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How to Have Honest Conversations

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True Talk

If you’re craving more authentic connection with others, these five conversation strategies can help.

In some ways, it’s never been easier to connect with the people in our lives; we’re all just a text message or social-media post away. Yet, while these tools enable us to stay in touch with each other — liking vacation photos or exchanging casual banter — truly meaningful interactions can sometimes feel scarce.

We can, of course, feel closely connected to others without having deep conversations all the time. We might bond over baseball statistics. We might joke around. We might enjoy each other’s silence.

But there are times when we want to be able to say what’s in our hearts, and it can be difficult to know how to cultivate deeper conversations. It might be scary to open up about things that really matter to us — and some people prefer not to engage on such an intimate level. Or maybe there’s conflict in a relationship, or certain topics have been swept under the rug, exactly where others want to keep them.

I often think of the dramatic scenes in movies and books when the protagonists, often on their deathbeds or hanging off the side of a cliff, finally reveal their truest feelings. We don’t have to wait until the end of our lives or some other critical moment to speak up about what is important to us, or to reach out to others in emotionally honest ways.

These five tips can help each of us enrich our relationships by having conversations from the heart.

1. Create the space.

Few emotionally rewarding conversations start with “We need to talk.” If you want to relate more deeply with another person, or share your own thoughts and feelings, think in terms of creating space — both physical and emotional — where real discussions can transpire naturally.

People feel comfortable in different settings, so consider where this person will be most at ease. Reflect on what feels good to you, too — the kinds of places and situations where you’ve felt safe sharing emotions or exploring ideas with someone else. Maybe a walk in nature lends itself to a deeper discussion. Perhaps the neighborhood coffee shop or your own living room feels more inviting.

You don’t necessarily need an environment devoid of distraction. While a blaring TV or pinging smartphone will certainly interfere with an intimate discussion, sometimes it’s nice to have little “escape hatches” for people who find face-to-face conversations a bit too intense: Shooting baskets with your teenager might allow him to relax and share what’s on his mind better than inquiring at the dinner table about his day. Preparing a meal alongside your new sister-in-law may ease any sense of formality that could get in the way of a good talk.

2. Talk with, not about.

Sometimes we need to talk about other people. It’s good to catch up on family news, and it can be important to relay the details of a mutual friend’s illness or a spouse’s new job. But one of the easiest ways to avoid discussing our lives, our hearts, and our values is to focus on people who are not present.

In these cases, as long as you’re discussing someone who’s not there, you’re essentially looking past the person who’s right in front of you. Or maybe you’re hiding and don’t even realize it.

So how do you shift from sharing the news (or gossip) about other people to actually talking with your conversation partner? You could start by asking how he feels about his spouse’s job change, for example. Or you could explore your own emotions and thoughts about your mutual friend’s illness. Redirect your attention to the experiences and emotions of those who are present.

3. Speak from your heart.

We can talk about our favorite subjects all day: gardening or football, theology or furniture making, politics or rodeos. We can conceal ourselves behind our pet topics, too, never delving deeper into why and how such things might touch our lives in meaningful ways.

Determining when it’s safe to introduce your real feelings or concerns into a conversation takes sensitivity, bravery, and a willingness to experiment. Let’s say you’re chatting about spring planting with a fellow gardener and sense that she may be open to a more personal connection. Here’s one way you might initiate a conversation about something that’s important to you:

You (testing the waters): “I’m really looking forward to my garden this spring. Especially now that I’m taking care of my aging dad, I’ll need a little garden therapy!”

Fellow gardener (picking up on your cue): “I didn’t realize you were a caregiver for your dad. How are you doing with that?”

If your conversation partner expresses interest in your personal feelings and experiences, you can feel confident sharing more. On the other hand, you’ll know pretty quickly if she isn’t willing or able to go deeper. (“Yeah, I can’t wait for spring, either.”) If that’s the case, set aside your concern for now, and keep your eyes open for other opportunities to connect with someone else.

That said, it’s vital to find people with whom you can share how you really feel. If there is no one in your life you can really open up to, consider reaching out to a therapist or minister.

4. Listen from your heart.

Conversation is a two-way street, and just as you must be bold enough to tell your own stories and express your own concerns, you must also be receptive enough to listen to another person’s stories and concerns.

Deep listening isn’t easy. It requires concentration, compassion, and self-awareness. You know how good it feels when you realize someone truly hears what you have to say — and how lousy it feels when the other person seems distracted, more interested in sharing his perspective, or intent on “fixing” you.

So when your conversation partner says something that triggers a strong emotion, whether that be sadness, envy, boredom, or excitement, challenge yourself to stay present rather than insert yourself into the narrative. When that person is struggling with a challenge that seems to have an obvious solution, resist the impulse to advise. Try to recognize your own motivations or expectations so you can instead focus on the other person. (For more on how to be a compassionate listener, go to “5 Ways to Be a Better Listener“.)

5. Let go of outcomes.

Even if the only thing you want from a conversation with another person is a deeper connection, you may not get it. Insisting on such an outcome when the person is not interested or emotionally ready isn’t just ineffective; it’s unkind. (And if your goal is to convince or influence in any way, you’re trying to control the relationship, not deepen it.)

It takes courage to initiate authentic conversations, to essentially say to someone: “This is how I feel; this is what I need. Would you be willing to go there with me?” Similarly, it takes bravery to let go of what you’ve hoped for in a conversation or relationship.

It also takes practice. The more you seek to connect with others in an authentic way, the more you will hone your skills of giving and receiving, inviting and releasing. You will learn to approach your conversation partners — and yourself — with greater patience and compassion. Over time, these relationships will feel less like a series of casual touch points and more like the authentic connections you desire.

This originally appeared as “True Talk” in the December 2017 print issue of Experience Life.

is a Soto Zen teacher and secular-mindfulness instructor based in Minneapolis.

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