Don’t Be Boring. Time-Proven Advice on the Art of Conversation.

Jake Wilder
Jan 16, 2018 · 8 min read
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Photo by Greg Raines on Unsplash

“Why do we feel it’s necessary to yak about bullshit to feel comfortable?” Mia Wallace poses this question to Vincent Vega, breaking up an uncomfortable silence in a Jack Rabbit Slims booth, while also questioning the value of a disturbing percentage of our daily conversations.

Perhaps small talk has it’s place. It offers a comfortable way to start talking with someone. And for everyone who finds silence uncomfortable, it offers a way to pass the time.

But it’s not a conversation. It doesn’t build connections or develop relationships. Where conversation provides depth and connection, small talk is shallow and forgettable.

Would you listen to a podcast where the host and guest talked about the weather and their commute the whole time? Then why do we fill so much of our own time with this meaningless drivel?

We’ve all had great conversations before. Those where we’re engaged and connected with another person. Times where we walked away energized and inspired.

We all know the benefits. And yet, we seem to keep falling back into the relative safety of small talk.

Perhaps in a world that continues to become more polarizing and more divisive, we resort to small talk as a safe, comfortable means of avoiding the ever-growing list of emotionally charged issues of today.

But where does this end? If we’re unwilling to brave the difficult task of holding real conversations, we resign ourselves to a world where new views are rarely shared. And deeper connections become more and more fleeting.

The good news is that we don’t need to reinvent the wheel. This isn’t a new issue and it doesn’t require an innovative solution.

Over 150 years ago, Arthur Martine published Martine’s Hand-book of Etiquette, and Guide to True Politeness, giving us a trove of advice on navigating the social arts of conversation and other areas of life. Among his timeless, and timely, guidance, I’ve found the following ideas are well suited to navigating even the most difficult topics and braving real conversations.

Welcome Silence.

“The power of preserving silence is the very first requisite to all who wish to shine, or even please in discourse; and those who cannot preserve it, have really no business to speak.” — Arthur Martine, Martine’s Hand-book of Etiquette, and Guide to True Politeness

The biggest impediment to conversation is our general inability to keep our own mouths shut. We’d rather be talking than listening.

We’re always interested in what we have to say. The other person? Not so much.

But as Martine advises, preserving silence is critical to holding a meaningful conversation. And not just with our mouths, but with our minds as well.

Steven Covey famously said, “Most people don’t listen with the intent to understand; they listen with the intent to reply.”

We need to quiet our minds so we can understand the other person. Not drift off trying to craft a counterargument. People notice the difference. And as Carl Buehner once said, people “may forget what you said — but they will never forget how you made them feel.”

People may forget our response. They’ll remember our presence.

Resist the Urge to Self-Promote.

“If you are really a wit, remember that in conversation its true office consists more in finding it in others, than showing off a great deal of it yourself.” — Arthur Martine

We all want to contribute to the conversation. So when someone tells us about a struggle or a story, it’s tempting to jump in and relate a similar experience of our own.

Maybe it’s a mix between our need for constant one-upsmanship and an earnest desire to relate.

But no matter our motives, once we jump in with our own experiences, we start making the discussion about ourselves. And conversations are not opportunities to boost our own ego.

The anabolic acrobat, Jon Call, aka Jujimufu, says that he used to suffer from this same tendency. Someone would tell a story and his immediate impulse was to respond to with a bigger or more dramatic experience of his own. As he stopped this impulse and started focusing on better understanding others’ experiences, he found the benefit to be remarkable. As he told Tim Ferriss in Tribe of Mentors,

Don’t Preach.

“No well-bred man goes into society for the purpose of sermonizing.” — Arthur Martine

Those who disagree with us, are typically knowledgeable of the same facts that we are. Hence, preaching the rationale behind our decisions isn’t nearly as enlightening as we believe it to be.

More often than not, it’s condescending. And boring for everyone involved.

As one of the things Dave Berry learned in his first 50 years, “People who want to share their religious views with you, almost never want you to share yours with them.”

Good conversations aren’t one-sided. They require an open exchange of information.

Avoid Gossip.

“If you happen to fall into company where the talk runs into party, obscenity, scandal, folly, or vice of any kind, you had better pass for morose or unsocial, among people whose good opinion is not worth having, than shock your own conscience by joining in conversation which you must disapprove of.” — Arthur Martine

I’m convinced that most people fall into the topic of gossip not due to ill will, but because they see it as an easy way to say something interesting.

