Four Great Questions To Ask People

Image of a question mark drawn in black marker with a red dotIn our information-overloaded civilization, the value of answers is plummeting. The compendium of human knowledge lies a few keystrokes away. Anyone with a question can easily find an expert answer in a matter of seconds. Because of this, the value of questions is rising. School teaches us that having the right answers at the right time is the prime determinant of success. While that was the case in the past, today the pathway to creating solid, enduring value lies in the asking of great questions.

This article is going to show you four great questions to ask people. Questions provide a conversation with impetus. I rely on them heavily when engaging in conversation. Asking questions shows others that we are interested in hearing what they have to say. They establish a foundation on which a trusting relationship can be built.

Now on to the four questions.

1. “Where Are You From?”

I was unconvinced about this question for a few years. I believed it was overused. It was the question new acquaintances awkwardly ask each other at the beginning of a cocktail party, only to be left stranded after answering it, the conversation on life support.

I did my best to avoid asking this question for a number of years. But recently I’ve discovered that the question, if properly followed up, has tremendous potential to shed light upon a person’s depths.

Having lived in 7 different cities in 4 different countries over the past dozen years, I have experienced my fair share of living disruption. It was only recently that I realized that the place we grow up in deeply shapes our world-view in ways most of us are utterly unaware of.

For example, people, especially men, who grow up in a culture of honor are more likely to react aggressively when confronted with an insult which would damage their reputation. Cultures of honor develop in places where the rule of law is not upheld by a central authority, such as the Wild West in the 17th century, inner city neighborhoods controlled by gangs or countries where the government is so corrupt and ineffective the populace cannot rely on it for protection.

Image depicting a cowboy riding a stallion with two others following close behind in front of a cloud in orange light

Cultures Of Honor Rely On Testing

People in any such culture, especially men, continuously test each other to see who can do what to whom and get away with it. The more a person accepts being pushed around by others, the more he/she will experience it. Therefore, minor affronts, to the eyes of a cultural outsider, are more likely to be met with aggression.

Mexico, where I was raised, has historically been home to a culture of honor. Growing up, I remember learning through cultural conditioning that if anyone ever insulted your mother (a common type of insult in cultures of honor), it was your responsibility as a man to stand up for yourself and resort to violence to do so, if necessary.

Naturally, like with all cultures, Mexico’s is in a constant state of flux. As the rule of law has solidified, the culture of honor has weakened. But it’s still around and will remain as long as anyone reading this. Culture dies hard.

By asking someone where they’re from you get an idea of what their upbringing was like. We acquire a tiny window into their past.

If you know about the history, ecology or geography (or anything else) of their hometown, it opens the door to even more questions! I can’t tell you the number of times I’ve met a person, learned where their from, and then immediately followed it up with a question relevant to their cultural upbringing.

It never fails to elicit a smile. I sometimes even get asked “How do you know about that?” Most people I’ve met love to answer questions about their culture. And when people talk about what they love, it builds trust and grows the relationship.

Speaking of things we love, that leads us to the next question.

2. “What Do You Do For Fun?”

One question I stay away from is the infamous “What do you do?”

In my opinion, asking that question is likely to lead to a conversational dead end. Due to the fact that a surprising amount of people don’t like what they do for work. Asking them about it only serves to remind them of the job they abhor.

So I avoid it like the Amish avoid cars.

Instead, I tack on two extra words to the end of the question. Instead of asking a person what they “do” I ask them what they “do for fun.” This puts the answer into a positive frame. You are asking a person to look through their life and come up with the parts of it that bring them joy. It’s guaranteed to steer the conversation into a realm of conviviality and sincerity.

Image showing a person jumping into a lake after swinging from a rope with another person watching him from the branch of a tree


Additionally, that person will then associate you with the positive emotions he/she experienced when answering the question. Which, again, builds trust, which leads to lasting, deep relationships.

Sometimes It Can Backfire

Writing all this, I must admit that it’s possible the question will lead to a dead end. The question often takes people unawares. I have met people who respond to the question with “I don’t know.” Everyone does something for fun, so that answer was a lie. But they didn’t want to admit to me what they actually did for fun.

We only lie when we feel guilty about something. If a person feels guilty about what they do for fun they won’t tell you about it. But that doesn’t mean you shouldn’t ask the question! If a person responds with “I don’t know”, you will be nudging them along the process of self-examination. It’s likely that person will remember and reflect on why they answered the way they did.

There’s nothing wrong with pushing people, as long as you do so gently and politely. Of course, some people can take more pushing than others.

For example, it might not be pleasant for someone to realize that they feel guilty over dedicating all their free time to watching television, but becoming aware of that guilt is the first step in changing its cause.

In fact, asking ourselves the question “What do I do for fun?” is a fantastic way of examining how we spend our free time. I’ve written about how dedicating our time to “creative fun” is an excellent way of increasing our power to create a life we love (read about it here).

On the note of creating a life we love, the next question prompts growth.

3. “Have You Learned Anything New Recently?”

How I wish more people asked me this question! Since I’m constantly learning new things, I always have a new answer for this question.

This question is wonderful for a variety of reasons. One, it gets people thinking. Rather than remaining at the surface of a person, asking this question encourages people to go through their life and pick out a moment when their curiosity was tickled. By drawing their attention to their curiosity you feed it, you actually make people more curious by asking them about what they’ve learned recently.

