The Time is NOW for the Second Question

Brad HughesBlog, Connect Better


  • The first thing you ask someone is as important as the second.
  • Following up the first question with a second deepens relationships and shifts our attention OUTWARD to serving, supporting, and connecting.

I was more than a little intrigued when host Martin Silverman invited me to check out his podcast, “The Second Question.” (Now THAT’s a GREAT title, Martin!)

Martin is an educator and fellow school principal from beautiful San Antonio, Texas.

Martin’s second question for every teacher interview is, “Who is the best teacher you’ve ever had, and why are they the best?”

To Martin, the second question:

  • uncovers their vision.
  • shifts the conversation from content to relationships.
  • reveals what they value and what they want to become.

From there, Martin says his job is to help them be able to fulfill that for themselves, so that for some student in the future, they are the answer to the second question.

The first question gets the ball rolling. The second is our opportunity to get to the heart of matters, to someone’s needs, values, aspirations, and purpose.

This got me thinking about the power of the second question, and why we might NEED that second question now more than ever.

Sometimes you may craft the second question on the spot based on what you hear and feel, especially if you're willing to pause, increase your wait time, and be patient. Click To Tweet

The Second Question: From Acknowledgement to Empathy

Quite often our first question to someone we encounter is “How are you?” We typically hear socially acceptable replies like “Not bad.” “Fine.” “Doing good.” We may repeat these interactions many times in a day.

Now, my motto is Let no one pass by unacknowledged. And certainly, the exchange above passes as an acknowledgment. It’s a start.

Let’s be real. We lead busy lives. We’re doing all we can to get by during the stress and peril of the global pandemic. It’s understandable that the script of our day—where we need to be, what we need to do, what we have to remember—drives our attention and our capacity to be present for others we encounter.

Especially our capacity for others that could really use an extra few moments for a second question.

Empathy in Action

You see, stress shifts us into self-protection mode. We put on our blinders and we keep our heads down. We stick to the inner script lest we get distracted and off-track. Our focus is INWARD.

Stress is a barrier to empathy. Empathy is what worship leader, teacher, and leadership developer Dan Wilt calls, “That ability to freely enter the experience of another.”

How CAN we enter that experience, Dan asks, “if we’re tucked safely inside our own feelings, our own experiences, our own worlds, and our own needs?”

Dan believes that asking the second question physically embodies that virtue of empathy.

It’s the second question that deepens relationships and shifts our attention OUTWARD to serving, supporting, and connecting.

Questioning as a Gentle Art

As we seek to uncover a little more with our second question, author and faith community-builder Rodney Duttweiler evokes an image of this gentle art as someone drawing water from a well, as opposed to a power excavator breaking up hard-packed earth to reveal what’s underneath.

Indeed, both techniques seek to retrieve something from below the surface. But drawing water from a well is done gently and deliberately. It invites and embodies hope, trust, safety, and restoration in the cool water promised at the end.

And What Else?

If your first question is, “How are you?” try this:

  • pause.
  • make eye contact.
  • soften your eyes and posture.
  • really listen to the answer.

If the answer is, “Not bad,” “Fine,” or “Doing good,” then your second question might be, “No really…how ARE you?”

For Michael Bungay Stanier, author of the award-winning leadership book, The Coaching Habit, the first question is, “What’s on your mind?” The second question is always, “And what else?”

You can even repeat the second question, And what else? a number of times to gently uncover what’s underneath.

My go-to second questions are, “What do you need?” and “How can I help?”

The second question I’m experimenting with lately is, “How can I support your work today?”

Sometimes you may craft the second question on the spot based on what you hear and feel, especially if you’re willing to pause, increase your wait time, and be patient.

Your gentle, encouraging presence lets your companion know you’re not rushing away, and leaves space for them to tell us more.

The Second Question Is Transformative

Making the second question a habit has the potential to be transformative.

Dan Wilt writes that, over time, entire friend networks may be transformed when we start to make asking the second question a new norm.

My mind goes to the potential transformation within families, schools, workplaces, and communities.

And it starts with a personal commitment to be ready to pose the second question.

It uncovers the vision, shifts from content to relationships, reveals what others value, and what they want to become…

AND positions us to help fulfill all of those for another person.

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What’s YOUR Second Question?

And what does it say about you and what you value?

What’s the second question YOU need someone to ask, right now?

Could you take time, make time, for that second question today? Today, could you be the person to help someone uncover their vision, their values, and their needs?

I truly believe the time is NOW to ask the second question.

About Brad Hughes

Brad is an elementary school principal with 25 years’ experience in education. He is currently at Forest Hill Public School in Kitchener, Ontario, Canada, designated a HERO Generation school in the Waterloo Region District School Board. Prior to becoming a school leader, Brad taught for 16 years in classrooms from Kindergarten to eighth grade, most recently teaching middle school Visual Arts, French and Special Education.

Brad is a certified Self-Reg School Champion and has an ongoing commitment to reframing the joys and challenges of school life through a Self-Reg lens. Brad and his wife Jennifer are proud parents of a son and daughter both in university. He describes himself as an optimist and recovering perfectionist who is passionate about #LeadingWithLove and improving the lives of kids by supporting the adults that serve them.