A headshot has one job
It has to make a stranger, looking at a small circular crop for less than a second, decide that you seem competent and approachable. That is the entire brief. Almost everything else people worry about in a headshot is secondary to it.
This is why the most common failure is not a bad photograph. It is a technically good photograph of someone who looks uncomfortable, or unapproachable, or like they were photographed for a different purpose entirely.
Where it will be seen changes what you need
A headshot for a professional network is cropped tight and viewed tiny. It needs a clear face, strong separation from the background, and an expression that reads at thumbnail size. Subtlety is wasted here.
A headshot for a company website or a speaker profile has more room. It can include shoulders and some environment, and it can carry a bit more personality.
A press or author photograph can be looser still, and often benefits from looking less like a corporate portrait and more like a photograph of a person.
Tell your photographer which of these you need. They are different crops, different lenses, and sometimes different sessions.
Expression is the whole thing
The difference between a headshot that works and one that does not is usually the expression, and it is the part people least expect to be difficult. A held smile looks held. No smile at all often reads as cold at small sizes.
What works is a genuine, slight expression, which cannot be performed on command. Good portrait photographers get it by talking to you until you stop performing, then shooting. If someone photographs you in silence for twenty minutes, you will look like someone who was photographed in silence for twenty minutes.
Practical preparation
- Bring more than one top. Two or three options in different tones cost you nothing and give you real choice afterwards. Mid-tones photograph more forgivingly than pure white or pure black.
- Avoid getting a haircut the day before. Two or three days of settling looks more natural.
- Skip anything new and untested on your face. A shoot is a bad time to discover a reaction.
- If you wear glasses, bring them, and mention them when booking. Reflections are manageable but the photographer needs to know.
What to ask for in the deliverables
Ask for the files in more than one crop: a square or circular-safe tight crop for profile pictures, and a wider version for websites and slides. This is a trivial request at edit time and saves you cropping badly later.
Also agree on retouching. The useful standard is removing what is temporary and leaving what is permanent. A blemish that will be gone next week can go. Lines that are simply your face should stay, both because they are you and because heavy retouching is obvious and undermines the credibility the photograph exists to build.
When to redo it
A headshot has a shelf life. If your appearance has changed noticeably, or the photograph is more than a few years old, it is working against you: anyone who meets you after seeing it experiences a small mismatch. That is a poor first impression to have engineered.
Booking
Portrait work is widely available on the platform. You can compare photographers at portrait photography. When reviewing portfolios, look past lighting quality and ask a simpler question about each image: does this person look like someone you would want to work with? That is what your own headshot has to achieve.