Headshot Photography Tips That Actually Help (From the Photographer's Side of the Camera)

Most headshot tips articles are written for the person being photographed. Wear navy. Get a haircut a week before. Stand up straight. Useful but shallow. The advice that actually changes how your headshot turns out comes from the other side of the lens: what the photographer is thinking about while shooting, and what you can do (or your photographer should be doing) to make it work.

These are the tips I use on every headshot session. Half of them are things subjects can do to make their own photos better. The other half are things photographers do, included so subjects can tell whether their photographer actually knows what they're doing.

Tips for the person being photographed

1. Eat before the session. Hungry faces look hungry. Tired faces look tired. The two hours before a headshot are not the time to be heroic about skipping lunch. Eat something real, drink water, show up at neutral.

2. Get the haircut three weeks out, not three days out. Fresh haircuts read as fresh haircuts. Hair grows in for two weeks before it sits naturally. Plan accordingly. If your hair grows fast and the cut needs maintenance, a touch-up at week 2.5 is fine.

3. Pick the wardrobe by what frames your face, not by what's trendy. Solid colors at the collar. No logos, no busy patterns near the neck, no scoop necks unless you're going for a specific look. Navy, charcoal, dark green, burgundy all read as professional. Cream and ivory read as approachable. White in direct sun blows out and steals exposure from your face.

Bring two options. The photographer will tell you which one wins. Most of the time it's the one you weren't sure about.

4. Practice the half-smile in a mirror once. Most people have two smiles: the polite tight one and the real laughing one. Headshots usually want something in between. The half-smile. Mouth closed or slightly open, eyes engaged.

The shortcut: think of someone you actually like and look at the camera as if you've just spotted them across a crowded room. The face you make is the headshot face.

Don't "practice smiling" in the literal sense. Practice the look-of-recognition. The expression you want is involuntary.

5. Show up 15 minutes early. Headshot sessions are 30 to 60 minutes. The first 5 minutes are always tense. Arriving early gives you time to settle, drink water, breathe. The photos from minute 15 onward are almost always better than the photos from minute 3. Give yourself the runway.

Tips for the photographer

6. Light from above and to one side. Always. The single biggest separator between professional headshots and amateur ones is light direction. Light from directly in front (a phone flash, a ring light, a webcam) flattens every face. Light from above and to one side gives the face structure: a slight shadow under the brow, a highlight on the cheek, a defined jawline.

For outdoor work: face the subject toward open sky but not toward direct sun. The sky itself becomes the soft light source.

For indoor work: a window to the subject's side is the cheapest version of this rule. Move them until the light shapes the face.

7. Focus on the closer eye, not the face. At wide aperture (f/2 or wider), depth of field is shallow enough that one eye can be in focus and the other slightly soft. The eye closer to the camera should be sharp. The eye further away is allowed to drift.

This is a small detail that separates serviceable headshots from professional ones. Every time you frame a shot, single-point focus on the near eye. Move the focus point manually if the camera puts it on the wrong spot.

8. Shoot at 85mm to 135mm on a full-frame camera (or 56mm to 90mm on APS-C). Wider than that and faces distort. The nose looks bigger than it is. The ears look smaller. Telephoto focal lengths compress the face and produce flattering portraits.

For iPhone users: use the 2x or 3x telephoto lens, not the 1x main camera and never the 0.5x ultra-wide. Step back, zoom in optically, not digitally.

9. Talk through the session, don't just shoot. Silent photographers produce stiff subjects. The face you photograph is the face the subject was making while you talked to them.

This isn't small talk for its own sake. It's directed conversation that produces the expressions you want. Ask about their work. Ask what the headshot is for. Ask what they want their colleagues to think when they see this photo. The face that answers "what do you want people to think when they see this" is more interesting than the face that smiles on command.

10. Shoot more frames than you think you need. Headshot sessions usually produce 200 to 400 frames. The final delivery is 5 to 15. The math is brutal: 95 percent of what you shoot will not be delivered. That's correct. Headshots live or die on the moments between the moments. Catching them requires shooting through them, not waiting for them.

The practical rule: when you think you have the shot, take three more frames. The fourth is the one with the right blink, the right micro-expression, the right tilt of the head.

What goes wrong on most headshot sessions

Trying to make the subject smile bigger. The bigger the smile, the faker it reads. Quiet expressions photograph better than forced energy.

Shooting at noon in direct sun. Hard shadows, squinting, blown-out highlights. Schedule for the first or last 90 minutes of daylight, or find open shade.

Letting the subject choose their best side without challenging it. Almost everyone has a "good side" preference that's based on what they see in the mirror. The mirror is the reverse of what others see. The side you think is your good side is often the one others find less natural. The photographer should shoot both sides, deliver both, and let the subject discover.

Over-retouching skin. Modern audiences read heavy skin smoothing as fake. Light retouching (a spot here, an eye-whiten there) is invisible and looks better than no retouching. Heavy retouching (porcelain skin, removed lines, sharpened jawline) is visible and reads as filtered.

What to look for when hiring a headshot photographer

Good signs:

• Their portfolio shows the same person across multiple shots, not just one image per subject
• Their portfolio has a consistent light direction (above-and-side, not on-axis)
• Their pricing is public and the package includes a specific number of retouched images
• They ask what the headshot is for before quoting

Warning signs:

• All-portfolio shots taken on the same overcast day at the same location
• Heavy retouching across the portfolio (skin looks plastic)
• No specific image count in the package
• Pricing only available after a phone call

Booking the session

If you're booking a headshot session on the SF Peninsula, the headshots page has the package details. Outdoor sessions start at $425 including 8 fully retouched final images, 45 minutes at a Peninsula location of your choosing, and personal + LinkedIn + company website licensing. Reach out with what the headshot is for and your target date.