Am I Boring You?

Can you recall the most painfully boring conversation you’ve been a part of?

Was it with a telemarketer who rambled for 10 minutes straight before you could even interject a simple “Sorry, I’m not interested.”

Was it with a colleague who spoke non-stop about his new hobby—extreme ironing?

Or was it with a neighbor who chatted incessantly about his mowing schedule while you tried desperately to sneak back inside your house?

On the contrary, I’m sure you can recall FANTASTIC conversations—ones with your significant other in the early stages of dating, a conversation with a teacher or boss that encouraged you, or a conversation you were still thinking about days or weeks later.

study in Britain found that people have an average of 27 conversations every day and 43% of those conversations were deemed pointless.

So how do we have more meaningful conversations? And what can you do to become a captivating conversationalist?

Keep reading to find out!

“A good conversation is like a mini skirt; short enough to retain interest but long enough to cover the subject.”
— Celeste Headlee


Last week we shared the questions you should be asking during a conversation. But this week, we are going to dive into six habits you should cultivate to achieve conversational greatness.

Celeste Headlee, host of Georgia’s Public Broadcasting, wrote a book called We Need to Talk: How to Have Conversations That Matter, after her wildly popular TED talk had over 10 million views.

In the TED Talk, Headlee shares 10 tips for better conversations, but for our purposes, we’re going to hone in on 6 of them.

Here are 6 Tips For Better Conversations:

  1. LISTEN MORE, TALK LESS: This is obvious—especially when you remember the most boring conversations you’ve been a part of. In each of those instances, YOU probably weren’t doing much talking. We MUST be better listeners if we want to be incredible conversationalists.

  2. DON’T INTERJECT YOUR EXPERIENCES: When someone is sharing a story—whether uplifting or tragic—don’t make it about you. When we take someone’s story and use it to shine the spotlight back on ourselves, it detracts from making a meaningful connection.

  3. DON’T BE A KNOW-IT-ALL: Bill Nye once said, “Everyone you ever meet will know something that you don’t.” If you aren’t sure about something, say so. And while you’re at it, be enthusiastically prepared to learn something new from each encounter.

  4. READ...A LOT: Mark Levy, author of Accidental Genius: Using Writing to Generate Your Best Ideas, Insight and Content, said expert conversationalists, “seed a conversation with jolts.” He explains, “If you’re talking about, say, workplace productivity, it’s fine to talk about Pickett’s Charge or black holes or an idea from an Elizabeth Gilbert book that, in some way, relates to workplace productivity. Bringing in ideas from other domains keeps people awake and interested, and it’s actually how paradigm shifts are born.“

  5. READ THE ROOM: Listen, not only with your ears, but also with your eyes. Non-verbal cues are a telling way to determine if your conversation is on the right track. If someone is disengaged, change the topic. If they are responding positively, keep the train going!

  6. DON’T SWEAT THE DETAILS: You know when you’re in the middle of storytelling and you can’t recall the exact name or date or details you think are vital for the story?


Details are more important to remember than to recite. If you forget a detail when sharing, don't let it stop you in your tracks. In her TED Talk, Headlee says, “What they care about is you. They care about what you’re like, what you have in common. So forget the details. Leave them out.”

However, if someone does take the time to highlight key details in THEIR storytelling, make note! This is a great opportunity to map those details in your Contact Mapping app and bring them out during your next conversation.

By cultivating these 6 habits, you’ll be well on your way to expert conversationalist status!

Keep track of your meaningful conversations.