So if you’re not Mike Wallace, how do you ask the hard questions? Here’s my top 10 tips for conducting tough interviews:

• Do your homework. The more information you have, the better prepared you’ll be to ask any kind of question, hard or easy. And it’s easier to steer the conversation back to tough topics when you’ve got your facts down cold.
• Write questions down. In an age when everyone seems pressed for time, it’s not uncommon for interview subjects or their PR handlers to ask for questions in advance. That’s fine, especially since it forces you to prepare. But once you’re talking, don’t feel obliged to stick to the script. When you’ve got a subject comfortable, go with the flow and toss out a couple juicy questions that aren’t on the list.
• Don’t ask “yes” or “no” questions. Don’t give an interview subject the opportunity for monosyllabic answers, otherwise you’ll be stuck with no good quotes. Ask open-ended questions that makes them think, such as “What led you to that decision?” or “How did you solve that problem?” or “What else can you tell me about that?”
• Don’t be afraid to look stupid. What if you have the opposite problem and your subject is a know-it-all who talks in circles all the better to intimidate you? If what they’re saying isn’t obvious to you, it won’t be obvious to your readers either. So swallow your pride and ask, “Can you run that by me again?” or “I’m not sure what you mean by that?” or “Can you explain why?”
• Don’t let a subject off the hook. You ask a question, they won’t answer. Ask a different way. Or ask why they won’t answer. I get this a lot because I interview executives at private companies who don’t want to talk about revenue or other money matters – and if they’re privately held, there’s nothing forcing them to divulge it. Coax it out of them by asking “Can you give me a range?” Or “What do companies in your industry generally charge?” or “How much did sales increase over last year?”
  
• Get specifics. Don’t be satisfied with pat answers or industry jargon. This is especially true if you’re writing about a field or subject with a language all its own, like business, medicine or technology. If you don’t understand the terminology an interview subject is using, don’t be afraid to ask “Can you explain that for me?” or “I’m not familiar with that term, what does it mean?”
• If you’re pressed for time, front load. If you’ve only got a celebrity or CEO for a couple minutes, cut to the chase. Ask your three or four most important questions right away so you’re sure to get the information that you absolutely positively have to have or your editor will kill you – or your story.
• Play good cop/bad cop. Interview subject not cooperating? Or do you have to ask someone about something they’ve been blamed for or accused of? Start out polite and only get more assertive or aggressive if you need to. In these cases, save hard ball questions for the very end, so you have time to soften them up and they let their guard down. What’s the worst thing that could happen? They refuse to answer or walk out of the interview – at least you got answers to your other questions.
• Circle back. The subject won’t answer a question the first time around. Let it go, move onto your other questions, then come back to it at the end. Approach it by saying, “Now that you’ve had more time to think about it, what did you really want to say about Topic XXX?” or “I’d like you to reconsider talking about XXX.” All they can say is no. Then again, your solid interview skills may lead them to reconsider.
• Psyche yourself up. Football players get pumped for the big game by listening to a pep talk or their favorite up-beat song, praying, jumping up and down or performing some other ritual. Figure out what psyches you up and use it. Then pick up the phone.