#088 Vicki Tan: Ask Better Questions - An Interactive Approach to Life's Decisions

You're stuck in life because you're navigating uncertainty without understanding the invisible geography of your mind.

Tech design maverick Vicki Tan (Google, Spotify, Headspace) transforms decision-making with a powerful insight that revolutionized her career: most people struggle to make choices that lack self-coherence. They don't align with who they truly want to be.

Discover how cognitive biases influence all aspects of your daily life, from perception of time to how you navigate life's most pressing questions. Through thought-provoking stories—including how her 125-pound dog taught her more about self-discovery than moving to NYC—Vicki maps the quiet ways we approach uncertainty.

She reveals why changing jobs, cities, and relationships sometimes fails to deliver satisfaction, while explaining why well-intentioned advice from friends might not resonate with your unique mental shortcuts.

From her interactive guide "Ask This Book a Question," learn the playful approach to decision-making that empowers you to understand yourself in a new way. This journey of self-discovery helps you view your questions in a different light, making you surprised by how clear your path forward becomes.

ℹ️ About the Guest

Vicki Tan is a San Francisco–based digital product designer and behavioral science expert whose work has shaped user experiences at leading tech companies. Currently a Staff Product Designer at Pinterest, she has previously held key design roles at Spotify, Headspace, Lyft, and Google. Her approach blends psychology and design to create meaningful products that help people find inspiration and build healthy habits. In April 2025, Vicki released her debut book, Ask This Book a Question: An Interactive Journey to Find Wisdom for Life's Big and Little Decisions. This innovative guide reimagines decision-making by encouraging readers to explore their questions through the lens of cognitive biases and storytelling. The book offers interactive visuals and prompts to help readers navigate choices with greater clarity and self-awareness. 

• Instagram - http://instagram.com/vickiheart
• LinkedIn - https://www.linkedin.com/in/vickitan/
• Twitter - http://twitter.com/vickiheart
• Bluesky - https://bsky.app/profile/vickiheart.bsky.social

Get your copy of "Ask This Book a Question" today: https://vickitan.com/book

👨‍💻 People & Other Mentions

• Vicki Tan - Product designer who worked at Google, Spotify, Headspace, and Pinterest; author of "Ask This Book a Question"
• Ask This Book a Question by Vicki Tan - Book about decision-making through questioning, available April 8, 2025
• Daniel Kahneman - Behavioral economist mentioned in relation to cognitive biases
• Amos Tversky - Collaborated with Kahneman on cognitive bias research
• Thinking, Fast and Slow by Daniel Kahneman - Book on behavioral economics and cognitive biases
• Viktor Frankl - Referenced regarding the space between stimulus and response
• James Clear - Author of "Atomic Habits" mentioned regarding tiny habits creating life shifts
• Atomic Habits by James Clear - Book about building good habits and bre

Chapters

• 0:00 Introduction: The Power of Questions Over Answers
• 1:16 Vicki's Journey: From Behavioral Science to Design Innovation
• 5:00 Umami Metrics: Where Psychology Meets Product Design
• 14:47 The Question Revolution: Why Questions Matter More Than Answers
• 18:19 The Friendship Paradox: Why Advice Often Fails
• 22:21 Cognitive Bias: The Invisible Force Shaping Our Choices
• 28:25 Survivorship Bias: The Hidden Danger of Success Templates
• 33:57 The Charlie Effect: External vs. Internal Change
• 42:31 Micro Habits vs. Major Leaps: The Science of Everyday Decisions
• 46:43 Living With Bias: Integration vs. Elimination
• 52:14 AI as Decision Partner: Augmenting Human Thinking
• 58:59 The Ultimate Question: Finding Your Central Why
• 1:01:52 Conclusion & Resources: Your Decision Journey Starts Now