Crucial Skills®

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Crucial Conversations for Mastering Dialogue

How to Approach a Suspected Thief

The following article was first published on January 23, 2008.

Dear Crucial Skills,

Someone stole money from me and I have a hunch it was a roommate. How would you approach this confrontation? Our relationship is neither strong nor bad, just fairly new.

I’m not sure how to ask her without making her feel unsafe. And I definitely can’t imagine her saying “yes” even if she really did take the money. What should I say?


Dear Baffled,

I sympathize with your situation. Something bad has happened. You can’t generate any plausible explanation other than theft. And yet, it’s hard to see this new roommate as a thief.

One of the hardest times to motivate yourself to speak up is when you aren’t whipped-up in righteous indignation. You doubt yourself and you don’t want to cause pain to a potentially innocent person. On the other hand, this is also the best time to speak up because you are in exactly the right frame of mind for real dialogue. You’re humble enough to be wrong and caring enough to worry about the impact of your approach.

Of course, what you do depends upon the strength of the story you’re currently telling yourself. So I’ll offer some advice for three scenarios. You choose which fits:

1. No evidence. The only reason you’re even thinking your roommate may have taken your money is by process of elimination. In other words, you don’t think she stole it but you can’t think of any other explanation.

In this circumstance you should bring up the missing money. Share the facts—not your story (that you wonder if your roommate stole it). If your roommate had nothing to do with it, this will help involve her in the search or alert her to problems that could continue to plague both of you. Simply say something like, “Last night, I had two $100 bills in my purse. I left it in the kitchen and this morning they were gone. Have you had anything come up missing recently?” If your roommate was involved, this conversation will either put her on notice that you’re aware of something fishy or lay the groundwork for a future, more direct, conversation. But, I don’t recommend this very vague approach if you have more reason to suspect your roommate.

2. A little more evidence but a lot of fear. You have a number of reasons to suspect her (e.g., she had two $100 bills when you went out to eat last night) but have reasons to believe a conversation would do more harm than good (she has a hot temper and carries a Taser).

In this situation, you’ve concluded that the potential upside of a conversation is not worth the downside risk of conflict. The big mistake people make in this situation is indecision. They waste time feeling resentful about reality rather than simply accepting their own assessment and making a hard choice to either a) adapt to the insecure environment by securing your valuables; or b) move. Get over it—if you’ve decided you aren’t going to speak up, accept responsibility for that choice and decide how you’ll deal with the future.

3. A little more evidence but nothing to lose. You have a number of reasons to suspect her and nothing to lose by trying the conversation. The worst that can happen is that she denies it, resents you, and you move out. The only difference from the second option is that you’ve opened up the possibility for her to acknowledge her actions and for you to come to some resolve. Here are some ideas for holding the conversation.

  • Don’t open your mouth until you’ve committed to Plan B. Decide what you’ll do if either she denies it and you’re still suspicious or she denies it and the relationship sours. If you’re prepared for this eventuality, you’ll feel a bit less stress in the conversation.
  • Begin with a sincere and emphatic apology. “I have a concern and I feel terrible about even bringing it up. But I know if I don’t, it will nag and bug me and get in the way of our relationship. May I talk with you about it?”
  • Take her carefully down your path to action. Carefully and non-judgmentally share your data. Take all the time you need and don’t skip any element of what feeds your concern. Then, very tentatively, share your conclusion. “The other night I had two $100 bills in my purse when I left it on the counter. I know I did because I opened my billfold to remove $5 for cab fare when I got home. The next morning it was gone. I racked my brains to think of what could have happened to it. Then when you and I went out to eat that night you had two $100 bills.”
  • Acknowledge your suspicion but be tentative. At this point she knows what you’re leading to. You must very quickly restore safety in two ways: 1) by letting her know you hate this conclusion—even though you worry about it; and 2) by letting her know if she made a mistake you can still respect her. “I know this sounds horrible for me to even ask. But can you see why I’d be wondering? Since I can’t come up with any other explanation about how it could be missing, I decided I needed to talk to you rather than leave it festering between us. And I want you to know if you did make a mistake, I’ve done so in my life too.”
  • Open the dialogue. Now it’s her turn. “Did you—for any reason—take the money from my purse?” Be prepared for her to be hurt and defensive. If she is, do not back down. Continue to ask her to help you reconcile the concerns while assuring her all you want to do is work it out.

