Want to Break Out of Your Shell? Ask Questions

by: Shannon McNay

I have a friend with a special skill: she can make anyone love her. She’s friendly and warm, cheery without being too perky, and creative without seeming over the top. When she meets people, she at once puts them at ease and sparks their interest. One of the most interesting things about her? She’s a total introvert.

Surprising, right?

There’s a common misconception that all outgoing people are extroverts. That an introvert could never work a room or comfortably talk to strangers. But it’s not true at all! For one thing, being introverted doesn’t always equal shy. And if it does for you, then you can push past your shyness with one simple thing: questions.

Want to Break Out of Your Shell? Ask Questions

I tend to be a combination of shy and outgoing. When I’m in a room full of people I know, I have no problem mingling. But if I walk into a room full of strangers, I want nothing more than to hide. It’s so bad that sometimes I even get a queasy feeling in the pit of my stomach and count the time until I can go home.

This persisted until I met Claire, the friend I mentioned above. I was in awe of Claire from the moment I met her. No matter where we went or who she met, she could get anyone to open up and talk to her. Even the most curmudgeonly of all the people I know (I know a lot of curmudgeons) couldn’t defend themselves against her charm. How did she do it? Through three questions:

What’s your spirit animal?
What’s your spirit era?
Bagel or donut?

Can you believe that asking totally random questions is all it takes to get people to engage with you? I’ve seen it in action and it worksWhy? Because the questions are surprising, they’re thought-provoking, and they’re fun. They’re so weird that you can’t not take part in them. Go ahead, give it a try (and answer in the comments below):

What’s your spirit animal?
What’s your spirit era?
If you could only ever eat bagels or donuts, which would you choose?

For fun, here are my answers:


Think this is silly or too simple to work? Try it! The next time you meet someone new, ask these questions (or come up with your own). They blow right through the awkwardness of small talk (the worst) and jump to fun and engaging conversation. Even other shy people come out of their shells because of the surprise factor, fun, and thought-provoking nature of the questions. Everyone (shy or not) likes to talk about themselves – this helps!

Want some more proof of concept? Vox recently did a study on pickup lines to see which ones worked best on a dating app called Hinge. Every high-performing pickup line was a novel and thought-provoking question. There were no “What do you do for a living?” or “What do you like to do on the weekends?” questions. Instead, things like “Katy Perry or Taylor Swift?” and “Sunday priorities: exercise, sleep, or aggressive mimosas?” were the questions that garnered the most engagement.

Think about it. These types of questions instantly tell you a great deal about the respondent, as they will almost always be followed up with an explanation for the answer given. (For example, my spirit animal is the meerkat because I have only two modes of energy: I’m either extremely hyper or passed out cold. I also like to see what’s going on around me at all times.)


My favorite thing about the questions? They eliminate one of the most painful parts of networking: figuring out what the hell to say to people you don’t know besides, “Hi. So….what do you do?” Blech.

Try the Question Method Yourself!

Want to give this a try? Here’s how you can:

Hi, my name is …. (they respond with their name)

Whenever I meet someone, I like to ask them three specific questions to get to know them better. It’s my way of getting to know people without small talk. Are you game? (the other person will probably say yes simply out of curiosity if nothing else)

Your questions….

See, it’s pretty simple! Watch how it works in action the next time you go networking. It’ll take the pain out of meeting new people (a pain only shy people understand) and can make networking fun!

Image Credits: David Siu, Mathias Appel

2 responses to “Want to Break Out of Your Shell? Ask Questions”

  1. Claire says:

    Amazing post, Shannon! I know I’m biased, but the question strategy has truly been my biggest win in creating new connections and a wider network. I’m getting a great set of data, too.

    Keep on questioning!


    1. Squirrel
    2. 70s
    3. #Donuts for life.

    • Shannon says:

      Ever since I’ve adopted this strategy from you, it’s made a huge difference in my networking life as well! Thanks for leading by such a creative example :).

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