How to not be boring

If you find yourself searching for something to say beyond small talk, try these tactics to find more interesting approaches to conversation.

How to not be boring
[Photo: Luigi Manga/Unsplash]

Recently, I was at a gathering of colleagues when someone turned to me and asked, “So, what’s new with you?”


Ordinarily, I think I’m a good conversationalist. After all, it’s literally my job to talk to people and tell their stories or share their advice. And that’s not exactly an unexpected question. Still, the only “new-to-me” topics that came to mind were my daughter’s basketball tournament and my feelings about that morning’s political headlines—neither scintillating or appropriate topics at that moment.

Oh, no, I thought. Have I become boring?

But sharing our experiences in an authentic way to connect with other people is what makes us interesting, says Michael Pirson, PhD, associate professor of management systems at Fordham University. The hesitation I felt in not sharing the ordinary things that were happening in my life, and the frantic mental search for something more interesting, may have backfired and made me seem less interesting.

“If someone is contriving some conversation that might be interesting, it’s probably not going to land well,” says Pirson, whose expertise includes trust and well-being, mindfulness, and humanistic management. “It’s going to feel like a contrived conversation that people don’t necessarily want to tune in to.”

Find wonder in the ordinary

The most interesting people aren’t those who’ve gone on some Eat, Pray, Love journey to find themselves. Instead, Pirson says, they’re those who examine the ordinary. “Often, the ‘boring things’ are maybe not that trivial. Maybe they’re not that boring. Maybe they are actually little miracles,” he says. Share your observations about the world around you—interesting stories you saw or things you noticed–and you may be surprised by the universal connection they inspire.

This is essentially how Jessica Hagy starts her day. The creator of Indexed, a website where she creates and publishes interesting and amusing charts that relate to her own observations, and author of How to be Interesting: an Instruction Manual, Hagy spends a lot of time thinking about what’s interesting to her. People who are interesting are relentlessly curious, she says.


“That curiosity really sort of spurs a cross-pollination of, ‘Oh, I’m going to go test this out, and see what this is going on, and go on this weird little adventure, and meet these people who know things that I absolutely don’t,'” she says. Think about the everyday things around you and ask questions about them.

  • What is that roadside monument I see on my way to work every day?
  • Who built that interesting building in my city?
  • What nearby attractions haven’t I visited?
  • Why do people do things that way?

Use what you find to ask more questions and learn more about the world around you. “Having that sort of curiosity is almost like a protective armor from getting into those doldrums of just waking up and saying, ‘Is this all there is?'” she says. And when you find things that are truly interesting to you, share them.

Television veteran Audrey Morrissey, executive producer of NBC’s The Voice, is always looking for what will make a person or story interesting to viewers. It’s usually a matter of individuality. “Having a strong point of view, signature style, or being an uber-enthusiast in a particular field makes someone interesting,” she says. That means embracing what is truly interesting or unique about yourself. “Many people are ‘not boring’ in the way that they can carry a conversation or [can] be good at a social gathering, etc. To be interesting means that you have lived life, taken risks, traveled, sought out experience to learn for yourself and share with others,” she says.

Rules of engagement

Of course, it’s possible to be a font of knowledge and a boring person, says public relations consultant Andrea Pass. Paying attention to the listener is an important part of having a conversation that’s interesting to both parties. Droning on and on about what’s interesting to you isn’t going to make you an interesting person, she says.

“If the listener is not paying attention, it’s your sign to shorten the story or change direction. Make sure to bring the audience into the conversation so that it is not one-sided,” Pass says. Be a better listener yourself, and give others opportunities to participate in the conversation by inviting them with questions or invitations to share their own experiences or thoughts. (e.g., “Now, tell me about your favorite book,” or “Have you ever been to that attraction?”)

Questions are a powerful tool, especially when they encourage others to disclose information about themselves. A 2012 study from the University of California, Santa Barbara, found that roughly 40% of the time people are talking, we’re disclosing subjective information about our experience. And when we’re doing so, our brains are more engaged. So one tactic to leave others with the impression that you’re a sparkling conversation partner is to get others to talk about themselves.


Being relatable is also essential, Morrissey says. “The best entertainment and storytelling comes from people who are relatable–those who don’t shy away from opening up and freely share who they are and what they care about. These are the people to whom viewers most relate and find interesting. Being authentic, honest, and vulnerable is always interesting.”


About the author

Gwen Moran writes about business, money and assorted other topics for leading publications and websites. She was named a Small Business Influencer Awards Top 100 Champion in 2015, 2014, and 2012 and is the co-author of The Complete Idiot's Guide to Business Plans (Alpha, 2010), and several other books