Law Ten

Always Make Your Questions Bigger Than Your Answers

Questions are essential for lifetime growth. As children, when we’re all growing at a rapid rate, we ask lots of questions. As we get older, we gradually begin to think we have a lot of the answers. For some people, their entire sense of security and self-image depends on having all the answers—on never being wrong. As a result, these people try to understand everything in terms of what they know. But all growth lies in the territory of the unknown. What we already know is in the past. What we have yet to discover is the future. Always make your questions bigger than your answers, and you’ll keep drawing yourself into a bigger future with new possibilities.

There is nothing more powerful than a question. The reason is that the mind can’t ignore a question. It may choose not to answer, but the question will still be there, provoking new thoughts. Answers, on the other hand, are closed-ended. You can know them and file them away and never think of them again. They don’t require any further thought. That’s probably why people find them comforting.

Engaging with a Great Question

Questions open the doors to inquiry, which is how we imagine and discover new possibilities. Growth comes not from having the definitive answer but from the activity of being engaged in the conversation around a great question.

So what is a great question, and how do you make your questions bigger than your answers? Great questions are open-ended—that is, they don’t have easy answers. A really great question can keep you thinking and growing for a lifetime.

Dan shares this story:

When I was nine years old, I was walking in the cornfields of my family’s farm in Ohio. It was a beautiful, clear late afternoon in winter. The sun was still out, but you could see the moon coming up, and there was snow on the ground. As I walked, a plane flew overhead. Looking up and watching it pass by in this big open sky, I suddenly had an expanded sense that anything was possible, and I thought to myself, “I wonder, how far can I go?”

It was one of those moments you never forget. That plane and the whole scene symbolized something much bigger to me. Getting off the farm. Getting out of that town. Traveling to other places. An overview of things much broader than what I had experienced in my life until then. It was global in scope. That question became the defining question for my life. From that point on, I kept asking myself, how far can I go? And I’m still asking, and still going. Even though I couldn’t have possibly envisioned then where I am now, there’s really no end in sight, as long as I keep asking that question.

Questions Connect Us with the World

However, a question doesn’t have to be of this scale to keep you growing. Any question asked in a genuine spirit of inquiry will help you to grow. If you really want to know the answer, you’ll grow just by asking the question—even if you don’t ever get the answer. This is because questions open dialogue. They connect us with the world in a new way.

When you ask a genuine question and do get an answer, you have new knowledge that usually increases your understanding. That new knowledge can lead to other questions, and it can also lead to new ways of acting, new perspectives, and new confidence.

Jon Singer, an entrepreneur from New Jersey, has tirelessly fundraised and advocated for the rights of children with autism, driven by his passion to provide a quality education for his daughter Rebecca, who has autistic tendencies. He has this great story about an unexpected by-product of his and Rebecca’s experiences together when she was younger: Rebecca liked to get up very early, earlier than her mother and her brother, so when she lived at home, Jon, who is also an early riser, would get up and take her to Starbucks so that they wouldn’t wake the rest of the family. Like a lot of kids with autism, Rebecca has a tough time being in a new place. But with practice, she was able to be there for 10, 15, and then 20 minutes.

There was a nice young manager, Tommy Sherwood, who was there early and would open the door for them. He would say “Hi” to Rebecca, but she wouldn’t make eye contact. Eventually, Tommy went up to Jon one day and wanted to know if he could ask him a few questions about Rebecca, because he had seen that she was struggling in the beginning. He said, “How can I make my associates, my partners in the store, be more sensitive to anybody with special needs?” More questions followed, about autism and about raising children, because he wanted to have kids of his own.

Jon sometimes came in not just with Rebecca but with his six-year-old son as well. Tommy and the Singers got to know each other, and Tommy even supplied coffee for one of the visiting days at Rebecca’s school. Then one day he called, very excited: “Jon, you won’t believe it. I hired this young adult with autism to work in the store. And he’s one of my best workers!”

Tommy went on to tell Jon that a year earlier, an agency had come to him looking to place someone, but after discussing it, they had agreed that the working environment might not be suitable. But after meeting Rebecca, learning more about autism, and seeing what she had accomplished with all the time and effort, he had the confidence to hire Chris when the opportunity arose. He thanked Jon for that.

