Wait, What?: A Thought-Provoking Guide To Asking The Right Questions

by James E. Ryan

The first suggestion is to spend more time thinking about the right questions to ask.

For many of us, however, fretting about the right answers persists throughout our lives. It is a common feature of our professional lives, where we don’t want to feel incompetent around our colleagues. It also pervades our personal lives, where we don’t want to seem clueless to those who might be depending on us. New parents, for example, want to have answers for and about their kids.

It is only by asking questions of others, for example, that you can articulate a vision that is compelling to those with whom you work.

The simple truth is that an answer can only be as good as the question asked. If you ask the wrong question, you are going to get the wrong answer.

Good teachers, for example, appreciate that well-posed questions make knowledge come to life and create the spark that lights the flame of curiosity.

Effective leaders, even great ones, accept that they don’t have all the answers. But they know how to ask the right questions—questions that force others and themselves to move past old and tired answers, questions that open up possibilities that, before the question, went unseen.

Einstein, who was a big believer in the importance of asking questions, famously said that if he had an hour to solve a problem, and his life depended on it, he would spend the first fifty-five minutes determining the proper question to ask.

Good friends ask great questions, as do good parents. They pose questions that, just in the asking, show how much they know and care about you. They ask questions that make you pause, that make you think, that provoke honesty, and that invite a deeper connection. They ask questions that don’t so much demand an answer as prove irresistible. Posing irresistible questions, I believe, is an art worth cultivating.

It’s important to listen for good questions. It is a cliché to say that there is no such thing as a bad question.

Whether these questions remain bad, however, often depends on the listener. And the suggestion I want to make is that you, as listeners, can turn most bad questions into good ones, provided that you listen carefully and generously.

You will get, if you haven’t already, some hostile questions in your life—some from strangers, others from colleagues or supervisors or relatives. The trick is to distinguish the hostile ones from the innocent but clumsy ones. Clumsy questions might really be the questioner’s way of seeking to get to know you better, or they could just be the product of anxiety and ignorance, neither of which is morally blameworthy. The only truly bad questions are not really questions at all. They are statements disguised as questions that are meant to be demeaning or designed to trip you up. It’s worth being wary of those “questions,” but I believe it’s also worth remaining open to, and generous toward, all other genuine questions, including the clumsy ones.

Questions are like keys. The right question, asked at the right time, will open a door to something you don’t yet know, something you haven’t yet realized, or something you haven’t even considered—about others and about yourself. What I am suggesting is that the five questions that follow are like five crucial keys on a key ring. While you’ll certainly need other keys from time to time, you’ll never want to be without these five.

“Wait, what?” is first on my list of essential questions because it is an effective way of asking for clarification, and clarification is the first step toward truly understanding something—whether it is an idea, an opinion, a belief, or a business proposal.

Too often we fail to pause for clarification, thinking that we understand something before we do. In doing so, we miss the opportunity to grasp the full significance of an idea, an assertion, or an event.

Asking “Wait, what?” is also a good way to avoid jumping to conclusions or making snap judgments. Too often we decide very early whether we agree or disagree with someone or with an idea, without making an effort to truly understand the person or the point.

Even if a better understanding of an idea or perspective doesn’t change your mind, it is likely to make you respect or at least appreciate the person proposing the idea more than you would otherwise.

In almost every instance, it is better to ask clarifying questions first and to argue second. Before you advocate for a position, be sure to ask “Wait, what?” Inquiry, in other words, should always precede advocacy.

Rakesh, however, taught us not to be so sure, and he demonstrated how prone we are to make arguments and judgments based on false assumptions.

It is especially worth remembering in difficult situations, whether at home or at work. When faced with difficult conversations or emotionally charged situations, it is always a challenge to pause to ask if you have all of the facts you need to draw fair conclusions. It is easy—too easy—simply to react, often passionately and often based on assumptions rather than facts. Reminding yourself to ask “Wait, what?” is a way to guard against jumping too quickly to conclusions.

