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In this episode, Elizabeth Weingarten shares how leaders and individuals can navigate uncertainty by embracing better questions, practicing vulnerability, and fostering authentic community connections. She explores her “questions practice” framework, the importance of open-ended inquiry, the mindful use of technology and AI, and strategies for creating psychologically safe spaces where curiosity thrives. The conversation offers practical, actionable tools for building emotional intelligence, strengthening teams, and leading with intention.
Embracing Uncertainty, Vulnerability, and the Power of Questions in Leadership
If you have ever felt stuck in the face of uncertainty, hesitant to admit “I don’t know,” or unsure how to navigate life’s biggest questions, you’re not alone. Whether you are leading a company, guiding a team, or simply making critical decisions in your own life, uncertainty is an inevitable part of the journey. Many leaders and individuals try to avoid it, clinging to quick answers for comfort. But what if the real key to growth, connection, and resilience is in learning to live with, and even love, the questions themselves?
This perspective is at the heart of what applied behavioral scientist Elizabeth Weingarten, author of How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty, explores in her work. Through a blend of personal storytelling, emotional intelligence principles, and evidence-based insights from positive psychology and coaching, she reveals how vulnerability, curiosity, and intentional self-leadership can help us thrive during ambiguous times.
Weingarten challenges the common advice to simply “embrace uncertainty” by offering something more actionable, the concept of a “questions” practice. This involves intentionally making space for meaningful, open-ended questions that expand possibilities instead of narrowing them. In both leadership and personal growth, these practices not only deepen your self-awareness but also strengthen community, foster psychological safety, and improve your ability to guide others through challenges.
Building a Practice for Asking Better Questions
If you want to improve as a leader, grow personally, and navigate uncertainty with greater confidence, you need an actual practice for asking better questions. Elizabeth calls this a “questions practice,” and it’s one of the most transformative tools for self-leadership and leadership alike.
Unlike random moments of curiosity, a “questions practice” is intentional. It’s a structured way of making space for meaningful, open-ended questions that deepen self-awareness, spark better decisions, and build stronger communities. Think of it like meditation or yoga; it’s a skill that strengthens over time.
There’s four key elements of a strong questions practice, the “Four Cs”: Curiosity, Conversation, Community, and Commitment.
1. Curiosity: Shift From Fear to Openness
Most of us have default questions that limit our thinking. They’re often binary (“Should I do this or not?”) or loaded with urgency, which triggers anxiety instead of insight. In positive psychology, we know that the quality of your questions shapes the quality of your solutions.
Weingarten suggests reframing your question so it opens possibilities rather than shuts them down. For example, instead of “Should I leave my job?” ask, “What steps could I take to make my work more fulfilling?” This moves you from a trap of two unsatisfying choices into a space of creative options.
Next time you feel stuck, pause and check:
- Is my current question too narrow?
- Does it invite exploration or force a quick yes/no answer?
- Is it rooted in my values and goals, or in someone else’s expectations?
2. Conversation: Talk to Yourself and Others Differently
Questions are the starting point for self-reflection, but they’re also an invitation for dialogue. The challenge? Without intentionality, big questions can spiral into anxiety.
In self-leadership, it helps to treat inner dialogue like a constructive coaching conversation. Replace judgment (“I should have figured this out by now”) with curiosity (“What can I learn from feeling uncertain right now?”).
Applied in leadership, this means creating “question-friendly” conversations with your team.
3. Community: Don’t Do It Alone
One of the most surprising leadership insights? The people who navigate uncertainty best rarely do it in isolation. Community is a powerful stabilizer when living with big unanswered questions.
When you talk through your uncertainties with trusted peers, mentors, or coaches, stress levels drop, clarity improves, and you feel more supported. Neuroscience backs this up: strong social bonds reduce cortisol and activate parts of the brain associated with safety and reward.
4. Commitment: Know When to Stay, Know When to Let Go
Finally, a “questions practice” requires commitment, to sit with a question long enough for it to teach you something, as well as recognize when it’s time to let go.
Weingarten uses a “fruit tree” metaphor to categorize questions:
- Peach questions ripen quickly into answers.
- Pawpaw questions take years to bear fruit.
- Heartwood questions (like “What kind of leader do I want to be?”) grow with you for life.
- Dead leaf questions no longer serve you and should be released.
Regularly reviewing your questions through this lens helps avoid rumination and keeps your self-leadership practice focused and energizing rather than draining.
