Elizabeth Weingarten is an author, journalist, and applied behavioral scientist specializing in the intersection of human behavior, communication, and decision-making under uncertainty. A graduate of Northwestern University’s Medill School of Journalism, she has served on the editorial staffs of The Atlantic and Slate, held the role of managing editor at Behavioral Scientist, and led research initiatives across organizations like New America, ideas42, Torch, and Udemy. In her book, How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty, Weingarten draws on behavioral science and personal narrative to explore how cultivating curiosity and reframing open-ended questions can help people navigate life's biggest unknowns.
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The Art of Asking: Why We Need Curiosity in an Answer-Obsessed World
What They Talked About
Elizabeth breaks down what inspired her to write her book, How to Fall in Love with Questions. The idea first sparked from a frustrating pattern in her dating life: going on date after date with people who never asked a single question.
That curiosity deepened during the pandemic, when Elizabeth faced huge, overwhelming life decisions about her failing marriage and a shifting career path. Instead of rushing to quick fixes, she found comfort in a quote by poet Rainer Maria Rilke about "loving the questions themselves." The speakers reflect on how modern society rewards people who appear to have all the answers, making it hard for people to sit with uncertainty or simply admit, "I don't know."
Key Takeaways
The Power of Curiosity: In an era defined by fast changes and instant answers, asking thoughtful questions is one of our most effective tools for navigating life and work.
Overcoming the Answer Trap: Our culture often praises quick confidence over deep inquiry, creating a environment where people feel afraid to express doubt or ask questions.
Embracing Uncertainty: Learning to live with big, uncomfortable questions can guide us toward genuine personal growth and deeper connections.
"The worst thing that you could do is just not ask any questions, right?"
— Elizabeth Weingarten
Why High-Stakes Curiosity is So Hard: The Brain's Fight for Certainty
While many leaders praise curiosity in theory, high-pressure environments often force them to demand immediate answers instead of encouraging questions.
Weingarten explains that our brains evolved to save energy. Predictability and certainty take less metabolic power (calories) to process, whereas living with uncertainty requires more cognitive effort. Because of this, our minds tend to treat uncertainty as something uncomfortable to avoid.
Psychologists measure our urge to resolve ambiguity through a scale called the "need for closure." This urge isn't fixed—it changes based on the situation. Someone might handle high uncertainty at work easily, yet feel uncomfortable with it in their personal life.
Personality traits like "openness to experience" help explain why some people tolerate uncertainty better than others. While cultural backgrounds and life circumstances also play a role, Weingarten notes that people react to uncertain environments in diverse ways—some build resilience, while others seek tighter control.
Key Takeaways
High Stakes Kill Curiosity: When anxiety or stakes are high, we are most vulnerable to grabbing fast, easy answers that might not actually be the best decisions.
Uncertainty Costs Energy: The brain defaults to certainty because autopilot uses less energy than navigating complex, unanswered questions.
Context Matters: Your comfort with unanswered questions isn't a fixed trait—it shifts depending on whether you're at work, at home, or facing a specific trigger.
"Uncertainty takes more calories... as a result, we're coding uncertainty in our environments as something that is aversive, something that we want to avoid."
— Elizabeth Weingarten
Building the "Uncertainty Muscle" in the AI Era
Alex shares how background experiences—like being a startup founder, navigating immigration, or traveling without a set plan—help build a higher tolerance for the unknown. However, major life responsibilities like parenting and managing a team often bring people back to needing structure and predictability.
Elizabeth points out that modern convenience, especially AI tools and instantly accessible information, removes micro-moments of friction. When we can look up restaurant menus in advance or get immediate AI answers to any question, we lose daily opportunities to practice being okay with not knowing.
The seamless availability of information feeds our tendency to "maximize"—turning small decisions, like picking a place for lunch, into research projects instead of quick choices.
To prepare for high-stakes decisions, Elizabeth recommends intentionally creating small moments of uncertainty in daily life—such as walking into an unfamiliar restaurant without reading reviews first.
Key Takeaways
Uncertainty Tolerance Can Be Trained: Facing unpredictable situations acts like resistance training for your mind. Over time, it raises your comfort level when navigating life's larger unknowns.
Convenience Has a Cognitive Cost: While AI and instant search engines make life easier, relying on them to remove every trace of ambiguity can weaken our ability to handle real-world unpredictability.
Start Small: Building resilience doesn't require drastic life choices—small everyday shifts, like making decisions without researching every detail, help keep your uncertainty muscle active.
"Having devices and agents around us at all times that are able to alleviate any uncertainty... takes away these everyday moments and opportunities to strengthen our uncertainty muscles."
— Elizabeth Weingarten
Navigating High-Stakes Uncertainty: The Personal Is the Professional
Modern tools like ride-sharing apps give us a hyper-detailed sense of predictability, which slowly conditions us to expect control everywhere. When things become unpredictable, we reflexively push for immediate solutions to calm our anxiety.