Cultivating the habit of understanding first and making judgments second will also help you avoid pointless conflicts and create deeper connections with those around you.

7 habits: Seek first to understand...

“I wonder . . . ?” Before you object, I recognize that this is, technically, not a complete question. It is instead the first half of a series of questions. “I wonder” can be paired, at the very least, with both “why” and “if.” This chapter is about these two variations on a single theme, namely the questions “I wonder why?” and “I wonder if?”

I am only suggesting that you take the time to look around you—whether at the people near you or your physical surroundings—and remember to ask “I wonder why?”

Learning these stories will inevitably enrich your life. It might even lengthen it. Curiosity, it turns out, is conducive to health and happiness, as scores of social scientists have documented. Curious people, not surprisingly, are likely to learn more and to retain more of what they learn. Curious people are likely to be more attractive to others, as people are attracted to those who seem interested in them. Curiosity also leads to empathy, an emotion that seems in short supply today. Curious people are likely to be healthier, and to experience less anxiety in particular, because they see new situations as an opportunity to learn rather than an opportunity to realize that they don’t know enough. Curious people are also, according to some studies, likely to live longer, presumably because they are more engaged with the world around them.

But if you never stop asking “I wonder if I could do that,” you are bound to find things you love to do.

Once you start asking “I wonder why?” and especially if you get an unsatisfying answer, you are inevitably going to ask “I wonder if things could be different?” Put another way, to ask “I wonder why?” about the present naturally raises the question “I wonder if?” about the future.

The lesson I draw from this example, as well as others, is that even the most stubborn facts of life surrounding you are worth questioning.

I believe it’s healthy and productive to remain curious about yourself. Why do you have certain habits? Why do you like certain places, foods, events, and people, and what if there are others you would like just as much, if you gave them a chance? Why do new experiences make you nervous? Why are you quiet in meetings or shy at parties? Why are you easily distracted? Why do you sometimes lose your patience with certain members of your family? And what if you tried to change those things about yourself that you would really like to change? Or, just as importantly, what if you just accepted some of those things as part of who you are?

“Couldn’t we at least . . . ?” is a good way to get unstuck. It is a way to get past disagreement to form some consensus, as in, “Couldn’t we at least agree?” It’s also a way to get started even when you’re not entirely sure where you will finish, as in: “Couldn’t we at least begin?” No matter its specific form, asking questions that begin with “Couldn’t we at least . . . ?” is the way to make progress.

Both groups find confirmation for their existing opinions. Our virtual worlds are becoming so segmented that we can even choose from different broadcasts of the same sporting event—one that favors the home team or one that favors the visiting team. More and more, we can choose to see only what we want to see.

Asking “Couldn’t we at least agree?” will not resolve all disagreements, of course, but it can at least reduce their scope. Finding some common ground, in other words, can help isolate true areas of disagreement. This is especially helpful in preventing opposing sides on a particular issue from wasting time questioning the motives of their opponents, which happens far too frequently in public debates.

To assert that those who disagree with you must have dubious or immoral goals is basically to announce that there’s nothing left to discuss.

Too often—whether because of procrastination, fear, or a desire for perfection—we hesitate to begin a project at home or at work if we cannot see precisely how or when it will end.

“Couldn’t we at least get started?” on something—whether it was a new project or new initiative. I have discovered, consistent with Goethe’s observation, that once you commit to something, you often end up mobilizing a stream of resources, ideas, and assistance that you never imagined would come your way.

Diversity has the potential to make institutions and organizations stronger, but it also has the potential to create divisions. This conversation was aimed at understanding how to ensure that diversity is a source of strength rather than a source of division. It would also help all of us become more comfortable having hard conversations about race, identity, and equity—conversations that we insist are necessary but too often put off to the future.

But even efforts that failed or were disappointing had something to teach us. Getting started does not guarantee success, but it does guarantee that you will not live with regret about failing to try, which is the last point of this chapter.

