Quest for Questions
Always on the hunt for better questions.
I’ve always been on the hunt for better questions. Some people just have a way with asking questions. Ones that are deep, funny, inspiring, eloquent, right on point. I’ve always struggled with asking questions. I love it when other people ask good questions and then I get to reap the benefits of listening and learning. Since it’s been hard for me, I made it my life goal to ask better questions. Ever since I was in college, I set out on this quest for questions to get people talking about things that really matter. I started a note in my phone in 2021 where I keep all these questions. It currently has 87 questions and is always growing. Some are simple and silly, others are personal and profound.
Finding the right level of invading someone’s personal space in a way where they can reveal a little or lot is a truly a gift. It’s hard to find that perfect question. So I’ve given up on finding the perfect question. Because that doesn’t exist.
Just curiosity exists.
Seeking to understand, to learn more. Test alllll the questions. Some will hit home, others won’t. There’s a data point in my quest and I keep going.
So I invite you to join the quest of asking questions.
The world needs more questions and less answers. When you can be ok with that, all will be well. All shall be well.
Here’s a compilation of my favorite ones…
Personal Reflection Questions
What is your favorite time of the day and why?
What makes you tick? What are you hot topics?
What’s your story? (Instead of, what do you do?)
How do you recharge when you're stressed out during the week?
Do you like your name? What’s the story behind it?
Where are you putting your time and effort in life? Why?
Are you a long-term or a short-term thinker?
What’s the most out-of-character thing you’ve ever done?
What’s the most spontaneous thing you’ve done this week?
What area of your life is most organized?
If someone wrote a book about you what would it be titled?
How have you been growing most recently?
Are you a doer, dreamer, or thinker?
What makes you happy? What’s your “hot topic” you love to talk about?
Where do you need help in your life right now?
About You Questions
Do you have a treasured piece of clothing you are not willing to give up?
How did your family make tacos growing up?
What are you famous for among your friends and family?
What’s the last thing you bought yourself other than groceries or gas?
What did you have for dinner last night?
What’s one of your favorite scents? Do you notice scent a lot?
What’s a meaningful object you keep in your home?
What’s special about the place you grew up?
What’s your walk-up song?
When was the last time you ate a meal alone in public?
Goofy Questions
Who’s your guy? (The inaugural TND question)
What’s your favorite kitchen utensil?
What’s your go-to weird snack combo?
If you had to eat one meal every day for the rest of your life what would it be?
If you were a vegetable, what vegetable would you be?
What color is each subject?
What would you give up first: pasta, rice, or potato?
If you could transport yourself to any place in time just for this weekend, where would you go?
If you could create your own breakfast cereal, what would it be? Shape, flavor, and color.
One last note. Open-ended questions lead to more depth and insight, so aim for those. Like David Brooks says “The quality of conversation depends on the quality of questions”. Check out his whole video about “The Art of Seeing Others” or try out a few of his questions for meaningful relationships…
What crossroads are you at?
If these 5 years of your life were a book, what would this current chapter be called? What’s it about?
What would you be doing if you weren’t afraid?
What’s the no or refusal you keep postponing?
What’s the commitment you’ve made but no longer believe in?
What’s the gift you hold in exile? The talent you have that you are not using?
How do your ancestors show up in your life?
As you’re on your quest for questions check out these inspiring hosts + creatives: Sarah Wilson | Priya Parker | Esther Perel | WNRS
What are the questions you like to ask to get the conversation flowing?
Let us know the comments.
