Skip to main content
🔖 Read in 5 mins ·

How many times per week do you find yourself in a situation participating in small talk about topics you don’t really care about – just to cover the awkward silence?

Whether it’s waiting for a really slow elevator in your condo, talking to an acquaintance at a party, or chatting with a complete stranger at a networking event, it happens to all of us.

It’s the same old questions that drain all the energy out of me and make small talk feel like torture sometimes… “Please someone! Get me outta here!!!”

When I first went to networking events after moving to Toronto I wanted to meet like-minded people and then I wonder why I didn’t remember anybody of these people that handed me their business card the next morning. What happened?

I ended up doing the “small talk tango”.

I don’t have anything against dancing, but this felt like a dance that neither of us wanted to be in.

"Introverts don’t hate small talk because we dislike people. We hate small talk because we hate the barrier it creates between people"

~ Laurie Helgoe

Looking back we probably missed out on a lot of opportunities to connect with interesting people because neither of us was able to move BEYOND the small talk.

To make it worse I even stopped going to networking events because I wanted to avoid those boring conversations.

It wasn’t until a few years later when I created my ASK DEEP QUESTIONS cards and mastered the skills to go from meaningless to meaningful conversations in a matter of seconds that I started going out again to events.

Since then I’ve also learned that having a healthy social network contributes to our health and happiness in a huge way. So now I’m excited to share some of my favourite strategies with you.


I realized that I just couldn’t do small talk because it felt like I had to be fake and pretend to be interested in the weather, sports and celebrity gossip. The same time authenticity is one of my core values. So I needed to find a way to turn this BARRIER into a BRIDGE.

So first let’s reframe small talk from always being the end of a conversation to the beginning of a new relationship that only lasts a minute.

Think of small talk as the light appetizer before the main course, and approach it with renewed purpose ?

I believe that nobody actually enjoys chit-chat, but it’s a necessary gateway to a deeper and more meaningful conversation when you meet someone new. It’s a way for people to feel comfortable and safe, so they can start building trust with you before you go deeper.


Most small talk revolves around the same old questions, so I started asking people unexpected, thoughtful questions that couldn’t be answered with a simple yes or no. The results were awesome: I learned super interesting facts about other people that I would’ve never picked up in “normal” conversation – and as a bonus we became closer.

So instead of:

  • What do you do?
  • Where do you work?
  • What’s your day job?

Ask one of these questions:

  • How did you end up in this line of work?
 How do you keep a good work life balance?
  • What is the most interesting part about your job?
  • If you could have any job in the world, which one would you choose?

👉 Get even more thought-provoking questions in my DEEP CONVERSATIONS GUIDE that also includes my new SMALL TALK CHEATSHEET

And sometimes I wanna go even deeper, so I started asking people:

“Hey, I just started this small talk detox and my doctor prescribed me more meaningful conversations. Could I ask you a deeper question instead?”

And nobody ever refused! ?


During your next casual conversation pay attention to your thoughts when your friend is telling a story.

  • Are you thinking about your own story that you could share as soon as our friend pauses?
  • Or are you thinking of a question to ask to better understand your friend’s story?

I believe the true art of listening is when we can listen to understand instead of listening to respond.

We all want to talk ourselves, so next time you meet someone new I challenge you to follow your natural curiosity and keep asking follow-up questions that let the other person share their story. Whenever you see them “light up” that is a good sign to go a level deeper.

You’ll be surprised by how suddenly you have skipped small talk with just going deeper on one question. I promise you the other person will feel so much more connected to you because you gave them the gift of being heard. Something that happens rarely these days.

"Every Conversation is an Invitation to Risk Revealing the Real You"

~ Keith Ferrazzi

My goal with this post and my DEEP CONVERSATIONS GUIDE is to support you never get stuck in boring small talk ever again, teach you how to have a meaningful conversation so you can easily connect meaningfully with strangers.

There are a lot of tips I didn’t cover in this post that is going to be part of my BEYOND SMALL TALK WORKSHOP, so keep an eye out for the next one.

If you have any of your own strategies, please post them below in the comments.


Learn how to skip the smalltalk and get to the deep and meaningful conversations.

Jan Keck

Jan Keck

Trainer | Facilitator | Experience Designer · Turning Meetings into Inclusive, Engaging and Memorable Experiences 🙌