is this aspect of his personality appropriate for his business brand?

After pausing on that question, he responded no. 

We all have many sides to our personalities; some aspects are not appropriate for certain areas of our lives.  It was important to have this discussion with Douglas during the review session, because we were able to select images that maintain the integrity of his business brand while also staying true to who he is.  

Although he only chose three final headshots, he was able to walk away with the other ones and can use them on his social media pages.  After all, a good picture is still a good picture, and it would be a waste to let those images never see the light of day.

Selecting the most appropriate headshots from a session is a game of minutiae;  a slight turn of the head, lean towards or away from the lens, squint in the eye, hair flip or mouth smirk can completely change the entire dynamic of the expression.

It doesn't take much muscle movement to elevate one headshot above the rest.  

Although the session and review can be long and arduous, the results are extremely gratifying for clients since they know that they just wisely invested their time and money into their career and brand.