How to Make Every Conversation Better

From great leadership to great relationships, it all starts with great conversations. Read to the end for 3 foolproof conversation fixes!

Amanda Warton Jenkins
The Startup
7 min readNov 13, 2019

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Image courtesy Shutterstock.com

“So. What are your thoughts on Justin Bieber?”

I was out to dinner with a new friend, who self-applies the term “reserved.” We were on a totally different topic when she threw this zinger at me from left field.

“Ummm … what?”

We laughed, she admitted her non-sequitur, and then confided: she’d been working on becoming a better conversationalist.

“That’s one of my go-to questions,” she said. “I have a few.”

She listed the others, which included:

  • What’s your favorite meal to cook?
  • Young Elvis or jumpsuit Elvis? and
  • If you could time travel, where would you go?

They were awesome questions, and I was grateful for the lightened mood. I hadn’t thought about how to be a good conversationalist for quite some time.

But it’s true — great conversations can transform our relationships. Empathy, connection, and acceptance are some of the biggest things that we all crave — but it’s impossible for us to give this to each other when we are horrible conversationalists.

There are valuable business rewards for being a great conversationalist, too. If you are in any role that requires you to influence others or convey your point of view, a conversation is critical.

Are you making mistakes in your everyday conversation? Are you participating in conversations that are on the road to nowhere? Here are six surefire ways to know when you’re in a conversation that’s gone horribly wrong — and three simple things to keep in mind to help elevate the conversation.

Six Common Conversational Mistakes:

1. You put your mouth in motion before putting your brain in gear.

Instead of thinking through your response when someone else is talking, do you take a pause to focus on the other person’s words and what they’re actually saying? When it’s your turn to speak, do you allow for some quiet? If you just start talking without thinking first — hashtag. You’re doing it wrong.

2. You’re St. Elsewhere.

Let’s admit it. We all get bored, especially when we are talking to someone we know well. Sometimes I think I can predict exactly what my husband will say, so my mind wanders when we talk.

3. It’s all about you.

Do you go on and on about yourself in conversation because you genuinely think you’re The Most Interesting Man on Earth? Or, do you domineer conversations because you’re overwhelmed by your own feelings and justhavetogetthemalloutnevermindtheconsequences?

Debby Downer will talk and talk about her problems looking for guidance or advice. Narcissist Nick doesn’t realize that he already knows everything about himself, and could learn something by shutting the hell up.

Neither of these people ever ask you how you’re doing, or what you did this weekend. They assume that their problems or triumphs are more worthy of airtime and that it is your obligation to listen to them.

4. You’re judgemental.

What we really want as human beings is love. But since we’re human, at some point in our lives, we’ve been separated from it — usually through some childhood trauma. Making fun of, writing off or judging others is sometimes our knee-jerk reaction when we feel inadequate.

Gossip is an especially nasty version of conversation mixed with judgment. It gives us the feeling that we’re bonding with others — when we’re actually banding together to condemn another person. We can choose to judge rather than deal with our own pain. But this only takes us farther from love and empathy. The people we gossip with will only ever be suspicious that we’re doing the same to them behind their backs.

In this way, judgment always backfires. When it is your belief system, you’ll always feel unsafe, under attack and defensive.

5. You have a hidden agenda.

This is where first dates often go wrong. Many successful people have been trained to focus on the outcome of every interaction. They might get what they want in business, but often “check out” when speaking to a friend, spouse or loved one. The conversation may seem irrelevant because it isn’t taking them to their desired goal.

On a first date, this is when one party tries to impress the other endlessly in a (usually fruitless) quest to get them into bed. Yammering on and on about oneself typically doesn’t get us where we want to be (see Narcissist Nick, above).

When we’re in a relationship with someone but are out to lunch on their feelings, needs, hopes or wishes — the things they deem of utmost importance — we’re not connecting with that person. We might get our agenda in the short term, but in the long term, the relationship will suffer.

6. You can’t let sleeping dogs lie

I used to pride myself that I could pick up the thread of any conversation at any time, at will.