Later, Jon saw an article about Chris, the young man Tommy had hired, in the newspaper. In it, Chris was quoted as saying that the job at Starbucks had been his first real break. They subsequently promoted him, creating a new title—café manager—and put him in charge of rearranging and organizing the store. He made a great contribution. Jon called Tommy to applaud him, saying, “Look what you did for this guy! He had such a tough life, and because you took the time to want to learn about Rebecca, and learn about these things, you’re changing his life.” He cannot say enough about Tommy and what a great person he is. And all of this happened because Tommy took the initiative to ask some genuine questions.

So what is not a genuine question? Sometimes people ask rhetorical questions, or ask questions not because they want to know the answer but because they’re trying to corral someone into agreeing with their point of view. Questions that are asked with a genuine desire to know the answer, without a preconceived idea of what that answer will be, are good, growth-promoting questions.

Embracing What You Don’t Know

To keep asking good questions, you have to give up any fears you might have about not already having the answers or appearing ignorant. However, there’s another way to look at this. If you value great questions above great answers, then whether or not you know the answer is immaterial. In fact, the best questions may be those that have no answers at all. Making your questions bigger than your answers means always being open to the possibility that your understanding has some flaws in it and always being willing to entertain the idea that there’s a better way to do something than the way you already know. Learning and improvement happen when you’re open to these possibilities.

At St. John’s College in Maryland, where Dan studied the great books, the teaching method is based on asking great questions. Everyone reads the same book. Then 18 people get together with two tutors in a room, and one of the tutors reads a passage and asks a question about it to start the discussion. The most skilled people at St. John’s are the ones who can answer a question with a question. Those people keep deepening the conversation and expanding the question so that it becomes even more comprehensive. After two and a half hours of questions, you’ve heard all kinds of points of view that you never would have thought of on your own. It makes you humble. You realize that no matter how bright you are, you’re never going to have the definitive perspective on anything. Life is created out of everyone’s perspectives through a constant conversation.

Approaching life by always asking bigger questions allows you to create for yourself a constant sense that there’s always more to discover and greater depth to the things you thought you knew. It keeps you open to all kinds of possibilities for greater learning and increased contribution. It forms the basis for all cooperation, shows the way to better performance, and allows us to have a deeper sense of gratitude, compassion, and appreciation for others. Being a great questioner can make life more fun and can also increase your confidence by making you see that the unknown, while sometimes a source of fear, is also a source of excitement, adventure, and opportunity for growth. Big questions help us to define our purpose and give direction to our lives.

In almost every story in this book you will find a key question, or series of questions, behind the person’s growth in that moment. This is because always making your questions bigger than your answers is an essential ingredient for every kind of growth. The question is the one form of thought that always actively leads us out of the past and into a bigger future.

Where Do I Start?

  Engage your curiosity. If you’re having trouble asking genuine questions, go out and find something new that takes you into an area you know nothing about. Read a book or watch a documentary about a subject you’ve never explored before. Go somewhere you’ve never visited. Start a conversation with someone you wouldn’t normally talk to. Start or join a discussion group to talk about articles or books you haven’t read before, preferably on subjects you know little about. Approach these new subjects with a genuine spirit of inquiry—what Zen masters call “beginner’s mind.” This will give you lots to ask questions about.

  Challenge yourself to keep the discussion going. When you find yourself in a conversation with someone and you both have some time, make it a challenge to try to keep the conversation going by asking great questions. You can even do this with someone you’ve never met before, like a cab driver or the person sitting next to you on a plane. Really listening to what the other person is saying will give you clues about what to ask next.

  And a few great questions you can ask yourself to get you started:

If everything I’ve done up to now is just the beginning, what’s next?

What new habit would I like to create for myself over the next 21 days?

If I had 25 years to do something great, what would it be?

What are the ten achievements I’m proudest of over the past year? What could I do as a next step to build on each one of them?

What is no longer acceptable in my life?

What do I want to do more of in life? What do I want to do less of?

How far can I go?