"The biggest reason somebody will avoid answering a question is because they don't trust you with the answer." - Debbie Millman

Debbie Millman has spent 21 years asking questions on Design Matters, the show she started in 2005 before podcasting had rules. In episode 100 of Curated Questions, she takes the receiving chair.

Debbie traces her craft from a survey-style list she asked everyone, work she now calls terrible, to a method she describes as storytelling through questions, where each question carries the context a guest needs to respond to a fully realized moment in their life. She explains why she avoids false wisdom language, multiple-choice framing, and interpretation the guest hasn't offered yet, and makes the case that people withhold answers when they don't trust you with them.

The conversation ranges across branding, her clients, the questions she brings to any redesign, the rebuild of The Rumpus with Roxane Gay, and what AI costs students who skip the difficulty. She closes with the question consuming her at 65: how to live this last third.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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Keep questioning!

"You were the most interested person in the room, and you're gonna get love." - Maury Rogow

Maury Rogow is all about storytelling. He is the CEO of the Rip Media Group and creator of the Story2Sales methodology that's generated over $150 million in trackable revenue for clients. I appreciate the tag line, "Your brand will thrive or die, based on the story you tell."

Maury's unique journey spans high-tech success and Hollywood storytelling. He built his business career at companies like Avaya, Lucent Technologies, and GeoTel—a startup that sold to Cisco Systems for over $1 billion. He then pivoted to Hollywood, serving as executive producer for feature films like "Bedrooms" and "Enter The Dangerous Mind," and working with industry legends including the creator of the Batman franchise.

Today, Maury combines business acumen with cinematic storytelling to help Fortune 1000 companies like Comcast, Kaiser Permanente, and Ben & Jerry's create compelling brand narratives. His approach recognizes that in our noise-filled marketplace, every company must master storytelling to survive and thrive.

Maury has proven that great stories don't just entertain—they sell. He's written several books, with his latest on the horizon being "Your Story Can Be Your Superpower - Selling in an AI world." He has been featured in Forbes, Inc., and Entrepreneur magazines.

In this episode of Curated Questions, host Ken Woodward engages with Maury Rogow, CEO of RipMedia Group, to explore the transformative power of questions in both personal and professional contexts. Maury shares pivotal moments in his career, from telecommunications to Hollywood, emphasizing how a single question can change a transactional relationship into a meaningful connection.

The discussion covers the importance of storytelling, the benefits of embracing unique traits, the impact of framing on emotional responses, and effective strategies for leveraging questions in sales and daily life. Maury also offers practical advice on finding balance in business, the role of AI in asking the right questions, and shares key resources and techniques for developing better questioning skills. Listeners are encouraged to take on an audience challenge to spend a day asking only questions and to reflect on the impact it has on their interactions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

#100 Debbie Millman: Earning Trust & Storytelling Through Questions

#47 Maury Rogow: How Questions Create Instant Trust in Any Conversation!