
Design Matters with Debbie Millman Surprising First Questions
Oct 6, 2025
In a special anniversary compilation, various past guests share their quirky answers to Debbie Millman's signature first questions. Eric Spiekermann discusses a climber’s harness that recalls childhood treehouses, while Roman Mars recalls attending college at 15. Jessica Hische humorously explains her cat’s name change to Olivia Benson. Other guests like Chip Kidd, Isaac Mizrahi, and Roxane Gay offer amusing and insightful anecdotes about life, creativity, and personal quirks, making this reflection on a two-decade tradition both nostalgic and entertaining.
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The Power Of A Playful First Question
- Debbie Millman explains she researches guests deeply and begins interviews with playful, personal first questions.
- She uses these to signal preparation, relax guests, and prompt candid conversation.
Surprise Funk Drummer Moment
- Ben Schott tells of unexpectedly playing drums in a funk band when asked at an event, surprising friends.
- He self-describes his performance as perfectly mediocre white drumming, enjoyed by attendees.
Stylish Slobbery Is Authentic
- Isaac Mizrahi and Debbie Millman banter about being stylish even while lazy, claiming slovenly moments reveal true style.
- Mizrahi argues the most stylish moments happen when you relax and still maintain chic personal details like cute slippers.






