Portrait - 1st to be paid for

OK here goes... let me have it!

I was asked to go to his home to take this for a website (hence small size).
Below this is the "Original" and "setup".

I didn't move around his furniture and he had plain "Magnolia" walls. I have a cheap umbrella with 420EX and 580EX hand-held bounce on cable (pointing approx 45 degrees up). I chose to use my 30mm f1.4 Sigma, stopped down a little.

I had to take a lot of shots to get anything like a smile. Perhaps this was the hardest thing, trying to gently amuse him as well as composing my shots. His eye area is very dark - I didn't do anything about this. I did some cutting and pasting (some shirt from an other photo) to even up the shoulders a bit - he is shaped a bit unevenly.

I am pretty happy with this but I'm sure you can tell me what I could have done better (or could still do?).

Camera Model Canon EOS 500D
Lens 30mm
Focal Length 30.0mm
Image Size 4752x3168
Image Quality RAW
Flash On
Flash Type External E-TTL
E-TTL II flash metering Evaluative flash metering
Flash Exposure Compensation 0
Shutter curtain sync 1st-curtain sync
FE lock OFF
White Balance Mode Auto
AF Mode One-Shot AF
Picture Style Standard
Sharpness 3
Contrast 0
Saturation 0
Color tone 0
Color Space sRGB
Long exposure noise reduction 0:Off
High ISO speed noise reduction 0:Standard
Highlight tone priority 0: Disable
Auto Lighting Optimizer 0:Standard
Peripheral illumination correction Disable
File Size 19580KB
Dust Delete Data No
Drive Mode Continuous shooting
Live View Shooting OFF

1) Next time ask him to wear something without stripes. (And preferably something that doesn't show his chest)
2) Sit him with his shoulders facing about 45 degrees away from the camera and have him look at you instead of getting a dead pan straight face shot
3) Fix your white balance BEFORE shooting. Also it's a bad idea to mix lighting it tends to throw off white balance.
4) Add depth to your shot by using 3 point lighting
5) 30mm is a little wide for a portrait. Wide lenses make noses look big and are generally considered unflattering.
6) Don't cut and paste shirts on people. It makes them look like football players. Do it in camera.
7) Relax him by making him puff out his mouth and hold if for a few seconds. Then take the shot after he releases.
8) Turn his body to get the best angle.

If you took this for a passport photo ask him not to smile and ignore everything else I said.

Thanks for these valuable tips.
3) I shoot Raw - so I don't need to worry about white balance(just leave Auto so mostly ok but easy to change later)? I doubted there would be a lot of light from the window - actually I did try using a reflector on the left as I don't have a good 3rd flash but i am not sure it did much + I walked to the location so I couldn't carry too much! Where would you put the 3rd source?
5) I think you are right - I usually use 70-200 for portraits of children in the open. I did take my 17-55 I should have used that.
6) I didn't change his shirt - just used a tiy bit of extra "material" so I could even up his shoulders a bit.
7) not heard this one - I'll try it.
Not a passport photo.

Thanks again!!

I agree with Drumsfield, especially the need for a longer lens. Those of us who are gifted with a bigger honker dont need any extra help. You rarely ever want the shoulder square to the camera, this adds some bulk, often makes for rigid looking poses (fortunately he appears loose), Have him turn his shoulder so 45 degree and then look back into the lens.

There’s really nothing here that screams or even whispers "this is a professional portrait". Just to try and add to whats already been said.
1) I find the lighting to be real flat and well not very flattering. Try and use your lighting to add shadows and depth.
2) Bring a backdrop or two so you don't have to use the wall.