Ask Paired Questions
How to use paired, contrasting questions to break out of conversational ruts
(Pairs are awesome)
Most interviews come to a point where you’re invited to ask questions. The next time you’re in this situation, try asking a pair of contrasting questions rather than just one.
Example:
“What kind of people do well here . . . and what kind of people don’t do as well?”
This approach applies to all kinds of conversations in work and life. Here’s why it works:
Paired, contrasting questions can really open things up. They signal that you’re open to a range of responses. They encourage the respondent to think creatively. You will come off as someone with critical thinking skills, a cut above, particularly if you practice word economy and keep things tight.
Paired questions communicate, “Instead of me asking you a specific question, and you answering, let’s just have a conversation.”
Also, because paired questions invite the negative in addition to the positive, you’re more likely to get helpful feedback, which you can then address.
Paired questions aren’t limited to interviews. Here are some scenarios:
Icebreaker | social situation
“What’s a trip you’ve made that was amazing? What’s a trip that turned out kind of ‘meh’?”
Team meeting
“What went well in our meeting today? How could we improve things next time?”
Trying to get your kids to talk to you
“What was your favorite thing about school today? What’s something you didn’t like about school today?”
Informational interview | seeking feedback on a pivot
“What are strengths I have that companies might value, and what’s an obstacle I might experience in making this pivot?”
Business development
“What would be attractive to your colleagues about this approach? What hesitations might they have?”
Talking to doctors
“What would be the benefit of getting the procedure? What would happen if I don’t get the procedure?”
Your turn: Try out some paired questions and let me know how it goes! And also, so that I walk my talk:
“What did you like about this essay, and what would make it better for you?”
About Your Invisible Network and M2Leaders
Building better networks and richer relationships with others are lifelong career and leadership advantages. I demystify all in “Your Invisible Network,” described by Herminia Ibarra as “The best book on networking, one I recommend to all my students.”
M2Leaders is my awesome company. Our 25 coaches partner with companies, firms, and major nonprofits to help leaders reach their full potential and do great things. We’re kind of a big deal, so check us out!
Copyright 2026 by Michael Melcher. All rights reserved


I love this piece, Michael. Simple but brilliant. It spans so many topics and sparks curiosity and thoughtfulness.