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Crucial Conversations for Accountability

How to Confront Someone Who Has a History of Evading Responsibility

Dear Crucial Skills,

How can you confront a manipulative roommate who has a way of talking their way out of situations and a history of gaslighting? I caught them stealing food from other roommates.


Dear Roommate,

Two of our most popular Crucial Skills articles are “How to Confront a Liar” and “How to Approach a Suspected Thief.” You might want to read both for additional ideas on approaching your roommate. You’re not alone in living and associating with people who don’t always act responsibly. It’s a challenging world out there.

It sounds like your concern centers on the fact that you’ve caught your roommate stealing, but their history of manipulation and gaslighting gives you little confidence in confronting them with good results. I’ll share three skills I think will help.

Ask the Humanizing Question

When you’re facing bad behavior, one of the principles we teach in Crucial Conversations is to ask yourself, “Why would a reasonable, rational person do what they did?” We call this the humanizing question, and we suggest that you spend time reflecting on it before engaging in dialogue. But what happens when history indicates the other person isn’t reasonable or rational? How do you proceed?

The humanizing question is so important because its purpose is two-fold. Yes, it helps you humanize the other person you’re about to dialogue with. But also, and maybe most importantly, it keeps you human. You’ll find that the cognitive process of generously diagnosing someone’s behavior helps to neutralize your own heightened emotions, slow your desire to act harshly and reactively, and remind yourself that you’re safe. This process ensures that you enter the conversation both reasonably and rationally.

If you can’t understand why your roommate acted the way they did, consider why another person—one who is reasonable and rational—acted that way. Perhaps they were out of food and in a hurry but planned to replace the items later. Or perhaps they asked permission when you weren’t around. In any case, when you practice the humanizing question, you’re taking time before the confrontation to both act humanely yourself and see the humanity in the other person.

It’s important to note that we don’t give people the benefit of the doubt because they are in fact innocent. Often, the other party is guilty and that’s why the confrontation is necessary. Which brings us to our next skill.

Start with Facts

As you approach your roommate, be sure to stick to the facts about what you observed and nothing more. Resist the urge to pile on additional frustrations or add conjecture about what the incident means about the other person. Instead, simply and factually describe what you saw and then let them explain.

“Yesterday, I saw you drink Fred’s milk. The carton was clearly labeled but you poured a glass anyway. Did he give you permission to do that?” And then listen to understand. Some simple, factual dialogue might just help them reset their behavior or provide the explanation you were lacking.

Sticking to the facts is particularly important with someone who gaslights. You’re not talking about your feelings or perceptions that are debatable; you’re simply describing facts that can’t be denied. In the future, I strongly suggest you speak up quickly and in the moment so that the facts hold their power. The longer you wait to speak up, the more the facts grow fuzzy—sometimes degrading into a game of he-said-she-said. And this may be why you’ve struggled with your roommate in the past. You’ve had concerns, you’ve remained silent, and your silence gives them leeway to debate history as it grows fuzzier and less certain. Any hope of salvaging this relationship will depend on your willingness and ability to speak up candidly and quickly.


If your roommate’s behavior doesn’t change despite you speaking up in the moment, then you’ll want to elevate the conversation from Content (a singular incident), to Pattern (the history of bad behavior), and eventually to the Relationship. This skill is called CPR and it helps you decide which conversation to hold so you can solve problems rather than get stuck having the same conversation over and over.

Instead of narrowing in on a single incident of stealing, talk about a pattern of behavior that is unacceptable in your home. You might need to set some boundaries. For example, “Since this is a pattern, maybe it’s best that we label our food so there isn’t any confusion about who it belongs to.”

If, you’ve held a pattern conversation and reached some new agreements, but your roommate continues to behave poorly, then it’s time to elevate the conversation to the third level: Relationship.

At this point you’ll want to talk about how they have violated your trust or created such a toxic environment that you need to renegotiate the relationship. Many people who gaslight or manipulate are rarely confronted about THAT behavior. The other person tends to beat around the bush, addressing small content issues but never addressing the impact of these toxic behaviors on the relationship.

Relationship conversations are not easy, but if things are as challenging as you describe, it’s probably where you need to go. This is when you’ll want to talk about finding new living accommodations for you or them. Or maybe even ending the relationship because it’s no longer healthy for you. The best approach is to proceed tentatively. Continue to share facts that support your conclusions and concerns. Make sure it’s clear why you feel the way you do, and that your accusations aren’t based on conjecture or stories, but real behavior. Then ask them how they see it? Listen to understand their view and then decide what that means for you.

If they feel remorseful, maybe there’s room to work things out. If they are defensive and resistant, you may want to find a new living arrangement. Whatever the result, your thoughtful actions should help you move forward with your decision confidently.

Best of luck,

You can learn more insights and skills like this in Crucial Conversations for Accountability

5 thoughts on “How to Confront Someone Who Has a History of Evading Responsibility”

  1. Wendy Clarahan

    This response is so brilliant Brittney. It was a pleasure to read as the sequence just flowed & the writing was pithy but informative the way my brain needed to understand. I know I can apply what I have learned here to situations in my personal & professional life. The way you have layed it out is so rational & reasonable in & of itself so the emotions were taken out of the picture, I could focus & I could just let my prefrontal cortex go to work unimpeded lol👍

    1. Brittney Maxfield

      Thank you Wendy! Your kind words mean a lot. Thank you for reading.

  2. tom benzoni

    This is an important idea; the premise needs to be very clear, however. Just Culture has a good model here. (I refer to the original Just Culture, not the one I see in the punitive section of HR manuals, leaving out the responsibility up the chain.)
    First: Are the rules clear ad agreed to? In a communal environment, it can become confusing in a hurry. “We are communal in Area A but not in Area B.” We do not share food, no exceptions, no grace. We do share utilities, all grace. (4 people in communal space: one uses only one’s own food but uses 50% of the hot water…)
    Next: Are the rules followed? I don’t label the carton of milk that I want just for me, clearly, with my name, using is up before it stinks up the refrigerator and I don’t crowd out others.
    Last: Now ask the “bad intent” question: “I bought that milk yesterday, I labeled it, it was alone on the shelf. It’s empty now, back on the shelf. Any idea what happened?”
    I find the first 2 steps are frequently neglected as we seek to canonize ourselves. This is lazy thinking.

    1. Brittney Maxfield

      Thank you Tom – really good insight.

  3. Corinthia Emanuel

    Succinct, functional, and effective! Thank you.

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