I had him lean forward with his chin resting on his fist rather than sitting straight up — that lean-in changes the whole read of the shot, making direct eye contact feel more engaged and confident instead of stiff. It's a small adjustment, but leaning toward the camera instead of away from it is what gives a headshot some presence.
The plain grey backdrop and simple black tee keep everything focused on his expression, no wardrobe or background detail competing for attention — a deliberately stripped-down look that fits a founder or startup headshot better than a suit and tie would.
It's the kind of direction I lean on for headshot sessions built around a more casual, confident brand — the wardrobe and setting stay simple, so the posing and expression carry the whole shot.
1/200; f/2.8; ISO 500; 85.0 mm.