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Daily Inspiration Quote by Chuck Klosterman

"You're trying to find new ideas in people. I always think to myself, what question I am least comfortable asking the person? And then I make sure I ask it early in the interview"

About this Quote

Klosterman is admitting, with a critic's smirk, that “new ideas” rarely arrive dressed as novelty. They show up as discomfort. The line reframes interviewing as a kind of controlled social trespass: if you stay inside the polite perimeter, you’ll get the publicist-approved story, the personality brand, the rehearsed anecdote that flatters both parties. The uncomfortable question is a crowbar. It pries loose the person from the version of themselves they’ve been performing.

The strategic detail - ask it early - is the tell. He’s not chasing confession for its own sake; he’s managing the power dynamic. Early discomfort prevents the gradual warm-up from becoming a contract of mutual niceness. It also blocks the interviewee from “getting into character,” from using momentum to steer the conversation into familiar grooves. Klosterman wants to puncture narrative autopilot before it hardens.

There’s subtext, too, about the critic’s job in a culture drowning in access. When everyone can get the same backstage pass, differentiation comes from asking what others won’t. His method acknowledges that originality is often negative space: the topic avoided, the premise taken for granted, the self-justification left untested. It’s a small philosophy of intellectual risk, dressed as interview technique.

Contextually, it fits Klosterman’s late-20th/early-21st-century lane: pop culture treated as a serious arena for ideas, and “seriousness” measured by willingness to complicate the comforting story. The move isn’t cruelty; it’s a bet that friction reveals more truth than rapport.

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APA Style (7th ed.)
Klosterman, Chuck. (2026, January 17). You're trying to find new ideas in people. I always think to myself, what question I am least comfortable asking the person? And then I make sure I ask it early in the interview. FixQuotes. https://fixquotes.com/quotes/youre-trying-to-find-new-ideas-in-people-i-always-47515/

Chicago Style
Klosterman, Chuck. "You're trying to find new ideas in people. I always think to myself, what question I am least comfortable asking the person? And then I make sure I ask it early in the interview." FixQuotes. January 17, 2026. https://fixquotes.com/quotes/youre-trying-to-find-new-ideas-in-people-i-always-47515/.

MLA Style (9th ed.)
"You're trying to find new ideas in people. I always think to myself, what question I am least comfortable asking the person? And then I make sure I ask it early in the interview." FixQuotes, 17 Jan. 2026, https://fixquotes.com/quotes/youre-trying-to-find-new-ideas-in-people-i-always-47515/. Accessed 12 Feb. 2026.

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Ask the Uncomfortable Question Early in Interviews
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About the Author

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Chuck Klosterman (born July 5, 1972) is a Critic from USA.

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