Most headshots taken by a professional photographer meet the technical standard. Correct exposure. Clean background. Subject in focus. These things matter, but getting them right is expected, not exceptional. What separates a good headshot from a great one happens above the technical level.
What 'works' actually means
A headshot that works looks like the person at their most credible and at ease. Not stiff. Not performing. Not trying to project a version of themselves they've constructed for a camera.
When someone looks at a photo and thinks, 'that's a good headshot,' what they're registering is usually a combination of three things: the expression reads as genuine, the subject looks comfortable in their own skin, and nothing about the photo is distracting from the person.
Getting there requires direction, connection, and selection. Each of those is a distinct thing.
Direction
Most people don't know what their face is doing in a photo until someone tells them.
A slightly tight jaw reads as tension. Chin too high reads as guarded. Eyes slightly unfocused suggest distraction. None of these are things a subject notices in the moment. They're what a photographer sees through the lens and corrects in real time.
Good direction isn't about posing. It's about reading what the camera is picking up and making small adjustments until the photo reflects how the person actually carries themselves, rather than how they carry themselves when they're aware of being photographed.
Connection
There's a difference between an expression that looks inhabited and one that looks performed.
Trying to look confident usually produces the opposite: a kind of effortful seriousness that reads as stiffness. The best headshots tend to capture a moment when the subject stopped thinking about the camera. Something the photographer said landed. They looked away and then back. Something shifted.
That's not luck. It's what happens when a session gives the subject enough time and attention to get past the part where they're self-conscious.
Selection
In any given session, there are frames that are technically fine and frames that actually work. The difference is often subtle: a fraction of a second between an expression that's slightly strained and one that's at ease, the camera catching something real rather than something constructed.
Knowing which is which is a skill. It's why the number of frames shot in a session isn't a reliable measure of quality. A high-volume session produces many technically adequate images. A more deliberate one produces fewer frames and better selection.
What this means in practice
If you've had a headshot session that felt rushed, that's useful information. If you've seen your photos and thought they look like you but not quite like you at your best, that's usually a direction and selection problem, not a technical one.
A great headshot is the result of time, attention, and a photographer who knows what they're looking for. Those conditions aren't accidental. They're built into how the session is structured.