Two Questions to Ask in a Great Conversation

Want stress?  Try networking.  The prospect of networking used to really freak me out.  Talk to people I don’t know?  About what?

Truth is… its incredibly easy to talk with someone about easy subjects:  the weather, where they live,  how old their kids are…  But these are only surface questions.  How do you really get to know someone?  How do you find out if you connect with them as a friend or if you are a good fit with them in the business sense.

Recently, I heard an amazing talk given by Chris Brogan, the CEO of Owner.Media at the Disney Social Media Moms Conference.  Having a great conversation simply boils down to two questions. 

• What are you working on right now that makes you really excited?
• (Think of a problem you are having)  I’ve really been stuck with this.  What would you do?

Easy, right?  Yes and no.  If you are someone like me who simply had trouble even starting a conversation, these two questions delve deep and are a little off putting if you start a conversation with them.  

Since I am a huge fan of food, I like to think in terms of dinner courses for metaphors. Every conversation has an appetizer portion.  Some convos never go past the appetizer.  Its like tapas and a glass of wine and you are off.  Appetizer questions show you are polite and welcoming, both necessary things, they just don’t have staying power.  These are questions and comments like:

• This weather is gorgeous.
• Where are you from?
• Do you have kids?  How many? How old are they?  Boys or girls?
• What are you doing this weekend?
• Whose class is your son/daughter in?
• What’s your blog about? (This is always big for me at conferences)

Politeness.  Niceities.  Some may lead to an interesting conversation. Most of the time you will find something you have in common, but usually they won’t lead to anything of substance.  

However, once you have discussed these easy topics for a few minutes and you decide that this person seems interesting and you want to know them better, you can ask:

What are you working on that you are most excited about?

The beauty about this question is that you can use it in a personal or a professional setting. You can discuss a project that the other person is working on around the house, maybe a hobby or maybe their career.  This question is amazing because it gives your conversation partner a chance to brag in a very socially respected way.  You did ask after all!  

Also, you can find out the coolest things going on in other people’s lives – future vacations, awesome hidden talents, cool people they know.  It can really bring up a wealth of information that will keep the conversation going.

I’m really stuck with this.  What would you do?

I love giving advice.  Other people love giving advice too.  With this question, you show that you value the other person’s experience as well as gain incredibly useful expertise.  I love using this at blogger conferences because I am usually surrounded by blogging rockstars who have been doing this for a number of years.  I can pick their brains and use all their secrets.  Muah haha.  Well, not really secrets, since they told me.  Still… you can see how powerful this one is.

This also works incredibly well at school pick up with parenting advice.  And if the advice isn’t that spectacular?  A simple “Thank You for that advice” will work well.

To really delve deep into conversations, these two simple questions will tell you tons about other people and make the conversation an incredibly useful one.   The dessert in my whole conversation metaphor is a new friend or business connection at the end!

This post is part of my Shy Girl’s Guide.  I am a former shy girl who has figured out the world and uses lots of tricks to help my inner introvert talk with people.  Read more Shy Girl’s Guide posts. 

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