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4 Conversational Habits Every Entrepreneur Should Learn

Actively listening means asking the right questions.

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I’ve seen it a hundred times. In coffee shops, by the water cooler and in networking events everywhere. An eager young entrepreneur attempts to impress a potential client with a lengthy monologue about their exotic experience. “I just can’t say enough good things about Bali,” they say, flipping out their phone and scrolling through an endless barrage of images. 

I get what they’re doing: They’re trying to foster connection. And what better way to build rapport than by making yourself appear more interesting and offering up a bevy of videos of your exciting escapade?

But here’s what’s actually happening as you enthusiastically harp on about your latest trip: People’s eyes are glossing over — you’re losing them. 

The reason this happens, according to researcher Gus Cooney, a social psychologist at the University of Pennsylvania, is due to something called the “novelty penalty.” The gist being that talking about something completely new alienates people who might not be familiar with your topic of conversation. Sure, Bali is exciting, but folks can’t relate to a place they’ve never been to before.

“The novelty penalty might explain why a description of an exotic holiday can often fall flat with your colleagues unless they have been to that location themselves,” writes David Robson for BBC.

Building better connections is essential for entrepreneurs; you could even say it’s our lifeblood. But just like the above scenario, there are plenty of conversational pitfalls we can easily fall into. That’s why I’d like to offer some strategies for remaining conscious of how you’re communicating.

Related: Why Mastering the Art of Conversation Will Make You More Money

Be sensitive to the times

Writing for Harvard Business Review, Robbie Samuels asks us to acknowledge that we’ve all been through a lot in the last 18 months. 

What this means is that we’re also a little ill-prepared for small talk. 

Our personal journeys have varied widely over the last year, Samuels writes, so it’s understandable if that makes us cautious. “The usual, ‘What did you do on vacation?’ conversations won’t suffice, but that doesn’t mean we need to resort to ‘Hey, how many emotional breakdowns did you have in 2020?’ either.”

Many leaders will try to systemize their communication, but all this does is make you robotic and tone deaf. At my company, Jotform, we’re a team of 300+ employees spread over different continents. I can’t pretend that this pandemic hasn’t changed the way we relate to one another. Each person has faced different challenges and therefore has different needs. What this means is that my conversations won’t be the same with each individual. 

If I can get anything across, it’s this: We should humanize our conversational habits to build better connections. And that starts with the following:

Ask questions, but also actively listen

“If you want to have a meaningful dialogue with someone – rather than two ‘intersecting monologues’ – then you should make the effort to ask some questions,” Robson emphasizes.

Rather than overshare about your latest sojourn to Bali, ask the other person (whether a colleague or potential client) about their own experiences — what’s new with them? But remember to be genuine with your asking. Don’t just wait for their answer and immediately change topics, either. Listen intently with earnest curiosity.

When I go on a walking meeting with an employee, I ask about their family and how they’re managing their workload. How are you adjusting coming back to work? Is there anything you’re especially looking forward to over the holidays?

It’s as simple as this: asking + active listening = care.

“The first key to being well spoken is making others feel well heard,” writes Jane Chin for Inc. “We focus too much on what we should say next, formulating witty responses in our heads instead of giving full presence to the person talking.”

The art of listening, she notes, is as important as the art of speaking. “When the other person feels truly ‘heard’, that person will perceive you are caring about what s/he is saying, and this may make you appear more likable and better spoken.”

Related: These Tips will Help You Rule any Conversation

Center shared human experiences

I’ll never forget a college mentor who took time after class to ask an awkward Turkish transplant like myself about my experiences moving overseas. He was from the West Coast and spoke about feeling homesick at times. How even though it wasn’t the same, he understood what it felt like to be an outsider.

These small moments weren’t just simple mundane small talk — they were meaningful exchanges that made me feel less alone. 

At its finest, leaning on shared experiences gives us common ground and  strengthens our ties to one another — whether we’re acquaintances or even strangers. Nicholas Epley, professor of behavioral science at the University of Chicago, tells BBC, “In these deep conversations you get access to the mind of another person, and you get to recognize that the other person actually cares about you.”

Related: 7 Ways to Have a Pleasant Conversation With a Negative Person

Leave your ego at the door

This seems like it should go without saying, but try to limit how much you talk about yourself. Easy right? But it’s actually one of the biggest barriers entrepreneurs face when communicating. It’s natural to try to hype you and your business up, thinking this is the way to garner interest in your audience. But it actually has the opposite effect.

The trouble is, many leaders conflate ego with confidence. But talking a mile a minute and constantly interrupting the other person only makes you appear pompous, not confident.

My advice to young and seasoned entrepreneurs alike is to dial it down. Take a breath and pace yourself. “Humility and gratitude are cornerstones of selflessness,” write HBR co-authors Rasmus Hougaard and Jacqueline Carter. 

“Make a habit of taking a moment at the end of each day to reflect on all the people that were part of making you successful on that day,” they add. “This helps you develop a natural sense of humility, by seeing how you are not the only cause of your success.”

And it’ll also make you a far more interesting conversational partner.

Related: 15 Ways to Command a Conversation Like a Boss

Aytekin Tank

Written By

Entrepreneur Leadership Network VIP

Aytekin Tank is the founder and CEO of JotForm, the easiest online form builder. JotForm was ranked in the 2016 Entrepreneur 360™ List, an annual ranking of the most entrepreneurial private companies in the U.S.