Insights from an Interviewer:  Lessons I've Learned Interviewing People Over the Last 20+Years

Over the last 20+ years, I've interviewed everyone from Rock and Roll Hall of Famers and NBA Hall of Famers to high school athletes, CEOs, and small business owners. I’ve conducted interviews in a variety of settings, too – in MMA gyms, on golf courses, in ballrooms, in people’s homes, in parking lots, on the grass at Wrigley Field during batting practice, just to name a few.

While not all of these experiences were great (some I’d like to forget), these interactions have helped me learn quite a bit about how to prepare for an interview, how to read the person I’m interviewing, and how to maximize the time I have while interviewing someone. So I’d like to share a few of those lessons here:

  • Be prepared.  This seems pretty obvious, but for anyone who’s conducted an interview without doing their homework on the person they’re interviewing, you understand how challenging it can be to have a meaningful conversation. I try to learn as much as possible about the person I’m going to interview so I feel like I already know them before we talk. I’ll read any articles I can find about the person or locate publications where they’re quoted; I’ll see if they’ve written anything (and read it, time permitting); I’ll review their LinkedIn profile, CV (if it’s available online), Facebook page and Twitter feed to learn about their education, professional experience, interests, etc. All of this definitely takes time, but by preparing yourself, you not only show your interview subject that you’re taking the conversation and their time seriously, you should also be ready to ask solid questions and take the interview in a new direction if need be.

  • Be ready to pivot.  I used to have a prepared list of questions in front of me when I conducted interviews to help ease my nerves and to serve as a checklist so I didn’t forget to ask anything, but I found that being married to my list of questions was often a conversation killer. I’d ask a question. The person would respond. I’d ask another question. The person would respond again. Repeat. Sometimes you just need to ask a few specific questions or someone’s PR team has limited your interview time to a few minutes, so going through your questions list can sometimes be the best approach. For the most part, though, I will write down the general areas I’d like to discuss during the interview. From there, I’ll just let the conversation flow as my focus is more on the interviewee’s words and expressions than my notes. Is my interview subject bringing up something I didn’t expect? If so, and if it’s relevant and I have the time, I should be prepared to guide the conversation in a new direction. There is no script when you interview someone, and you never know what you could find out, so you really do need to be ready to go in whatever direction it takes you – which is why the first bullet in this list (Be prepared) is so important.

  • Be observant and listen for non-answers. When you're face to face or doing a video call with your interview subject, be sure to pay attention to their expressions. Are they smiling or do they get a sad or stern look on their face when you ask them a question or when they’re responding? If so, ask them why. Are they avoiding responding directly to a question or are they regurgitating talking points or offering “coach-speak” that really isn’t providing much substance? If so, rephrase the question or request that they clarify their response.

    Are they preoccupied with something and not giving you their undivided attention? If so, maybe this is just not a priority or a good time for them (which is fine, unless of course you’re on a tight deadline). So you can either ask to reschedule, or if that isn’t a possibility and this is you’re only crack at the interview, don’t try to force the conversation or create a connection with your interview subject that just isn’t there – just get whatever information you can and try to be ok with that.

  • Be engaged and try to be yourself. Interviews are not simply asking questions and writing down quotes. They should be conversations. A give and take. This took me a long time to learn. For many years, I thought interviewing was simply about getting the information I needed from someone so I could plug quotes into my story. I’ve learned, though, that good interviewing is really a dialogue and it’s creating a level of comfort so the person being interviewed can talk freely instead of pausing after every question so they can gather the right words to respond. As I’ve gained more experience and confidence, I’ve found that just being myself, smiling more, and being vulnerable – sharing details about my own fears, weaknesses, and worries – has helped people feel more comfortable opening up to me. It has also made for much more enjoyable conversations.  

  • Be appreciative. People are busy, and when they take the time to answer your questions, it's good practice to follow up and thank them (or whoever organized the interview) for giving you the opportunity. This also opens up the door for additional dialogue should you need to ask follow-up questions about the piece you’re working on, or if you need to reach out to them again for a future assignment. A simple “thank you” can be a great way to develop your network.

Not every interview is going to go as planned or be as enjoyable as you hoped. And not every person you interview is going to become one of your go-to sources … in fact, you may never speak to your interview subject again. And that’s ok. What’s more important is that you prepare yourself so you’re making the most of each interview opportunity that comes your way.

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