The Art of Asking The Right Questions In Life

After retiring from my position as co-CEO of Chipotle, I didn’t know what my next big move would be. I had become a pilot, and I was working on some business deals, but metaphorically, I was in a holding pattern. During this period of time, I met Wendy, a woman in her 70s with severe Parkinson’s disease. (I’ll tell you more about her later.) “I know what you need to do!” she told me. “You need to ask questions!” She said it as though she had solved the greatest mystery in my life. In a way, she had. I’ve been asking questions my entire life, and I’ve always believed in their power.

But Wendy made me realize that I had developed something special in my ability to ask questions. Asking good questions is one of the best skills you can develop as a leader, and as a person. It’s how you develop relationships and gain new knowledge. Though asking questions may sound simple, there is an art to it. Ask questions in the wrong way, and you can easily offend or annoy. In looking back at my experiences, I’ve identified a few key lessons that have helped me to ask questions in the right way—a way that leads to greater connection and understanding.

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Lesson #1: You must ask from a place of loving curiosity

On my fifteenth birthday, I landed a job at Dairy Queen. This was where I received my first lesson in the art of asking questions: you must ask from a place of loving curiosity. We had several customers that came from a nearby mental health treatment facility. I was fascinated by their stories and spent breaks talking with them. They’d often had difficult lives and found themselves alone and homeless. I’d ask questions, trying to find out where and whether their choices and actions had led to their present situation, and what could be done to improve things. I’d ask why they smoked cigarettes when they had so little money. I’d ask why they chose to eat ice cream and drink coffee when they were not very healthy.

While these questions may sound judgmental or offensive, the opposite was true. I actually cared about them and wanted to better understand them. I truly was curious and wanted to learn from them. They knew I cared, as they could hear it in my voice and see it in my eyes. So, they would answer me with total authenticity. Rather than being offended, they were touched by my concern, and they felt honored to be seen and understood as having important information to share with me. It was remarkable to see how the simple fact that I was interested in them—that I cared about them—lifted their spirits. I learned from these new friends the power of listening with a curious heart.

Lesson #2: Don’t shy away from the difficult questions

Before becoming co-CEO of Chipotle, I spent many years as a trial lawyer. One of the major tools I used to win my cases was the deposition—a.k.a., asking questions of a witness who is under oath. The goal of the deposition was pretty clear. It was to obtain admissions from the plaintiff that would enable me to prove in court that their claim was baseless or fraudulent and that my clients shouldn’t have to pay. To accomplish this, I became fearless about asking difficult questions. Since the job required it, I was given latitude to ask, without offense, questions that society would otherwise deem quite inappropriate. For instance, I got comfortable asking people if they were lying. I asked them if the pain from the accident had affected their sex life. I asked the tiniest details about their medical treatments and then asked why their recollection wasn’t consistent with their medical records. As I asked hard question after hard question, they’d become exhausted, sick and tired of lying. Then, I would ask them about that! I would say, “I can see you are tired of this, aren’t you?” They’d say, “Yes!” Then I would say, “It’s a lot of work to keep this whole story straight, isn’t it?”

But I would ask this question with genuine compassion for them. I didn’t hate these people or even look at them as criminals. I looked at them as people who had allowed bad judgment to get in the way of living a good life. I saw my job in the deposition not only to get the truth from them, but to help them see that bad judgment was not something that had to continue to be a part of their life in the future. Questions have the power to radically change people’s actions and lives, but the only way to achieve that is to ask the hard questions. You shouldn’t shy away from the difficult questions, but you should approach them with compassion.

Lesson #3: Questions are meant to be empowering

Now it’s time to return to Wendy. I met Wendy while visiting Germany with my mother. Wendy and her husband, Jorge, were friends of my mother’s. I suspect few others would risk it, but I asked Wendy about her Parkinson’s disease. At first, I worried that I may have offended her, but as I asked more questions, a wonderful lightness suddenly fell over the room, and the conversation that followed blossomed. At some point, I asked Wendy and Jorge how often they were able to get outside for a walk together, since I had noticed on my way up to their second-story apartment that there was no obvious handicapped access, and Wendy was confined to a wheelchair. Jorge explained that it was difficult to get Wendy downstairs. They actually had to use three different wheelchairs to navigate the narrow passageways and stairs. “Why don’t you guys move to a building with handicapped access?” “Well, we have lived here for ten years now,” he continued, “and the real estate market here in Berlin is tough. There are not many places for sale and very few that would suit our needs.” “You’d only need to find one,” I gently challenged.

I remember feeling that I’d said enough to plant a seed. I really wanted them to be able to get Wendy in and out easily, as I saw that as the key to them both feeling a life of freedom. Two weeks later, my mom called me. No, Jorge and Wendy hadn’t moved as I’d hoped, but they’d told my mother that our visit to their apartment had been the most powerful visit that they had in twenty years and that they were asking fresh new questions about their relationship and their lives. This is the power of questions. With questions, you can change someone’s life. It may not be in the exact way you want, but that’s part of the beauty. Done right, asking questions isn’t about sneakily telling someone what to do. It’s about empowering them to think more deeply and make their own decisions.

Finding answers

When you ask questions, you find answers. They’re not always the answers you expect, but they’re often the answers you need. In asking Wendy and Jorge questions, I got the answer to what direction my life should take. When Wendy told me I needed to ask questions, she meant her words in the broadest, most profound way. She meant that I needed to get out in the world and ask questions, to put my curiosity and intellect to work solving problems in this world. Taking her advice, I’m now filming a docuseries in which I ask questions to elicit the wisdom from people from all walks of life. While asking questions may not be the focus of your life in this way, I guarantee that mastering the art of asking questions will serve you well. By approaching people with genuine curiosity and love, leaning into the difficult questions, and seeking to empower instead of dictate, you can build deeper relationships. And you just may be surprised by the answers you find. For more advice on the art of asking questions, you can find my book, Love Is Free, Guac Is Extra, on Amazon.