How to Have Difficult Conversations with Friends

The answer to this question is very context-specific. What you would say to a bunch of guys on the basketball court is very different from what you might or might not choose to say to somebody in a boardroom. There are political realities to the context that everyone is subject to. It’s very tough to speak truth to power, and it’s not always advisable. My friend Esther Perel coined a phrase I like a lot: responsible honesty. You want to be responsible.

That said, there are situations where you’re a cad if you don’t speak. If somebody’s being overtly disrespectful, say, to a woman or a man of lower status or a younger man and it’s harsh or it’s rude, it’s incumbent upon you to say something. And short of some dire consequence, you want to say something in real time as it’s happening. If that’s not available, you pull the person aside. But you don’t want to sit in silence while somebody is mistreating someone else.

My kids confront me all the time. They’re perfectly capable of saying, “Dad, that shit doesn’t fly anymore.” Or “Dad, that’s an old, white male talking.” They’re not shy. Or “Dad, only somebody with privilege would say that.” But they’re vocal, and I’m their father.

Again, it’s all about the specifics. If what was said was racist or elitist or misogynist and/or insulting to you in some way, you can go back and say, “Hey, listen. I’d like to bring something up with you. Is that okay?” The first rule of doing this in a way that the person will more likely be receptive to is to not dump on them. Instead, you need to contract: “I have something to get off my chest. Is that okay with you?”

Or: “I want to clear the air. Is that okay with you, and is this a good time?” Contracts are there to protect you. It’s much harder for the person to turn around and act like a big, angry victim, if they’ve agreed to hear it from you.

That’s the first step: to ask, to contract. Second, you take ownership. Speak from the pronoun “I.” Don’t blame the other person for your feelings. It’s not “You did this.” It’s: “I was uncomfortable with…” I ask people to outlaw the phrase “makes me,” as in, “You made me angry.” No. You’re responsible for your own feelings. This happened, and I got angry. Cut the causality. You speak with humility about yourself: You are holding up the mirror of behaviors that you are uncomfortable with or that don’t match your value system.

It’s very important, through all of this, to lead with vulnerability. You do not want to lead with anger, and certainly not with indignation. Righteous indignation is intrinsically shaming. There’s a difference between saying, “That’s not my value system,” and saying, “You’re an asshole.” One is clean, and the other crosses onto the other person’s side of the street. Crossing the boundary is intrusive. Be kinder; be more compassionate. It’s what I call standing up for yourself with love. It’s a revolution to be strong and loving at the same time. To find a firm and loving voice is to step beyond patriarchy. The delivery can be very loving and very firm in the same breath.

Practice holding the person in warm regard, even while you’re confronting the difficult trait or behavior. They’re a good person; this is a difficult part of them. Once you start seeing them as bad people, you’re done. They’re never going to listen to you. This piece of it can help you stay centered, while casting a cool eye on the behavior: “You’re a good person; I know you’re a good person. This is beneath you. This behavior is not the best of you.”

It’s all relational. My kids started correcting me when they were like six and seven. But I couldn’t correct my father. He was uncorrectable. He was closed off and angry. There are lots of sons with fathers who would not, could not tolerate a conversation that was that emotional and personal and honest.

One way of speaking—if it’s not a violation playing out in real time, if it’s softer than that—is to talk about yourself. That gets the message across. If someone says something objectifying about a woman, you can talk about how you see it, and the message is extremely clear.

You also need to be centered. That’s the most important part of confronting somebody: your own self-esteem. If you’re in the one-down, shame position and you need to confront somebody with difficult behavior, they’ll blow right by you. They won’t listen—you’re too weak. If you go one up, and you start judging them, looking down your nose at them, holding them in contempt, they’ll smell it and they won’t listen to you. They’ll protect themselves from your attitude.

One of the great traditions in male friendship is giving each other shit. Most men love to do that and fall right into that. And it goes both ways. You can give somebody shit for saying something misogynist. You just look at them, and you go, “Oh my god, you are so retro. When are you going to step into the twenty-first century, man?” And it’s like, you know, that’s the way guys talk to each other.

If a man moves from inflation to deflation, from grandiosity to shame, it’s like you pop their balloon and they deflate. What I tell my guys is this: When you’re up in grandiosity, when you’re acting out on somebody, you’re shameless. It’s a form of preoccupation and entitlement. When you go down into toxic shame—which is “I’m a terrible person; don’t talk to me because I feel so bad” or even “Come comfort me because I feel so bad about what I did to you”—when you move from shamelessness to toxic shame, you just move from one form of self-preoccupation to a different form of self-preoccupation.

Guilt or remorse is what’s in the middle and what pulls you up out of yourself. I say to the guys I work with: “I want you to get over yourself. It’s not about you; it’s about the person you hurt. Remorse pulls you out of self-preoccupation and back to the person you hurt. You want to make amends; you want to repair with them; you want to help them feel better. Get over yourself. This wallowing around in shame is no favor to anybody.”

I say to people: “It’s tough to come out of shame. I’ll give you sixty seconds.” And they do. But I have to teach most of the men that I work with what healthy guilt and healthy self-esteem look like. It’s the capacity to hold yourself in warm regard in the face of your screw-ups and imperfections.

Feel bad for your behavior, hold yourself in warm regard as a flawed person, and learn from it, and move into repair. That’s what a grown-up does.