Had the good fortune to shoot for Time 100 recently- a really wonderful guy Matt Berg, who has developed a text messaging system to track children’s health that is being used in Africa-ChildCount+.
Got an email back from him saying he was really happy with the picture and felt it reflected who he is, which is interesting- you spend a couple hours with someone and try to put that into a picture. From experience I know that the way I see someone in their picture is often very different from how they see themselves. Nice when the two dovetail.
Another view;

