Crucial Skills®

A Blog by Crucial Learning

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,

Develop Your Crucial Skills

Image for

What's Your Style Under Stress?

Discover your dialogue strengths and weaknesses with this short assessment.

Take Assessment

Image for

Subscribe Now

Subscribe to the newsletter and get our best insights and tips every Wednesday.


Image for

Ask a Question

From stubborn habits to difficult people to monumental changes, we can help.

Ask a Question

23 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

    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?

  9. These People Shared The Worst Moments Of Their Lives…And They’re Utterly Brutal

    […] VitalSmarts […]

  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

  13. These People Shared The Worst Moments Of Their Lives...And They're Utterly Brutal

    […] VitalSmarts […]

  14. Heartbroken People Share Their Very Worst Breakup Stories

    […] VitalSmarts […]

  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.

Leave a Reply

Get your copies
The ideas and insights expressed on Crucial Skills hail from five New York Times bestsellers.


Take advantage of our free, award-winning newsletter—delivered straight to your inbox