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Written by Laurie Hillis

Hi, I’m Laurie Hillis, I love what I do: the learning, the process, and above all, seeing how my clients grow as leaders.

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February 15, 2023

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We are so much more than what we do for a living

How to strike up a deeper conversation with someone you just met

“Hi, I’m Laurie. It’s nice to meet you. ……. {awkward silence} ……. Umm, so, what do you do?”

Does this sound like every first meeting you’ve ever had?

Even in non-workplace situations (like the airplanes I was on a few times this week), when meeting someone for the first time, we often default to this question. Surely, we all know that we are much more than what we do for work. As Brené Brown, and many others in different words, says: “We are hardwired to connect with others, it’s what gives purpose and meaning to our lives…” 

So why the reluctance to move quickly to a deeper connection?

Is it too personal to ask about someone’s personal life so soon? Is the inevitable pause that follows an unexpected question uncomfortable? Is it the only “safe” question we can come up with? I suppose so. But seriously, how is it the only question we can think of? And why are we so in favour of staying safe in our new connections? 

Can you accept the awkwardness if it means a potential deeper connection?

For me, it’s the people I meet who try to get to know the whole me that I feel a deeper connection to. It might feel a little off-putting at first when someone asks me a question that is beyond “What do you do?” but it immediately signals to me that this person is different from most and cares about getting to know me.

Now don’t get me wrong – I am very proud of the work I do and I love talking about it, but it doesn’t need to be the first thing I share when meeting someone. I have so much more to share!

Of course, you want to be mindful of your approach and choose questions that don’t feel like an invasion of privacy or an inquisition. Questions with only yes or no answers can stop a conversation dead in its tracks if someone isn’t a natural conversationalist. And stay away from topics like religion and politics – we’re not trying to scare people off! 

So here’s a challenge for you – the next time you meet someone for the first time, stay away from work-talk, at least in the beginning. Ask a different question. If you’re met with a little silence or awkwardness, let it be. And then listen to the response. Ask follow up questions. Stay present and curious. If it gets really awkward, share something about yourself first. Going first will make the other person feel more comfortable sharing something about themself.

Need help getting started? Here are some conversation starters that are sure to get you into a deeper conversation and connecting with that other person quickly:

  • What do you do when you’re not working?
  • Where did you grow up? What was that like? What brought you here?
  • Do you do any sports or hobbies? Tell me about them!
  • I’m planning to do some traveling this year, but haven’t decided where. Where would you suggest I check out? 
  • I’m looking for a great podcast. Have you listened to anything you’d recommend? 
  • Do you have any pets? (Animal lovers can connect with other animal lovers instantly!)

If it still feels like the only right question to ask right off the bat is “So, what do you do?”, or someone doesn’t seem to be enjoying your ‘get to know the real you’ approach, ask about their job, and then follow it up with questions that dig a little deeper:

  • What do you love about what you do?
  • What drove you to this career?
  • I’ve always wondered (            ) about that industry.
  • Do you envision doing anything different at some point?

Yes, you may receive hesitation or a head tilt, and it may take the person a little longer to answer your question, but what have you got to lose? More importantly, what have you got to gain?

Let’s connect:

If you want to know more about Megatrain and how we can work together, drop me a line:

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