How to Choose a Headshot Photographer (From Someone Who Does This Every Day)
I've been a professional headshot photographer in Boston for years. Headshots are not a side service for me. They're my specialty. And I hear the same story all the time: "I booked the cheapest option, I felt awkward the whole time, and I've been hiding behind a photo I hate from two jobs ago."
That's usually why someone's LinkedIn photo is a decade old. It's not laziness. It's that the last experience was uncomfortable, and nobody wants to repeat it.
This guide is for you.
Make Sure You Actually Like Them
This matters more for your headshot session than almost any other kind of photography. The camera reads discomfort instantly. If you don't feel at ease with your photographer, everyone feels it when we see your jaw locked up, your shoulders shrugged to your ears, your eyes looking distant, and no amount of retouching fixes a tense expression.
Look for patterns in Google reviews and testimonials. Do clients mention feeling comfortable? Do the words "easy," "fun," or "put me at ease" keep showing up? Over 600 of my reviews are five stars, and the thing clients mention most is that the session was actually enjoyable, even for people who dreaded it. And then talk to them to see if this remains true.
You should be able to feel out if your photographer has the right vibe in the first minutes of a phone call or Zoom. Trust your gut.
Look for Headshot-Specific Experience
Not all photographers are the same. Wedding photographers excel with couples on an already romantic evening. Commercial photographers do magic with professional models paid to look ‘photogenic.’ Headshot photography is its own skill set. It's about lighting one face well, directing a person who hates the camera or who's nervous, and producing an image that works hard for you on LinkedIn, speaker panel bios, and everywhere your name shows up.
Ask to see a portfolio of headshots, specifically with regular people. Not portraits with hands holding boutiques. Headshots. Look for variety in the faces, not the backgrounds. A great headshot photographer can make a software engineer, a CEO, and a nonprofit founder all look like people you'd trust with your business.
You Shouldn't Have to Know How to Pose
While other photographers just expect you to know how to pose and smile, you probably don't. Most of my clients walk in saying some version of "I'm not photogenic" or "I never know what to do."
The photographer's real job is coaching. Before I was a photographer, I was a teacher of 13 years, and that training helped me to read if a kid is hiding his struggles from across the room. I notice. And I’ll tell you exactly what to do with your chin, your shoulders, your eyes. You are never left guessing in front of a camera while someone silently clicks away.
I say a bunch of stupid jokes (but I think they're hilarious) which relaxes all the facial muscles, your eyes light up, your body lifts another half an inch in joy and confidence, and then I snap a succession of pictures to capture the best micro expressions.
Ask any photographer you're considering: how do you direct someone who feels awkward in front of a camera? If the answer is vague, the session will be too.
Ask: ‘Will the Stylist Stay for My Whole Session?’
A $100 headshot and a $700 headshot are usually not the same product, and the difference isn't ego. It's everything that happens around the photo. Does your photographer help you find your vibe to reach the your target audience. How conservative or wide your smile is? Are you looking to impress Venture capitalists or are you inspiring a room of women in tech with your mentorship?
Some other questions worth asking before you compare prices: Do you have professional guidance choosing your final images together during the session, or wait days for a gallery link and have to figure it out by yourself? How many outfit changes, and does taking off a jacket count as one? If hair and makeup is offered, does the stylist leave after prep or stay through the whole session? What does retouching include, and will you still look like yourself? And when do the finals actually arrive?
Every one of those questions exists because someone got burned. The gallery link sounds fine until you're alone on your couch trying to pick between 200 nearly identical photos of your own face. The hour in the makeup chair is wasted if nobody's there to catch the flipped collar in shot 40. And the retouching question is really asking: will my coworkers still recognize me?
You're usually getting a headshot because you need it for something, like a new role, a speaking engagement, or a website launch.
There's no single right way to run a session, and I have strong opinions about how I run mine. But whoever you hire, know exactly what you're buying before you buy it.
Choosing a headshot photographer comes down to a simple question: will this person make me look like the best version of myself, and will I actually enjoy the process? Ask good questions, look at the work, read the reviews, and trust how the conversation feels.
If you're in the Boston area and want to talk through your headshot, I'd love to help.