I am confident, from my own experience, that every time you attempt to lend a hand, or to right a wrong, or to speak up, you will feel better—about the world and about yourself. When you act, you may make a mistake; when you speak, you may say the wrong thing. But it is much better to fail while daring greatly than to be a bystander, to borrow a line from Teddy Roosevelt. If you fail, often the worst thing that can happen is that you will have a funny story to tell. I have never heard a single funny story about failing to try.

Dare greatly!

The trick is to help others without believing yourself to be, or acting like you are, their savior.

All of which is to say that how you help matters just as much as that you do help, which is why it is essential to begin by asking, “How can I help?” If you start with this question, you are asking, with humility, for direction. You are recognizing that others are experts in their own lives, and you are affording them the opportunity to remain in charge, even if you are providing some help.

when they offered to help, they always asked how they could help. By asking her how they could help, she explained, they were allowing her to retain her independence and dignity.

Asking how you can help is also an effective way of nudging others to identify, express, and confront their own problems.

Asking how you can help is equally effective in less dire circumstances, though for similar reasons. If you ask others how you can help, you are inviting them to take some ownership of their own problems. For this reason, it is a useful question to ask friends, family, and colleagues. It is a particularly useful question, I have found, to ask kids and young adults.

by asking him to tell me what he needed, I shifted the burden to him to identify and begin to address what, exactly, was bothering him.

As parents (and teachers), you try to help solve problems, both big and small. Very often, you think you know what the solution is, so you offer your idea—or a whole slew of ideas. Yet sometimes offering solutions simply fuels the anxiety or stubbornness that your kids or students are feeling, just as occurred with the boy in ski school. If you instead listen patiently and silently to their concerns and complaints, and then ask how you can help, it changes the conversation. It usually causes my own kids to pause. They think about whether I can actually help them and, if so, how. More often than not, they eventually tell me that I can’t really do anything. But in saying this they are already starting to figure out the problem for themselves. What they most needed to do was vent, get some sympathy, and figure out a solution for themselves.

Finally, if you ask how you can help, you are entering a conversation and a relationship on more equal footing. You are likely to be open, as you should be, to the possibility that the person you are offering to help will likely have something to offer you in return. After all, you are inviting them to teach you enough about their situation or their lives to enable you to help them. In this way, asking how you can help is an invitation to begin a genuine relationship, one based on the notion of reciprocity.

In other words, who knows what all of this ultimately means, but our most important task for now is to notice and appreciate the fleeting beauty around us. In my experience, if you offer to help others and leave yourself open to their help in return, you will come to appreciate that, in Frost’s words, “this is love, and nothing else is love.”

“How can I help?” is an essential question. It is the question that forms the base of all good relationships. It is a question that signals that you care. It signals a willingness to help. But it also signals respect, humility, and the likelihood that, in the end, it is you who will be helped just as much.

The fifth and final essential question asks, “What truly matters?” This is the question that can just as effectively guide you through a meeting with colleagues as it can guide you through the biggest decisions in your life. It forces you to get to the heart of issues at work or school, and to the heart of your own convictions, beliefs, and goals in life. It’s the question that can help you separate the truly important from the trivial and can help you maneuver through the minutiae in pursuit of the momentous.

detailing ways to save time at work. Professor Pausch’s underlying premise was that you should be as efficient as possible at work so that you can do all of the things outside of work that matter just as much, like spending time with family and friends, or pursuing hobbies and other passions.

What I have discovered in reading memorials is that every one of them usually hits on the four areas of life mentioned above: family, friends, work, and acts of kindness.

“Wait, what?” is at the root of all understanding. “I wonder . . . ?” is at the heart of all curiosity. “Couldn’t we at least . . . ?” is the beginning of all progress. “How can I help?” is at the base of all good relationships. And “What truly matters?” helps get you to the heart of life.