How to be a more curious person

Transform your life, leadership and relationships with better questions and a deeper connection to your curiosity.

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Voltaire said that it is wiser to “judge a man by his questions, not by his answers.”

Tony Robbins said that “the quality of our life is determined by the quality of the questions we ask.”

If you have ever wanted to become a great question asker, or more curious person, this post is for you.

I believe that our curiosity is a compass. A compass that guides us towards connection with others and ourselves. To me, this connection is the foundation of a life well-lived.

Additionally, asking great questions is one of the best ways to earn influence, learn quickly, and lead effectively. The benefits of being curious at work are well researched and practical.

The post below synthesizes several of my favorite techniques and helpful mental models that I’ve used to cultivate a deeper relationship with my curiosity.

Before we begin, I’ll admit that my relationship with curiosity started on shaky ground. It was less of an honest exploration and more of a tactic.

How my journey with curiosity began…

I was very fortunate to grow up with entrepreneurial parents. My mom is a 12-time author and keynote speaker who has dedicated her life to teaching communication best practices to people. One of the perks of having her as my mom is that I was exposed to innovative and alternative thinkers at a young age.

I remember being the errand boy at the Hawaii Writers Conference while I was still in elementary school. I spent my weekends delivering breakfast to Mitch Albom (Tuesdays with Morrie) and doing odd jobs for folks like Jack Canfield (Chicken Noodle Soup books)  between sessions.

As I got older and worked my way through college, I began to feel pressure to contribute in these high-performing circles as an adult. I could no longer lean on the cute factor of being a kid amongst grown ups.

As this transition was taking place, I remember the early traces of social anxiety and limiting beliefs that began to crop up around these “high-value” people. Things like…

“These people aren’t going to care about what I have to say.”

“I’m not going to be interesting to them.”

I’m not smart enough to be here.”

And then one day, I discovered a strategy to counter the jerk in my head. I noticed that many of these authors and speakers were asking people bigger questions about things like passion and purpose. I thought that I’d give it a shot.

I started to ask deeper, more personal questions when I’d meet people that I perceived to be successful or important. Things like, “What’s your purpose?” or  “What are you most passionate about?” and “What’s your dream?” were several staples.

My interactions immediately started to shift. The conversations that I was creating were more interesting and people started to respond positively to my deeper line of inquiry.

They started to comment on how refreshing it was to hear these types of questions from a young person. This praise was just what my ego needed to feel like I belonged. 

I didn’t trust myself to contribute  ideas or opinions because I was so hypercritical of myself and specifically my intelligence. I felt much more comfortable contributing by asking questions and listening than I was talking and sharing ideas.

At the time, my “enoughness” was so predicated on being liked and accepted. Asking these types of “big” questions was working…so I ran with it.

Fast forward over the next 5 or so years of my early professional life, and I got pretty dang good at asking questions. I gave a TEDx talk entitled “What if questions are the answers,” I started to give talks to young people about the most important questions they can ask themselves to find their dream career. I started my first company and started to get invites to cool business conferences on my own (no more riding mom's coattails.) As I developed this skill, I started to get recognized for it socially and professionally. Employees would comment about how much they appreciated my inquisitive leadership style and the communal questions/prompts I would ask in meetings. I would frequently get strangers telling me “that I asked great questions.”

Then I had my wake up moment. The first time I truly asked myself WHY I was operating this way.

I was attending a conference for entrepreneurs, called the Summit Series, on behalf of my children’s nonprofit Dreams For Kids. They had taken over an entire Virgin cruise ship for the event.

Forbes called the event a Davos-like conference for millennial changemakers. This was exactly the type of environment where I typically devolved into my validation-seeking habits. Wanting to be liked by others to prove to myself that I deserved to be there, and was good enough.

On the first day of the event, I found myself locked in a one-on-one conversation with the General Partner of a well-known Silicon Valley venture fund. I remember asking the man a question about what he cares about, and several minutes later he looked at me and asked me a question. “Ohh, shit,” I thought. It was obvious that while he was answering the question, I had completely zoned out and was in my own head thinking about something else. It was an awkward moment that disrupted our flow, and shortly thereafter, we went our separate ways.

I walked up to the fairly empty top deck for an introspective moment.

“Did you actually want to know what he cared about? Or were you just asking it out of habit? Are you asking these questions because you want to? Or, simply because you want to be perceived a certain way?”

