How to Ask Better Questions

5 keys to asking better questions and the #1 mindset shift you need to make to enable better connections.

People often ask me…how do you ask better questions?

For years I have been told I ask really good questions.

It’s probably one of the things I get told most often. 

Well, the truth is, I worked at it.

Even though I was always innately curious, it was a big ah-ha moment when I realized that the way to ask questions was absolutely critical to sparking an interesting and powerful exchange.  

Turns out, the questions we ask are scientifically proven to affect the quality of our relationships.

A study by psychologist Arthur Aron, as referenced in the New York Times, explored how the relationship between two strangers can be accelerated by having them ask each other a specific series of personal questions. Since our relationships - at work and in life - are critical to impacting our success and fulfillment, I felt this was something worth prioritizing. 

So I studied it.

Just like some people invest years in learning a new language, how to be a better public speaker or how to be a designer. 

I spent years studying the art of question design.

I learned from some of the greatest teachers - including the David Cooperrrider - the originator of Appreciative Inquiry - and various thought leaders of Conscious Communication. 

I experimented with my own questions.

I would ask a question in different situations - when meeting people at a “networking” event, in the office, at the start of a business call, at a dinner party with friends, at a reunion - and would observe how it connected us and how interesting the conversation became.

Through all this, I unlocked how to ask questions in a way that is exponentially more powerful. 

Here are the top 5 keys to asking better questions:

1. Insightful & thought-provoking  

Make sure they are “generative” questions that allow you to better understand who a person is & what they believe below the surface, invite a broader way of thinking and that can inspire change. 

When I became a Certified Facilitator of The Xchange Method, I learned how to design & ask questions that quickly enable conversations that drive exponential change & meaningful connection.

These are based on 6 different question types: Purpose, High-Point Story, Continuity, Future Image, How Might We, Action or Commitment.  

Any time I am guiding an experience I spend hours strategizing on the best ways to ask questions, which types to incorporate and what cadence to ask them to accelerate desired outcomes for the group.  And I love teaching people in the experience how to do this themselves too! 

2. Open Ended  

People need options and the ability to express their ideas, perspectives and emotions.  This is critical to move into an engaging dialog, otherwise it’s easy to get a one-word answer “yes” “no” that can often shut a conversation flow down.  

“Open-ended” questions will allow more context to come through and give an easier opportunity to ask a follow up question to learn more. 

According to data published by Harvard Business Review, “closed” questions can introduce bias.

For example, maybe you are checking in with a colleague at the start of a meeting or a family member at the end of the day.  

How often do we have a brief conversation that feels boring or disconnected?

We can easily shift this by being more intentional with what we ask…

Instead of asking….”how are you?”

Ask…”what’s been a highlight or lowlight of your day?”

3. Not leading 

We often unknowingly ask a question that already has an underlying bias in the way we ask it.  

Others can quickly pick up on this and sense your own opinion or judgment, just by the way you ask it. 

This will shut someone down from answering it in an open & candid way - maybe out of concern or fear for what you will think of them or their perspective.

For example, you may ask an employee “you totally agree that we should move forward with launching this initiative, right?”  

Versus if you ask, “we are at a point we should make a decision if we should move forward with launching the initiative, there’s been a lot to consider and I value your perspective, what do you think we should do?” 

Do you notice the difference between the two examples?

Leaders often think they are asking questions of their team to get input, but if it’s not done in an effective way it leads to a fear based & follow-the-leader culture.  This can demotivate people as they feel their voice in not truly heard.  It can also decrease creativity and they feel less empowered to share their true beliefs and ideas. 

4. Sequence matters

The cadence in which you ask questions matters significantly. 

It’s important to warm people up by increasing the level of depth and vulnerability as you go.

This helps build comfort, psychological safety and trust. 

The aforementioned research published by the New York Times was specifically designed in this way - the questions started with more approachable levels of emotional connection and then increased in levels of intimacy that elicited more vulnerable responses.

Doing this in our conversations is part art, part science and part intuition.  

We designed a proprietary framework for key questions to ask anyone to accelerate & deepen connections that increase in the levels of depth as you go.  Each question has been tested for years and proven to be effective with coworkers, business partners, clients, friends & family.  

The key learning of ours is that it’s important to practice questions in different situations so you then also can learn to gauge what is appropriate when, and also what you might need to say to lead into asking the question to make sure someone is ready and open to sharing.  