This is tough, but the costs of not speaking up will be much higher than the risks of taking action now. Be humble and honest and you’ll have done all you can. Finally, if you decide to leave, do so quickly and graciously. When you refuse to let others paint you as a villain, you enable them to examine themselves rather than justify their transgressions using your vengeful response.

Best wishes,

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33 thoughts on “How to Approach a Suspected Thief”

  1. Anthony Kerwin

    Did you ever hear the results of later crucial conversations? I wonder that about a lot of your stories.
    Thank you for all your work and the stories – you always provide helpful suggestions.

  2. Douglas Harrell

    What about asking, “Did you see it?” and “Did you need to borrow it?”
    This asks for help, and gives them an easy out if they really did take it. They can say yes, and you can say, “Okay, but next time please ask first.”

  3. rochellearellano

    This is so helpful!

  4. Jill Paulson

    Yes, this is helpful, BUT….has anyone considered that critters may live in the house, looking for paper and cloth to build a nest? Money is paper, after all. I mention this because I ran into a similar situation as a child, living in the woods. We had no idea there was a RAT in the house, but things kept disappearing. The rat hideout was discovered 30 years later during a remodel, explaining it all. I can’t imagine assuming guilt in a situation like this. Missing items are not always by human hand. My thoughts…

  5. Harlan Cohen

    For the future, buy and use a safe. Lightweight ones can be hooked to a stationary object with a cable.

    Who knows who may be in and out of the apartment down the road. Suggest your roommate get one too.

    1. Kim

      I agree totally

      1. Michael

        Nope, one should not have to bank money, valuables or items from anyone. If it’s not yours leave it alone.

        1. Christine

          I don’t believe coddling someone who steals is the path forward. It’s a bad sign. People who feel entitled to your hard earned cash should be confronted. Move her ass out. You did nothing wrong other than not seeing the signs of a deeply disturbed person.

          1. Arlene

            I fully agree! My l (now ex) best friend of 32 years stole a $54 lipgloss. She lied when I confronted her saying she didn’t meanwhile I had used it before going to meet her at hair salon and know exactly where
            I put it. We came to
            My house and about 45 mins later I saw her using it. I immediately went to check my purse and it was not there. She said she had found the one she
            Lost weeks ago when she went to get all her stuff from her car (in my driveway) to stay over at my house. I didn’t want to start a war so I let it go and asked her about it two days later and it was not same story she told me the first time I asked. I let two more days go
            Buy and asked again to which she did a copy and paste of what she said the second time. I ended up telling her I do not want this friendship anymore. That I cannot have a friend who
            Lies and steals especially since I have been extremely kind financially to her and her kids. I cannot believe that she lost a 32 year friendship over a $54 lipgloss, I cannot have her in my life because she just keeps lying… 100%.
            You Should NEVER steal especially from your best friend. That is disgusting.

        2. obaleana belvona

          Isn’t that the truth! who told you as a child it’s ok to steal? a teacher, a grown-up, your mom? no. as children we learn right from wrong. good and bad. I’m sure as a child there’s a lot of people that remember what it’s like to take something that didn’t belong to them. fear of punishment, embarrassment, guilt. and when you grow-up its law, a crime with punishment for a reason! I have no patients or respect for theives. just because you want something, doesn’t make it yours. how hard is that to figure out

        3. Kimturner

          My thoughts exactly if it ain’t for you don’t touch it you ain’t got no business touching you are a thief

    2. Lynn Robbins

      I’m not replying – have a question. I have a woman who cleans my home every other week. I had my jewelry in a winter coat pocket for months. Anytime I want to wear a piece, I too k it out and replaced it in the same place. I did this even before my cleaning woman. I usually never leave her alone and I did twice for about 1 hour. This past weekend Inwent to get an item and the entire box was missing. She is coming on Wednesday and I don’t know how to approach this. I live alone and nobody has a key, never had a break in.

