Lesson number 9: Do most of your homework.
It always feels like a balancing act. You want to be able to talk intelligently with the guy or gal, want to know something of who they are and what they do, but don't want to come off as a raving fanboy. You really don't want to try to know them better than they know themselves or know so much that what they have to say is uninteresting.
For me, as has been painfully pointed out, if I'm not all that interested in who I'm talking to or the subject I writing about, it shows like a pizza stain on a white t-shirt. I'm trying to fix that. I'm working not so much on faking finding everything interesting, but broadening my horizons so more things might actually be interesting. Hell, it might even work.
Other, more well-known interviewers, don't necessarily agree on the whole only sort of knowing the other guy idea. They want you to study your subject like it's a big test. Read all the interviews. Read everything about them. Listen closely to every, single song. Go through their garbage. That's not me. While digging and digging you might be able to unearth something special out of someone, you also don't get the person you're talking to.
Presumably, that's what you want and not to reduce them to quivering tears. Let Dr. Phil or some other television preacher do that.
Most people live pretty close to the surface of who they are. Musicians particularly often force a lot of their deep issue stuff close to the surface with what they do. The weepy singer/songwriters make their living picking at their own scabs. The metal guys make their living eating them. It's there.
The only real exception to this is the manufactured pop singer. Most of the time, they're sort of artistic mercenaries. They do their one thing, usually sing, and leave the rest of the heavy lifting (writing songs, writing music, playing instruments, conceptualizing their image) up to other people.
I've talked to a few of certified pop singers (Carrie Underwood, Martina McBride, Hilary Duff). They were the hardest interviews from my side of things because it's hard to see the actual surface. Their bios are also the most likely to be peppered with bullshit filler and talking points. Talking to them, at points, was a little like talking to cartoons, though I still got a sense of who they were even though what I knew about them was suspicious.
Underwood, for instance, had a remarkably well-developed ego, but was still in awe of being famous. She liked, at least at the time, the treatment from everyone and was quick to point out the sizes of her audiences numbered not in the hundreds, but in the thousands.
McBride seemed to have a growing disatisfaction for the industry that gave her the life she has. She didn't like the political correctness of country music, which she felt was personally limiting. I think she was being encouraged to conform to what is marketable, not what is necessarily representational of who she exactly is.
Duff wanted to feel normal, wanted people to think of her as normal, even though by her own casual statements that was obviously not true. Regular people, even regular rich people, don't have to close down a store in order to do recreational shopping as a break from touring.
I think if I'd focused too much on the homework, on the research about their careers and personal life, I might have let that be enough. It is easy to drown in information, but I'd have learned very little about them other than what they already wanted me to know.