Tip 1.

Always remember that bigger questions lead to bigger answers, and thus bigger conversations.  Simply be conscious of what you are asking, and consider whether there is room for better questions to be asked.

Tip 2.

Try to ignore the inner voice that says, “You shouldn’t ask people such personal questions!”.  While we definitely believe there is a time and place for everything, trust that people aren’t as afraid of answering deeper questions as you think.  

For example, if during a conversation someone tells you their parents are divorced, there’s nothing wrong with asking, “How did that affect you and your siblings growing up?”.

Tip 3.

If during a conversation someone shares something personal about their life, don’t close the door, but rather take it as an invitation to walk through it.  

For example, if they say something like, “I don’t really love my job”, instead of saying, “That’s too bad”, try asking a bigger question like, “What part of your job bothers you the most?”.

Tip 4.

When talking to others, look for ways to communicate the reason why you are asking the questions you are asking in the first place.  You can accomplish this by adding precursors such as…

“I’d be curious to know why you chose that path over another”

“I would love to learn more about how that turned out for you”

“I would be interested in understanding what you learned from that experience”.  

In the examples above, you are incorporating your reason for asking the question into the question itself. You are “curious”, you want to “learn  more”, and you are hoping to “gain understanding”.  

This dissuades those being asked the question from wondering what your motive is.  It puts them at greater ease, where they think, “Oh, I see now.  You’re asking me that question because you want to learn more, and not because you are trying to pry.”.

Tip 5.

Another way of approaching Tip #4 is to simply state your reason for asking the question before you ask it.  

Examples of this include… 

“I think you have such a cool job, can I ask you a few questions about it?”

“The risks you have taken are so uncommon, I’d love to ask you more about that if you’re ok with it?”

“I’ve never met someone who grew up in that part of the world, can I ask you what that was like?”.

Tip 6.

The final way of approaching Tip #4 is to share your personal fondness of people in general, and your love of meaningful conversation with others.  Again, this helps people understand why you ask questions that are different than what they are used to hearing, as opposed to thinking you have some sort of “agenda”.  

An example of this would be to say something like…

“You know, I really find people fascinating, which is why I like to ask unconventional questions that go beyond where you work and live.  Do you mind if I ask you a few questions about yourself?”.

Tip 7.

When someone shares an experience they had with you, look for ways to help them expand.  When we say things like, “That must have been so cool, really fun, unexpected, memorable”, etc., we cut the conversation off from going further.  

Instead, look to say things such as…

“That must have been so cool, what did you learn from that experience?”

“That sounds really fun, is there any way you would have done it differently if you could?”

“I can only imagine that was unexpected for you.  How did it change you as a person?”

“What a memorable moment for you.  Are there any other moments in your life that compare?”.

Tip 8.

Create a space where vulnerability is welcome, by being vulnerable first.  

Instead of saying, “How did your parents’ divorce impact you and your siblings?", try saying, “When my parents got divorced, my siblings and I were devastated.  What was the experience like for you and your brother?”.  

By taking this approach, you are going first, which creates a safe space for them to join you.

Tip 9.

Look to turn predictable information into something more interesting, by getting a little creative with your questions.  If you find yourself asking traditional questions such as…

“What do you do for a living?”

“Where do you live in the city?”

“What school did you go to?”

“When did you get married?”

After they answer these types of questions, try getting creative with your follow up questions by asking things such as…

“You’re an accountant? Cool.  So, what’s your favourite thing about your job?”

“You live in that neighbourhood?  Great.  What’s one secret people living over there know about that part of town, that others don’t?”

“You studied at Michigan State?  That’s a great school.  What do you think makes Michigan State unique?”

“You’ve been married for 20 years? Congratulations!  Are there any stories from your wedding that stand out?”

Tip 10.

Look for the questions that put a smile on people’s faces.  No matter what someone is sharing, see if there is a question you can ask that will make them feel happy.  

Some examples below include.

“You grew up close to a beach?  Awesome!  What’s one of your favourite childhood memories from that time?”

“You work with celebrities?  Neat!  What’s one of the funniest things a celebrity has ever said to you?”

“You manage that many people?  Well done!  So, what’s one of the nicest compliments you have ever received from a co-worker?”