  6. Kim

    There was this girl who was slamming dope and she was on a sick one when she and her boyfriend broke into a house and got gold and diamond jewelry from the master bedroom before getting scared off and ended up in the house behind the first house when people came home. At second house she went through a window that was open. There was a woman sleeping and money on desk in hall she took. It was 5 grand. I think about the sleeping woman what her life like trying to convince someone shpe really had left it on the desk. Crazy stuff like that happens more than you know. And the reason I always keep my doors locked, windows only part way open. & money hidden if I have it ( Only on a few occasions have I ever had large sums of money in my house) from anyone’s view coming inside my house.. so there’s always that possibility of some weird thing like that happening you don’t even know about.

    1. Kim

      And my best friend told me this story it was her cell mate when my friend had to do a weekend for a DUI.?

  7. Alfred

    If you think your roommate has been stealing from you, you can gather evifdence by turning your phone into a security camera. At least you’ll have proof in case your roommate denies it altogether!
    YouTube #AlfredCamera

  8. mitch

    a gave someone money to hold for me till i needed it and now they wont give it back. what do i do

    1. Younes

      hi im really interested to know what you have done.

    2. Younes

      Hi, can you please tell me what you ended up doing?

    3. Juan Lerm

      1. Whether in your family home, apt with a roommate(s), a business partnership, even places of worship and so forth , if one suspects theft , the use of grifting ( drawing on emotions to obtain money they likely intend not to repay – this is Fraud punishable by 2-5 years in prison. Mainly because of intent, and likely wire fraud if money is deposited in their bank and transfers it to pay someone for what they owe, etc, each payment is potentially one indictment. Prison time, severe fines, slanderous lawsuits usually connected, conspiracy to commit a state/ federal crime, esp if others involved, and civil lawsuits , where proof is not as important…). happen to thousands of people everyday. Most walk away only to repeat the crime bc the victim refuses to confront their concern, creating a behemoth of a criminal.

      Speak to a criminal attorney who these days provide at least 30 minutes of free advice . If its a good, provable case, attorneys will usually do a quick investigation for free and call you back giving you their findings. This is plan B, possibly , C and D.

      If a civil discourse has con. Sideways in an attempt to find non- legal resolution, the next step is to get a quote from the lawyer to handle the case step by step. First, they will have you give full. Details, aby prove , including security cam footage of crime… documents like contracts, recorded phone conversations in one-party states, like Texas. If your intimately involved. with the alleged criminal as business partners or living together…then its not only legal to record using phone Apps that are free or for 10-20 dollars. I have one and use it when i am speaking to a partner or people you find suspicious. Texts and emails are admissible in. Court’s . If u record via your cell, u can start the recording at anytime; whether you call or they call. They can hear the recording sounds.
      Recording with your phone close by is something you can also do in person when attempting resolution. * just know that in 1 party states, only one person needs to know of the ongoing recording. And that person can be you. You do not have to mention anything to the person(s) in group talk, as long as all of you are involved in the issue necessitating clarification and resolution.

      1. Thank you for coming together to resolve this issue(s). Im sure all of us want resolution and without the beed to get upset or threaten. So, who would like to begin in giving a general overview as to why we have been called to meet. If no one says anything, then you can have a synopsis written from which you will read. Make copies for all.
      2. The agenda should be concise.
      3. Have proof if any including conversations. Do not use recorded ones at first.
      4. Stay calm but don’t backdown. U can have a meeting in a coffee place away from people.
      5. Then, move to the list of solutions, first asking them how they feel and how they would want to fix things.

      The above shows great leadership capabilities, and protect you from the culprits from stating you took to long to discuss your concern(s) or you didnt take any step forward to protect the relationship… personal, business… etc

      6. After the meeting, email and text all parties thanking them for meeting and for their input. If things go sideways, stay calm and try to set up a followup meeting in person or by phone ( always record) , asking if they would like to rediscuss or come up with new solutions. A second meeting is usually needed. People need time to ruminate over what issues were discussed and if they are ready themselves for plan B.