After sitting with my thoughts for a while, I got honest with the reality that I was leaning on these questions  to be liked and connect with people, it was a subconscious tactic to connect. In that way, it was sometimes an inauthentic strategy. “Ugh, gross,” I thought.

After getting real about my relationship with curiosity as a tactic, I asked myself the same question, “Do you really want to be asking these types of questions?” The answer was a crystal clear “yes.” Asking deeper, more meaningful questions just felt like the most interesting and aligned way to be in the world.

They made my conversations more dynamic.

They helped me to get to know people on a deeper level.

They helped me to learn new things and grow.

They typically made people feel valued and appreciated.

They helped me to be more present.

They often felt like an act of service. Helping others to learn about themselves and uncover valuable insight.

For most of my early professional career, I had embraced my curiosity as a tactic. A way to control situations and achieve in the world.

In this moment, I was able to choose my curiosity as a way of being that was aligned with my values. The fact that it was historically effective for connecting with people on a personal and professional level was just an added bonus.

From that day forward, the questions just came out differently. That’s because they were being expressed from a place of intrinsic motivation, and no longer from a place of external validation or control.

In my opinion, this is one of the biggest lessons we can learn about becoming a more curious person and asking better questions.

Our curiosity is just one facet of our authenticity. When we connect to our curiosity and give it a voice, we are expressing the authentic self in real time. When people connect to that realness, we earn their trust and respect with much less effort.

This is when my intentional journey with curiosity began. It was inextricably linked to my journey with being authentically me in the world.

The best techniques to develop our curiosity 

1. The most important question there is - “What do I want to know?”

The #1 thing anyone can do to cultivate a deeper relationship with their curiosity is quite simple.  Ask this question, “what do I want to know?” before any experience where you want to connect with other people. It could be a business meeting, social event, or casual hang.

When we answer it, we naturally articulate the questions that most directly represent our curiosity. We become clear on the authentic questions that we want to bring forth in conversation. We don’t need to remember them explicitly, even becoming slightly aware of them will make us more likely to share them naturally in conversation.

We shift our attention off of self-consciousness and into other consciousness. We make it easier to be present in conversation because the questions we ask are those that we actually want the answer to.

Earlier in my professional career, I would take 60-seconds to write down these questions before any important meeting. Each time, I would notice my body relax. The exercise would fill me with an authentic confidence that I could guide the conversation in a meaningful direction.

Next time you prep for an important  social engagement, simply ask yourself, “What do I most want to know about the person(s) I’ll be with?”

If you find yourself in a dialogue that is dragging or boring, you can also direct your attention back to this question to shift the direction you;re headed.

I find that it is good to get yourself to at least three questions when you answer the prompt. There is a mnemonic device called “the power of three,” and simply put, our mind remembers things in threes more effectively.

We should think of curiosity as a muscle; the more we work it, the stronger it becomes. The more we practice this before a conversation, the more naturally we will start to do it without even thinking about it. As we do it more, our capacity to find the right question on the fly, moment to moment will expand.

We are what we do consistently. Answering this prompt is how we build the habit of curiosity. 

2. Establish your “BIG 5” and discover your curiosity template

Each of us has a curiosity template. Our curiosity template speaks to our fundamental interest in other people and the world.

Some people are more drawn to the personal, the “Who are you?” questions.

Some people are more interested in the practical, the “What are you doing and why does it matter?” questions.

Some people are more fascinated by the intellectual, the “What do you know about the world?” questions.

Some people are intrigued by the topical, the “What do you think about this thing?” questions.

Your Big5 are the five questions you generally find yourself interested to know about anyone you meet. It could be a coworker, friend, or family member.

My Big5 at the moment are:

What are you most excited about right now?

What is challenging right now?

What is your dream? If you knew you couldn’t fail, what would you do?

What have you learned recently?

What do you care about?

When you write down your Big5, it is more likely that you will default to these interesting questions and not surface-level fodder that leaves both you and your counterpart bored and looking for the eject button.

So, take a second and write down your Big5. Feel free to steal mine if they connect for you.

Just because these are your questions now does not mean that these will always be them. Your Big5 will change as you change.

3. Practice the Golden Rule of Curiosity

You know the golden rule. You’ve heard your parents say it over and over growing up.

“Do unto others as you would have them do unto you.”

The Golden Rule of Curiosity is simple, “Ask questions to others that you would like to be asked yourself.”

