I loathe small talk.

It’s why I tend to go 10-15 months between haircuts, because I prefer split ends over the thought of 60 minutes of “so…do you have any vacation plans for this summer?”

Small talk bums me out because it doesn’t create much value. I don’t discount the fact that it’s an essential social tool… becayse jumping straight into “tell me what your deepest fears are” on a sales call might *not* earn you a new client. Small talk itself isn’t bad, but when we never progress past it, that’s what makes me want to call out sick.

When you’re at an industry event, whether that’s a conference, a mastermind, a mixer, whatever, one of your jobs is to be memorable. And that’s hard to do when you’re asking the same four questions as everyone else in attendance (you know the ones I’m talking about- “what do you do?”, “how long have you been in business?”, “where are you from?”, and “how long did it take you to get here?”).

Real connection doesn’t happen at the surface- it happens when we care to plumb deeper, to get to know the person we’re talking to beyond just their occupation, place of residence, and years in the industry. The goal here isn’t to bear your soul or find your new BFF, but to have conversations that lead to relationships that benefit both you and the one you’re talking to.

But what if networking makes you sweat, or you’re worried about saying something dorky (#itsme), or the thought of asking anything OTHER than surface-level questions makes you want to hide in a corner?

I got you!

Here are 10 questions you can ask at your next industry event to go deeper without invading someone’s sense of security:

1. What’s going well for you right now?

I love that this invites someone to reflect on what IS going well, because so often as business owners we’re quick to focus on what ISN’T going well. So it’s a way to bring out the positive, and then chances are, they’ll ask you the same question, and you’ll get the chance to reflect as well!

2. What are you passionate about outside of work? 

This is always a fun one that seems to catch people off-guard! Sometimes you’ll get snarky answers, but my favorite part about this question is how it opens the door to get to know someone outside of JUST what they do for a living. SO many fun rabbit trails can open up with this one simple question!

3. What are you hoping to get out of this conference? 

This is something I love that my mastermind does every time we get together- setting intentions. It forces me to pinpoint one specific takeaway I’m looking for, instead of touching on a bunch of different surface-level areas of my business. And you never know- whatever answer the other person gives? It might be something you’re able to help with!

4. What’s something you’re learning right now? 

This is another good reflection question- sometimes we’re so in the thick of our own businesses that we haven’t taken a step back to ask ourselves, not just what am I DOING, but what am I LEARNING?

5. If you could have any super power, what would it be and why?

This is just a fun one to break the ice- less personal than the previous questions, and I love hearing people’s answers. Mine is a toss up between the ability to fly and the end-of-day ability to blink and end up in my bed with my face washed, teeth brushed, and contacts out. I don’t know why I hate getting ready for bed, but it’s such a drag.

6. What’s the best business book you’ve read recently?

I’m always on the hunt for a can’t-miss book rec that changed someone’s life, so this is an especially good one for when you’ve met someone whose business you admire- I want to know what influenced them, what voices are speaking into their head in the form of a book. 

7. How are you being challenged right now?

Ok so this one is maybe a question to save for like… the second or third day of a conference, maybe not a question you ask someone within the first couple of minutes of meeting them. It’s not overly intimate, but it is personal. Use this one selectively- it may catch some people off-guard. 

8. In a movie about your life, who would you choose to play you?

This is another just-for-fun question, but it DOES give you some insight into how a person sees themselves! I love hearing people’s answers, especially when it’s someone I’m already familiar with- I love hearing how their answer might differ from who I would pick to play them in a movie.

9. If you could have dinner with any person in history, who would it be? Why them?

You could sub out “any person in history” for “any person alive” or “any celebrity”- pick your poison. People’s answers here will surprise you and maybe make you rethink your own!

10. What made you sign up for this event?

This one goes hand in hand with question 3 of “what are you hoping to get out of this conference.” Sometimes it’s a specific speaker they wanted to hear from, or a friend was coming and asked this person to tag along. Sometimes they’ll tell you about a specific project they’re working on and they selected this conference to help them succeed with the project, and that opens the door to ask more questions about what they’re working on, which shows you how much might be able to point them in other helpful directions.

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Even as an extrovert, I know how intimidating it can be to walk into a room of people you don’t know. It can be tempting to stick to small talk, because it’s low-risk, and you’re already nervous. 

But you’ve already done the hard work of signing up and physically getting into the room. So why not make the most of it by asking questions that will lead to deeper conversation, and stronger connections?

Want more content like this? Check out my podcast, The Artisan CEO!

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