How to ask the right questions

When it comes to parenting, friendships, dating, partnered relationships, the skill of asking the right, mindful questions can enrich conversations and allow for intimacy. The art of asking mindful questions is intrinsic to certain careers such as therapy, coaching, consulting or being a facilitator

A 23-year-old woman who has been in therapy for a while tells me, “You know what the biggest turn-on for me on the first date is? When the other person asks me thoughtful questions. I can’t even begin to tell you how rare it is to find that. Sometimes that one simple question allows me to go beyond the surface level conversation and think deeply about my life. This guy whom I met for our first date asked, ‘What’s the part that I most enjoy about my job?’ No one has ever asked me this, and I had never thought about it. That conversation suddenly made me feel closer to him and left me with a good feeling.”

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When it comes to parenting, friendships, dating, partnered relationships, the skill of asking the right, mindful questions can enrich conversations and allow for intimacy. The art of asking mindful questions is intrinsic to certain careers such as therapy, coaching, consulting or being a facilitator. But it’s not about careers alone-- it’s one of those skills that’s key to every important relationship in our life. I consistently see a pattern where clients reach out and feel a void when people who are most precious to them seem to ask questions that are experienced as judgmental or seemingly offer unsolicited advice, instead of asking how they want to be helped.

Adults across age groups tell me in therapy that whether a question is asked or not itself begins to impact the trust and safety they feel in the relationship. Teenagers and young adults who are just beginning to navigate the world, talk about it as one of those criteria that allows for ease in communication and comfort when they are nervous.

No matter how old you are, you can cultivate the art of asking great questions. Questions that allow for conversations that can foster a meaningful connection. Just as we can learn to actively listen, the same way we can learn to ask questions that bring more empathy and openness to a conversation.

Based on my experience, the mindfulness in relation to asking questions has four components: the timing of when a question is asked, the tone and the nonverbal cues used when asking and how much openness and exploration the question allows for, and lastly, the pace of asking. Good conversations feel like a dance where both people get a chance to talk, so pacing the questions and creating space for the other person to engage with you is crucial.

Given that we assume so much about people based on their social media, the questions we ask then assume greater significance. We all have experienced moments where a question is asked but we can sense that the other person isn’t really interested in our answer.

So, the task of asking a good question begins with creating an intention to deeply listen and being patient as the person begins sharing their perspective. Leaning forward, nonverbal cues that convey interest, curiosity, making eye contact, choosing to keep the phone away, they all allow the person speaking to feel what they are saying is important. I remember I was meeting a CEO whose work I loved, and they asked me, “Tell me your story, I want to know about you”. Questions that are open-ended, as compared to close-ended questions allow scope for exploration. Be mindful to not ask questions that can feel invasive or threatening. I remember a friend going through divorce and one of our friends would always gently ask, “Is it okay to ask how the court process is making you feel, or do you prefer not talking about it now?” Making space for silence, pauses is part of good conversations.

In a world, where work seems to have taken so much prominence, choose to ask questions that focus on you knowing the person, rather than their work. If conversations also begin to become too centered about your work and one-sided, learn to pause and gently move the focus back on the other person.

As the playwright Eugene Ionesco wrote, “It’s not the answer that enlightens, but the question”.