Dear Crucial Skills,

How do I ask my former sister-in-law for money that she owes me?

My former sister-in-law is a high powered attorney in NY. Her son and my son are the same age and are good friends. I suggested to her they attend camp together for the summer and she asked that I go ahead and register both boys and also pay the registration fee, which I did. She said she would follow up with payment. A month later she still had not reimbursed me, so I sent her an e-mail reminding her. Still no response.

We are not very close and I have never really felt that she respected me. How do I confront her without getting hostile?

Signed,
Repo Woman

Dear Repo Woman,

Your last two sentences say it all. It was appropriate for you to include all that you did in that final brief paragraph. You first disclose that you believe she doesn’t respect you. Then you add that your challenge is to confront without hostility. My first point is that these two issues are inextricably connected. You will be hostile to the degree that you a) believe she doesn’t respect you; b) believe her disrespect of you actually means something about you; and c) use a & b to assemble a story that has her avoiding repaying you because she is intentionally trying to stick it to you.

In other words, your hostility will be driven by the story you’re telling yourself about her and her behavior and not by the behavior itself.

You first must work on your story. Some options you have are to find a way to tell a story that:

• Has her feeling some degree of respect for you. (Hint: what are three pieces of evidence an objective outsider would give you to demonstrate that she holds you in some level of esteem? For example, she allows/encourages her son to spend significant amounts of time with your son.)

• Makes you less dependent on her feelings about you. (Hint: Why does it matter that she doesn’t totally respect you? Who cares? What stories do you tell about yourself that make you suspect she shouldn’t respect you? Are these stories true?)

• Explains why a reasonable, rational, and decent person would not have repaid you. (Hint: it’s a small amount and she’s forgetful; you’ve done something to bug her in the past and this is her way of needling you; she’s strapped for cash living her lavish, lawyerly lifestyle; etc.)

What I’m suggesting is that you provoke, assault, soften, and challenge your story about her, about your relationship, and about what’s going on. At the end of the day the only way you can avoid being hostile is to stop feeling hostile. And the only way to stop feeling hostile is to master your story.

Now, how do you hold this conversation? Person to person. You have now exceeded the utility of e-mail and will only get into trouble by taking this next step electronically. Call her up.

Now that you’ve got her on the phone (or in person), hold the right conversation. This is a pattern issue. Talk about the pattern, not the money. Describe the gap between what you expected and what you are getting in a way that illustrates the pattern of neglect. As you “describe the gap” be sure to create safety–don’t attribute bad motive–and affirm your basic respect for her:

“Two months ago you asked me to sign your son up with mine for summer camp. I was so glad you agreed because your son and mine have such a special relationship. At that time you asked me to cover the deposit and promised to pay me back soon. After a month lapsed and I didn’t get the deposit from you I sent an e-mail. When I covered the deposit, I expected you’d pay it back soon so I wouldn’t have to ask because I don’t want to have the burden of nagging. What’s up?”

Hopefully you can see in this sample script my attempt to show respect, clarify my concern, and open up the right conversation–not just one about the money, but one about a pattern of her not keeping the commitment and pushing the problem onto you.

You may also want to build a little more safety by demonstrating that you are not attributing bad motive about her failure to repay:

“When you didn’t respond I wondered if maybe you didn’t get my e-mail. Or perhaps you’re short on cash in the short term. If there are any issues I’m happy to try to work this out in some reasonable way. What’s up?”

When you demonstrate your willingness to attribute good motive, or to show understanding for challenges the other person faces, you aren’t letting her off the hook. You’re simply making it safe for her to open up about what she’s facing. Then with full information about what’s going on, you can agree on a solution that suits you both.

Good luck!

Joseph