5 Questions for Better Small Talk

Have you ever been talking to someone and just run out of things to say or ask?

The awkwardness starts to build and you're ready to dip.

Learning to ask better questions can help you avoid these dreaded moments.

Here are 5 questions you can build into your small talk to keep the conversation flowing and help you make more meaningful connections.

1) If you had a full free day, what would that day look like?

I love this question. It's focused, yet open enough for people to take it any which direction they're most comfortable with. This question provides an opportunity for others to share about what recharges them and what brings them joy.

The best part of this question is watching others light up as they express their passions.

With everyone being so "busy" these days, getting to even daydream about a free day is quite lovely. You may even help someone realize that they need to prioritize a day off soon.

2) What did your journey to (X) look like?

X could be any number of topics..typically I like ask this question about how people ended up their jobs,  "What did your journey to Apple look like?"

It's pretty wild how some people end up in their roles. You may even learn that someone you know introduced them to the company. I love these moments where you get a glimpse of the connectedness and serendipity of life.

X could also be a recent vacation "What did your journey to Vietnam look like?"

Reminiscing about a trip, even long after it's over, can bring deep pleasure in the present. Asking this question gives people a chance to relive these moments.

3) What did life look like for you growing up?

I used to ask "What are your parents like?" but realized that this question is a bit too pointed and that everyone's parent situation looks different.

Asking, "What did life look like for you growing up?" is more open ended and allows people an opportunity to share joys, hardships, and be more vulnerable if they're comfortable.

I really enjoy hearing other's response to this question as it helps me understand more of the people, places, and things that have molded them into who they are today.

4) What's been the highlight and lowlight of your week?

This one is an easy one to incorporate into conversations and can often be used when breaking the ice with someone you just met at an event.  

I'm not completely against asking someone "What do you do for work?", but I'd prefer to open with a question like this one prior to the former.

Many (maybe even most) people work to live, rather than live to work. So asking about work right off that bat may not be the most exciting intro.

5) What's something that most people don't understand or misunderstand about (you/your industry/your work, etc.)?

You can learn from anyone. The trick is finding where other's expertise and experience exceed yours.

What I love about this question is that you're trying to go beyond common sense and towards a deeper understanding. Many new businesses and opportunities are created by going against the grain and common practice.

For example, before Airbnb, it'd be really odd to let random strangers rent out a room your in house. Now, we don't bat an eye at the concept. But there was a time when only a handful of people understood the opportunity of renting out your own home.

This question has a ton of potential in helping you understand the people and world around you better.

One Multiplier Statement for Better Small Talk

"Tell me more about (xyz)!"

Once you have someone talking, ask them to go deeper. Polite people will usually not want to rant and bore you, so they'll often just give you a high level summary to keep the conversation going back and forth.

Saying, "Tell me more about (this or that)" gives them permission to keep going! By saying this and asking follow up questions, you'll be making the shift from small talk to having an engaging conversation.

And once you show interest in getting to know someone at a deeper level, they'll naturally want to get to know you at a deeper level as well.

Learning to ask questions and follow up questions is the foundation of building deeper and more meaningful relationships.

What questions do you like to ask to help you move from small talk to deeper more meaningful conversations?