      If no resolution is attained, then for as little as 500dollars, a lawyer can send a demand letter and cease desist. A time limit on causations and resolutions will be on the letter. This does not mean the alleged enemy must attain a lawyer. But he now knows he will have to respond. A restraining order maybe needed if one perceives a threat.. usually very effective. The letter will remain amicable .

      C. If the party presumed defendant (s) are dismissive, then a full legal letter will be sent. It is worth it if they plan to hurt others and the minies owed are high. After all, the lawyers will seek to have all legal fees paid. Usually. 10-15k dollars are what lawyers charge. More if it goes to court. But you have the right to change your mind anytime.

      D.criminal lawyers will usually take cases they have a high likelihood of winning. It improves their image. And that is extremely valuable to all lawyers.

      Lets protect each other by seeking justice. Not vengeance.
      Dr. J

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  10. Louisa

    Ive been saving money in my piggy bank. Lately, I found out that the piggy bank was not on its right place. I knew something is wrong so I opened it then I found out that half of my money savings were lost. I immediately told about this to my cousin and suddenly the house helper suddenly appeared in the moment and keep telling me that she didnt do it even if I never named her. Is it possible to suspect her?

  11. Olivia

    I have a lot of money I have saved up over 6 months And only told 2 of my close friends and my sister all of a sudden my sister says she “found” 70 dollars should I believe her or see if it was her

  12. Matthew

    I had a friend stay the night and when I was woken up by him he gave me my wallet .not till a HR has gone by and I notice 500 100$ bills are gone .how do I prove that .He did go pay off a drug det he said he had his stimules check com in then the story changed he said his unemployment check is what he said he payed it with . but just yesterday he had no $ and asked to barrow 40$ isn’t that enough proof .once he left he he didn’t replied to my messages .if I put my hands on him I go to jail .

    1. younes

      hi bro, im going thru the same thing except its less money for me, what did you end up doing

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  15. Abigail azi

    Last night buglars came to my house and stole some valuables.i could not and still can’t fathom how they did it. This morning I saw my neighbor sitting outside his house and he wierdly smiled at me. I’ve never had a conversation with him. so I suspect him and some of his friends and I don’t know how to approach them

  16. Ann

    My neighbor/friend took our shih tzu overnight while myself and my daughter went away. When we came home our dogs $70 Seresto collar was gone. Neighbor says” I had to give the dog a bath, and the collar got tangled in his hair, so I had to cut it off and I threw it away..but I bought you this replacement one, no box, just a collar in a plastic bag! …and yes he has a dog.. !!

  17. Esther

    I opened my bag when my bestfriend was there cos we wanna eat. I took out some money for food and then kept the bag in my wardrobe and gave her the key. Then, the next morning, all the money was gone. I don’t know what to do and this has been happening for a while now.

  18. Nick

    This is really useful . I cant say anything else about it . I successfully caught the class thief that was stealing from everybody’s food and money . Thank you Joseph Grenny for creating this .

  19. Guest Poster

    I asked a friend to cat sit while we went away for a few days. When we returned there was a loooot of food missing and also my motorcycle helmet. Nothing else was missing. I made sure I didn’t leave any valuables in the house before we left, I took them to the house of a relative who I trust but who couldn’t look after our cat. I confronted my friend and he got a hurt look and said, we’ve been friends for years how could you possibly believe such a thing of me? But I know he is a thief because many people had similar experiences with him, still we had hoped that he had reformed now that he has a job and doesn’t “need” to steal anymore in order to have money. Needless to say I don’t consider him my friend anymore but I don’t know what to do to get him to admit that he stole our food and the helmet and give them back to us.

  20. AH

    How can you tackle this with a manipulator roommate who you actually caught stealing food but has a way of talking their way out of situations and a history of gaslighting?

  21. Jane Chepkorir cheruiyot

    I’m afraid to do so cause he’s almost 5 times my age

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