How to Avoid Soul-Squashing Small Talk

Guest Post by Bobby Powers

Where do you work?
What do you do?
Where are you from?

How many times have you been asked these questions?

The sheer lack of imagination applied to most conversations makes it seem like our species only developed speech a few decades ago and we’re still trying to figure it out. Either that or we’re so hamstrung with worry about asking the wrong thing that we decide to only ask the safe questions — the ones we know won’t offend anyone or reveal anything too personal.

In every conversation, we’re given a rich palette of colors to paint with, but we dip our palaver paintbrush into the same boring hues time and again, resulting in the same boring conversations.

Probably due to my hatred for small talk, the art of asking questions has always fascinated me. Questions are the key to making conversations more interesting, so if we want to improve our conversations, we need to improve our questions.

Two years ago, I attended a leadership conference in Texas that profoundly influenced the way I think about questions. In a room packed with 5,000 people, the conference hosts kicked off the first icebreaker with a bang:

“We know that all of you are used to getting asked the same three or four questions every time you meet a new person at a conference: ‘Where do you work? Where are you from? Is this your first time attending this conference?’ So we’re laying down a ground rule for this conference: You can’t ask any of those questions. We’re passing out cards around the room that contain deep, meaningful questions, and you’ll be asking each other questions like that all week. No fluff.”

Sure enough, thousands of little conversation cards circulated around the room bearing questions like the following:

  • What is one thing you want to accomplish in your lifetime?
  • What is one thing life is teaching you right now?
  • What is the most adventurous thing you have ever done?

For the first icebreaker, we were instructed to pair up with someone we didn’t know and ask each other one or two questions from the cards. I was sitting next to an older gentleman who didn’t look too scary, so I asked him to pair up. “Gary” and I asked each other the questions on our respective cards, and we were suddenly painting with all of the conversational colors on the palette.

In every conversation, we’re given a rich palette of colors to paint with, but we dip our palaver paintbrush into the same boring hues time and again.

Within five minutes, I had opened up to Gary about my career aspiration of becoming a leadership author and speaker — a dream that only a few people knew at the time. And Gary told me about the pain of losing his older sister when he was only 15. He talked about how much she taught him in those 15 years and that he’s a better person from having known her.

After our short conversation, I felt closer to Gary than to many people I had known for years. I left the conversation with a feeling of warmth and connection, not boredom and disinterest.

That experience taught me that small talk is a product of our own laziness and comfort. It’s 100 times easier to ask a common question than to dig deep and ask something more meaningful.

If we want to improve our conversations, we need to improve our questions.

Asking deeper questions not only requires you to exercise creativity but to take a genuine interest in another person’s story. It demands vulnerability and openness because if you’re asking deep questions, you’re going to be asked deep questions in return.

Here are five ways to avoid soul-sucking small talk:

1. Learn How to Ask Better Questions

“Without a good question, a good answer has no place to go.” -Clayton Christensen

Thoughtful questions are the scaffolding of every worthwhile conversation. We can improve our dialogue by asking open-ended questions, posing one question at a time, becoming comfortable with silence, and not “leading the witness” by hiding advice in our questions (“Don’t you think it would be best to just…?”).

A question that is 20 percent better can often yield an answer that is 200 percent better. In this way, questions have a disproportionately large impact on the quality of a conversation.

There’s a world of difference between asking someone “Did work go well today?” versus asking “What was the highlight of your workday today?”

The former question puts the other person into autopilot, eliciting a yes/no answer or a bland response like, “Yeah, it was fine.”

The latter question catches people off-guard in a positive way. They think. They smile. They remember that amidst their hectic and stressful day, a customer gave them a kind word or a genuine thank you. An otherwise forgotten moment is remembered and appreciated.

Invest the time, effort, and curiosity to ask better questions.

2. Develop a List of Go-To Questions

“Answers are closed rooms; and questions are open doors that invite us in.” -Nancy Willard

In 2015, a team of researchers led by Arthur Aron conducted a study to see whether two strangers could quickly and intimately bond with each other by asking a specific series of questions. The researchers’ results have been adopted into the popular press, including a popular New York Times article with the provocative name “The 36 Questions That Lead to Love.”

The researchers concluded that in order to bond closely, people need to ask and answer questions that require some level of vulnerability. Merely putting two people in the same room to gab for 45 minutes wasn’t enough.

A question that is 20 percent better can often yield an answer that is 200 percent better.

What are your go-to questions? If you find yourself reaching for the same tired questions over and over, consider developing a go-to list of questions. Consult lists like the 36 questions from Aron’s study, the “200 Questions to Get to Know Someone” from Conversation Starters World, or one of the million other lists online.

