The Three Most Common Issues in Executive Headshots (And How to Fix Them)

Many executive headshots fall short for the same reasons. When a headshot feels off, it often comes down to one of three things: expression, lighting, or intention.

Here is a simple breakdown of each issue and how I address it in the studio.

1. Forced or held expressions

Most people try to hold a smile the moment the camera comes out. The smile looks okay at first, but it’s still the canned version someone might have practiced in the mirror. It’s never a natural look - we call it the “half-assed-smile”.

Because of this, I never ask people to smile. I avoid the “s” word on purpose.

Instead, I keep the session conversational. I use humor and questions to help you forget about the camera for a moment. When a real reaction breaks through, I shoot through that moment. A big laugh is not a usable headshot, but the expression that follows it often is. It is unforced, genuine, and clear. That single moment carries more weight than an entire series of posed smiles.

2. Lighting that flattens features or adds harsh shadows

Lighting shapes the entire image. Poor lighting flattens the face, hides the eyes, or creates heavy shadows that draw attention to the wrong places.

I use what I consider the best headshot lighting in the world. If a better technical setup existed, I would use it.

The system is based on the Hurley Triangle using the highest-end cinema LED panels available. It creates dimensionality and shape in the face while removing unflattering shadows. Most importantly, it lights the eyes. Eyes communicate emotion, so they carry the image. I use constant lights rather than strobes because constant lights shrink the pupils. When the pupils shrink, the iris shows more color. This gives the eyes a punchiness and striking impact that strobes do not provide.

3. Lack of intention or direction

A headshot should have a purpose. When that purpose is missing, the image may look fine, but it does not say anything. It lacks direction.

I spend time listening before I start shooting. I want to know how the headshot will be used, who will see it, and what message the image needs to convey. Once we understand the goal, choices about lighting, backdrop, posture, and expression become simple. Without intention, those choices are guesses. With intention, they support a clear message.

Intentional images have more impact. They feel steady and focused. They help people understand who you are and what you want them to take away when they see your headshot.

A strong executive headshot is not an accident. It comes from natural expression, expert lighting, and clear purpose. When these three elements work together, the result is a headshot that feels honest and confident.


If you want to learn more about the process, I am always happy to share how each part of the session works.

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How to Book Full-Day On-Site Corporate Headshots in Boston

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The Anatomy of a Headshot Session