Elizabeth emphasizes that handling professional uncertainty begins with self-awareness and personal emotional regulation. A leader’s comfort with unanswered questions depends on their ability to manage feelings of fear, anxiety, or low self-worth without rushing to forced decisions.
Instead of compulsively reacting when stakes are high, effective leaders pause, regulate their emotional state, and evaluate whether they are framing the right question or setting up the right conditions for their team.
Alex shares how his personal background influenced his reactions to conflict at home, showing how unexamined expectations make us react with rigid demands rather than open-minded curiosity.
Key Takeaways
Self-Regulation Is Key to Curiosity: Your response to uncertainty directly reflects your relationship with yourself. Managing your internal emotional state allows you to stay open-minded when external pressure rises.
Pause Before Deciding: In tense, high-stakes moments, step back to calm your initial reaction so you can ask the right questions rather than pushing a quick, forced answer.
The Personal Shapes the Professional: You cannot fully change how you handle workplace ambiguity without first examining your personal triggers and emotional patterns.
"Your relationship to uncertainty and these kind of big questions is a direct reflection of your relationship to yourself... because your relationship to uncertainty at the end of the day is all about how do I regulate my own emotions."
— Elizabeth Weingarten
The "Master Move" for Staying Curious Under Pressure
When faced with chaotic or tense situations—whether it's screaming children or a high-stakes board meeting—our default reaction is often to regain control. Elizabeth notes that this desire deflates curiosity because we stop listening and start projecting our own immediate fixes or demands.
Drawing from Judson Brewer's work on anxiety, Elizabeth shares a simple behavioral reset: taking a brief pause and making a mindful sound, like "Hmm." This small break creates mental space between the initial trigger and your reaction, opening the door for curiosity.
Alex and Elizabeth discuss how anxiety is often driven by "time travel"—either dwelling on past failures or catastrophizing potential future outcomes. Curiosity grounds you firmly in the present moment.
Weingarten compares this mindful state to action heroes escaping danger: they don't panic or get lost in the past or future; they observe their surroundings with keen awareness to make the best possible choice in real time.
In tense moments—such as a board member grilling you with tough questions—the goal of curiosity is to look beyond the immediate pressure and ask, "What's really behind this question? What are they actually concerned about?"
Key Takeaways
Pause Before Reacting: When you feel overwhelmed, take a brief breath or pause to disrupt your automatic stress response before offering a forced answer or reaction.
Stay Grounded in the Present: Anxiety pulls your focus forward to worst-case scenarios or backward to past mistakes. Curiosity grounds you by asking what is actually happening right now.
Uncover the Real Question: In high-stakes conversations, focus on understanding the underlying need or fear driving the other person's behavior rather than responding defensively.
"How do you just create a little crack in that... and so you can just like, 'Hmm,' and then asking a question... it's something that can keep you kind of anchored in the present moment."
— Elizabeth Weingarten
Uncovering the Subtext: Asking Expansive Questions in a Broadcast World
Alex notes how high achievers often rush to answer a question immediately just to get a mental checkmark. However, simply checking off an answer often fails with clients or team members because it misses their underlying worries.
Elizabeth emphasizes that true communication goes beyond hard technical facts. The real skill lies in noticing subtext—picking up on hidden anxieties, emotional cues, or unstated fears, and asking thoughtful questions to bring them into the open.
Modern culture encourages constant sharing and self-promotion ("Look at me"). Alex reflects on how easy it is to get caught up in pitching a product or narrative instead of stepping back to ask what the other person actually cares about.
When preparing to ask a key question, Elizabeth shares her first core filter: avoiding binary (yes/no) traps. Binary questions limit options to just two outcomes. Instead, reframing them as open-ended questions unlocks far more possibilities and insights.
Key Takeaways
Look for the Question Behind the Question: Answering the literal words someone says isn't always enough—pay attention to the underlying emotions and concerns driving their inquiry.
Ditch Yes/No Questions: Binary questions narrow your thinking. Reframe your questions to be open and expansive so you don't accidentally limit potential solutions.
Shift from Pitching to Asking: Great leadership and sales aren't about broadcasting how much you know; they come from asking sequenced, well-timed questions that build real connection.
"Being able to get the subtext... picking up on cues from somebody that they're concerned... that's this real ninja skill, the people that are able to see and understand like, 'Oh, there's something else going on here emotionally for this person.'"
— Elizabeth Weingarten
Question-Asking as a Strategic Tool: Reframing and Internal Values
Elizabeth shares a deeply personal example of reframing her question about divorce. Changing a rigid binary choice ("Should I get a divorce?") into a generative, open question ("How would I and my partner need to change to stay together?") opened up an entirely new path forward.
Alex highlights the subtle distinction between open-ended and expansive questions. While an open-ended question simply invites more information, an expansive question reframe the premise entirely—stretching possibilities and unlocking strategic insight.
The second filter in Weingarten’s framework asks whether a question acts as an internal compass. It challenges us to reflect: Is this question aligned with my core values (or our company’s mission), or am I answering a question inherited from outside pressure?
