Leading Better with Bigger Questions

By Meryl Herr

December 17, 2021

De Pree Journal

On December 31, 2017, I started a new New Years tradition. I grab my journal, my Bible, a few pens or markers, and make myself cozy under a warm blanket. I skim my journal entries, think about the books of the Bible I read that year, recall the struggles and heartaches, and try to list the lessons learned.

Then, I wonder what themes from the past year God invites me to carry into the next. I choose a word to represent each theme, and I write the words on a sticky note.

For 2018, my words were Flywheel, Inquire, Write, and Wall. (I also write sporadically on my blog. You can read about why I picked those words here.)

For 2022, I think one of my words will be Ask. Let me explain. 

On a scale of 1 to 10, how would you rate your ability to ask good questions? 

For me, it depends on the context.

I get paid to ask good questions. A substantial component of my work as a researcher is to develop questions that will help me get a sense for how someone understands a concept or how they experienced a particular event. Sometimes my questions allow me to hear stories of deep joy and gladness. Sometimes my questions elicit painful memories and answers obscured by heavy sighing, even tears. Other times, my questions yield only numerical responses that have to be counted and analyzed in order to hear the story the data tells. 

Sometimes my questions allow me to hear stories of deep joy and gladness. Sometimes my questions elicit painful memories and answers obscured by heavy sighing, even tears.

I feel a deep sense of satisfaction when I craft a good question, or when someone I’m interviewing says, “That’s a good question, Meryl.” In the world of research, I’d give myself a solid 9. 

Interestingly, I don’t feel as confident in my ability to ask good questions in everyday conversations. In those contexts, I’m maybe a 5 or 6. 

Someone recently asked me why I thought that was. Good question! I responded by saying that I think it’s because I can be pretty task-oriented. (I’m sure fear of failure and fear of rejection also play a role. What if someone thinks I’m weird for getting too personal? What if I fumble the asking, the listening, or the response?) My default mode is to ask questions related to projects and processes: Did you get your lunchbox and your jacket? When can I expect that report? How can I support you on that task?  

The doing questions are good and necessary, but what about questions that help us think about being–or better still, the connection between our being and our doing

Questions and Meaning-Making

In the social sciences, we call that quest for integration between our being and our doing “meaning-making.” In her book Big Questions, Worthy Dreams: Mentoring Emerging Adults in Their Search for Meaning, Purpose, and Faith, Sharon Daloz Parks describes meaning-making this way: “In our meaning-making, we search for a sense of coherence, connection, pattern, order, and significance. In our ongoing interaction with all of life, we puzzle about the fitting, truthful relationships among things. We search for ways of understanding our experience that make sense of both the expected and the unexpected in everyday life” (p. 20). 

Did you catch that? We’re searching. We’re puzzling. We’re looking for connections and patterns and significance. Whether we know it or not, deep down some part of us is always asking questions.

Daloz Parks shares a list of some of those big questions—questions she says many young adults (and older adults) ask. Here are a few that resonated with me:

  • Who do I really want to become?
  • Will anyone be there for me?
  • What is my society, life, or God, asking of me? Anything?
  • What constitutes meaningful work?
  • When do I feel most alive?
  • Where can I be creative?
  • Why is suffering so pervasive?

While those questions may drive our meaning-making, our quest to integrate our being with our doing, sometimes we can’t actually articulate them. We don’t always sit down to ponder those exact words. For example, I had to wrestle with the question, Why is this job so unfulfilling? in order to get to Where can I be creative? And I’m pretty sure those questions came late in a long line of other questions. 

Breaking through to the big questions wasn’t easy. It meant pausing long enough to answer the other questions along the way–the ones I scribbled in my journal, the ones my therapist and spiritual director posed. But the tears and the angst and the doubts were worth it because breaking through to those big questions helped me better understand who God created me to be and what God created me to do. The big questions helped me to see that I thrive in spaces that have a culture of innovation and experimentation. That’s because I have an entrepreneurial spirit and a natural bent toward improving systems and processes. 

But the tears and the angst and the doubts were worth it because breaking through to those big questions helped me better understand who God created me to be and what God created me to do.

Daloz Parks believes that young adults “are being cheated” precisely because “they are not being asked big-enough questions” (p. 179). She continues, “They are not being invited to entertain the greatest questions of their own lives or their times” (p. 179). 

I wonder if the problem is more extensive. I wonder if we’re all cheating each other by not asking big-enough questions—or at least the questions that get us on the route to the bigger questions. I want to get better at asking those big-enough questions. I want to take that 5 or 6 up a few notches. I want to grow in this area because it seems like asking good questions and patiently listening to their answers could help me be a better friend, a better mentor, a better manager, and a better leader. 

Learning to Ask Bigger Questions

But how do we develop a repertoire of good questions and the skill to ask them artfully? Here are three strategies that I’m trying:

Learn more

I recently interviewed someone who said that asking good questions is a learned skill. So, some of us have some studying to do. 

I’ve come across several articles and books on asking questions. Recently I downloaded a copy of How to Ask Great Questions: Guide Discussion, Build Relationships, and Deepen Faith by Karen Lee-Thorp. I like how she categorizes different types of questions, and she gives several examples. 

Another place we can go to learn more about asking questions is the Bible, specifically the four Gospels. Jesus was a master at asking good questions. Look at the interchange between Jesus and the teacher of the law in Luke 10: What is written in the Law? How do you read it? (Luke 10:26). Notice this question Jesus put to the disciples: Who do people say the Son of Man is? (Matthew 16:13). Pay attention to the types of questions he asked and how people responded. 

Make notes

When I hear or read a good question, I write it down or flag it so that I can remember it for the future. If it prompted me to think deeply, maybe it would work on someone else. Or I could turn it into a template to develop my own questions. 

I paid attention to a question De Pree Center Executive Director Michaela O’Donnell posed recently. Instead of asking our team, What do you need to end the year well? she asked, What do you need to end the year whole? That’s a big question because it doesn’t focus merely on my doing but rather on my being and doing. And it’s catalyzed some additional conversation about some rhythms that I need to build into my work life in order to thrive. I’ve made a mental note to think about how I could make a subtle change in a common question to make it a bit deeper, a bit bigger. 


Being “book smart” about asking questions probably won’t result in my being “street smart” in conversation. I have to practice asking bigger questions and the associated bigger listening. Yes, it’s risky, but I think the return on investment is worth it. 

You could start small, closer to home. Practice asking better questions with your family. Instead of What did you do at school today? ask your kids, What made you laugh today? or What was something hard you faced at school today?

At work, maybe take a few extra minutes to check in with a colleague or direct report. What’s energizing you in your work these days? What have you done recently that’s given you a sense of accomplishment? 

What Was the Original Question?

On a scale of 1 to 10, how would you rate your ability to ask good questions? That was the original question. Let’s change it up a bit.

On a scale of 1 to 10, how would you rate your ability to ask the bigger questions? If, like me, you do a little self-assessment and identify an opportunity for growth, what are you going to do about it? What’s the next step on your journey to becoming better at asking the bigger questions?

Meryl Herr

Director of Research and Resources

Dr. Meryl Herr is the Director of Research and Resources at the Max De Pree Center for Leadership where she designs and conducts research studies that add to the understanding of what helps marketplace leaders flourish. She also oversees the team’s efforts to convert research findings into r...

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