Three ‘gotcha’ job interview questions
Read Time: 7 mins
Written By:
Donn LeVie, Jr., CFE
You’ve been hired to examine a case of suspected embezzlement in a small business. Your client, the owner, suspects that one of his employees is behind the scheme. He’s given you the name of the suspected employee, and you get to work right away gathering as much information as you can about the employee and why your client suspects them. You learn whether others were involved in the alleged scheme, how much money was possibly stolen and how it was — or if — perpetrated.
The information you obtain in this early stage of the engagement lays the foundation for the interview with the suspect. The facts and evidence you’ve already collected will help you construct effective questions to ensure a productive interview and meet your client’s objectives. Asking the right questions, in the right way, at the right time can get truthful information from the suspect to resolve the case. But preparing for this type of interview requires more than just formulating good questions. You’ll need to develop an interview strategy that considers what can go wrong and understand that how you structure your questions can minimize errors and encourage the truth from suspects. Most importantly, this careful planning will help you avoid interview contamination — anything that can negatively influence a suspect’s responses. This includes taking stock of your biases and prejudices ahead of the interview.
Fact-finding interviews, in which you facilitate an exchange of information that promotes truthful and factual responses from a subject, require considerable planning to eliminate “noise”— all those things that may harm the dynamic and outcome of the interview. Contamination — a negative influence during an interview that may cause a subject to provide incomplete or inaccurate information — can happen at any point during the exchange, turning a strong case into a weak one. From the time you enter the room until the time you conclude the discussion, you risk introducing elements that can derail the interview. By carefully planning and preparing ahead of time, you decrease any opportunities for contamination. In my experience, I’ve found that one interviewer and one interviewee is the best dynamic to minimize distractions. The room setup is important too — ensure that the subject’s focus is on you and not the door or window. The interview will be far more productive if you’re able to control and reduce distractions.
But the questions you ask and how you ask them can also contaminate an interview and provide the perfect opportunity for a suspected fraudster to evade the truth. The following sections detail how to carefully construct fact-finding interview questions so you may collect the critical information about the case.
The goal of the fact-finding interview is getting accurate information straight from the suspect, but your questions may provide the subject with an opportunity to obfuscate, or relay imprecise information. Consider how the following two questions elicit different responses depending on how they’re worded:
I asked the pastor, "May I smoke while I pray?"
The pastor said, "Absolutely not."
I asked the pastor, "May I pray while I smoke?"
The pastor said, "Absolutely."
Other questions that can affect responses begin with phrases such as “Would you say …?”; "Can you say ...?”; "To the best of your knowledge ...?” or “What can you tell me?” These questions have the propensity to contaminate the interview because they invite the subject to their own interpretation. Asking someone, “What would you say …” encourages them to say anything. They’re able to rationalize that they’re providing truthful responses because they are, in fact, telling you what they’d say. A question asked in this manner doesn’t require a factual response.
Questions that lead with phrases such as “to the best of your knowledge” are also contaminating questions because the meaning of “knowledge” is open to interpretation. A person may interpret that to mean any number of things — did they deduce, observe or infer the information? Questions should be precise, simple and direct to get the subject to lie, to tell you the direct opposite of the truth. If I ask a suspect, "Did you take that money?" then I must define "take" and "money" to meet the requirements of a simple, precise and direct question. Otherwise, if those words aren't mutually understood, the subject can "wiggle" out of a response without lying.
The following 2016 interview between journalist Chuck Todd and Wikileaks founder Julian Assange on the news show “Meet the Press” demonstrates how a poorly worded question allows the subject to provide a poor, and possibly dishonest response. During the interview, Todd uses the phrase “would you be able to say.” Assange uses it to his advantage and repeats Todd’s phrasing.
Todd: I understand that, but the easiest way to clear this up, Mr. Assange, would you be able to say categorically that a foreign government did not hand you this material?
Assange: I can say categorically that we have published proof that the election campaign of Bernie Sanders was sabotaged in a corrupt manner by Debbie Wasserman Schultz and others within the DNC [Democratic National Committee]. We can say that categorically.
Every interview involves an exchange of information. The questions you ask must get truthful responses that aren’t influenced by any word or phrase. You may not be able to eliminate all instances of contamination — some things may be out of your control — but you can minimize the likelihood that an interview will be derailed by your questions.
