Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Accountability

How to Let Others Learn the Hard Way

Joseph Grenny

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


Crucial Confrontations

QDear Crucial Skills,

My sister-in-law is in a cycle of denial and anger at having lost her home and many possessions. She is also on the verge of losing her business. She is lashing out toward family members because they aren’t stepping up to the plate.

I am resentful because she isn’t taking responsibility for the role she played that brought her to this current crisis. She believes her family should be bailing her out of trouble physically and financially. I honestly would help if I thought I could, but I’m afraid I’d simply be enabling her bad habits and keeping life from teaching its lessons.

How do you deal respectfully and compassionately with others, when the guilt of watching them sink deeper and deeper into trouble becomes uncomfortable?

Helpless Spectator

A Dear Helpless,

What a wonderful in-law you are. The fact that you are agonizing over your response is evidence of your compassion for your sister-in-law. Here are a few thoughts about your dilemma:

1. Learn the difference between guilt and pain. You talk about feeling guilt, but if you truly feel you are doing what is best, what you’re feeling is not moral guilt. It could be that you’re feeling social guilt—a worry that your sister-in-law doesn’t approve of you or that others may judge you harshly because you aren’t doing what they think you should do. This isn’t moral guilt, it’s dependency. If this is the case, you need to look inward rather than outward. Be comfortable and confident with your response and affirm your own choice rather than looking to others for approval.

You may also be feeling simple pain. You sympathize with your sister-in-law’s predicament and hate the fact that she is creating this misery for herself. If this is the case, then you’re human. This is the right way to feel and there is no solution for it other than to stop loving her, which I don’t advocate or believe you want to do.

2. A little distance makes pain manageable. I think it’s perfectly appropriate to protect your own happiness by giving yourself a little distance from someone who is on a self-destructive path. Have a little less contact, talk about her less with others, but be careful about too much distance. Stay close enough to be accessible, and far enough to avoid excessive misery. When you put yourself too far out of contact you could be slipping into selfishness rather than self-management.

3. Develop a message that expresses both your love and your boundaries—and deliver it consistently when she attempts to draw you into enabling her. If you are comfortable that you are doing the right thing, then your guilt will turn into a cleaner and more manageable kind of pain—and you’ll be able to confidently and compassionately express two messages: 1) that you love her and will help her; and 2) that you won’t participate in things that won’t truly help. This is a tough message to get across, and many people who are intentionally blind to their own role in their misery won’t hear it from you until the 100th time you say it—perhaps many years down the road.

One dear friend didn’t truly hear it from me for four years. But when he did, we began to work together in a healthy way. This is a bit wordy, but here’s what I said over and over again to him:

“I know you think I should help you in ways that I don’t think would truly help. I know you resent me for that. But I want you to know that any time you are willing to engage in a plan I believe will be healthy, I will do everything in my power to help. Until then, I will maintain a little distance because I think our disagreement about what I should or shouldn’t do will hurt rather than help our relationship. But please don’t mistake that distance for a lack of affection. If anything, it is my way of protecting our relationship. I will always love you.”

Don’t make the sucker’s choice of maintaining your boundaries by becoming cold. And don’t become an enabler in order to avoid seeming cold. Express both your love and your convictions—over and over again. Someday she will hear them both and appreciate your wisdom.

You have my admiration. I hope my words help, too.


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