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Conducting Difficult Interviews or Conversations: 10 Tips

Updated: Mar 16, 2021

At home or at work, there will be a time when you will be called upon to do a difficult interview (perhaps even an exploratory conversation) involving multiple individuals. It may be among members of your own family, friends you know, people you manage, or it is part of your work responsibilities.

For some, this process comes naturally, for others it can be difficult. Here are some tips to prepare and conduct an interview based on the Authors' decades of experience in the business, human resource, and forensic arena:

1. Know your role. Are you the collector of the facts so that others will act on the information you gather in the interview or will you be the person who will act on the information? As a parent, you gather the children and you gather the facts – fairly straight forward. But in business it gets a little bit more nuanced where interviewing individuals separately and in a timely manner is not always easy. At home you may be the final arbiter, while at work, the final arbiter may be a person once or twice removed which means the facts have to be accurate. You may want to consider getting a written statement from those involved if they are several layers removed.

2. Have a clear purpose. At the end of the interviews or focused conversations, are you supposed to take action, make a report, castigate someone, or are you merely a sounding board? It is important to know what you are collecting the information for. Are you doing the interviews to arbitrate, to deal with an ongoing issue, to discover what happened, to improve practices, or to prevent something from happening in the future? Interviewing is nothing more than “effective communication with a purpose.” Make sure you understand what that purpose is.

3. Be neutral. Are you seen as an unbiased and fair collector of the information or will one or both individuals see you as somehow biased or leaning in a certain direction? In other words, does one child think you favor one sibling over another? In a work setting, is there a perception that HR favors management and that employee issues are hushed away? Only you can answer that question but never imagine that if you are biased that it is OK or it won’t matter, or it won’t be noticed. It will be noticed, it will be a factor, and it affects the actual mechanics and process of the interview. If you are honest and ethical you will try your best to be neutral in thought, tone, and questions.

4. The reality of recall. When gathering information in an interview, remember that time and emotions affect recall. But perhaps more importantly, as clever as we humans think we are, our brains are not video recorders. We interpret reality as we perceive it and it may be not just a little flawed but very flawed. Our ears and eyes can deceive us. As a former FBI agent, I have been to so many bank robberies where the bank tellers and managers could not agree on whether the suspect had a gun and if he did what color it was, nor what size of weapon was displayed. In one robbery in Phoenix, six witnesses all had different descriptions. Imagine going to court with that kind of testimony? We seek perfection in recall from those we interview and from witnesses but remember their recollection, no matter how emphatic, can be wrong.

5. Body language matters. As a collector of facts, it is important to remember that the information you will gather, unless it is by phone, is both verbal and nonverbal. What is said is important, but so is the body language. Sarcasm, cynicism, or emotions such as anger, apprehension, or even fear, are often revealed not in the words but rather the body language. While we often think of a quiet setting for the interview, we should also think about one where all of the body language can be observed from the feet upwards. As I noted in What Every BODY Is Saying, oftentimes the feet are more honest than the face.

6. Listening is not hearing. Listening is very important in an interview and you should be focused at all times. Listening requires analysis and interpretation in context. How well you listen matters. A quick synopsis of what was said by you lets others know you got it precisely and if not, you were attempting to and now is the time for them to correct you. Remember, that emotions, shock, fear, apprehension, or lack of verbal skills affect what we say; and so our thoughts and intentions sometimes don’t come out perfectly. Be patient. Seek to understand what is meant, not just what is said. As interviewers we want clarity, it is up to us to ask for it. “What do you mean he was hassling you?” Ask for clarification. “Hassle” may be a word that for this person covers a variety of things, make sure you understand. Once more, some people express themselves very well, but many don’t. And so, we ask for clarity—patiently and politely.

7. The importance of primacy and emphasis. What things are mentioned first or foremost by the person being interviewed are important. There may be a priority of revealing information to you due to emotions or urgency. Listen to what is said first and what is repeated. Note where emphasis is made. Are they telling you a story or are they trying to convince you of their story? This is significant. Some people go over-the-top trying to be believed, and if they do, we must wonder why? As Shakespeare said in Hamlet Act III, Scene II, “The lady doth protest too much.” If you are a neutral listener, there usually is no need for trying to convince you of what took place—they merely have to convey what took place.

8. Time garners clarity. Whether it is a management issue, parental issue, or interpersonal issue, give people time to say what they want to say without interruption. Ask, “What happened?” And allow them adequate time to say whatever they wish to say. When they are finished, ask “is there anything else that you think is important that needs to be added?” After they are finished and have nothing further to volunteer to you, then and only then seek greater details. Details are key and if you make it known that you will ask for more and more details make them understand that it is for clarity, not that you are suspicious or that you do not believe them.

9. More may be needed. After you have gathered the facts, make it known that you may want to talk to them again. Also ask how they feel. Often times, when people don’t feel good about an interview it is because they feel the interviewer was unfair, uncaring, patronizing, haphazard, or perhaps the interview was not what they expected. Whatever their sentiments, try to determine how they feel immediately after the interview. Some may feel relieved while others they may never be satisfied. You never know. How they feel after an interview is something that both authors routinely ask as it serves a useful purpose in determining if there are underlying unresolved issues.

10. The helicopter view. One way to approach the interview is to look at it, as Anne-Maartje Oud, teaches at the Behaviour Company, by taking the “helicopter view.” In other words, examine the facts and conduct the interview as if flying above looking down. What that means is we listen carefully to what is said. But we also factor in how things were said by the interviewees, where the event took place, who else was there, where was everyone standing or sitting when it took place, what day and time it took place, and even consider environmental conditions such as weather, lighting, or ambient noise. We are the camera and pilot that can zoom in and out or focus on different aspect and we can hover, move about, come back, land for a bit, loiter on a topic, or cover a wide swath as we conduct the interview from that helicopter view. This view from above allows us to look at perspectives including the history of the individuals involved to see if the interviewees have a history of issues or if there are other external factors.

Conclusion: The purpose of an interview or a focused conversation, is to find out what we were not privy to. We want to find out what happened from each person as they observed it, or they perceived it. To achieve that we have to create the right environment and we have to be mindful of many things, including our own neutrality, our own focus, and our own purpose. Trust, openness, and psychological comfort all contribute to positive outcomes in most efforts—but especially here with difficult conversations.

This post was authored by Anne-Maartje Oud with Joe Navarro.

Anne-Maartje Oud is the founder and director of The Behaviour Company, a world-wide consultancy on best-practices and human behavior. Anne-Maartje Oud may be reached directly at: or follow on Twitter at: @BehaviourC Live Training events 2020. Facebook

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