The Lawyer’s Well-Being Brief. . .Why Questions — Not Answers — Unlock Breakthroughs and Well-Being
“Care for your psyche. . .know thyself, for once we know oursleves, we may learn how to care for ourselves.”-Socrates
Welcome (back) to the Lawyer’s Well-Being Brief! Each week, I share insights and practical strategies to help us cultivate well-being and thrive — both personally and professionally. Live well! Lawyer well!
This week we are looking at Questions are the Answer, A Breakthrough Approach to your Most Vexing Problems at Work and in Life, written by Hal Gregersen.
It seems like we live in a culture that celebrates always having the answers. Hal Gregersen challenges us to take a different approach: ask better questions.
Who is Hal Gregersen?
Gregersen is a senior lecturer in leadership and innovation at MIT’s Sloan School of Management, a former executive director of the MIT Leadership Center, a fellow at Innosight, and a cofounder of the Innovator’s DNA consulting group.
He has dedicated his extensive career, including prior teaching posts at INSEAD, London Business School, and Dartmouth’s Tuck School of Business, to create cultures of fearless inquiry and to help leaders transform their organizations into innovative powerhouses. Ranked as one of the world’s 20 most influential management thinkers by Thinkers50, and winner of the 2017 Distinguished Achievement Award for leadership, Gregersen regularly delivers inspirational keynote speeches, interactive and dynamic customized workshops, and transformational advisory experiences.
The Power of Questions
Gregersen emphasizes that the quality of our questions directly impacts the quality of our lives. Instead of asking, “What should I do to be happy?”, try asking, “What brings me joy?” This subtle but powerful shift invites self-awareness and helps identify the activities and relationships that genuinely support well-being.
In organizations, too, this shift is vital. Asking questions like “What are we not seeing?” can break through stale assumptions and open the door to innovation.
The Question Burst: Sparking Insight
One of Gregersen’s signature tools is the “question burst” — a short, structured brainstorm session where no answers are allowed, only questions. The goal is to generate at least 15 questions in 4 minutes around a single challenge. It’s simple, disarming, and surprisingly effective. By loosening the grip of conventional thinking, new insights emerge naturally.
Cultivating Curiosity
At the heart of Gregersen’s message is a mindset of curiosity over certainty. Each day, ask yourself, “What am I curious about today?” This opens the door to discovering new hobbies, perspectives, and people that enrich your life. Curiosity fuels learning, creativity, and connection — essential ingredients for growth.
Embracing Uncertainty
Rather than fearing the unknown, Gregersen encourages us to lean into it by reframing uncertainty as a learning opportunity. When faced with ambiguity, try asking, “What can I learn from this?” This approach builds resilience and helps us adapt with greater confidence — both personally and professionally.
Building Meaningful Connections
Questions are also a bridge to deeper human connection. Instead of small talk, try asking open-ended, reflective questions like, “What’s been the highlight of your week?” These kinds of inquiries spark meaningful conversations and help cultivate a sense of belonging — something we all need for emotional and psychological well-being.
Reflecting on Values
In moments of transition or stress, Gregersen suggests turning inward with questions that clarify what matters most. “What is most important to me right now?” This simple reflection can guide you to make aligned, intentional decisions — and help you act from your core values instead of just reacting to circumstances.
From Reflection to Action
Of course, great questions are just the starting point. Gregersen emphasizes the importance of following questions with action. Ask yourself, “What small step can I take today to improve my well-being?” Even tiny adjustments, made consistently, can lead to profound transformation.
Closing Thoughts
When we stop chasing answers and start asking better questions, we don’t just become more innovative — we become more human. As Gregersen reminds us, questions aren’t just a path to insight; they’re a practice for living well. The journey toward a more meaningful life begins not with a solution, but with a question.
Forward Always!
