Two tips to keep in mind if you want to be a better conversationalist

by Rachel

Image: Kiyana Salkeld / Just Good Shit

Image: Kiyana Salkeld / Just Good Shit

I recently read We Need to Talk: How to Have Conversations That Matter by Celeste Headlee, which I really liked. The book has a lot of great, practical tips for being a better listener and better speaker — based in scientific research, and Headlee’s career as a radio host.

Since I’m sure none of us want to turn into the living embodiment of “I am feel uncomfortable when we are not about me?”, I thought I’d share two of my favorite tips for talking a little less (or just a bit more effectively) from the book here.

01. Stay out of the weeds

Getting into the weeds when you’re talking means you’ve lost the main path of a story, and are instead “wandering aimlessly in a field of trivial details.” Here’s more from Headlee:

“Getting into the weeds often sounds like this: ‘We went to Italy in 2006. No, was it 2007? Wait, it must have been 2005 because it was just after I took that job in Boston. I think that’s right. Sharon would know for sure.’ By the time you get back to the real story, your friend is staring at you with glassy eyes and considering making a break for it to get a latte.

The business psychiatrist Mark Goulston says we only have about 40 seconds to speak during a conversation before we run the risk of dominating the exchange. He describes the first 20 seconds as the green light, when the other person likes you and is enjoying what you have to say. The next 20 seconds are the yellow light, when ‘the other person is beginning to lose interest or think you’re long-winded.’ At 40 seconds, Goulston says, the light turns read and it’s time to stop talking.

Take a moment to gauge just how long 40 seconds is. Look at the second hand on your clock or watch, start to tell a story, and stop when you’ve hit 40 seconds. That’s not a lot of time! If you waste it with superfluous detail, you’ll never get to the meat of your message.”

FORTY SECONDS!!! That is…not very many seconds! Here’s Headlee again:

“We can also end up there when we feel compelled to correct the fine print of someone else’s story. Imagine a friend is telling you about a scary skiing accident. He says that after he was airlifted to the nearest hospital, he received an emergency MRI to see if his ribs were broken. You jump in and say, ‘Well actually, the MRI wouldn’t show your ribs. An MRI only shows soft tissues. Are you sure it wasn’t an X-ray?’ You have just steered a conversation (and possibly a friendship) into the weeds.

The onus is on you to determine what information is essential and what is unnecessary. That can be difficult sometimes. But if you’re thinking about it, you’re already making progress. All too often, we continue to spout information without consciously considering if we should.

The next time you find yourself providing a lot of detail about a personal matter, take a close look at the other person’s face. Are they looking at something else besides you? Are they stifling a yawn? If so, they might be trying to escape. Forget about what year you bought your first Toyota, and move the story along. Your friends, family, coworkers, baristas, and cashiers will thank you.”

02. No repeats

I once had a boss tell me, “Take yes for an answer.” He was basically saying, I agree with you, you’ve won me over — why are you still talking about it? The comment made me a lot more aware of the ways I might be repeating myself in conversations, regardless of whether the other person is saying yes, no, or something else entirely.

Here’s Headlee on this topic (Italics mine):

“Repetition is the conversational equivalent of marching in place. It’s not interesting and it doesn’t move the conversation forward. We sometimes assume repeating information helps drill it into someone’s head. After all, we’re taught from a young age to repeat the information we want to learn. … These types of repetition [e.g, flash cards, repeating dates in your head] help you to retain new types of learning for one key reason: you’re the one repeating the information. Research shows that when we repeat something multiple times, it ups our chances of remembering it. The benefit increases if we repeat that information to another person, but the benefit isn’t shared with the person listening. So if you’re in a meeting and you repeat a deadline to your team four times, you’ll probably remember it well but your team members are no more likely to retain it than if you’d mentioned it only once.”

Basically: if you’re repeating yourself because you don’t feel like you’re being heard, well…you’re probably not doing yourself any favors. “Often, when someone hears the same thing for a second and third time, they think, ‘I already know this,’ and they stop listening,” Headlee says. So, why do we do keep doing it? Headlee says it’s often the result of wanting to keep a conversation going, but having nothing new to add.

Repetition is particularly noxious when you’re repeating negative statements. If you’re upset with someone and just keep saying, “You fucked up and I feel away about it” over and over again, they are likely going to get frustrated and tune you out — not suddenly have a light bulb moment and apologize the fifth time you say it.

And it doesn’t even have to be direct criticism to make the other person feel bad; even if you’re not saying “you, personally, fucked up,” repeating a negative comment about a situation can still bring the other person down. For example, if your friend selected a restaurant for lunch and then the server was rude, your order came out cold, and they forgot to bring you the refill you asked for…and you just keep repeating “ugh, this sucks” and “I’m so disappointed” and “I can’t believe how terrible that service was” over and over again…it can start to feel like criticism to your friend, who feels responsible for your displeasure, even if it’s clearly not their fault.

Here’s Headlee again:

“Try to become aware of how often you repeat yourself, and think about what might be prompting you to do it. Do you feel like you’re not getting the acknowledgement you need from the other person? Has he or she failed to follow through on things in the past? Are there too many distractions present when you’re trying to have a conversation (i.e., saying something important while your kid is playing a video game might not be a good idea)? Are you prone to ramble in your conversations?

Over the next few weeks, get into the habit of pausing for a couple of seconds before you respond to someone. Before you repeat yourself, take a moment to find something new to say. You can even ask your friends to tell you when you’re repeating something. I had my son say ‘echo’ every time I started repeating things, and after hearing it a few dozen times, I began to break the habit.”


The whole book is very good; I really recommend it, especially if you’re a manager! You might also want to check out Celeste Headlee’s TED Talk: 10 ways to have a better conversation. ✨

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Living, Showing Up, Friendship, Work