Technology’s Role in Meaningful Questioning and Community Building
The first step in using technology more intentionally is instead of only turning to your phone for certainty, use it as a tool for curiosity. This could mean resisting the urge to look up an answer right away so you can think, reflect, and ask better follow-up questions. It could also mean using AI-based tools as brainstorming partners rather than answer machines. For example, you might share a personal or team question with an AI assistant and ask: “What are some better, more open-ended ways to frame this?”
Using AI to Spark Better Questions
Start treating AI like a “thought starter” rather than a “thought stopper.” The goal is to receive new angles and prompts that you build on through your own reflection, conversation, and community dialogue. For leaders, this can mean feeding a complex team challenge into an AI tool and asking it to suggest new ways of framing it, then bringing those reframed questions into a team workshop to explore them together.
The danger lies in letting AI give you a single definitive answer without questioning it. That stops curiosity in its tracks and removes the human element from problem-solving.
"My heuristic right now for thinking about AI as a tool and helping us navigate questions and uncertainty is, are we using it as a thought starter or a thought stopper? And I get worried when we ask AI questions or use the tool and then we don't question it... or we don't get curious about it and just say, okay, well, it told me to do this and that's what I'm gonna do."
-Elizabeth Weingarten
Balancing On-Screen and Human Time
Of course, not all community-building should happen on screens. One hidden benefit of a good tech strategy is knowing when not to use it. Practicing small doses of uncertainty, like walking into a restaurant without reading reviews, applies here too. Sometimes the most meaningful connections come from in-person conversations where no one is fact-checking in real-time and every participant brings their lived experience to the table.
Leadership Strategies for Creating Safe Spaces for Inquiry
Creating a culture where questions are welcomed, and not shut down, is one of the most powerful things a leader can do. It shapes trust, boosts innovation, and increases team engagement.
Here are bite-sized, actionable strategies for building safe spaces to ask questions:
Start with Self-Leadership
The way you handle uncertainty yourself sets the tone for your team.
- Get comfortable with your own big questions.
- Model curiosity by openly exploring things you don’t have answers for.
Pro tip: Your relationship with uncertainty is a mirror of your relationship with yourself. Lead that first.
Build “Question Time” Into Meetings
Even when schedules are tight, carve out a few minutes for inquiry.
- End meetings with: “What are the big questions on your mind right now?”
- Make it a routine, so asking becomes normal — not a special occasion.
Create Psychological Safety in the Moment
When someone asks a question:
- Acknowledge it immediately (“That’s a great question to explore”).
- Avoid rushing to answers — encourage reflection.
- Show openness even when you can’t provide certainty.
Use Assigned Roles to Lower Risk
Give team members “permission” to challenge assumptions by assigning roles:
- Devil’s Advocate
- Curiosity Captain (dedicated question-asker)
This removes fear of judgment and normalizes inquiry.
Respond With Curiosity, Not Closure
Instead of shutting down a complex question, try:
- “Tell me more about what’s behind that.”
- “What’s another way we might frame this?”
- “Who else’s perspective could help us here?”
Ready to take questions, vulnerability, and community to the next level?
- To get practical tools and actionable tips that will jumpstart your journey, download the Leadership in Uncertain Times Kick Starter Booklet here.
- Join the newsletter to be notified when a new episode is ready for you to listen and get every Kick Starter Booklet for all future episodes.
- And if you’re looking to elevate your entire C-Suite leadership team, learn how Craig Dowden can help your leaders perform at their highest-level visit https://www.craigdowden.com/executive-mastermind
- For a deeper dive, listen to the full-length episode of the Do Good to Lead Well podcast featuring Wes Adams & Tamara Myles:
Did you like this article on Questions, vulnerability, and community? Does it help you become a better leader? Then check out these articles to help hone those skills even further:
- Positive Leadership for Innovation and Resilience with Jason Tham: Leading with Authenticity, Agility, and Purpose in a Fast-Changing World
- AI Therapy: Lessons on Vulnerability and Listening: Why Leaders Should Create Judgment-Free Zones Like AI Therapy: Lessons on Vulnerability and Listening
- Lead your team or company in the future with ethical AI practices: AI Driven Leadership Strategies for the Future with Geoff Woods
- Create an environment for Meaningful Work: Exploring the Science and Practice of Meaningful Work with Wes Adams and Tamara Myles
- Reveal and fill blindspots in your daily professional life: Seeing with New Eyes: Martin Dubin on Leadership, Self-Awareness, and Blindspotting
Craig Dowden
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