Get In the Habit of Asking Better Questions

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He had tied his hands behind his back and was standing on the outside of the railing, preparing to jump. He shouted at me: “One step further and I’ll jump!” He sounded hoarse and it was clear he had been crying.

I had been having quite an emotional night of my own. It was my senior year of college and to survive the combined stresses of a recent break-up and trying to finish my senior thesis, I was out for my nightly “sanity ride” – biking at top speed around about 10 minutes of Portland’s Columbia River. I might have just whizzed on by the man on the bridge, leaving him unnoticed. But for some reason, I slowed just then and did notice him.

I remember vividly the calm that passed over me. Maybe I can just chalk up the explanation to the endorphins that were no doubt coursing through my system from an exhaustive bike ride. Maybe it was my wilderness responsive medical training. By good fortune, training or happenstance, when I dismounted I was in a state of serenity which I now think made all of the difference in what came next.

The man shouted down to me to come no closer. I stopped and waited. I don’t know what inspired me to ask the question: “How are you feeling?” But that question has shaped my life since.

I’ll cut to the chase: the man didn’t jump. I spent the rest of the night with him asking him questions and being present. It took two hours, sometimes in silence, and sometimes with a few quiet questions, for him to calm down enough to untie his hands and come down off of the bridge. I remember very little of the specifics of our conversation, just his apathy and disillusion. He had hit rock bottom and wasn’t sure if he wanted to be helped or just end his miserable experience. I eventually walked him to a local homeless shelter, where he was a well-known public figure. About the time I might otherwise have been getting up that morning, I pedaled home.

It has been eight years since I found that man on the bridge and asked him “How are you feeling?” I can only speculate but by his report and my experience that simple question made the difference is his deciding to live.

I once heard Tony Robbins say:

“Thinking is just the process of asking and answering questions.”

This message encapsulates a good deal of the value I see in asking questions. While leading questions are frequently taught to lawyers and teaching questions to educators, we pay very little attention to questions specifically designed to help someone understand their internal landscape.

Types of Questions to Ask

Here is summary of the different types of questions:

Judgmental Questions

Judgmental Questions are very common. While the intonation of a phrase will imply a question, tone and attitude might express outrage or scorn. “Why did you do that?!” doesn’t actually inquire as to the reasons for an individual’s behavior. Instead, the purpose behind the question is to accuse. Though it might as well be included, we usually leave the “you idiot” left unsaid.

Similarly, we ask ourselves judgmental questions. “Why did I eat that pint of ice cream (when I know I feel sick after eating ice cream)?” is just veiled self-criticism. What I’m actually saying is that I think I’m dumb for having eaten ice cream and that I should have known better. Judgmental questions are useful to recognize because we do ask them regularly, and often without realizing it.

It is important to become aware of our judgmental questions. These are all around us and the most common type of question in the world today. And as we become more able to spot our own and others’ judgments, we will be better able to support friends and family with less judgmental, more loving questions, too.

Questions to Learn

Questions to Learn are the second most common form of a question. Imagine a reporter interested in learning your story and you have an accurate sense of “learning” questions. These questions are directive, with a very clear intent from the questioner, but they need not be accusatory.

The primary drive behind these questions is to gain new information: learn why something has happened or why someone behaved in a specific way. A police officer interviews a witness: “What happened after you saw the car speed through the red light?” An interviewer asks for more details: “Tell us something of your backstory. Where did you grow up?”

Questions to learn are a very useful form of questioning, whether you are asking or the subject of the inquisition. Unfortunately, these questions, too, are often intertwined with judgment. As you become increasingly aware of the different types of questions that people employee, you’ll be more able to distinguish between questions sincerely asked out of a desire to learn more, and those that have some amount of inherent judgment.

Questions to Teach

Questions to Teach are the most commonly taught style of question. We most frequently see these questions employed by a teacher trying to help a student reach the answer. We might also call these “leading” questions.

A teacher might ask their students subtle or even blatantly leading questions like “Why do you believe that is the best answer to this math problem?” or “How would you go about solving it?”

These questions are usually intentionally asked, resulting from the questioner considering the impact of their question on their audience. Leading questions are also recognizable in courts, where a prosecutor might be subtly manipulating a witness to share a previously unheard testimony or shape the jury’s decision.

One further note about leading questions: they are by far the most effective method of helping another individual uncover a specific desired answer or outcome. By leaving “bread crumbs” a teacher is able to help a student to discover their own answer.

Questions to Explore

Questions to Explore are the least common type of question. That night on the bridge I used what I’ve come to call an exploring question, which is just a question asked with no agenda and with love.

These are rare because they are non-directive and accepting. Guided by instinct or luck I asked the bridge jumper how he felt, which might seem an odd thing to ask someone crying on a bridge. I don’t know what would have happened if I had told him “Don’t jump!” or tried to teach him. I would guess that things might not have gone so well.

Ask More Loving Questions

We all have opinions that we are all too willing to share. Most of us have agendas that we would like others to adopt. We rarely set aside our own biases to practice presence with another person. Loving questions provide the person being asked the opportunity to discover an internal answer about themselves and the invitation to fully accept themselves in that moment. All of us have the ability to connect with other people, intimately and lovingly, just by listening and asking questions.

Most of us go through our daily lives without considering the impact of our questions or noticing the attitudes that underlie our daily communication. Simply by attending to the questions we ask, we can make a substantial difference in another person’s life.

Get curious. Listening carefully. And ask more loving questions.

Finally, if you want to ask better questions, then watch this short, 20-minute course to learn how to have a great conversation with virtually anyone.