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

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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RE: "When You're Under Attack" (January 2, 2008)

I think the letter answered by Emily Moss, from "Attacked" is a good example of the difference in conversational style between men and women. Men, are generally more direct than women.

Certainly the question, "Why are the analysts afraid to ask you for a work product?" is direct but I'm not sure I would frame it as attacking. Direct or "pointed" is not the same thing as "attacking." Unless there were additional comments not reported here, then I would suspect that the attack lies in the mind of the receiver rather than in the intent of the speaker. Having to communicate with people who read things not intended into comments is often a big communication issue with married couples and with mixed gender workplaces.

From the writer's comments it appears the manager has been unhappy with the level of service his group has received for some time now. Perhaps the first thing to do is to solve the response problem, and then attend to the directness of his comments. If her group were providing superlative service I suspect she would not get so many "pointed" questions.

I don't think the issue, in this case, is primarily one of communication. It sounds as if the primary issue is one of providing adequate service to a client group. First things first!

Patricia P.

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RE: "The Unreasonable And Irrational" (January 9, 2008)

Kerry,

Thanks for a wonderfully insightful column.

I think you left out an important piece of the answer to the person who asked "But what if the answer to the Humanizing Question is that this is not a reasonable, rational and decent person?"

They may not be reasonable, rational or decent NOW; however in treating them that way, you are helping to create a reasonable, rational and decent person in the future. We must treat people the way that we believe they can and should be, not the way they "are" right now or have been in the past (even if for their entire lives.)

Stephen

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RE: "Moving The Needle" (January 16, 2008)

Wow! Tell Kerry I want to work for HIM!

Imagine, actually being appreciated for one's efforts at work.

It is true that often times the most effective reward an employee can receive is the cheapest, yet rarest—genuine praise and/or thanks for a job well done.

I've been working almost 30 years now. Companies have "attempted" to thank/reward me, and almost without exception they fall flat. I say "almost" because there was one instance, about 20 years ago, that still stands out in my mind.

A group of us at a small flight simulation company had worked on a proposal for a contract. Some time after we had finished the work and the proposal had been submitted (and before we learned we had indeed won the contract), one of the managers personally came to the cubical of each of us who had worked on the proposal and thanked us, shook our hand, gave us a copy of a letter of thanks for our effort that was being placed in our personnel files, and gave us a ballpoint pen with the logo of the project we had worked on. The pen was the most expensive part of the reward and probably only cost the company a few dollars each, but that didn't matter. It was the personal thanks and handshake and the fact he came to me instead of just delivering some collective "thanks" in a meeting room, or just sending around a memo of thanks.

This gesture cost the company next to nothing, but I think it will stick in my mind as one, if not the, best example of true thanks I've ever received.

Tom T.

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