“What was it I was talking about?” someone would say.

“You were talking about your Aunt Bertha’s knee surgery,” I’d happily interject.

Over the years, I’ve learned that sometimes it’s better just to let the conversation run its course. Whatever we were talking about couldn’t have been that important anyway, especially when it’s the other person who’s changed the subject. Obviously they want to talk about other things.

An exception to this rule: when you’ve actually interrupted someone’s story with your own. Then it’s great to bring the conversation back to what they were saying!

When we make any of the six mistakes above, a genuine conversation never takes place. We’re actually participating in a strange kind of psychological game. We might make others feel obliged to listen to us, praise us, or even feel sorry for us. Our bond with these people is not authentic. This conversational faux pas is not a death sentence. In fact, some of them might make you appear magnetic and charming at first. But if you consistently make these mistakes, mark my words. People will see you coming — and run.

How to Make Every Conversation Better: 3 Tips

1. Listen

“Being listened to is so close to being loved that for the average person, they are almost indistinguishable.” ― David Augsburger

It seems counter-intuitive, but to have a really great conversation, you hardly need to talk at all. You mostly need to listen.

To truly listen, you’ll need to let go of control and simply “be” in the conversation. Not only will you begin to enjoy the conversation more, but you’ll probably get more out of it, too. There certainly are times to steer a conversation towards a goal or desired outcome, but our loved ones need to be listened to without prejudice or agenda.

Anyone who manages or leads others needs to listen closely. The most creative, successful people are experts at leading this way. They’ve mastered the art of inquiry, raising questions no one else is asking and really listening to the answers.

If my mind wanders when my husband is talking, no matter how repetitive I think he is being, I’m trying out mindfulness. I focus on the words that are being said, and the present moment. When I do this well, I begin to hear things I’ve never heard before.

2. Find Common Ground

As a kid, I was blessed with a big family full of grandparents, uncles, aunts, and cousins — all of whom are great conversationalists. They remembered my birthday, kept tabs on my sports, asked me about school, and let me go on and on about myself when we talked. It was great at the time, but it didn’t even dawn on me that conversation was supposed to be a give-and-take. For these dear family members, all we needed to have in common was blood.

These days, I’ve learned to have much more interesting conversations with practically anyone when I can find some common ground. When we find it, that’s all we have to talk about! What a relief.

These days, when I see my family members, who are still so gracious, I make sure to ask about our shared interests. I always learn so much.

3. Elevate the Conversation

Martin Luther King, Jr.’s “I Have a Dream” speech was powerful because it spoke from individual experience, yet was fluent in a language that appealed to shared values.

“I have a dream that my four little children will one day live in a nation where they will not be judged by the color of their skin, but by the content of their character.”

Granted, his was a monologue. But with it, MLK elevated the conversation. His voice resonated with all Americans because almost everyone could identify with his vision.

The idea is to use shared concepts to nudge conversations in a positive direction. So if I’m talking to a family member, I try to remember to talk about how great it is to simply spend time together.

When I’m talking to a Mom friend, I throw in something about how lucky we are to have such a great school, community, and green spaces.

When I’m at a loss, a one-liner that works great to turn things positive is, “Life is good.” This usually swings things toward more gratitude, less complaining. We can all usually agree that life is pretty darn good.

During my conversation with my “reserved” friend out to dinner that night, we covered a lot of ground. At one point, we touched on the heavy topic of grief. I’d lost my Dad, and she’d lost her Mom. Something we had in common. But my loss was about twenty years prior. Hers was a mere two.

When she brought up Justin Bieber, it was funny — it lightened the mood!

We laughed about it being out of nowhere, but I saw that it may have been intentional.

She wasn’t ready to open up about her grief. Or maybe she didn’t want to dwell on it. So she gracefully changed the subject. I let her and realized what a fantastic conversationalist she already was.

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Amanda Warton Jenkins
The Startup

Yoga teacher, MPP UChicago "rewilding," living from the neck down, cultivating Albert Einstein's "sacred gift," intuition. My book: https://amzn.to/3mTwXlZ