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Asking Purposeful Questions.

Updated: Jun 25, 2023

The relationships in our lives — whether with friends, family members, or romantic partners — are one of our richest sources of joy, meaning, and purpose. And when we take the time to invest in them by asking creative, meaningful questions, we create long-lasting bonds that are both deep and fulfilling.

At WAW we cultivate the art of conversation: asking questions, holding the silence, being present.

Please find below 10 powerful and purposeful questions, gather from a community of good "conversation partners":

What are you excited about right now?

“I like asking this question because it helps me connect with others. When I read or hear any new content, it gives me an opportunity to share and reconnect. I also listen for how long it takes for the person to answer this question. It often speaks to the individual’s state of mind. I find passion to be contagious. Unleashing passion within others helps us ignite it from within.The answer also often introduces me to new places, experiences, or learnings.”

Stacy Cassio, CEO, Charlotte, N.C.

How can I support you?

“This is my favorite question to ask in both my personal and professional relationships. Support can mean different things to different people. For some, support might mean not inviting them out for a happy hour while they commit to a no-alcohol month. Or it might mean testing a new product or service that they want to sell. It could even mean being a listening ear throughout a tough health situation. Everyone has a goal or need that comes to mind right away, and it’s helpful for me to know and understand how I can show up for others.”

Alyssa Towns, business operations specialist, Denver, CO

What’s something new or different you’ve done recently?

“The answers to this question are always fascinating and I find it to be a good conversation-starter. It also prompts people, including myself, to think about what we have done, learned, and accomplished lately. It doesn’t need to be something big. It’s the little things that count the most.”

—Lily Woi, career and leadership coach, London, U.K.

What do you want to be celebrating in five years?

“I like to ask people, ‘Imagine we are celebrating your accomplishment or goal five years from now. What would be celebrating?’ We all have goals and aspirations. This question lets me know what they are ultimately working toward. It also allows me to see if I can help connect them with a tool, resource, or person who can help them achieve their goals.”

Dan Chan, virtual magician, San Francisco, CA

How are you feeling today?

“I make a conscious effort to ask people how they’re feeling, especially now. This one question is a direct but subtle way of getting friends to share what they are going through. More often than not, people open up when asked this question, leading to a conversation which gives me a chance to listen and offer support.”

Bhakti Talati, certified empowerment coach, Mumbai, India

What’s your favorite book?

“My dad is a successful salesperson and taught me the secret to being good at his job is being interested in people. It helps him offer solutions to customer problems, and it’s also a personality trait that he carries into his personal life to establish meaningful relationships. Following his example, I like to try out different dinner table questions with family and friends to open up conversation. One of my recent favorites is asking for their favorite books. At a family reunion, I learned about my cousin’s love for fantasy and my aunt’s love for historical fiction and, more importantly, why they love these books. It helps me better understand who they are.”

Becca Carnahan, author and career coach, Littleton, MA

What is most important to you right now?

I love asking this question because it builds an instant connection between myself and the person I am talking to, and it makes people think intuitively. Sometimes we are all so busy doing, that we don’t take the time to consider why we are doing what we’re doing. Re-assessing what is meaningful now refocuses our energy and attention on being in the moment. This question is a quick and memorable energy refresher and a thought-provoking way to foster a trusting and more intimate interaction with the people in your life.”

Randi Levin, transitional life strategist, N.J./N.Y.C.

What gifts or opportunities have you received recently?

“Instead of a generic, ‘What’s been going on?’ or ‘What have you been up to?’ I like to ask a more perspective-based question. It usually catches the person off-guard, causing a moment of pause. The response tends to be more thoughtful and sometimes even leads to a complete reframe of something perceived as negative going on in their life.”

Julie Bronsteater, personal and executive coach, Chicago, IL

What’s your family like?

“I believe that talking about family is one of the most effective ways to break the ice. I personally have an interesting relationship with my family where we don’t necessarily get along all the time and it is okay! I am certain most people can relate, but they don’t talk about it. Bringing this up in a natural way and even making jokes makes others comfortable to speak up instead of being ashamed or shy about it. I love my family, but we are all human, so why not talk about it and normalize the ups and downs?”

Martin Sevillano, architectural designer, Los Angeles, CA

What’s one gift this past year has given you?

“A lot of people are feeling that the forced separation of the pandemic has had a negative impact on some of their relationships. As the world begins to open up, there is some anxiety about how to bridge the gaps that may have been created, which is why I would consider asking something that conjures joy and hope. For example: ‘I know this has been a challenging time, but I’d love to know about a gift this past year has given you, big or small.’ As humans, we all have a deep need to feel heard and understood, so while they’re sharing their experience with you, make sure to listen and give them your undivided attention.”

Adriane David, mindfulness-based coach, Calgary, AB, Canada

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