In fact-finding interviews, you’re getting information directly from the suspect. In doing so, you ask questions with specific words and terms related to the case. The problem is that using specific terms without mutual understanding allows the interviewee to interpret terms any way they like. I call this "wiggle." When a person is being deceptive, they may provide answers they can later "wiggle" out of and explain away by what they "really meant." They purposely misinterpret a word to their advantage. Questions like “Did you follow procedures,” or terms like “slip and fall,” “embezzlement” or “assault” may return misleading answers if you don’t have confirmation that the subject understands and agrees with your definition. During litigation, the suspect could explain away their answer by saying, “I took that question to mean …” To avoid contaminating an interview with misinterpreted information, you must ensure that everyone shares the same definitions, that there is a mutual understanding of terms. You create a record of mutual understanding by forcing the suspect to define all the words used during the interview. Prevent the "wiggle."
You may not be able to eliminate all instances of contamination, but you can minimize the likelihood that an interview will be derailed by your questions.
Minimize the suspect’s ability to “wiggle” out of a truthful response by asking them to explain their understanding of key terms and phrases. For example, after they respond to your prompt, follow up with a question such as, “What do you mean when you say …” so there’s no doubt about the meaning of any word.
When you use terms without confirming the subject’s understanding, you assume the subject knows what you’re talking about. I recall attending a deposition (testimony under oath) where an attorney asked a department store salesclerk if they had any “chattel.” The salesclerk answered: “No.” But there was no follow up question to clarify if the salesclerk knew that chattel is tangible personal property that can be moved from one place to another. If the clerk was unfamiliar with the word, they might provide an unreliable answer.
Here’s a better approach to that question:
Attorney: I'm going to ask you about “chattel.” “Chattel” is personal property and not real property like land, cars or boats. Do you have any chattel?” Asking the question in this way confirms mutual understanding, and the attorney may now rely on the salesclerk’s response.
Let’s return to the embezzlement case from the beginning of this article. Consider that you’ve determined the money was embezzled from a customer’s bank account, but you don’t know how much was taken or how the suspect did it. With that in mind, you don’t want to ask the suspect, "Did you embezzle money from the Smith account?"
You can’t assume the employee knows the definition of "embezzle" or the nature of the relationship between the employee and Mr. Smith. What if they’re working together and the employee is helping Mr. Smith hide or launder illicit funds? A better question is "Tell me about these entries in the Smith account."
Then, you build knowledge from their response by defining the words they use and asking follow-up questions such as, "Tell me what you mean when you say …”
Once you’ve established mutual understanding of terms, you’ll ask more specific questions using those mutually understood terms.
Don't be afraid to look stupid or naive with your questions. Your objective is to gather reliable facts and evidence, not to look good in the interview transcript.
Before there were female ornithologists, there were no known female birds that sang. What does this statement have to do with developing an interview strategy for a fraud case? Our biases influence how we understand the world. In 2021, Scientific American reported on research about the song of the female barn swallow. Barn swallows are one of the most-researched bird species, but until this study, the focus of researchers had been on male birds. In the early days of ornithological studies, most of the researchers were men who focused on male birds that inhabited the surroundings of their universities in the Northeastern United States. Female birds in this climate have different song patterns than male birds, but because most avian experts of the day — men — didn't study female birds, their biases guided our understanding of birds for decades, and many people thought female birds didn’t sing.
Implicit bias, an unconscious negative attitude to a social group outside our own, can manifest during interviews. An essential part of your interview planning is to take inventory of your biases. Being aware of them helps you to avoid going into an interview with preconceived notions about the subject, including their guilt or innocence. When you’re aware of your biases, you’ll approach interviews with an open mind to probe for the truth. Consider the following questions to examine your own biases:
Your biases and prejudices will affect how you interpret the facts. By knowing and understanding your biases, you’ll be able to conduct a good, fact-finding interview.
Just as we need to be aware of our biases and prejudices, we also need to understand the nature of lies and how people construct them. I define lies as partial truths — there’s a kernel of truth in every lie. As we mature from child to adult, we hone our skills as partial truthtellers by weaving some truth into the lies. People often rationalize this by convincing themselves that because they’ve included some truth they haven’t lied completely. Statements with no truth at all are actually rare — deceptive statements often include a little bit of truth. This is what makes the fact-finding interview process so difficult. You might hear some truth in a statement and assume that the rest is truthful. A deceptive person knows this and uses it to their advantage. We all want to hear the truth; the default is to believe what we’re told. It takes extra effort to detect the subterfuge in a message.
