Silver-Halide wrote in post #17428287
Thanks all for the brutal honesty. The truth hurts--but not as much as not knowing.

I am embarrassed to admit that I forgot my large parabolic shoot through umbrella. For the key light I had one of those pocket diffusers on hand, but obviously the light is too harsh in summarizing the comments.
Right now I'm planning to print these out and take them too him and offer to reshoot. With the umbrella I should mitigate most of the spectacle shadows as well as soften the overall complexion, right? Worth doing with only two off camera flashes? These were shot at night so maybe if we tried for an afternoon shoot the reflector could become a third light source. I would guess he will just take his favorite of the three and call it good--he was just planning on using his iPhone at first

Thanks for accepting the comments graciously.
To expand a bit on quality of light: it's both perfectly possible and perftectly valid to use hard light only for portraits and obtain good results –for both men and women. It's all a matter of position of the light (learn the portrait patterns –Rembrandt, open loop, closed loop, Paramount...) and the right ratios.
I wouldn't call this photo superb, but it's an adequate example:
I used a 12" bowl reflector and went for an open loop pattern. I used a white reflector on the opposite side of the light to fill in shadows a bit and lower the ratio. Season to taste, depending on the mood you want to go for. Traditionally, higher ratios are preferred for portraits of men, as it adds more character.
A word on hard light: it will make the texture(s) of a subject more prominent, thus emphasising skin blemishes. That's one reason photographers don't use it for wrinkled subjects –however, this might be just what you want, to convey experience (that mood thing again). On the other hand, you can deftly use deep shadows to hide other 'problem' areas, such as double chins.
One last thing: the smaller your light source, the more noticeable any hot spots will be: you can see that in the photo above, on the model's forehead. A good reason to always keep skin towels handy.