A headshot has a job. It sits on a LinkedIn profile, a company bio page, a conference programme, a book jacket. It gets looked at for about two seconds by someone deciding whether to take you seriously.
That makes it different from portrait work. A portrait can be interesting. A headshot has to be effective, and effective is a narrower target.
What a good headshot actually does
Three things, in order of importance:
It looks like you on a normal day. This sounds obvious and it’s the most commonly broken rule. If your headshot is so polished that people don’t recognise you when you walk into the meeting, it has failed at its only job. Heavy retouching is the usual culprit.
It matches your field. A litigator, a therapist, a startup founder, and an actor need visibly different photographs. Lighting, expression, wardrobe, and background all shift. A photographer who shoots everyone the same way is giving you a generic result and hoping it fits.
It reads at small sizes. Most headshots are viewed as a circle roughly a centimetre across. Busy backgrounds, low contrast, and clever compositions all collapse at that size. Squint at any candidate photographer’s portfolio images — if they still work, the lighting is doing its job.
How to judge a photographer before booking
Look for consistency, not peaks
Anyone can produce one great frame. What you want to know is whether they produce good frames reliably. Look for a portfolio with many different people in it — different ages, different skin tones, different face shapes — and check that the quality holds across all of them.
If a portfolio is all one demographic, that’s worth noticing. Lighting that flatters one skin tone doesn’t automatically flatter another, and it’s a skill that shows.
Ask how they handle expression
This is the part people don’t anticipate. Most of a headshot session is not about the camera — it’s about getting a genuine expression out of someone who is self-conscious about being photographed.
Ask directly: how do you get people to relax? A photographer with a real answer will describe a process — conversation, prompts, showing you the back of the camera early so you stop worrying. “I just make people comfortable” is not an answer.
Ask what you’ll actually receive
- How many final retouched images, and can you choose which ones?
- Do you get crops for different platforms, or one file?
- What’s the retouching approach — blemishes and stray hairs, or reshaping?
- Are outfit changes included, and how many?
- What’s the turnaround?
- Do you get usage rights for your own professional purposes?
That last one matters more than people realise. If your employer will use the image, or if you’ll need it for press, make sure the licence covers it.
What to wear
Solid colours in mid tones. Avoid tight patterns, which can shimmer at small sizes, and avoid pure white or pure black, which are harder to light well.
Bring two or three options in different necklines and colours. Necklines change a photograph more than people expect. And bring something a shade dressier than your normal working wardrobe — you can always dress it down on the day.
Get a haircut a week out, not the day before. Same principle as skincare: give yourself time to look like yourself again.
Studio or location?
Studio gives you clean, controlled, consistent light and a neutral background. It’s the safe default, and if your company needs matching headshots across a team, it’s the only sensible option.
Location or environmental puts you somewhere with context — an office, outdoors, a workspace. It’s warmer and more distinctive, and it works well for founders, consultants, creatives, and anyone whose brand is personal rather than corporate. It’s less flexible about weather and time of day.
If you’re unsure, ask which the photographer prefers and why. The reasoning tells you more than the choice.
Red flags
- Portfolio full of heavy retouching. If everyone has poreless skin and a reshaped jaw, that’s what you’ll get.
- No range of subjects. One demographic, one lighting setup, one expression.
- Charging per image with no included count. Fine if disclosed up front. Unpleasant if discovered at the gallery.
- No conversation before the shoot. Someone should ask what the photo is for.
- Rushed sessions. Fifteen minutes is rarely enough to get past the first stiff expression.
Frequently asked questions
How often should I update my headshot?
Every two to three years, or whenever you’ve changed something noticeable — hair, glasses, weight, facial hair. The test is whether someone would recognise you from it. If the answer is “mostly,” it’s time.
How long does a session take?
Anywhere from twenty minutes for a straightforward single look to a couple of hours for multiple outfits and setups. Longer sessions aren’t automatically better, but very short ones leave no room to relax, and the first few minutes are almost always the stiffest.
Should I get professional hair and makeup?
Optional, and more useful than people expect — particularly for anyone who’ll be photographed under studio lights, which are less forgiving than daylight. If you go without, keep it close to your everyday look so the photo still resembles you.
Can I use a phone photo instead?
For some contexts, honestly, yes. Phone cameras are good now. What they don’t give you is controlled lighting, and lighting is most of what separates a professional headshot from a good snapshot. If the photo is doing real work — winning clients, getting you hired — the difference is visible.
What if I hate being photographed?
Most people booking headshots say this. Say it out loud when you book, because it changes how a good photographer runs the session — more conversation, more direction, more time before anything serious happens.
Booking in Monmouth and Ocean County
I shoot headshots and professional portraits across the Jersey Shore — studio work, on-location sessions at your office, and outdoor environmental headshots around Rumson, Red Bank, Spring Lake and Point Pleasant. Team bookings welcome. Get in touch and tell me what the photos are for; that determines almost everything else.