Alex notes how easily teams and individuals absorb trends or external expectations without reflecting on whether they matter. Using questions as a values-check prevents people from fighting battles that don't align with their long-term goals.
Key Takeaways
Move Beyond "Yes/No" Dilemmas: When stuck between two rigid options, reframe the inquiry around the conditions needed for success or growth rather than a simple binary choice.
Check Your Motivation: Ensure the questions you are trying to answer serve your personal values or company strategy, rather than social pressure or industry hype.
Sequence Your Inquiry: Start with broad, open questions to gather context ("Tell me what you're experiencing"), then transition into expansive, reframing questions to generate actionable paths forward.
"Is this question leading back to my values? Is it guiding you back to your north star? And if not, pick a different question."
— Elizabeth Weingarten
Pruning Your Mind: Elizabeth Weingarten’s Tree Framework for Questions
In this final segment, host Alex Shevelenko and author Elizabeth Weingarten unpack her Tree Framework—a tool for categorizing the questions we ask so we can set realistic expectations, drop unhelpful thoughts, and navigate life's uncertainty.
The Tree Framework
/\
/ \
/ \ [ PEACH QUESTIONS ]
/ \ Quick answers (Weeks / Months)
/ \
/__________\ [ PAWPAW QUESTIONS ]
|| Slow answers (5–7 Years)
||
|| [ HEARTWOOD QUESTIONS ]
|| Lifelong / Core Values (Evolves Over Time)
//\\
// \\
~~~~~~~~~~~~~~~~~~~~~~~~~~ [ DEAD LEAF QUESTIONS ]
🍂 🍂 🍂 🍂 Unhelpful Rumination (Release Them!)
Key Categories of Questions
| Question Type | Time Horizon | Meaning & Examples |
|---|---|---|
| 🍑 Peach Questions | Short-Term (Weeks to months) | Quick to resolve. Questions that ripen fast and yield concrete answers relatively soon.
• Examples: "Will I get this job offer?", "Will we close this funding round?" |
| 🥭 Pawpaw Questions | Medium-Term (5–7 years) | Slow-growing. Complex questions that require patience, persistence, and continuous effort.
• Examples: "Will this career pivot bring me purpose?", "Will my startup succeed?" |
| 🪵 Heartwood Questions | Lifelong (Evolving) | The core trunk. Universal questions that are never permanently "solved"—they guide stability and evolve as you grow.
• Examples: "Who am I?", "How do I balance high performance with well-being?" |
| 🍂 Dead Leaf Questions | Past-Focused (Release) | Unhelpful rumination. Past-oriented, "what if" queries that keep you stuck, drain energy, and offer no path forward.
• Examples: "Why didn't I raise money earlier?", "What if I hadn't made that mistake?" |
Key Takeaways
Drop the "Dead Leaves": A huge portion of mental exhaustion comes from replaying past failures. Reframe dead leaf questions ("Why did that fail?") into forward-looking lessons ("What can I carry forward into my next attempt?").
Align Expectations with Reality: Anxiety often triggers when we treat a Pawpaw or Heartwood question like a Peach question—demanding instant clarity on a 5-year venture or a lifelong identity choice.
Calibrate Your Urgency: Recognizing which category a question falls into helps you let go of the artificial pressure to find fast answers to life's biggest unknowns.
"Recognizing that... we might feel a lot of pressure and urgency to get those answered, but recognizing that they might never be answerable, or they're going to take time, takes the pressure off."
— Elizabeth Weingarten
Cultivating Patience: Giving Big Questions Time to Breathe
Elizabeth explains that recognizing a question as long-term (a Pawpaw or Heartwood question) gives us permission to slow down. Instead of anxiously grasping at the first answer that comes along, patience creates space for richer, more thoughtful choices to surface.
Rushing to resolve ambiguity usually leads to impulse decisions. Sitting with a question longer opens up a far wider set of possibilities.
As her final reflection, Elizabeth challenges listeners to reframe how they interact with their unanswered questions: What would it look like to treat a question in your life like a person? Rather than seeing a big question as an obstacle to conquer, we can learn to build a relationship with it over time.
Her book, How to Fall in Love with Questions, is available everywhere books are sold. You can also find her work at elizabethweingarten.com and on her Substack newsletter, Time Travel for Beginners.
Key Takeaways
Resist the Urge to Cling: When anxiety pushes you toward an immediate answer, pause and give yourself time—the best solutions rarely appear under self-imposed pressure.
Build a Relationship with Uncertainty: Treat your life's big questions as ongoing partners in your growth rather than problems that need an instant fix.
Patience Is Practical: Allowing time between asking a question and reaching a conclusion leads to stronger decisions, better self-awareness, and less overall stress.
"What would it look like for you to start to treat a question in your life like you would treat a person? That's the big reframe around curiosity and questions."
— Elizabeth Weingarten
Check the episode's Transcript (AI-generated) HERE.
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