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Crucial Conversations QA

To Confront A Thief

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Joseph Grenny

Joseph Grenny is coauthor of four New York Times bestsellers, Change Anything, Crucial Conversations, Crucial Confrontations, and Influencer.

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Crucial Conversations

QDear 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?

Signed,
Baffled

A 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 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 of 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 leaving 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,
Joseph

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Joseph Grenny

Joseph Grenny is a New York Times bestselling author, keynote speaker, and leading social scientist for business performance. For thirty years, Joseph has delivered engaging keynotes at major conferences including the HSM World Business Forum at Radio City Music Hall. Joseph’s work has been translated into 28 languages, is available in 36 countries, and has generated results for 300 of the Fortune 500. read more

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