Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

How (Not) to Lend Money to a Friend

Dear Joseph,

About a year and a half ago, a friend approached me about borrowing a significant amount of money. Over the years, he has paid back previous loans faithfully. At the time we talked about this, he offered to pay back with interest. I told him paying interest was not necessary and that he could just pay back the original amount of the loan whenever he could.

It has been a year and a half, and he has paid nothing back. He also hasn’t mentioned the loan. The relationship means more to me than the money. But now I’m wondering if he may have misunderstood and thought I didn’t need him to pay back the loan. How do I approach this? Thanks for your help.

Deeply Concerned

Dear Deeply Concerned,

Yuck. I hate it when I do this. I leave expectations vague, assume the other person will meet my expectations, then procrastinate discussing it when they don’t. When I do, I end up feeling a little sour toward them, and a little guilty toward myself. Sound familiar?

The fix is straightforward and can be said in three words: Clean. It. Up.

You’ve made a mess. So has he. But you can’t do him. You can only do you. So, clean up your side of the street in two easy steps:

1. Tell yourself the right story. First, acknowledge to yourself that you might need to kiss this money goodbye. You were reluctant to clarify your agreement the way you should have, and you’ve left so much room for misunderstanding that you might need to accept you have flushed your resources. Once you have accepted that possibility, and your own culpability in making it happen, you can . . .

2. Have a cleanup conversation. Don’t overthink this. What makes these conversations so hard is that we make them so hard. We obsess over them for days prior to having them. Just reach out to your friend and say, “I have a hunch you and I are on different pages about the money you asked to borrow 18 months ago. Can we talk about that?” That’s all it takes, and you’re off and running.

Start the conversation by asking, “What did you understand our agreement to be?” Then listen. Ask questions. Clarify. Then say, “Here’s what I thought was going on . . . ” and share your recollection.

This is where you get to own your part—as much as you are willing. If, for example, he comes back with, “I assumed the money was a gift,” you’ve got a decision to make. Is the relationship more important than the money? If so, it’s time to grieve the loss and move on (assuming, of course, you believe your friend is telling the truth—but that’s an issue for another column!).

With conversations like these, the longer you think about it the more miserable you get. Stop thinking and start talking.

And next time, put it in writing!

Good luck,

Want to master these crucial skills? Attend one of our public training workshops in a city near you. Learn more at

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

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