Client unhappy, not sure how to do better

I took some headshots for a client, all the shots turned out great except one person in particular, the boss, isnt happy with his headshot. He wants to reshoot, im not sure i can do better, meaning he doesn't like the way he looks and i'm not sure I can make him look better not that he looks bad or anything. He is happy with all the other staff and office shots i provided, he just doesnt like his pic...

here are the images... thoughts? do i just do a reshoot for just him? not sure how to handle this...

Maybe ask him what he doesn't like about his shot and then decide if its a processing issue or if you need to reshoot it. The boss will decide if you get future work from them after all.

The first seems reasonably well done to me; the second uses a background that doesn't really work for a headshot.

Can the boss get more specific about what he doesn't like about his photo ?

Agree with the above ^

Only thing realy bad about this is his wrinkled lab coat and shirt..... maybe he could use a comb too

the shots were done in the office and the the second shot they wanted the pictures in the background, so i did.

i'm going to talk to his assistant tomorrow, she is the one who asked me if they could get a reshoot of just him.

I think it's him more than you. As others already said - more attention by the client to grooming and wardrobe will help a lot. The only other thing I can think is to try to do something to de-emphasize his chin and the area beneath his chin. Also, I would go with a different background color if possible.

Excerpt from "The Portrait Photographer: Corrective Techniques"

Double Chins. To reduce the view of the area beneath the chin, raise the camera height so that area is less prominent. Tilt the chin upward and raise the main light so that much of the area under the chin is in shadow.

http://portrait-photographer.blogspot.​com …orrective-techniques.html

ask him to show you a few pic of himself to get an idea of his taste?

I think most people don't like themselves in pictures. Ask him what he doesn't like about it. And don't use the cluttered background with all the pictures.

He may never really like his photo, but some other things to try - have him give you some different expressions. Maybe he doesn't like his smile. It does look slightly awkward to me like he's not opening his lips enough. So capture a few different smile variations.

Do you have an off camera flash? Maybe get a back/hair light.

I would reshoot if i had the time, and take a bit longer to connect with him and get to know what he doesnt like about himself. Its a good opportunity to build a stronger business relation.

Off the top of my head though, the light feels low, like youre lighting his chin instead of his face, shoot with a 85mm if youre that tightly cropped, shoot from eye level, chin out and down.

Don't have him sitting down.

maybe have him make more of a smirk with his mouth closed, his smile is odd. his eyes looks a little independent like his left is a little lazy maybe find an angle where its less noticeable

The more I look at that photo - that white coat he is wearing is pretty horrible.

His chin is a bit too high in the first photo, and his shoulders should be more relaxed in the second. Have him push his whole head forward for more pronounced jawline (ala Peter Hurley). And perhaps a bit more natural looking smile.

thanks for the tips. i'll try a bunch of different poses, i need to mimic the lighting and the background of the other head shots so that needs to remain, this isn't my preferred setup, but the room was small and i had decent window light supplemented with an umbrella and speed light, i'll try to raise it up a bit.

i didn't take as much time as i should have to get him to do more poses since had only their lunch break to get the entire staff and other pics of the office. I need to make sure he is happy so i will.

To the suggestions above about posing and angles, I would add that what we can see of his haircut is unflattering. He doesn't just need a comb, he needs a barber. Sideburn and long hair over left ear are overdue for a trim.

This sitter would look better (more dignified) with his shirt buttoned higher up.

Having the camera higher is especially important with the shape of his head, which is rather bottom-heavy.