As a former psychotherapist, I know a thing or two about conversations, the art of listening to another person and saying the right words at the right time. But I also know how many obstacles get in the way of thoughtful, meaningful conversations. If you find conversations difficult, here are some tips that might help.

Photo: Half Chinese

Whether you’re talking with someone in person or online, having a conversation with a friend or a complete stranger, or whether you’re talking about changing the world or what you’re going to have for dinner, try out these tips for improving communication with others.

1. Don’t assume you know the other person’s story.

A few years ago, I sat in a Boston courtroom to observe a day’s worth of drug cases. In the course of several hours, a couple dozen men–mostly young, mostly Black or Hispanic–took their turns before the judge to explain why each had drugs and what was at stake if the judge decided to send him to prison.

And every single time, the judge, exasperated, cut the man off midstream with a variation on the same dismissive theme: “Yeah, yeah, yeah. I know your story.” He’d bang his gavel and pronounce a sentence. Each man shuffled off, head down, looking years older in a span of seconds.

Granted, these men weren’t there to have a conversation with the judge. But the anecdote bears an important lesson: Never assume you know the other person’s story.

We’re all complex beings, shaped by numerous people, places, and life experiences. Our stories are similar, but there’s always some difference that distinguishes us. And often, that difference means everything.

When talking with someone, I like to keep these lines from an Adrienne Rich poem in mind:

“if you think you can grasp me, think again;

my story flows in more than one direction.”

2. Don’t put your conversational partner into a category.

We pigeonhole each other all the time. Classification is a convenient way for us to manage and understand the world and to try to engage with each other: Liberal/Conservative. Traveler/Tourist. Activist/Apathetic.

But when we think about each other in these dualistic categories, we’re setting up our conversations in a way that’s sure to be unproductive. If I think about you as an ultra-conservative, I’m already building up the defensive arguments I’m going to use to persuade you to adopt my views. And that means I’m not at all prepared to listen to what you have to say. I’ve already scripted your words for you.

3. Stop trying to fill the space.

One of the hardest lessons for me to learn as a psychotherapist was how to become comfortable with silence. If a patient was talking and seemed to be struggling for words or fell silent, it made me uncomfortable and my first impulse was to fill the quiet space. I’d fill in the blanks with words I thought the person would want to say, or chatter on about nothing in particular until the patient picked up the conversation again.

As I learned more about the art of conversation, I saw how I tended to fill the space in all of my conversations– at work and in my personal life.

Conversations aren’t always about words. In fact, the most important part of a conversation is often what’s going on in the pauses between what we say. Don’t rush to fill that space–and whatever you do, don’t try to fill in someone else’s words. Practice becoming more comfortable with silence, and let your conversational partner experience discovering what he or she really wants to say.

4. Don’t pretend or assume you understand what the other person is saying.

If you’re not following the conversation, say so. This skill is called reflective listening, and it’s as useful in everyday life as it is in therapy. When your partner has finished saying something, and you’re not sure you understand or you want to confirm your interpretation of what’s just been said, say something like, “So, what I think you mean is….” This gives the other person the opportunity to confirm that you interpreted the message correctly or to clarify the message so you understand it.

5. Get rid of distractions.

I was recently at a restaurant and noticed that the couple at the next table kept their cell phones on the table for the entire meal. Every few minutes, one or the other would pick up the phone–while the other was talking–and start messaging.

If you don’t have time for a conversation, say so politely and let the other person know when you have time to talk. But when you do, put the cell phone away. Really.

6. Ask yourself: Am I advancing the conversation?

What this means is simple: Are you contributing to the conversation in a meaningful way? Are you engaging the other person? Are you leaving them intact? This is a particularly relevant tip for online communication, where we’re prone to fire off messages that make us feel good, but which hurt the receiver.

7. Ask questions. Let your conversational partner shine.

Two tips rolled into one. Most people love to talk about themselves. And most people want to be recognized. There’s nothing that improves your conversational skills more than cultivating a genuine interest in other people and providing every opportunity you can for them to talk about themselves. And don’t worry– if they’re good conversationalists, they’ll give you the opportunity to talk about yourself, too.

Community Connection:

Travel provides some incredible opportunities for conversation. Traveling alone and want to start a conversation? Check out Eva Holland’s advice for “gutsy girls” who are on the road solo. Or if you need some advice about how to deliver difficult messages to people you care about, check out “How to Tell Your Partner You Want to Travel…Alone” and “How to Tell Your Family You’re Leaving for a Year to Go Travel.”

Feature photo: mark sebastian