This is the fifth post in my series of daily posts for the month of April. To get the best of my writing in your inbox, subscribe to my Substack.
Not enough people appreciate the art of skillful listening. This is unfortunate because we would all have a much easier time dealing with our problems if we were surrounded with good listeners.
The advice below is what I’ve learned from my experience coaching and just helping my friends with their problems. It’s most useful for thorny personal problems like “my partner is not giving me enough attention” or “I’m feeling undervalued at work” or “I keep getting distracted from the projects I care about”. A friend who recently went through a breakup, and had many conversations with me about said breakup, said: unlike all my other friends, you never once said the wrong thing. So while no prescriptions for human interaction are universal, the advice below can, when used in the right context, make you a better listener.
1. Don’t tell them what to do.
I get it, you so badly want to solve your friend’s problem. If only they meditated more, or they broke up with their partner, or they confronted their tiresome boss.
But there are two reasons you should abstain from jumping into advice. The first is that your advice is probably something they’ve already considered. Remember, they’ve had a head start compared to you: they’ve been dealing with this problem for days (or maybe weeks or even years) and you only heard about it five seconds ago. The more obvious the solution seems to you, the more you should resist prescribing it, unless you’re sure that they actually haven’t considered it before. Better to ask “what have you tried so far?” and perhaps a follow-up “what about meditation?” instead of starting with “you should meditate more.”
The second (and perhaps more important) reason to avoid telling them what to do is that even if your advice is exactly what they should be doing, they are much more likely to follow the advice if they can somehow arrive at that conclusion themselves.
Part of this is an ego thing: when we feel like we’ve come to a conclusion ourselves, we’re more excited to act on it, because doing so establishes our agency and autonomy. But there’s something deeper going on here: when you come to a conclusion yourself, you understand it in a much deeper way. Hearing someone else say “you should break up with your partner” is a fundamentally different experience than hearing yourself say “I should break up with my partner.” Help them get to the point where they say the solution themselves.
2. Don’t make it about you.
When your friend says “I’ve been really stressed at work lately”, resist the impulse to say “oh man me too!!!” Someone who is stressed about work is probably aware of the fact that there are other humans who are stressed about work. You may think you’re helping them feel less alone, but I assure you they already know they are not alone in having this problem. (The main exception here is if you think they would be genuinely surprised to hear that you’ve struggled with the same thing, in which case go ahead and tell them.)
If your goal is to help them, rather than bringing the conversation to your experience, try to maintain the center of gravity on them. One good way to do this is to reflect what they said back to them. You can say “that sounds really hard”, or “seems like you’re getting burnt out”.
Telling them what you’re hearing does three things: (1) helps you confirm that you actually understood what they said (if not, they can correct you); (2) it helps them feel validated; and (3) it can also lead to insights. You’d be surprised at how often what seemed to you like a straightforward summary of what they said actually triggers some revelatory insight for them. “Well, when you put it that way, it’s not so bad” or “when you put it that way, it’s way more depressing than I realized and I need to do something about it.”
People are so mired in their particular framings and rationalizations of things that hearing another person describe their predicament can unlock insight and motivate change. But of course, you want to do more than just restate what they’re saying, you also want to ask questions:
3. Be willing to ask challenging questions.
Your friend says “dang, I binged netflix again last night; but tonight I’ll stop.” Your first response might be “aw darn, you got this!” But you probably also want to ask “what will be different about tonight?”
Some of us are hesitant to ask questions like this, because we’re worried we might offend our friends. But I’ve found that people find questions much less offensive than I expect. Unless they’re literally in the middle of an emotional breakdown, people actually appreciate straightforward, direct questions about what’s motivating their behaviors or how they plan to change. Of course it also depends on your tone: you have to be asking your challenging questions in the context of a genuine desire to help them. It’s easier to convey a caring tone in real life conversations than over text.
One other behavior I find common: again in an attempt to be as inoffensive as possible, we often give people prefilled answers that they can choose from. We’ll say things like “what’s been hard about work? Is it the number of hours, or the work environment, or something else?” You don’t need to turn your questions into a multiple choice quiz. You actually want to give them as much freedom in their response as possible; you want to minimize the amount of projection you put into your questions. Just ask: “what’s been hard about it?”
You should view such conversations as an excavation of your friend’s mind. You want to give them open space to dig out as much as possible. You’re just guiding the digging, not bringing a whole truckload of your own baggage and projections to mix up with their gravel.
4. Ask them what they need.
This works surprisingly well. Ask: “What do you need most right now?” or “What do you think would help you most right now?”
Sometimes a friend needs strategic advice. Sometimes a friend is actively freaking out and they need to be reassured that they’re gonna be okay. Other times your friend needs validation and a sense that they’re not worthless. People need different things at different times, and instead of playing a guessing game here, you can help yourself and the other person by just asking.
Coda
Of course, this is not a conversational style to be taken up all the time. You shouldn’t be doing this during an introductory coffee chat, or even during most of your conversations with friends. (I’ve written before, for example, that conversations can have different “interruption frequencies”.) In most conversations it’s totally fine—advisable, in fact—to share about yourself and make it a back-and-forth.
But when a friend does call on you for support with a tricky personal problem—one that will take a lot of digging and thinking to sort out—these principles can go a long way. You want to center the conversation on them, playing the temporary role of good-empathetic-listener-friend. You want to alternate between being a mirror and an excavator, to help them understand themselves better and come to a solution on their own.
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