In diligence interviewing, the subject of your interview has likely spent just as much time anticipating the questions you may be asking as you have spent time preparing them. Perhaps similar to what you were told about wild animals at summer camp, interviewing is one of those situations where they are probably just as scared of you as you are of them; no one wants to be embarrassed by not knowing the data or having an answer, especially in front of someone they do not know or while representing their company. It is normal for people to prepare to be interviewed by compiling data and creating some general responses to the questions they anticipate being asked. Just like you, they may even have written down some notes.

So as an interviewer, how do you navigate around those canned responses and encourage authentic answers and insights? We have a list of a few key tips to help guide you:

• Build Trust: It is a common misconception that the diligence professional’s job is to create a “gotcha!” moment. In reality, diligence professionals are looking for information and insights to gain a more comprehensive understanding, and it is extremely difficult to get there if you and/or your subject’s approach the concept of an interview as adversarial. You and your subject are not opponents, you are two people having a conversation.

• Approach Questions from Multiple Angles: Your list of interview questions should contain a mix of larger, conceptual questions and more detail-oriented questions (depending on the project, of course). Your subject may be initially more comfortable with one kind of question over the other, so help build their confidence and trust by giving them questions they can easily answer before approaching a topic that may require a more candid or vulnerable response.

• Be a Student: Often in our own diligence interviews, we ask our subjects to “educate us” in their area of expertise or in their knowledge of a particular topic. This language is meant to signal to our subject that we are approaching them as someone who wants to learn from them rather than someone who wants to challenge them. This approach can go a long way not only in building trust with your subject but also in how you approach their insights and answers with a neutral, non-judgmental mindset.

• Lean Into the Conversation: While every question on your list is there for a reason, we often find that cutting off the conversation to move to the next topic or question limits the insight we might gain from a subject. Good insight can be gained from organic conversation: if the subject is willing to keep speaking on a particular topic, do not be afraid to ask follow-up questions or keep probing to find what else might be there. Of course, this is not an advisable tactic to use if your subject happens to be particularly chatty or distractable, so gauge your subject appropriately.

• Ask Meaningful Questions: A great way to get canned responses is to ask canned questions. One of our favorite interview stories (yes, we have favorites) comes from Cal Fussman’s 2008 interview with former head of the USSR, Mikhail Gorbachev. Fussman had prepared for a 90-minute interview with Gorbachev but was told shortly before he met his subject that his time had been cut to a mere 10 minutes. Instead of asking a pointed political or strategic question, Fussman surprised Gorbachev by asking about lessons he had learned from his father. Through asking such an authentic and meaningful question, Fussman earned Gorbachev’s own authenticity and meaningful responses in return, and the two spoke for over half an hour. While we do not generally encourage asking too many questions about peoples’ fathers in diligence interviews, we strongly recommend intentionally crafting questions to show meaningful interest and engage your subject.