Podcast Summary: This Is Woman's Work with Nicole Kalil

Episode: How To Ask Better Questions with Elizabeth Weingarten | 347
Date: September 24, 2025
Host: Nicole Kalil
Guest: Elizabeth Weingarten (journalist, behavioral scientist, author of How to Fall in Love with Questions)

Overview

In this episode, Nicole Kalil dives deep into the value, power, and practice of asking better questions with guest Elizabeth Weingarten. The conversation challenges our cultural obsession with certitude, highlights the dangers of certainty “charlatans,” and provides practical strategies for cultivating a meaningful questions practice in our personal and professional lives. The episode is rich with personal stories, actionable tips, and memorable quotes, all wrapped in a tone that’s both insightful and candid.

Key Discussion Points & Insights

Redefining “Woman’s Work” Through Curiosity

• Nicole opens by framing “woman’s work” as anything authentic and self-defined, not dictated by social “supposed-tos” (01:10).
• Curiosity is positioned as a rebellious, transformative act, especially in cultures that prize answers over inquiry.

Elizabeth’s Journey to Falling in Love with Questions

• Elizabeth describes her personal and professional relationship with questions, sparked by poor conversational experiences while dating in Washington, D.C. (04:16).

  “Questions are kind of this superpower, right? But a superpower that we don’t value as a society.”
  — Elizabeth Weingarten (05:50)

• She shares a story of navigating profound uncertainty after leaving her job and getting married during the pandemic.
• A pivotal moment: Reading Rainer Maria Rilke’s Letters to a Young Poet, which encourages “loving the questions themselves.”

Why We Struggle to Ask Questions

• Nicole and Elizabeth discuss how asking questions is culturally undervalued and often seen as vulnerability, especially for women in professional settings (09:24).

• Research shows women tend to ask fewer questions than men in high-stakes environments, in part due to fear of being perceived as less competent or knowledgeable.

  “Asking questions can be a form of vulnerability because you're acknowledging that you don't know something. And...in a culture where we are valued for what we know, admitting ‘I don't know’ can feel scary.”
  — Elizabeth Weingarten (10:10)

Uncertainty as Fertile Ground for Growth

• Elizabeth emphasizes that her book is less about escaping uncertainty and more about learning to sit with it.
• Fast, easy answers can make us vulnerable to “charlatans of certainty”—those who sell easy solutions to complex problems (11:51).
• Developing comfort with uncertainty helps prevent hasty decision-making and allows for more authentic self-discovery.

The "Questions Practice": Four Elements

Elizabeth outlines a questions practice designed to help people get unstuck and move forward in ambiguity.
The Four Elements:

1. Curiosity

   • Get curious about the questions guiding your life, even if they feel anxiety-inducing (15:16).

2. Conversation

   • Learn to have productive conversations with yourself, especially to avoid anxiety spirals.

3. Community

   • Surround yourself with people who support you as you wrestle with tough questions, not just those who offer answers.

     “Community actually reduces our cortisol and lights up the parts of our brain that makes us feel like we're getting a reward.”
     — Elizabeth Weingarten (30:28)

4. Commitment

   • Commit to the lifelong process of questioning—and also learn to let go of “dead leaf” questions (those rooted in regret or rumination).
   • Elizabeth introduces the “questions tree” framework:
     • Peach questions: quickly answered.
     • Pawpaw questions: ripen over years.
     • Heartwood questions: shape your life’s stability (e.g., “Who am I?”).
     • Dead leaves: outdated questions to be released.

Choosing and Framing the Right Questions

• Beware binary (yes/no) questions, which can close off possibilities. Expansive questions invite deeper exploration (27:13).

• Be discerning about external sources: Are they thought starters or thought stoppers?

• Always filter advice through your own inner wisdom and agency.

  “Is it a thought starter or a thought stopper?”
  — Elizabeth Weingarten (19:27)

• Example: When facing marital uncertainty, shifting the question from “Should I get a divorce?” (binary) to “What would it look like for us to stay together?” (open-ended) led to more valuable insight.

Outsourcing Answers & The Importance of Agency

• It’s easy and tempting to seek fast fixes through experts, books, or influencers—but this risks giving away your agency.

  “So many of us give up on our agency...we’re so eager to get out of discomfort that we seize on an answer rather than really doing the work to figure out, is this the right question?”
  — Elizabeth Weingarten (21:00)

• Instead, treat others’ answers as “breadcrumbs” or clues, not the final destination.

Tactical Tips for Asking Better Questions

• For yourself:

  • Make sure your questions come from your own needs, not external expectations.
  • Ask questions that lead you back to your own values and desires (32:01).

• Back Pocket Questions (for yourself or others):

  1. “What would I do if I wasn’t afraid?”
     — Elizabeth Weingarten (34:45)

  2. “How can I define my worth and value outside of my achievements or accomplishments?”

  3. Nicole’s go-to: “What would I want for my daughter in this situation?” (37:05)

     “If I put it in that lens, then it sort of forces me...if I want it for her, I should want it for myself.”
     — Nicole Kalil (37:20)

  4. “Can you tell me more about that?” for deeper listening and discovery.

• The best questions feel expansive—they “open up the windows and doors in a room,” as Zen practitioner Joan Sutherland says.

Memorable Quotes & Moments

• “Curiosity isn’t just cute or quirky, it’s powerful, it’s connective, and it’s leadership of self and others…And asking good questions isn’t a soft skill, it’s a smart one and, frankly, much harder than just having somebody give you the answer.”
  — Nicole Kalil (39:09)
• “Sometimes the most honest, brave and world-changing thing that you can say isn’t ‘I know,’ it’s ‘tell me more.’ And that is woman’s work.”
  — Nicole Kalil (39:43)

Timestamps for Important Segments

• 01:10 – Nicole introduces the episode and topic of curiosity.
• 04:16 – Elizabeth shares her journey into the world of questions.
• 09:24 – Discussion about cultural and gendered barriers to asking questions.
• 11:51 – The problem with chasing certainty – dangers of “charlatans of certainty.”
• 15:16 – How to identify the big questions currently driving your life.
• 19:27 – Treating external answers as thought starters, not stoppers; importance of right source.
• 27:13 – The questions practice: curiosity, conversation, community, commitment.
• 30:28 – Why community is essential for holding difficult questions.
• 32:01 – Committing to the lifelong journey of questioning and letting go of “dead leaf” questions.
• 34:45 – Back pocket questions for self and others.
• 39:09 – Nicole’s summary on the power of curiosity and good questions.

Takeaways

• Asking—and sitting with—good questions is a skill that leads to greater self-understanding, agency, and authentic progress.
• The process of questioning is ongoing and active, not passive.
• Beware binary, externally driven, or “inherited” questions. Choose expansive, self-guided inquiries.
• Build supportive communities who can help you hold space for uncertainty.
• Embrace uncertainty as a space for possibility, not just something to escape.

Further Information

• Elizabeth Weingarten’s Book: How to Fall in Love with Questions
• Elizabeth’s Substack: Time Travel for Beginners

This episode offers a powerful call to challenge certainty, ask better questions, and take ownership of the inquiries that shape your life, all while honoring your own intuition and building supportive relationships along the way.