5. Get the tone right

The words you use and the inclinations in your voice can immediately set someone at ease or feel your care, genuine curiosity and compassion, or cause them to feel you are being disingenuous or to get uncomfortable & go on high alert.

For example, let’s say you were at an event or conference meeting someone for the first time.  You may want to quickly learn a little about their background.   

The following are two different examples - each will also use italics on where the emphasis is being placed for you to imagine a different tone of voice…

Option #1:

“What’s your story?”

 Option #2:

“I find one of the fastest ways I can form a connection with someone is to learn a little about their experiences…would you be open telling me about yourself…what’s your story?”

 Feel the difference?

Why does this matter & what are the implications?

The implications are clear.  The questions we ask have the unique power to enable higher quality conversations that will accelerate higher quality relationship, desired outcomes.  They help us learn, co-elevate and dream bigger, together. 

It’s scientifically proven that better questions help move businesses forward faster with more aligned momentum. 

And research shows us that improving the quality of relationships is proven to increase our well-being by elevating joy and fulfillment.  

Oftentimes we play it safe.  We don’t want to “rock the boat” or we are afraid we may be “getting too personal” so we stay on the surface.

While the time, place and cadence to our to our questions matters, there are dramatic implications to our businesses and lives when we play it safe.

We may be in a work strategic session, creative meeting, or customer/client call and ask a question that doesn’t help us gain much insight to positively move something forward, so we stay in a constant spiral of indecisiveness -> slowing down productivity. 

We may ask a question that completely derails us from our actual mission or priorities - causing us to go down a path that costs time and money, only to have to redirect it and do lots of rework -> again reducing productivity and likely engagement.

We may recommend something to a customer that is just not right for someone -> reducing trust and likely company profit. 

We may never truly get to know someone and they are left feeling not seen, valued or loved -> impacting our well-being. 

We may come up against the frustration of others by constantly only being asked what the task at hand is -> reducing motivation and eventually will likely lead to turnover.

When we ask better questions, everything moves forward in a positive direction, well beyond what the simple tasks at hand are. 

The #1 mindset shift you need to make to enable better connections:

You are empowered to quickly shift the conversation to make it more interesting and impactful.

You may be thinking…this all sounds good in theory but I’m skeptical - it seems like it takes a lot of energy and I don’t have the time to always have these types of conversations.

The thing is, like any learned skill, once you learn how to do it effectively, it’s like second nature and it actually reduces time to get to know someone, determine if you want to pursue building a stronger relationship, and moving things forward. 

 For example, a client first came to me as she wanted to gain confidence in how to deepen connection with friends, her partner, team and when networking.  After participating in our signature online connection experience, she shared:

“I got SO much value from this experience! I am now way more intentional when I meet people in typical environments…instead of engaging in small talk and being bored, I now know how to quickly elevate the interaction to be meaningful.  I am amazed at how fast I am able to build better relationships with new people I meet, develop deeper connections with long term friendships, engage my team members at the office in meetings, and my family including my teenage kids.” 

Everyone can do this.  It just takes intention to learn and practice, so you can effectively ask better questions in any situation. 

That’s why I love teaching proven strategies to shift this.  Our clients are often amazed at how fast they are able to learn and implement these and take ownership for making the conversations more interesting, engaging and memorable.  

The impact has been increased social confidence, feeling more empowered to use their voice, stronger connectivity in virtual workplaces, more authentic and trusted relationships. 

I hope you take a moment today to be more intentional in your interactions. 

How might you start to ask better questions? 

Drop a comment on what resonates with you or any questions you might have 👇

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This blog post was written by Lisa Kalfus, Founder of Firestart Connections & an expert in human connection. After a successful 20+ years as a corporate marketing leader, she stepped into her calling to be in service to others and started Firestart Connections with one goal – to accelerate & create deeper connections in business & life. 

Through immersive team building & personal growth learning experiences, Firestart Connections empowers heart-led leaders, entrepreneurs, teams and seekers to gain social confidence and build stronger, more authentic relationships & deeply connected cultures & communities.

Want some more tips and examples of great questions to ask?  Click here to access a special resource on 3 Simple Ways to Connect Better.  Feel free to share with a friend or colleague this may support!