Business manager and chef talking in restaurant

The key to any successful conversation is being ready to engage. The more you know about the person you’re talking to, the easier it is. (jacoblund/Getty Images)

Accounting | The Profession

6 ways to get the most out of your next very important conversation 

Pro tips to keep interview subjects engaged and, most importantly, how to ask the right questions like a journalist

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Have you ever wondered how Barbara Walters always makes celebrities cry? Or how Christiane Amanpour makes world leaders squirm in their seats? It may seem like journalists have some secret talent at asking just the right question to provoke the response they desire, but in reality, that skill is something anybody can develop—and use to maximum impact in a variety of settings. Here are six fail-safe ways to unleash the power of questions in your day-to-day business world. 

Come prepared to the interview

The late entertainment journalist Brian Linehan was famous for the tremendous amount of preparation he’d put into each interview digging up little-known anecdotes or facts about a celebrity that, often, they themselves did not remember. “You’re making me very nervous,” Bette Midler reportedly told him during one interview. “Have you been listening down the drainpipe?” 

The key to any successful conversation—especially when there’s a power imbalance—is being ready to engage. The more you know about the person you’re talking to, the easier it is to engage. And remember: if all else fails, people love to talk about themselves, so make sure you’ve got their CV and career highlights memorized. 

Choose your setting carefully 

Often in a work environment, you don’t have much control over where a conversation might take place—in an office or in a boardroom being the two most likely options.

But know that, to the extent you can control the setting, it helps to control the narrative: that’s why interviewers from Barbara Walters to Anderson Cooper try to secure interviews in a more personable setting, like a celebrity’s home or in a politician’s favourite café (or a car, as Jerry Seinfeld’s Comedian in Cars Getting Coffee series has proved). It puts the subject at ease and gets him or her to open up.  

Know when to be open—and when to be closed 

Speaking of open, not all questions are created equal. If you want somebody to really open up, you have to ask an open-ended question: “Tell me about what it was like growing up in Croatia”; “How would you describe that first job experience with McDonald’s?”

Closed questions, by contrast, are intended only to get a fact straight—something that will solicit a simple yes or no answer. “Are you happy in your current job?” may get a fulsome answer, but it’s equally likely that somebody will simply affirm or deny—and expect you to move on.  

Listen up—and listen long 

It’s human nature to fill pregnant pauses in a conversation—but as the “interviewer,” don’t fill the gap. Let your subject do the work. As every good journalist knows, some of the best material comes out of those silences—when the person you’re talking to is forced to reflect on what they want to say next, and often elaborate to a degree which they normally would not. It’s not about making your subject feel uncomfortable—give them non-verbal cues that you’re listening, that you understand—but rather, making sure that they, not you, are filling those gaps. 

Have a script—but make sure to break from it 

Yes, you need to come prepared with questions for which you need answers. But don’t be rigid about how the conversation unfolds. And make sure to ask follow-up questions. Your ability to listen is critical in getting the information you need and keeping your subject engaged in the conversation. If you look like you’re reading from a script, you’re more likely to get scripted answers in return. 

Get the pace and order of questions right 

While you don’t want to appear scripted, you should have a sense of when to ask what. As a general rule of thumb, start with the easy stuff and save your “tough” questions for last. Not only will it give you time to put your subject at ease and make them trust you, it also protects you if they decide they don’t like a particular question and choose to end the conversation early.

That’s what happened in a famous 1994 interview by CBS’s Connie Chung with Microsoft founder Bill Gates. After some icebreaking questions—one that even got Gates jumping over a chair to prove a talent—Gates walked out of the interview near the end, when Chung asked tough questions about an antitrust investigation targeting Microsoft.