Adding another wrinkle to the fact-finding mission is that "truth" and "fact" don’t necessarily mean the same thing. Like bias, a person’s “truth” depends on their perspective. You can have someone who’s being truthful about their perspective even when they’ve gotten the facts wrong.
During the interview, your questions must force the subject to lie. This means that you structure your questions in such a way that the subject will either lie to you or provide a highly suspicious response. When you ask a question beginning with "what would you say ..." they aren't forced to lie; instead you're giving them an opportunity to say whatever they want. For example, if you ask the suspected embezzler, "What would you say if the records show that you didn't deposit the $500 you received on June 22, 2025?" The suspect may respond, "I would say you’re wrong." And, even if they didn’t deposit the money on the date in question, they’re still answering you truthfully — it’s truthfully what they’d say in response to a poorly constructed question.
If I've established a mutual understanding for the word "embezzle" and I ask the subject precisely, "Did you embezzle money from your company?" the subject tells the truth, provides a suspicious answer or lies. If they respond with "no," a precise response, but they did in fact embezzle from the company, then they've lied. If they respond with something like, "I couldn't embezzle from my company," that response is suspicious, especially in conjunction with a change in nonverbal behavior such as a change in tone, it's a signal to explore further.
Each person has a unique communication style or pattern — how they talk, how much eye contact they make, their facial expressions and body language. Your initial questions, such as “How long have you been with the company?”; “How about Saturday’s game?”; or “Where do you live?” help you identify the subject’s unique communication pattern and help you calibrate when they deviate from it. You’ll notice that your interview subject has a specific pitch in their voice and uses different tones, breathing rhythm and speaking pace when answering different questions. Early in the interview, while you ask the interview subject basic, non-threatening questions to build rapport, you’ll need to observe the interviewee’s communication pattern. Their verbal and nonverbal responses to these rapport-building questions are the baseline, and standard you’ll use to compare any change in pattern when you ask the hard questions about the case. As you begin asking these questions, you may notice pattern changes. You’ll need to question them and determine why they’ve changed.
A change in communication is a red flag signaling that further investigation is required. Lying is stressful on the body, and a body under stress signals that through changes in verbal and nonverbal communication patterns. It’s important to understand that any change in a communication pattern doesn’t necessarily mean the subject is lying; the interviewee might be distracted by noise in the hallway outside the interview room or something else, but it’s your job to find the cause so that you may glean reliable information from them.
Noticing these communication pattern shifts helps you calibrate your questions, ensuring that you structure them to allow truthful people to supply the complete truth and make it difficult for deceptive people to obscure it. Think about it this way: If the subject didn’t answer your question, they probably did answer it through omission. If they don’t expressly deny doing something, there’s a good chance they’ve committed the act in question. Innocent people want to tell the truth to exonerate themselves. People with nothing to hide are helpful. A person with something to hide won’t be helpful. They’ll try to confuse you.
When you do notice a change, ask why. For example, “You answered my questions earlier in the interview without hesitation, but you hesitated to answer the last two questions and your facial expressions suggest that you’re having difficulty with these questions. Tell me why.”
It can be difficult to detect deception in skillfully worded statements. As interviewers, we need to be aware of deceptive people’s wordsmithing skills and use that knowledge to our advantage. Asking subjects probing questions that give us precise responses, using mutually understood words that can’t be misinterpreted is how we do it. Typically, truthful responses are simple, precise and direct. Truthful people want you to know the complete truth. Deceptive people don't.
Consider the response, “I didn’t do it.” When it stands alone without explanation, it contains the components of a truthful response. The use of the contraction “didn’t” signals that the interviewee is relaxed. As lying is stressful, the more relaxed response means they’re likely being truthful.
But, you can’t rely on the use of “it” in this denial without knowing what "it" is and whether it’s consistent with the evidence and circumstances. Then, you consider the context of the response. Did the interviewee blurt it out or was it a response to a pointed question? Is it consistent with the subject’s baseline communication pattern or did something in their pattern change when they responded? If this was in response to a question probing whether they committed the act in question, the denial "I didn't do it" is precise, simple and direct — all the ingredients for a truthful denial.
