Creative Leadership

Want To Be More Interesting? Start By Asking Better Questions

Today’s post is a guest column from branding expert Krysta Masciale of Big Deal Branding. She’s brilliant at networking, and has pinpointed one of the biggest challenges people experience engaging other people. Ever felt awkward meeting an important professional in your business? Or struggled engaging people at conferences, parties, or other events? Chances are, you’re not asking the right questions. So here’s Krysta’s key questions you should think about the next time you cross paths with a thought leader:

I think one of the worst relational epidemics we face is the art of asking terrible questions. Let’s start with the obvious question: “So, what do you do?”

BORING. Why is that our default? I know it’s because we don’t want to think of something interesting on the fly, but man … it’s sooooo bleh. What does it actually tell us about someone? At best it helps us make immediate judgements and put people in a quick general category so we can decide if they’re worth investing more time into. The answer doesn’t necessarily tell us about the person. It only tells us what they happen to spend 8-12 hours a day doing which, often times, is not an indicator of their true passions or inherent talents. In an effort to have more engaging and memorable encounters, here are some questions I’ve been testing:

What have you learned/read/watched recently that blew your mind?
Are there any books/movies/TED talks you would recommend?
What has been your favorite work experience to date?
What do you spend most of your time outside of work doing?
Do you think the career you currently have will be the one you’ll have in 10 years?

What do you think will be the most rewarding thing about working for yourself?
What are your biggest fears in making this transition?
Is there anything I can do to support you in this transition?
What has been the most encouraging thing someone has said to you in response to this decision so far?

What most excites you about being a parent?
What’s your favorite thing about being pregnant?
What has been the most surprising thing about this experience so far?

(First of all, you don’t have to say anything. Sometimes silence is a much better companion in these situations. But if your friend wants to verbally process, here are some helpful questions)
What is your favorite memory of ______?
What part of their legacy do you hope to carry on?
What has been the part of this loss that you’re having hardest time dealing with?
Would you mind if I came over and (walked your dog, cleaned your house, did your laundry, mowed your lawn, brought you food, etc) so that you could relax?

Where is your favorite place to go to lunch around here?
What has been your experience with faith communities so far?
What’s the hardest part about getting to church on Sundays?

Notice that none of these things lead with YOUR opinion or a projection of YOUR fears. For instance, you aren’t saying to a friend transitioning careers, “Are you sure you want to do that? Aren’t you scared you’re not going to be able to buy groceries, pay your mortgage or find a real job when this one tanks?” Those aren’t questions. Those are your insecurities projected on their situation. Trust me, they’re worried about that stuff, but not as worried as you because they’re going for gold on this. Additionally, you’re not saying to a soon-to-be-mom, “Enjoy your sleep, you’ll never get it again.” First of all, that isn’t a question. Also, it’s not helpful OR encouraging. People aren’t stupid, they know having a kid isn’t easy, let’s not lead with the obvious or the negative.

If you want to build a relational exchange that will have a lasting impact, try and ask questions you would want to be asked. The societal defaults are fine if you get tongue tied, but when you have the chance to think first before you speak … ask questions you would like to be asked and you’ll be surprised at how much you both enjoy the conversation.

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  1. This is such good advice, especially the points about asking questions that don’t project your fears or insecurities but are open-ended and truly allow you to get to know the other person and their perspective. #bettercommunication

  2. I was just praying about this the other day – thank you! I will work at making changes on how I talk to people so that I don’t put any of my fears and insecurities on them just like I don’t like when people put them on me. Also, the part about grieving is so spot on!!

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