Professional models know how to produce such expression at photographer command, normal people don't.
Still good photographer are able to get it from famous actors/politicians/sportsmen.
I've been asked to do some portraits for a friend portfolio, what should I ask for? Of course I don't want to ruin our friendship.
This question is related to How can I get my portrait subjects to look natural and drop the cheesy smile?
but it's also different because I'm talking about formal portraits, so I don't want a "natural" expression but a meaningful one.
This is also true for my own self-portraits...
Answer
In my experience it's much harder in a more formal studio environment, I've found it much easier in more natural settings. However, in both cases, engaging in a thoughtful conversation may trigger the expressions you're looking for more naturally because, in general, I find that asking people to "look thoughtful" results in a very exaggerated look just as "look happy" will do.
As another suggestion, the angle of your shot is probably going to help this along alot more. If the shot is fairly direct, it won't look as natural, but a shot more to the side with the subject looking off to the distance a little will look a lot more thoughtful. You still want to see both eyes, so it's not necessarily a full profile shot. Something along this line, perhaps:
That was a candid portrait of my niece back in the spring and, at the time, she was running around with a bunch of other kids collecting up hidden candy in the backyard! I just happened to catch her in a pause that looked more contemplative than excited.
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