If you want to talk about the weather and where you’re from, then ask other people those questions. If you want to go deep, learn and truly understand people, then honor your curiosity and ask those types of questions.

When we practice the golden rule of questions, we find new confidence in our question-asking because we know that they are fun and interesting to us. When we can do that, we find newfound confidence and ease in conversation. It’s also more likely that our questions will land with greater resonance. When people feel that we mean what we are saying and genuinely want the answer, they are more likely to go there with you. 

If we want people to go deep with us, it helps to establish trust and this layer of authenticity will help with that.

So, what types of questions do you personally want to be asked? What would be fun, interesting or meaningful for you? Write down your answers and then share with others next time the opportunity presents itself.

4. Transform conflict into collaboration with curiosity.

Conflict is inevitable; how we respond to it is up to us. One of the simplest ways we can transition from reacting to conflict, to responding, is simply getting curious when we get triggered or find ourselves in reactivity. 

One of my favorite teachers on relationships, Annie Lalla says that “conflict is just a collaboration waiting to happen.”

One of the most common mistakes that we make when it comes to conflict is making assumptions about how others are feeling, what they are thinking and what they want.

When we make assumptions, we disconnect ourselves from reality and aren’t able to make decisions based on the real facts of what is going on.

Our curiosity is a tool that we can use to check our assumptions and brings us back in touch with the facts and reality.

Next time you find yourself in a heated moment with someone or a moment of reactivity with yourself. Take a moment and choose curiosity…

What am I assuming about how this person is feeling?

What do I want to know about this person and how they’re feeling?

What do they need?

What do I need this person to know?

When we ask these questions, we’re more likely to respond to a challenging moment, rather than react to it.

If we are in a conflict where we feel we need to reprimand or deliver hard news, our message is much more likely to be received if we start with questions. People tend to respond better to a two-way dialogue, than a one way monologue.

5. Leading with curiosity at work

One of my favorite ways to become a more curious leader comes down to one simple question…”How can I be most helpful?.”

Whether it is with your team, a prospective client, or a friend, this question will get right to the point. It takes the guesswork out of being helpful. It gives our counterparts an opportunity to show us exactly where they need support.

If you want to take this even deeper, you can pair the initial question with a prompt of “what is the biggest opportunity and/or challenge you’re currently seeing for the business?”

More than any other questions, I find that these will lead us towards a constructive and insightful dialogue with professional colleagues and prospects.

Even when people don’t need your help, the genuine offer of support and genuine interest will translate to meaningful rapport and connection. People want to work with those that they like and feel connected to, so this matters.

Leveraging curiosity with teams

One of the key forces that keeps teams from performing optimally is a lack of shared understanding around purpose and priorities.

Great leaders make it easy for a team to find clarity by asking clear questions. When the most important questions are answered directly and explicitly, shared understanding will follow. 

Here are my current Big7 for business. Six questions that every leader can leverage to focus the energy of their team on any important project. 

1. What is our primary goal or objective? How will we know we have succeeded (start with the end in mine)

2. What are the biggest challenges? (address challenges up front)

3. How are we going to accomplish our goal and by when? (strategy and tactics)

4. What is unclear or unknown? (Proactively identify blind spots)

5. Who is responsible (assign roles)

6. Tell me how this is this important? (purpose and context)

7. How can I personally be host helpful?

On top of creating shared understanding, research shows that asking our employees questions helps to build up a sense of trust between coworkers. This honest connection is essential for unlocking performance and team cohesion.

There is an art and skill to using the right questions, and one small shift is shifting from the Why to the How, What, and Tell me more.

Research has shown that asking people “Why” can come across as provocative and put people on the defensive. On the other hand, “How,” “Tell me more,” and “What” create an open environment where ideas are likely to flow more freely.

Helpful mental models to trust our curiosity

Anais Nin said we are not responding to the world as it is; we are responding to it as we are.

Our experience of reality is inextricably linked with our perception of it.

If we want to shift our behavior towards being a more curious person, it helps to address our beliefs about curiosity up front.

Our identity and beliefs are the greatest driver of sustainable behavior change. With that in mind, here are some mental models that you can try on for size. Each of these has been helpful for me and made it easier to trust my curiosity as a compass for meaningful connection and guidance.

1. Replacing self-consciousness with other-consciousness. Curiosity is an anecdote for social anxiousness.

It is natural for the brain to predict and assume how other people are going to perceive and respond to us. It does this to protect us from ostracization and rejection.

