4 key strategies for great conversations

Too often, conversations can feel like being trapped among Freleng doors. You may not recognize that name, which belonged to animator Friz Freleng, but you likely know the gag: A cartoon character chases another down a hall and through a doorway, but while the first character exits in one location, the second character pops out of a completely different door. They continue to chase each other through the surreally interconnected hallway until they give up and exit the frame. Neither has accomplished anything except for filling a few minutes of runtime.

Conversations can devolve into a similar farce when, like our animated counterparts, we’re too busy chasing the conversational door before us to consider how each one connects.

Of course, finding those connections can be tricky. People converse with each other naturally. We do it as easily as, well, walking through a doorway, so we seldom consider what elements make a conversation work well. And if we ignore those elements, great conversations and meaningful connections become more difficult to create.

A conversational conundrum

Consider just one element of a conversation: the conclusion. Ending a conversation seems simple. When both participants have reached their goals, they bid each other good day, maybe doff their caps, and go their separate ways.

It’s rarely so ideal, though. When one speaker is finally ready to raise their vital point, the other may already be checking the latest online updates. That disconnect stems from the fact that people aren’t great at expressing their desires or understanding the desires of others. We assume we’re more transparent than we actually are.

Research backs that up. A study published in Psychological and Cognitive Sciences looked at close to a thousand conversations — some between intimate acquaintances and others between strangers. It found that in both groups, the trend was for one participant to bring the conversation to a close when their partner wanted to keep going.

The researchers likened this problem to certain game theory thought experiments (such as the famed “prisoner’s dilemma”). As with those thought experiments, coordination problems between the participants can lead to less-than-optimal outcomes. Specifically, participants may not have compatible goals, and even if they do, they often don’t realize what the other person hopes to gain.

“[W]hen it comes to ending ordinary conversations, honest communication is apparently in short supply,” the researchers write. “Because expressing a desire to end carries a significant risk of offending one’s partner, people may generally mask those desires when they arise and may instead wait for the conversation to pass a suitably ambiguous offramp.”

The opposite may also be true. When one participant begins their “closing ritual” — a glance at their wristwatch, mentioning another responsibility, or a stock phrase (“Anyyywho”) — the other person may end the conversation to prevent offense even if they wants to continue. 

And let’s not forget: Concluding a conversation is just one of many elements we need to navigate to make it work.

“Conversation is common, but it is not simple,” the researchers point out.

Layer up with “affordances”

In the newsletter Experimental History, Adam Mastroianni, a psychologist and one of the above study’s authors, summarized his research on conversations. He concludes that many conversational woes materialize from an imbalance of give and take. Conversational givers only offer openings for their partners to continue talking. Meanwhile, takers consume the conversation with the uninterruptible subtlety of a person slurping the dregs of their soda in a quiet theater.

Investing too heavily into either strategy leads to dismal conversations. Givers feel charitable but make their partners carry the conversation. Similarly, takers feel they are saving others from awkward silence while not offering openings for a considered response.

“Neither givers nor takers have it 100% correct, and their conflicts often come from both sides’ insistence that the other side must convert or die,” Mastroianni writes. “Rather than mounting an Inquisition on our interlocutors, we ought to focus on perfecting our own technique.”

This process begins by recognizing that there is no magical ratio of give and take. You don’t need to count the minutes and make sure both sides receive equal time. You aren’t moderating a debate. Instead, whether we are giving or taking, Mastroianni advises layering your conversation with “affordances.” 

In psychology, affordance represents a property of an environment that allows someone the opportunity to act. Mastroianni gives the example of doorknobs. They are quickly intuited, easy to grasp, and allow a person to open a door. Have you ever been stuck wondering if a door is push or pull? That’s bad affordance.

When you provide your partner conversational affordances, you help them realize where and how they can contribute to the conversation. They grasp the doorknob and open the door, and you walk through together. When you are stingy with conversational affordances, the result is a pell-mell dash from topic to topic, each speaker hoping that the other is following. You’re now caught in a Freleng doors trap.

How to open conversational doors

It’s one thing to recommend using affordances; it’s another to create them in real-time without sounding awkward. 

Thankfully, Michelle Tillis Lederman has some experience here. As the CEO of the training company Executive Essentials and the author of The Connector’s Advantage, Tillis Lederman became a networking expert after growing disheartened by how poorly leaders in corporate America communicated.

In an interview with Big Think, she offered four strategies to help us open our conversational doors:

1) Ask a question

A good question is a great way to keep a conversation engaging. Such questions are open-ended. They ask your partner to share something: about themselves, their feelings, opinions, or expertise. They should also be driven by radical curiosity — the honest desire to understand something about this person.

“Ask a question you actually want to know the answer to and one that you might be willing to share a little information on, as well,” Tillis Lederman advises.

There are two pitfalls to avoid though. First, avoid questions that lock conversational doors. These are the perfunctory variety that invite one-word responses, only produce the answer you want, or set you up to take even more airtime.

Second, don’t overuse questions. As Tillis Lederman points out, this makes the conversation feel more like an interrogation — which is why they must be balanced with strategy two.

2) Listen and probe (or share)

Put another way, listen so you can identify places where you can give to the conversation and those where you can take. As Tillis Lederman puts it: “If you’re asking a question, you need to not think about what you need to say next. You need to think about what they are saying and where could that conversation take us.”

If their answer tangles a thread that makes you curious, feel free to probe with an additional question or two. But when you see an opportunity where you can share, take it. Use the opportunity to show your partner you are listening to them, reveal something about yourself, and leave room for their response as well.

3) Seek commonalities

Good conversations are intimate. You need to share something about yourself to open that door to connection, and you need to be accepting when your partner does the same. For instance, when psychologists need to “jump-start friendship in the lab,” Mastroianni reveals, they have people answer questions about themselves. These questions lead to a steady escalation of self-disclosure.

For Tillis Lederman, the best connection strategy is to seek commonalities. Did you grow up in a similar community? Do you have similar goals or needs? Do you both have the same work philosophy or difficulties? While such commonalities may not be obvious, finding them can make the act of self-disclosing feel easier, helping a connection to form.

While commonalities may start shallow — “Oh, I have the same belt. Nice, right?” — they shouldn’t stay there. Mastroianni points to research suggesting that people tend to overestimate how awkward rich, deep conversations can be, especially with strangers. That same research suggests that people feel more connected to those they engage in deep conversation with.

4) End with a connection

As we’ve explored, ending conversations is more difficult than it seems. To help, Tillis Lederman recommends worrying less about the time and more about managing “mood memory.”

“Mood memory is how somebody feels,” Tillis Lederman says. “They won’t remember [exactly] what you said, but they will remember how they felt in the conversation with you. And you want to make sure that you don’t ruin that mood memory right at the end when you’re looking at your watch or over your shoulder.”

To manage the mood memory, lean into exit strategies that deepen connection. Schedule a follow-up chat over coffee for next week, or give them your contact information and suggest they are welcome to reach out. 

Here, you have the advantage over people in a lab because your conversations don’t have to be a one-and-done affair. Any conversation, good or bad, is just one part of the relationship-building process. Learning to improve those conversations with the other person only helps to strengthen that.

By understanding how conversations work and how to create affordances, we spend less time chasing down the connections we want and more time enjoying the ones we have.