The Virtue Of The Second Question

The conversation between two friends began as usual. “How are you?” one asked the other. The answer came, “It’s been a hard week, but I’m doing okay today.” Then came the response the askee had, unfortunately, come to expect: “Wow. Sorry. Me too. I’m so looking forward to the weekend. I went out for coffee with….”

Photo by Jorge Saavedra on Unsplash

The friend who had asked the first question, like many of us in our generation, had never learned to ask the second question – and the practice of asking the second question is the beginning of empathy – and its companion, friendship.

You Can’t Have Friendship Without Empathy

A colleague of mine, many years ago, defined empathy as “the ability to imaginatively enter into the experience of another.” 

But how can we freely enter the experience of another if we’re tucked safely inside our own feelings, our own experiences, our own worlds, and our own needs – continually (and often unintentionally) turning conversations with friends back to ourselves?

We all want the kind of friendships that feel – powerfully, emotionally, and consistently – deep, lasting, encouraging, helping, supporting, and mutually caring. But how do we get there in our friendships, and help others around us to do the same?

After a few decades of being a friend, and having others be a friend to me, here is a simple tool that can help our conversations with friends become gateways to greater, more lasting connection.

I call it, The Virtue Of The Second Question – and it is a way of conversing that can be learned. 

The Virtue Of The Second Question

When we think of virtues, we often think of more concept-oriented words like integrity, generosity, self-restraint, wisdom, patience, and other ways of being that beneficially enhance our lives with ourselves and the world.

But if a virtue is a muscle that we work, a second-nature character trait that we practice until it overtakes a first-nature vice, then our list of virtues could grow quite long if we open the door to listing practices that carry a virtue into every day life.

In this case, if empathy is a virtue, then there is a path to acquiring it, practicing it, and developing it until it overcomes its natural enemy – apathy.

Asking the second question is a practice that physically embodies the virtue of empathy – and it is truly a spiritual practice we can begin to implement immediately.

The Practice Of Asking The Second Question

Try this simple “Second Question” process the next time you are beginning a conversation with a person you care about.

  1. Ask “How are you?”
  2. As they answer, look them in the eye and listen attentively.
  3. When they are finished, ask a second question, like “Wow, I hear you. That sounds challenging. Did it affect you all week or are you getting some perspective on it?”
  4. As they answer, simultaneously listen and prepare a third question in your mind. Feel free to pause before you ask it; they won’t mind waiting. You have made them feel cared for.

After the second question is asked, the person is feeling listened to, and has a sense of safety in sharing another layer deep of emotion, thoughts, and attitudes. They may even begin to answer their own internal questions as they verbalize more details and get them on the outside for the hearing.

At this point, they will also, most probably, perceive you as being genuinely interested in their wellbeing, and as an example of someone acting as a true friend to another.

It is not the first question, “How are you?” that triggers deeper relationship. People in companies and in situations where we are interacting with general acquaintances ask this question all the time – with no intent of the conversation going any deeper than the short, polite answer.

For lasting friendship to blossom and bloom, it takes the second question (and the third and fourth questions) to bring the sunlight and rain needed for true, lasting companionship to grow.

The Second Question Pays Forward

When someone begins to make asking the second question a new normal in their relationships, there is a high potential that, eventually, conversations will come back to you (do they need to every time?), and a second question may be asked of you.

Over time, we could see entire friend networks transformed as individuals within it practice asking the second question as a matter of course in the way they interact in conversations.

The “Second Question Day” Challenge

This week, pick one day to be your Second Question Day. On that day, intentionally interact with friends, in person, via text, in email, or on social media, asking a second question in all interactions.

If you like the results (or even if you don’t), pick a second day to try it again.

And if the change in conversations feels like something deeper could be happening, something good and right and renewing to all involved in the friendship, begin to make the second question part of your new normal for interacting with others.


Question: Have you seen the second question at work in your own life, or in the lives of others?

Resource: I’m thinking of writing a short booklet called The Virtue Of The Second Question. Comment below if you believe a tool like that would be helpful in the lives of others (especially young people) that you know. I’m also taking ideas for a title and subtitle. I’ll let you know here if the little project comes out.


Sheltering Mercy: Prayers Inspired by the Psalms

Sheltering Mercy, along with its companion volume, Endless Grace, helps us rediscover the rich treasures of the Psalms—through free-verse prayer renderings of their poems and hymns—as a guide to personal devotion and meditation.

The church has always used the Psalms as part of its prayer life, and they have inspired countless other prayers. This book contains 75 prayers drawn from Psalms 1-75, providing lyrical sketches of what authors Ryan Smith and Dan Wilt have seen, heard, and felt while sojourning in the Psalms. Each prayer is a response to the Psalms written in harmony with Scripture. These prayers help us quiet our hearts before God and welcome us into a safe place amid the storms of life.

This artful, poetic, and classic devotional book features compelling custom illustrations and foil-stamped hardcover binding, offering a fresh way to reflect on and pray the Psalms.