As most of us have felt, this often leads to tension, anxiety, and reactivity (T.A.R) that are counterproductive for feeling good and connecting with people.

When you look at the definition of self-consciousness, it loosely translates to a hyper-awareness of oneself and how others perceive us.

In contrast, I think of self-awareness as the healthy recognition of one's self and our surroundings. Self-awareness does not trigger the same worry that self-consciousness does.

To rebut the brain's natural tendency to focus on external forces in social gatherings ( I call it the R.O.P. - rejection, outcomes, and perception), we can replace self-consciousness with other-consciousness. I define other-consciousness as an awareness of what we want to know about others and how they are feeling.

When we allow other-consciousness to permeate our being, resistance drifts away – we show ourselves that our curiosity and the questions that follow are enough to start and sustain a meaningful conversation wherever we go.

We don’t need to have a trove of smart things to say or talk about; we can simply ask questions and let our partners fill the void.

When we ask questions we genuinely want the answer to, we make it easier to be present.

When we ask questions we’re genuinely interested in, we are able to listen intently with much less effort. Why? Because better questions trigger more interesting answers. We are more likely to spark meaningful responses from people we genuinely want to listen to.

People will feel our genuine interest and feel more comfortable going deep and getting real with us. We become more present without trying to be.

People feel valued when we ask them questions. We can trust this. 

Dale Carnegie famously said, “You can make more friends in two months by becoming interested in other people than you can in two years trying to get other people interested in you.”

Think about the last time someone looked you in the eyes and asked you questions they genuinely wanted the answer to.

Was your response, “Ew, gross”? Probably not.

You likely felt seen, heard, and valued. When people are genuinely interested in us, we feel they care. Their authentic interest creates a sense of safety that helps us relax with them.

When we ask questions and truly listen to the responses, people tend to trust us and feel good in our presence.

2. Asking questions is how we learn. When we are learning, we are growing and this leads to confidence. 

“When you talk, you are only repeating what you already know. But if you listen, you may learn something new.” – Dalai Lama

The Dalai Lama was right. In conversations, we often simply parrot things we know about ourselves and the world back to other people. Sure, this is a necessary part of connecting with others and sharing information, but it’s not taking us anywhere new.

One of the easiest ways to find new motivation for being with people is to adopt “a learner's mindset” in conversation. This means that we approach every interpersonal experience as an opportunity for learning.

With the learner's mindset, we lock ourselves into a perpetual state of growth that shows us that we are moving forward and improving. Over time, we will notice ourselves getting smarter and more capable of talking about the world knowledgeably. We become wiser.

We find a new well of energy when we choose to believe that our next conversation has a hidden piece of treasure in it for us.

3. Our curiosity is an act of service to other people and the projects that matter most to us.

Do you want the people around you to feel like they can be authentically themselves? Well, if you answered yes to that question, the only way to truly create that space for them is simply being authentic yourself. 

When we ask the questions that we are genuinely interested in, we create space for other people to do the same thing. 

On top of that, these types of big, meaningful, deep questions create the space for true connection to happen. They allow us to transcend surface level chit chat and get to the meat of what is really going on. 

They create space for true insight and understanding to emerge and accelerate everyone's ability to learn and grow around us.

Curiosity is an act of service. When we embrace that a behavior is in the service of something greater than the self, we will be much more likely to express that behavior sustainably. To actualize the self, it helps to have a goal that is bigger than the self. 

In closing…

This is a collection of the most helpful techniques and ideas that have been useful for me on my journey of cultivating curiosity. I hope they can be helpful to you on your path.

If you have other questions or techniques that have been helpful to you, I’d love to hear about them in the comments. 

A Lot of this blog has been focused on the practical application and benefits of curiosity. So, I thought I’d end with something that might be slightly less practical, while also being really meaningful for me.

I find that my curiosity has also played a pivotal role in my spiritual development later in life.

I don’t have a connection with a formal “creator” or higher intelligence per se, but I do feel infinitely grateful to be having an experience of life at all. I try to approach being human with a radical agnosticism, or not knowing what the heck is going on.

I relate to my curiosity as one of the primary tools that I have to explore the “great mystery” we call life and everything it comprises. When I am tapped into my curiosity, I am tapped into the gift of my life, and that’s a good place to be.

It is a way of being I trust as much as anything I know.

As Rilke says, “live the questions.”

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”