ISTM #27: Nine Tips on Conducting Great Interviews

I received a fan email the other day, a rather rare occasion for me. It was from a Brazilian woman who was researching ways to interview people and she had dug out a piece I wrote in 2012 when I was still a paid Forbes contributor. When I read through it, I felt it was still applicable –not just to those conducting media interviews, but many other forms of business conversations.

Here it is with a few small tweaks added:

In my career, I have conducted thousands of interviews, have been interviewed myself scores of times and as a media consultant, I have also observed thousands of interviews between clients and the press from a neutral seat. There are a few tips that have worked consistently well for both my clients and me and perhaps they will help you. I write this from a media professional’s point of view, but I think many of these points are applicable to business and employment interviews as well.

1. Start slow, safe and personal.


I usually begin with a question that focuses on the person and not the topic at hand, such as: “Where did you grow up,” or “what was your first job out of college?” First off, you relax your subject and you personalize the conversation. This often relaxes the interviewee and produces a sense of where your subject is coming from. Second, you sometimes get a surprisingly good story.

Years ago,  a veteran business magazine reporter interviewed Oracle founder Larry Ellison. The subject was corporate strategies related to database software. But the writer started by asking Ellison where he was born and raised. Ellison, known for his aggressive and independent style, revealed that he was raised by a single mom and spent much of his youth on the streets of Chicago. This, for many years, became a key component of the Ellison persona and explained Oracle’s street-tough competitive culture.

2. Coax, don’t hammer.


The “shock jock” interviewer may get daytime TV audiences to cheer and jeer, but chances are your audience is too sophisticated and businesslike for such low-rent tactics. I prefer interviews that have the up-close, but soft style that coaxes revealing, newsworthy, useful answers. For that reason, I am a huge fan of NPR’s Terry Gross, host of the long-running Fresh Air.

She coaxes the most revealing content out of her subjects, by adopting a very personal rapport and asking questions, in a “c’mon, you can tell me” style. People tell her the most amazing stuff. I’ll bet a few of them later wonder whatever possessed them to reveal certain matters on national television.

3. Make some questions open-ended.


All interviews require you to ask specific questions that get answered with narrow data points such as: “What was your last job title?” But, in my experience, the most interesting responses I get come from open-ended questions, such as, “What is your vision for your organization five years from today?” or one of my current favorites, “Do you worry about any unintended consequences from what you are trying to accomplish?”

I started my career as a General Staff Reporter for a Massachusetts newspaper. My first big interview was with Alabama Gov. George C. Wallace, a controversial segregationist running for the presidential nomination. I was no fan of his but made it my business not to show my personal animosity. I opened by asking him what he thought the voters of Massachusetts shared in common with him. “They are as tired as I am of big government stomping on hard-working folks,” he said. This is a tired old saw today, but that interview may be the first time a candidate personified “big government” bullying everyday people. Wallace almost won that Massachusetts primary. His campaign manager sent me a Thank You note for giving Wallace the chance to state his case. It was a dubious distinction since I despised the man, but my job was to tell his story so that people could decide on their own.

4. Ask what you don’t know.

Lawyers consider it conventional wisdom to only ask witnesses questions that they already know the answers to. I do the opposite. I ask questions on issues where I am clueless what the answer will be. Lawyers hate surprises. As a journalist–or reader–I love them. Surprises mean I have something that has not been previously reported.

5. Let interviewees wander a bit–but be careful.

Interviewers, in my view, try too hard to control the conversation, when the person in the other seat is the one who is the news.

Interview4I recently watched Oprah Winfrey conduct a TV interview with Sean Penn in a Haitian refugee camp. Penn was in an uncharacteristically reflective mood. He obviously wanted to talk about the recent dissolution of his marriage but Winfrey changed the subject on him. Then he wanted to talk about the suffering of children in refugee camps, but she changed subjects on him again. After that Penn seemed bored and detached giving her cursory answers. I didn’t blame him.

There is a danger, however. If you are conducting a business interview, the company representative may resort to talking points and what I call Corpspeak. When this happens, I often stop writing, fold my arms and look out the window. The subjects often trail off. I don’t want to seem rude or confrontational, but I need to assert that I am present to get something new and unique and have no intention of regurgitating or reusing website content.

Sometimes it works, and the subject changes to more candid tones. Other times it does not and I write nothing at all—a waste of time for all parties concerned.

6.  Don’t send advance questions.

Sometimes, time requires me to send email questions, and then I get written answers in return. These are often adequate, but the result is rarely as good as face-to-face interaction.  If I am going to have face time, I make clear the topics that I wish to cover and even ask if there are other subjects the interviewee would like to discuss.

But I never send questions in advance. The result very often looks scripted to readers, and the answers start feeling like they were written by a committee. As a tech business writer, I am looking for positive news, but I have no desire to be mistaken for the company PR representatives. And, it seems to me, that when that happens, the journalist loses the credible that the company had hoped for, to begin with.

Second, advanced questions eliminate the chance for follow-up questions, which often get to generate more newsworthy answers and clearer details.

7. Be prepared. Find the overlooked.

I used to spend days researching before conducting an interview. Thanks to Google, that has been reduced to approximately an hour or two. I see what the subject has told other reporters and bloggers and I figure out what can be added to those previous conversations.

I also look in forgotten cubbyholes. In searches, I often always go to result pages 3, 4 and 5, where I may find interesting content that no one else has recently discussed.

I go into the room knowing the topics I want to discuss and trying not to waste time asking for answers recently discussed. But I do look for updates and I do look for the questions that someone else forgot to ask. I recently was scheduled to interview Yammer CEO David Sachs for my Forbes column. I had planned to ask him about his $25,000 hiring bonus to Yahoo employees. Unfortunately, in the preceding week, other reporters got to ask him all about it. I read them all and started my interview by asking Sachs how many resumes he had received and how many offers he had made. As a result, I got a small scoop, by asking the missed question.

Quite often, a subject’s response to one question begs for a follow-up. Many times, the follow-up question reveals more than either the interviewer or interviewee expected. You just can’t make that happen when you are following a script. When you do that, your mind very often goes on to your next question and you are not listening carefully to what your subject is saying.

Sometimes, the interviewee says something unexpected and in that moment headlines and bylines can happen. If the reporter just sticks to a script—as Oprah did—great stories blow by like leaves in the Autumn wind never to be noticed again.

8. Listen. Really listen.

The value of my interviews comes out of what people say, not what I ask. If I ask a question and the subject drifts off, there is often a good reason. I can get feisty and retort “Please answer my question,” or I can see where the person wants to go. If it’s into Corpspeak and talking points, I simply stop writing and fold my arms. If it’s into an area that might interest my readers, then I let the subject take the lead. The key is to listen between the lines. I make on-the-spot judgments on why my subject skipped or glossed over a point.

9. There are dumb questions.

Try not to ask a question that your subject has already answered. It discloses that you really weren’t listening. Also, try not to ask questions that are answered in the interviewee’s online bios or company FAQ.


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