Beware of responses like, “I couldn’t do it,” “I wouldn’t do it,” “I’m telling you I didn’t do it,” “I can tell you there is no way I did it,” “I am not guilty” or “As God is my witness …” These responses suggest that someone is being deceptive.
I regularly employ a powerful interview technique in which the subject writes their statement by hand. You’ll need plenty of plain, unlined paper — purposefully unstructured and plentiful enough to encourage thorough responses. Once I’m in the interview room with the subject, I introduce myself. I ask the subject general, non-threatening questions such as their full name, address, time with the company, etc. As I’m asking these questions, I’m observing the subject’s communication pattern to calibrate the interview. Then, I tell the subject that I’ll handwrite my questions and ask them to respond in writing. I use different colored pens for my questions and the subject’s answers. Once I establish this plan with the subject, I launch into the fact-finding interview with the prompt, “Tell me what happened.”
I then tell the subject that I’m leaving the room and will wait outside until they notify me that they’re finished writing. This action minimizes contamination because I’m not sitting in the room fidgeting, looking at my phone or distracting them in any way. This strategy gives the subject space to be alone with their thoughts. In my experience, people write thoughts they’re uncomfortable verbalizing, especially when they’re alone. Indeed, the Hallmark company made a fortune selling greeting cards that say the things many things are afraid to say out loud. It's easier to write, "I love you," than to say it face to face.
The command to write out a response to “tell me what happened” with an unlimited supply of plain white paper is the set up for a complex process where the subject will hand write several pages of explanation detailing what happened. I review the statement for signs of stress in their composition, such as crossed-out sentences, rewritten passages and any areas where the flow of writing seems disrupted or where their handwriting changes.
To illustrate this method, the following is a portion of a five-page statement from an interview subject responding to “Tell me what happened.” The subject’s ex-wife accused him of forging her name on checks and cashing them for himself. In this example, there’s little I said or did to influence his response. Remember: Deception is stressful. It’s harder to lie than tell the truth.
Note how his handwriting changes with “She said to sign her name …” Why did his handwriting style change there? Was he being deceptive or was he disrupted or distracted? The fact that it occurs when he’s writing his defense suggests that he’s dealing with the stress of deception.
My first question to him once I returned to the room was, “You wrote, ‘She said to sign her name ...’ Please tell me about that.” I wanted him to know that I’d identified possible deception in his statement and to maintain his stress level after writing the statement. He later confessed that his wife didn’t tell him to sign the checks.
Well-constructed questions contain mutually understood words constructed simply and precisely. For example, the question, “Were you ever at 765 Moross,” could be further refined by showing the subject a picture of 765 Moross and asking, “Were you ever inside that building?” Why is this question better? “At” isn’t precise. “Inside” is precise. The subject might not even know the address of the building.
Here's another example: “What is your net worth?” This question doesn’t define “net worth.” The better question asks, “What does the term ‘net worth’ mean to you?” Then, you ask the question “What is your net worth?” First you get the mutually understood definition, then you get the response.
So, instead of “When was the last time you saw Nicole?”
Ask: “When did you last see Nicole?” This question is shorter, simpler and more precise.
Instead of: “What do you think happened?”
Ask: “What happened?”
Instead of: “Do you have any chattel not already listed?”
Ask: “Do you have any personal property not already listed?”
Instead of: “Do you know who took the money?”
Ask: “Who took the money?”
Instead of: “Can you say you did not take the money?”
Ask: “Did you take the money?”
(See: “The interview question checklist,” at the end of this article.)
There’s much to learn as you develop the skills necessary to conduct ethically sound fraud examination interviews. Preparing ahead of time with an outline, including critical questions and how you ask them will set the stage for a successful interview. Planning your interview strategy will also help minimize contamination. Asking well-constructed questions that define terms and ensure that you both share the same meaning of words will blunt the interview subject’s ability to deceive, because your goal as the interviewer is to prevent any opportunity they might have to evade the truth.
Joe Koenig, CFE, is the owner of KMI Investigations LLC, based in Grandville, Michigan, and the author of the books, “Getting the Truth” (2014) and “Getting the Truth: I am D.B. Cooper.” (2019). Contact him at Joe.Koenig@kmiinvestigations.com.
As you plan your interview strategy, keep this checklist handy to guide you in developing questions.
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