6 ways to ask better questions

Whether I’m conducting a live on-air interview with a CEO, or sussing out answers from sources on background, I’m constantly asking questions. And I love it. As long as I can remember, I’ve always been inquisitive, which has won me friends, who’ve been flattered by my interest, and annoyed others, who found it invasive.

Over the course of my career at CNBC, at Fortune Magazine before that, and even back to the high school newspaper, I’ve been working to figure out how to ask better questions. Questions for which I’ll get interesting, surprising answers. Answers which teach me something, break news, advance a story, reveal someone’s interests, or simply help me get to know someone better.

I try to learn every day how to ask better questions by watching my colleagues, the best in the biz, and talking through interviews with my patient and experienced bosses.

1. Inquire, don’t interrogate

The same question can sound like an attack or an invitation – it’s all about tone. And I am shocked by how much of a difference a smile makes when asking a question you know someone doesn’t want to answer. This is something that my colleague Carl Quintinilla is brilliant at: he doesn’t take an aggressive posture or change his tone when he’s asking something tough, he just smiles and puts his interview subject on the spot. But he’s doing it in such a graceful manner, the folks he’s talking to don’t seem to realize he’s just turned on an interrogation spotlight.

This is especially true when I’m asking questions on background (meaning the answers will never be attributed to my source but are to help me understand the terrain). In those cases, my curiosity must be evident – and true. When my sources feel I am pressing too hard for some confidential insight into their industry, my go-to defense is, “What?! I’m genuinely curious to know!”

2. Don’t underestimate the power of surprise

Back when I was a reporter at Fortune Magazine I learned my then-boss Andy Serwer’s effective technique: ask a question that’s out of left field. It worked when he interviewed everyone from Mick Jagger, to Larry Ellison, to Carl Icahn. People are often so surprised, they’ll answer frankly and honestly, before they have a chance to think to go with the prepared PR-babble that’s oh-so predictable and dull.

3. *Really* Listen

If I get through a list of questions I’ve prepared, it’s a sure sign that I’m not paying enough attention to my interview subject. What’s infinitely better is reacting specifically to what’s being said. I always need to do my homework to prep on everything I want to address in an interview, but if I don’t deviate from the plan then I’m not doing my job.

4. Don’t “Ask” with a statement – just get to the point already

Everyone has been at those Q&A sessions where someone inevitably stands up and “asks” a long, rambling question designed to demonstrate his own knowledge rather than seek to gain knowledge from the expert. It’s a waste of everyone’s time. Journalists do it all the time – and I suffered through this phase as well.

I found a certain security in burying my tough question in several sentences to show just how much homework I’d done about disappointing earnings or a failed corporate strategy. The mere desire to impress an interviewee with knowledge has, in the context of an interview, the opposite effect: it implicitly takes power from the interviewer and gives it to the interviewee. An incisive question can itself imply the knowledge that the interviewer brings to the table.

I remember legendary Fortune writer and editor Carol Loomis telling me: if you’ve done your homework, it’ll be obvious, you don’t need to spell it out.

5. Ask both the questions people are eager to answer, and those they’re absolutely not

I love to hear people talk about the stuff they’re most excited about – their eyes light up, they gesticulate and lean in. It may not be the most critical for a story or background reporting, but it’s always worth taking the time, because the answers may benefit from that passion. When I pause from asking Disney CEO Bob Iger about quarterly results to throw in some questions about Star Wars, his whole persona changes – you can tell he’s genuinely excited to share hints about the upcoming films.

And on the other end of the spectrum, don’t be dissuaded from asking about stuff people don’t want to discuss. Even if you know they won’t answer it, it’s worth trying. Sometimes I preface a question with “You know I have to ask.” If I don’t get an answer, I’ll just keep trying by asking smaller pieces of a question.

6. Break up big questions into little bites

If I ask big, sweeping questions, I often get long, rambling answers, where even the person I’m interviewing can lose track of what he or she was talking about. The alternative to asking “What’s the future of social?” is breaking that 30,000 foot question into something more manageable, like “Will Facebook still dominate social media in the future?” Or, “Will we see a focus on privacy as a backlash to the rise of social media?” A bunch of specific questions might lead to an over-arching question later, but I find it’s useful to help people build with concrete answers before they get to a big theory.

Published in collaboration with LinkedIn

Author: Julia Boorstin is a CNBC Reporter covering media, social media, entertainment & startups.

Image: A foreign journalist raises her hand to ask a question during a news conference with Jiang Weixin, minister and secretary of the CPC Leadership Group of the Ministry of Housing And Urban-Rural Development, during the 18th National Party Congress (NPC) in Beijing November 12, 2012. REUTERS/Carlos Barria