Executive portraits
Executive Portraits and CEO Headshots in Chicago
Executive portraits are photographs made for annual reports, investor decks, press pages and speaking bios — places where the audience is deciding whether to trust a judgement, not just a face. Kay Choi photographs leadership across Chicago and the western suburbs, in studio or in your own building.
What is an executive portrait?
An executive portrait is a photograph of a leader made for the contexts where their name arrives before they do: a proxy statement, a keynote programme, a board page, a press release, an acquisition announcement. Its job is to carry authority without performing it.
That is a harder brief than a standard headshot, and the reason is scale. A headshot is usually consumed at thumbnail size by someone who already knows who you are. An executive portrait is often reproduced large — a full page, a stage screen, a lobby wall — where posture, hands, tailoring and the room all become legible and every one of them is saying something.
It is also usually one photograph of several. A chief executive typically needs a formal frame for the annual report, a warmer one for internal communications, and something looser for a conference bio. Photographing those in one sitting is far cheaper than discovering in November that the only usable file is two years old and cropped from a group shot.
Photographed in your building, or in the studio
Leadership time is the scarce resource, so the session is built around it. Kay photographs on site — boardrooms, executive floors, atriums, manufacturing space — and plans the lighting and equipment around the room and around the day's meeting schedule rather than across them. Building access, visitor passes, facility guidelines and parking are handled before she arrives.
The alternative is a studio sitting in Naperville, which gives a controlled, repeatable result: useful when a leadership page has to look coherent even though the people on it were photographed months apart.
For a whole leadership team in one visit, with matched light and background across everyone, see team and corporate headshots.
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How an executive sitting is run
- Time on the day
- Planned around the diary — a defined slot, not an open-ended booking
- Set-ups
- Formal, warm and environmental frames from one sitting where the schedule allows
- Direction
- Guided posture and expression throughout; nothing is left to chance in front of a board
- Review
- Images on screen during the session, so approval happens in the room
- Retouching
- Professional retouching appropriate to a printed report and a stage screen
- Delivery
- Files prepared for web, LinkedIn and print
Corporate, team and larger branding projects are quoted on the size and needs of the project. Session length, the number of final images, editing, delivery, usage and the final price are agreed in writing before the day.
Why executives dislike being photographed, and what to do about it
The most common thing Kay hears from senior leaders is a version of I photograph badly. Almost nobody photographs badly. What people usually mean is that they have only ever been photographed by someone who pointed a camera at them and waited.
The fix is direction. Where to put your weight, what to do with your hands, where to look a half-second before the frame, when to breathe out. It is a small amount of instruction, delivered continuously, and it is the difference between a portrait that looks like a professional and one that looks like a person being processed.
The screen matters too. Seeing frames during the session removes the part people actually dread — handing over control and finding out weeks later. Clients say it turns the sitting into something they are steering.
Kay Choi is an excellent professional photographer and her shots are great! She has a passion and makes her models look great with her photography skills. I will recommend her for professional photos.
Questions
What should an executive wear for a portrait?
Whatever you would wear to the most senior meeting in your calendar, in a colour that separates you from the background. Structured shoulders photograph well. Fine stripes and small checks can shimmer on camera, so bring an alternative. Wardrobe guidance is part of the planning, and there is a fuller guide to what to wear.
How long does an executive portrait session take?
It is built around the diary rather than a fixed block, and the agreed length is confirmed in writing before the day. On-site sittings for a single executive are typically the shortest thing in their calendar that week; a full leadership team is planned as a scheduled rota so nobody waits.
Can you match portraits taken at different times?
Yes, within reason — this is the main argument for a studio set-up. When a leadership page has to stay coherent as people join, Kay can repeat the same background, lighting and framing for later arrivals so the page does not visibly stratify by hire date.
Do you photograph board members and non-executives too?
Yes. Board portraits are usually the most formal frame in the set and are often needed at short notice for an announcement. They are quoted with the rest of the project.
Arrange a sitting
Authority, photographed rather than performed.
On-site sittings across Chicago and the western suburbs, or a controlled studio set-up in Naperville. Corporate work is quoted per project.