I’ve developed my own list of my favorite questions to ask. Many of them aren’t even deeply personal, but I’ve found they’re good segways to learning more about someone and opening more conversational doors. Here are a few of my favorites:

  • What’s your favorite book?
  • Where are you hoping to travel next?
  • What’s something you’ve learned about yourself recently?

3. Ladder Your Way Up to Vulnerability

“One key pattern associated with the development of a close relationship among peers is sustained, escalating, reciprocal, personal self-disclosure.” -Arthur Aron, et. al.

In the leadership conference example above, the conference hosts had given Gary and me explicit permission to have deeper conversations, which was extremely helpful because it set the expectations for depth. But unfortunately, we won’t have that type of permission or shared understanding working in our favor most of the time in everyday conversations.

I know from experience: it can feel awkward to dive in and ask something unexpected. The key is to gradually ladder your way up to vulnerability. You can do this in two ways:

  1. Asking gradually more personal questions
  2. Answering the other person’s questions with more openness and candor than people generally expect

Let’s say you meet someone new at a friend’s house. The other person (“Mary”) asks you how your day is going: a simple question that generally yields a blasé response.

But you decide to give Mary a real answer: “You know, honestly it’s been a bit rough. I had a big sales call with an important prospect, and I botched the call. I don’t think we’ll sign them now, and I keep second-guessing what I should have done differently on the call.”

At this point in the conversation, you’ll find out whether Mary wants to have a real conversation. She’ll either tap out and find a new chit-chat buddy or she’ll ask more questions and truly engage.

Vulnerability yields vulnerability. Openness leads to openness. Once you’ve shared an authentic answer with someone, you’ve established that they can also share something authentic with you. And now you’re having a real conversation.

4. Ask People About Their Life Story

“What is love but listening to and wanting to be a part of another person’s evolving story? It’s true of all relationships — romantic and platonic. And listening to a stranger is possibly one of the kindest, most generous things you can do.” -Kate Murphy

I have a new habit when I use Lyft or Uber. After years of either riding in silence or having small talk with drivers, I tried an experiment a few months ago. After a few basic questions, I asked my driver, “I love learning people’s stories. I was wondering, would you be able to give me a five-minute version of your life story?”

Everyone has a story. Most of those stories go untold because no one asks the right questions. Give others a podium to share what makes them unique.

To my surprise and delight, my driver lit up and said she’d love to tell me her story. She shared how she had once been a star collegiate athlete, then later went on to have a successful business career before giving up corporate life to try something new. Minutes after meeting her, I learned the highs and lows of her life, what she loves to do, and what she wants in her career.

I’ve now asked several drivers this question, and I’ve been amazed by the stories I’ve heard. One of the most memorable was when I got the chance to hear the story of a Ugandan refugee who moved to the US several years ago, where he promptly fell in love with his boss’s daughter and spent the next year wooing her. They’re now happily married with two kids.

Everyone has a story. Most of those stories go untold because no one asks the right questions. Give others a podium to share what makes them unique.

5. Take the Plunge: Ask Something Interesting

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” -Dale Carnegie

Two years ago, my wife and I went out to dinner with another couple I didn’t know well. From what I knew about the husband (“Ted”), we didn’t share many hobbies, so I was unsure how the dinner would pan out.

During our meal, I asked Ted about his work. He said he did some private investigation work, which sounded fascinating. So I proceeded to ask Ted a bunch of questions: What type of people did he usually track down? What was the craziest case he had ever investigated? Had anyone ever drawn a weapon on him? What tips had he learned in the field about how to tell if someone was lying?

A run-of-the-mill dinner turned into a fascinating conversation, and all it took was a little curiosity and a few deeper questions.

The next time my wife talked to her girlfriend about the dinner, her girlfriend said that Ted was convinced I was a spy. He had never had anyone ask him thought-provoking questions like that before, so he assumed my job must involve some form of intrigue and espionage. (It doesn’t. I work in tech.)

People aren’t accustomed to getting real questions about their life and career. Stand out by asking something interesting.

You don’t need to resort to small talk at parties, happy hours, networking events, and conferences. There’s a better way.

The next time you’re tempted to ask a small talk question at a company event, conference, dinner party, or Lyft ride, dig a bit deeper. Make the conscious decision to paint with the full palette of conversational colors at your disposal. You may even be confused for a spy, and that’s pretty damn awesome.

Bobby Powers


Bobby Powers is the Director of Employee Experience at The Block, a cryptocurrency infoservices firm where he leads manager training, onboarding, and employee development. Before joining The Block, Bobby managed international teams as large as 160 people across fintech, software, and retail. He’s a total book nerd who reads over 70 books per year (and has been doing so for the past 10+ years). If you’re interested in becoming a stronger leader, learner, or communicator, check out Bobby’s website ( and monthly email newsletter.


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