Derek Jeter teaches a class on media relations and interviewing

It took me a while to get around to reading the much-discussed New York Magazine profile of Derek Jeter, but I think there are some nice insights about the media from the famously opaque shortstop who played his last game Sunday.

The story, headlined “Derek Jeter opens the door,” features relatively intimate pictures of Jeter, many of them taken in his homes in New York and Tampa by Christopher Anderson, whom Jeter commissioned to photograph his final year in baseball.

I found the passages where the Captain talks about his interactions with the media particularly interesting. Jeter is obviously a private person by nature—he mentions this at one point in the story—but he also has job-related reasons for not opening up. His job, and reporters’ jobs. New York’s Chris Smith writes:

“In New York there’s a lot of attention off the field, a lot of distractions,” he says. “My job on our team all along is to try to limit distractions and try to keep it about the game. I think a lot of times players get in trouble when they’re asked questions and they think they have to find a way to answer it. If you ask me a question and I say, ‘I don’t know,’ there’s really no follow-up.”

Pretty shrewd, but it’s also one of the reasons writers say Jeter can be a boring interview. “If I was giving them headlines all the time, I wouldn’t have been here for 20 years,” he says. “But they ask boring questions. Give me a different question, and I’ll give you a different answer.”

Jeter has been so committed to the first part of that equation that it’s hard to imagine things would have been different if the media had asked brilliant, fascinating questions, rather than the ones he calls boring. It’s also hard to imagine that in 20 years, all of the questions were boring. In two decades of daily talking, even sportswriters can come up with an interesting question from time to time, just by accident.

Still, I’m OK taking Jeter’s advice to ask more interesting questions. One thing I try to do is picture how I would react if I were on the receiving end of my question. Would I want to answer it? Would I be interested in engaging with it? Or would it be something I’ve heard a million times before, or wouldn’t want anything to do with?

I once got a lesson in this from Tony La Russa, when he was managing the Cardinals. I was talking to him near the batting cage before a game and I asked him some question or other about bullpen usage. “Now, that’s a bad question,” he said, and then he explained to me why it was a bad question: He had no way of answering it without saying something that would hurt the feelings of at least one of his pitchers, and he wasn’t going to do that. The question was a dead end.

I don’t know why he didn’t just blow the question off. I guess he was feeling expansive that day. But I appreciated the lesson and I still think of it often, not in the sense of “How can I ask a question that won’t put the subject in a bad spot?” but more like “How can I ask a question that will make this person say something interesting?” That approach might be different for different interview subjects.

There’s one other little gem in that answer from Jeter: “I think a lot of times players get in trouble when they’re asked questions and they think they have to find a way to answer it.”

I agree, and thank goodness for that, right? A related point is that one of the greatest tools an interviewer has is silence. Most people hate silence in a conversation, and will make an effort to fill it by speaking. Sometimes the best question is simply an interested look at the end of an answer, a social cue that says, “Yes? Go on. I’m listening.” On the phone, good old silence can do the trick.

At that point, clearly, Jeter’s done talking. Most people aren’t.