top of page

Becoming a Captivating Conversationalist

It's 2014 and I'm sitting in the office of the United States Secretary of Education, Arne Duncan. At 6'5", this cabinet member strikes an imposing presence. Despite this, his warm personality and light-hearted humor makes the tone of the conversation casual.

He asks us about our travels, the organization we're representing and what we hope to accomplish in life. Then he begins to tell us a about a goal he has for himself that year.

"I hope to become a more engaging person. I thought I was doing okay until I attended an event last week and met this woman. She was hosting the event and I watched her go from person to person, welcoming people and making jokes. After each interaction you could tell the person she had just spoken with was in better spirits, almost lifted up in some way."

"Eventually she came over to me. She was smart, inquisitive, and polite. We spoke for almost 30 minutes and the craziest thing is, I don't know a single thing about her. I've even forgotten her name!"

Secretary Duncan marveled at this woman's ability to engage people, but we were a little confused. Seeing the look on our faces, he clarified, "What I realized is that the most interesting people are first the most interested."

While it may not be a priority for some, I think we can agree there are benefits to being a more engaging person. However, in an effort to do so, most of us get it backwards thinking that we should try and curate interest about our own lives. Rather, people respond best to those that are interested in them.

There are three things we can do to be more interested (and hence more interesting) in a conversation.

Ask More Questions

Have a list of go-to questions to ask in a conversation. You should avoid binary (yes/no) questions and ensure you genuinely want to learn the information you're requesting.

Don't One Up

Chances are you'll have a story similar to the one you're hearing. Don't share it immediately. Letting others stories hold you rapt shows interest and validates others experiences.

End On Time

Holding people hostage in a conversation is an easy way for people to become disinterested. Know when to land the plane and move on to the next conversation.

Whether you're trying to woo a D.C. dignitary or talk to a friend at a party, if we want to be interesting, we must first be interested.


The small talk topics Americans dread most are sports and current events.


Create a list of three go-to questions you can ask in your next conversation to demonstrate interest.


What makes someone interesting to you?


"When two interesting people have a conversation, they completely forget to talk about themselves." - Ed Latimore

Recent Posts

See All


bottom of page