And curiosity is a hallmark of success. By following our curiosity we can achieve great things. So we actively make people more successful by asking them this question.

Additionally, this question is a great way of expanding your own store of knowledge. See, as humans we have to constantly update our models of the world in order to thrive and reproduce. Every human being you see has survived until today thanks to their skills and knowledge. Even a hobo has had to rely on their wits, and physical abilities to survive, after all.

Everyone alive is a participant in the game of life. That means everyone has something to teach us.

How Asking This Question Could Have Helped Me

For example, when I was living in Washington DC in my mid twenties I lived with a middle-aged Puerto Rican man. He lived a unique life; he owned his own one-person party planning enterprise and published a quarterly magazine which he wrote and edited himself. He managed his own time and dedicated himself to doing only things he found meaningful.

We lived together for almost two years. During that time he kept trying to convince me that there is a flow to life; he told me that forcing situations is unnecessary, if something is meant to happen it will. I, being a hard-nosed physical scientist at the time, swept his talk of “flow” away as superstitious drivel.

I have since learned that he had the right of it. We needn’t go through life forcing our way into and out of situations. It took me a few years, but I ultimately absorbed the lesson he had to teach me. We remain friends to this day and probably will for the rest of our lives.

==> Flow is a well-studied psychophisiological phenomenon. Learn how I access flow regularly by reading this article.

Of course, I could have learned the lesson sooner had I been more open to learning from him. Maybe I could have asked him about the most valuable lessons he had learned in life.

We all learn things at our own time. Being open to learning ensures we gain the most out of every experience.

This openness can also apply to serving others, as evidenced by the next question.

4. “How Can I Help?”

I got this question from the book “Wait, What?” by James Ryan, the dean of the Harvard University’s Graduate School of Education. The book lists the set of the most effective questions anyone can ask on an ongoing basis, according to the author. I highly recommend the book.

The question “How can I help?” is powerful because of two reasons:

  • It establishes us in open service to others.
  • It empowers the other person to reflect on what they need.

According to Stephen Covey in the book “The 7 Habits of Highly Effective People”, there are three levels of maturity for a human being. They are:

  1. Dependent – We depend fully on others to get what we want.
  2. Independent – We can get what we want on our own.
  3. Interdependent – We get what we want while helping others get what they want.

According to Covey, humans are at our most powerful when we are interdependent; when we can rely on others and they can rely on us.

We Evolved To Be Interdependent

Image shows six different pairs of hands on a tree trunk seen from below

Human beings evolved to live in close community with each other, supporting each other through thick and thin. When human beings come together under shared ideals and cooperate harmoniously there are no limits to what we can accomplish (both positive and negative).

Together we create something that is greater than the sum of its parts. Like how trillions of cells come together to form the body and brain of a human. The human (whole) is greater than the sum of its individual parts (cells).

So it is with groups of humans.

Asking “How can I help?” allows us to express our intention as a cooperative being, open to serving others. On top of that, it allows the other person(s) to come up with their own solutions to their challenges. The best solutions to our challenges come from us. So by asking others how we can help them we reinforce their agency to come up with their own solutions.

And when we reinforce others, they reinforce us in return.

I Recently Started Asking “How Can I Help?” – It Works!

I’ll give you a personal example of the last time I used this question.

Just last week my girlfriend and I moved out of our home in Calgary, Canada.

My partner is a meticulous planner. On top of that, she’s like the energizer bunny, always brimming with energy to do what needs to be done. Whenever a big change is coming up she simulates countless scenarios in her head, comes up with plans to deal with them and mobilizes herself to act. Se does this all over the course of the months leading up to the change.

I’m not at all like that. I’ll be the first to admit that planning things is not my strength. By the time I’m ready to act, my girlfriend is already miles and miles ahead of me. I cannot match her in this, our natures are utterly disparate.

So instead of trying to match her, throughout our move I constantly asked her “How can I help?”

I Added My Power To Hers

Every time I asked she had an answer ready for me. Remember, she had simulated everything in her head. She knew what needed to be done. That was her strength. I simply added my power to hers by asking “How can I help?”

By presenting myself to her in a spirit of open service I increased her power.

It worked beautifully. Our move flowed like honey out of a glass bottle. We did it all calmly, efficiently and harmoniously. It was hard work, and we did it together. The result was maximum change with minimized physical effort and expense. By working together we achieved something which we would not have been able to achieve alone.

We became greater than the sum of our parts. That’s a hallmark of healthy relationships.

I invite you to ask people “How can I help?” and see how your relationships are upgraded in every sense through your open service.

Final Thoughts: Questions Open The Mind

Answers are overrated. They really are. Answers leave us in the known. It’s a shame we’re conditioned to value answers so highly while ignoring the power of asking questions.

The truth is that the quality of our answers depends fully on the quality of our questions. All progress starts with a question. Only by asking the right questions do we arrive at he right answers.

That’s why it’s in our best interest to take some time to figure out what the best questions are for each of us.

My aim with this article was to showcase the power of questions and give personal examples on how I have applied them in my life. Have I gotten you thinking about including these questions into your conversations?

Asking people questions opens doors to realms unimagined. It gives us a chance to explore the depths of others and to learn about them and about ourselves, in turn.

So what questions do you usually ask people?

To our wealth and success.

Share the wealth!

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