And yet, gossip destroys trust, making conversations all the more difficult. Not through intended malice, but perceived malice all the same.

As Alain de Botton describes in How Proust Can Change Your Life,

Nothing stifles conversations, or general happiness for that matter, like unnecessary drama.

Seek to Understand.

“Don’t think of knocking out another person’s brains, because he differs in opinion from you. It will be as rational to knock yourself on the head, because you differ from yourself ten years ago.” — Arthur Martine

When someone’s made up their mind on a subject, there’s usually little that we can say to convince them differently. Yet we try. We give them the rationale that we’ve found so convincing. And are then dumbfounded when it fails to have the desired effect.

People are generally aware of the basic facts. It’s how they relate those facts to their values that determines their position. Mindlessly parroting out one side’s mantra rarely helps in changing someone’s mind.

But we can listen. And we can let people talk. We can understand their perspectives. And let them slowly come around to seeing our perspectives as well.

When we stop trying to win a debate, we give ourselves the opportunity to change our minds. And invite others to join us.

As Charlie Munger put it,

Be Brief.

“If you can express yourself to be perfectly understood in ten words, never use a dozen.” — Arthur Martine

Get to the point. Few people care about all of those extraneous details we’re trying so hard to perfectly remember.

Elmore Leonard’s 10th rule of writing has a direct parallel to conversation.

If you wouldn’t be interested to hear a laborious description from someone else, chances are, they’re not too interested in hearing it from you.

Meet People Where They Are.

“A gentleman will, by all means, avoid showing his learning and accomplishments in the presence of ignorant and vulgar people, who can, by no possibility, understand or appreciate them. It is a pretty sure sign of bad breeding to set people to staring and feeling uncomfortable.” — Arthur Martine

When I coach six-year-old soccer, I need to use different strategies than when I relate the same concepts to teenagers.

When I discuss work issues with my wife (and she pretends to care), I use different language than when I’d describe it to a technical expert.

True conversations are borne out of curiosity. People become curious when they have questions they want to answer. And people develop questions when we relate ideas to them in concepts they understand.

Chris Anderson captured it well with his advice on public speaking,

Be Truthful.

“You need not tell all the truth, unless to those who have a right to know it all. But let all you tell be truth.” — Arthur Martine

It’s often refreshing to hear someone say flat out, “you know what, I’m not entirely sure of that answer. Let me think about that for a while.”

Few things ruin someone’s credibility faster than preemptively taking a stand based on incomplete or inaccurate information.

If you don’t know, say that you don’t know. There’s no shame in it. And it will actually boost your credibility for those areas that you do know.

Throw Away the Script.

“You will please so much the less, if you go into company determined to shine. Let your conversation appear to rise out of thoughts suggested by the occasion, not strained or premeditated: nature always pleases: affectation is always odious.” — Arthur Martine

Great conversations rarely follow a set plan. It’s the spontaneity of arriving at a new view or a new conclusion that engage us within great discussions.

We’d do well to take to heart legendary artist Richard Diebenkorn’s third rule of painting,

Be Interested.

“He who goes out of your company pleased with himself is sure to be pleased with you.” — Arthur Martine

Above all, be interested in other people. Bill Nye said “everyone you will ever meet knows something you don’t.”

If we go into each conversation looking to be interested, we’ll rarely be disappointed.

If we go in hoping to just pass the time and avoid that uncomfortable silence, we’ll probably get what we expect as well.

But only one of these mindsets lends to real conversations. And connection. And growth.

So above all, be interested. Because as with any relationship, we get out of our conversations what we put into them.


None of these ideas are earth-shattering. There’s no secret formula.

Be present. Be interested. And try to understand.

As Celeste Headlee closed her fantastic TED talk on this same subject,

You do the same thing. Go out, talk to people, listen to people, and, most importantly, be prepared to be amazed.”

So look for those connections. Because doesn’t that sound more interesting than talking about the weather?

Let’s start the conversation. I’d love to hear your thoughts and suggestions. And if you found this helpful, I’d appreciate if you could clap it up 👏 and help me share with more people. Cheers!

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Jake Wilder

Written by

Enemy of the Status Quo.

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

Jake Wilder

Written by

Enemy of the Status Quo.

A network of business & tech podcasts designed to accelerate learning. Selected as “Best of 2018” by Apple.

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