How to Confront an Employee About Theft: Holding the Line Without Destroying the Person
DeShawn Mitchell trained three of the people on your floor. He stayed late during the holiday rush without being asked. When a customer collapsed near the registers last spring, he was the one who called 911 and stayed with her until the paramedics arrived. He has been with you for four years. He was promoted to senior associate eight months ago. And for the past month, he has been putting electronics in his bag after closing. Loss prevention sent you the footage this morning. $2,300 in missing inventory. The camera angle is clear. You called him into the back office. He thinks this is about the holiday schedule. He is sitting across from you right now, smiling, asking about Christmas Eve shifts. You have to say something.
Why This Conversation Goes Wrong
You open with an accusation. "We know you have been stealing." Even with footage, leading with guilt triggers the fight response. DeShawn will deny, demand a lawyer, and shut down completely. You will get no cooperation, no recovered merchandise, and a much harder legal process.
You soften it into meaninglessness. "There have been some inventory discrepancies and we just want to understand..." If you cannot bring yourself to be direct, DeShawn will play along with the vagueness forever. He knows why he is here. Pretending otherwise insults both of you.
You moralize. "After everything this company has done for you" or "I trusted you" makes this about your feelings of betrayal, not the facts of the situation. DeShawn is not stealing because he lacks gratitude. He is stealing because his rent is due and his divorce left him broke. Your disappointment is real but irrelevant to the conversation you need to have.
The Evidence-and-Exit-Ramp
Theft conversations fail in two directions: too aggressive, and the employee lawyers up and admits nothing; too soft, and the conversation dissolves into ambiguity. The Evidence-and-Exit-Ramp holds a firm center. You present facts clearly, you give the person a dignified path to the truth, and you follow your legal obligations without turning a human being into a case number. The goal is not confession. The goal is resolution.
Set the room
Close the door. Sit across from him, not behind a desk. Do not have security visible yet. "DeShawn, I need to talk to you about something serious, and I want to be straightforward with you." The word "straightforward" signals that you are not going to play games. It also, subtly, invites him to be straightforward in return.
Present the evidence without editorial
"Loss prevention flagged discrepancies in electronics inventory over the past four weeks. We reviewed the footage." Pause. Let it land. You have not said "you stole" or "you were caught." You have stated facts. The footage exists. He knows what is on it. The pause is where he decides whether to fight or talk.
Offer the exit ramp
"I am not here to ambush you. I want to hear what happened." This sentence changes everything. You have given him permission to tell the truth without it feeling like a trap. Most people caught stealing are not criminal masterminds. They are people who made a desperate decision and are terrified of what happens next. An exit ramp is not softness. It is strategy.
Listen without reacting
When he talks -- and if you have built the ramp correctly, he will -- do not interrupt. Do not shake your head. Do not say "I understand" prematurely. Let him tell you about the divorce, the rent, the items he sold online. Write it down. Your calm is what keeps him talking. Your reaction is what would make him stop.
State the outcome clearly
"Here is what happens next." Company policy, termination process, what loss prevention needs from him, whether you are involving law enforcement. Be specific. Be factual. And then: "DeShawn, I want you to know that four years of good work are not erased by this. This is how this ends here, but it does not have to define what comes after." That last sentence costs you nothing and gives him something to hold onto.
The moment that changes everything
He already knows he is caught. What he does not know is whether you see him as a person.
DeShawn walked into this office knowing exactly why he is here. The casual question about the holiday schedule was not confusion -- it was his last few seconds of normalcy before his life changes. When someone is caught, the terror is not about the act itself. It is about what the person across the table thinks of them now. DeShawn has spent four years being the guy who trains new hires, the guy who stays late, the guy who handles emergencies. In the next ten minutes, he becomes the guy who steals. That identity collapse is what makes people deny, deflect, and lawyer up -- not because they think they can escape the evidence, but because admitting the truth means accepting the new label. Your job is to separate the act from the identity. "You did something wrong" is different from "you are a bad person." If DeShawn believes you still see the four years alongside the four weeks, he will cooperate. He will tell you what he took, where it went, what he can return. Not because he is trying to reduce his punishment, but because the person sitting across from him treated him like someone who made a terrible decision, not someone who was always this.
What to Say (and What Not To)
Instead of
"We caught you on camera stealing."
Try this
"Loss prevention reviewed footage showing inventory being removed after hours. I want to hear what happened."
Instead of
"How could you do this after everything?"
Try this
"I know you well enough to know this is not who you are every day. Tell me what led to this."
Instead of
"You leave me no choice."
Try this
"Company policy requires termination for this. I want to walk you through the process so there are no surprises."
Instead of
"Security will escort you out."
Try this
"I will walk with you to collect your things. You do not need to explain anything to anyone on the floor."
The Bigger Picture
The National Retail Federation estimates that employee theft accounts for $50 billion annually in U.S. retail losses, more than shoplifting. But the data point that matters more for this conversation: a 2023 SHRM study found that how termination-for-cause conversations are handled directly predicts whether the departing employee cooperates with investigations, returns property, and refrains from retaliatory behavior. Dignity is not a luxury in these conversations. It is a risk-management strategy.
The remaining team watches everything. They may not know why DeShawn was called to the back office, but they will know he left and did not come back. If the rumor is "they caught him and walked him out like a criminal," your team sees a company that discards people. If the rumor is "something happened, and they handled it," your team sees a company that holds standards without losing its humanity. That perception affects retention, morale, and whether the next employee in trouble comes to you before it becomes a loss-prevention case.
Wrongful termination claims cost U.S. employers an average of $45,000 to settle, even when the employer is in the right. Proper documentation, a respectful conversation, and a clear process reduce litigation risk by over 60%, according to employment law firm analysis. The ten minutes you spend treating DeShawn like a person are the ten minutes your legal team will thank you for later.
Practice This Conversation
10 minutes · AI voice roleplay with DeShawn Mitchell
Reading about this is step one. Practicing it changes everything. Sonitura lets you rehearse this exact conversation with DeShawn Mitchell, a realistic AI senior retail associate, 4-year employee going through a divorce who reacts to your words in real time. It takes 10 minutes. You will not get a rehearsal for this moment. When the footage arrives and you have to make that call, you will already know how to hold the line and the human at the same time.
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