A Question of Questions

Why better questions matter more than most of us might believe

While researching vulnerability for last week’s essay, I stumbled across a directive from Ocean Vuong—the celebrated poet, novelist, and teacher—that urges us to “learn to question the questions.”

I’ve been thinking about his statement ever since.

Along similar lines, my friend Peter Block, the remarkable writer and philosopher, posits, “A good question works on you.” Here are a handful that have been working on me all week:

• Why does the quality of our questions have such an impact on the quality of our work?
• How can I learn, as Ocean Vuong advised, to better question the questions?
• What can I do over time to get better at asking better questions?
• What happens when an organization can collectively improve the quality of the questions it asks?

In his exceptional book Community (which I’ve read something like six times), Block writes that a great question is “ambiguous, personal, and stressful.” This has certainly been my experience with each of the four questions above. That said, I’m striving every day to accept that there will be no easy or quick answers to any of them. In fact, I have the feeling I’ll be at this work for the rest of my life.

What follows is an exploration of my own curiosity about questions, and about the impact of having an organization that learns to ask them ever more effectively.

To be clear, this is not the kind of essay that will arrive at a finite set of conclusions. My emphasis, instead, is my imperfect effort to better understand the import of asking better questions. The essay is only an entrée—a beginning—for a curious human (namely, me) who, in the spirit of vulnerability, has spent a lifetime both asking and being asked questions, yet has given relatively little thought over all those years to the craft of asking them well. If some clarity arises in the form of answers, that’s awesome. If not, then I’m working to align myself more closely with Peter Block’s wise words: “Questions bring us together. Answers divide us.”

Avoiding my own impulse to offer immediate answers is anything but easy for me. As the oldest kid in my family, I grew up feeling as if I was “supposed” to have an answer to nearly anything anyone asked. It’s not hard to see why, then, as an adult, my instinct still leans toward coming up with those answers. Undoing decades of conditioning will not, I know, be a quick process—but I’m committed to doing the work!

Why is it so important to take on this challenge? Nationally known speaker, leadership coach, and author Tony Robbins puts it pretty succinctly: “The quality of your questions determines the quality of your life.” Which means, then, the more effectively I can learn to bring better-quality questions to the fore—and come up with them when I’m feeling pressured and on the spot—the better my life and leadership are likely to be.

In the context of what I wrote about beliefs a few weeks back, what we believe has a huge influence on the kinds of questions we will ask. The insightful writer and environmentalist Wendell Berry demonstrates this well in his classic work The Unsettling of America, drawing the distinction between a person who comes to exploit the land and another who arrives instead as a nurturer:

I conceive a strip-miner to be a model exploiter, and as a model nurturer I take the old-fashioned idea or ideal of a farmer. The exploiter is a specialist, an expert; the nurturer is not. The standard of the exploiter is efficiency; the standard of the nurturer is care. The exploiter’s goal is money, profit; the nurturer’s goal is health—his land’s health, his own, his family’s, his community’s, his country’s. Whereas the exploiter asks of a piece of land only how much and how quickly it can be made to produce, the nurturer asks a question that is much more complex and difficult: What is its carrying capacity? (That is: How much can be taken from it without diminishing it? What can it produce dependably for an indefinite time?) 

Berry’s framing helped me see clearly how changing the question can completely alter the way things unfold. Two different approaches, with very different questions, driving diametrically different outcomes. Not surprisingly, I see our organization as a nurturer. As Berry explains, 

The exploiter wishes to earn as much as possible by as little work as possible; the nurturer expects, certainly, to have a decent living from his work, but his characteristic wish is to work as well as possible.

In another of his wonderful books, The Answer to How Is Yes: Acting on What Matters, Peter Block writes that a question that begins with the word “how” “looks for the answer outside of us. It is an indirect expression of our doubts.” With that in mind, Block offers a very helpful set of half a dozen questions to stop asking (I have certainly asked them all many times over the years), and also, for each, a more effective way to ask a comparable question.

How do you do it? becomes What refusal have I been postponing?

How long will it take? becomes What commitment am I willing to make?

How much does it cost? becomes What is the price I am willing to pay?

How do you get those people to change? becomes What is my contribution to the problem I am concerned with?

How do we measure it? becomes What is the crossroad at which I find myself at this point in my life/work?

How are other people doing it successfully? becomes What do we want to create together?

While each of the six original questions has some merit on its own, they are not, per Peter Block, anywhere close to optimal. The “how” questions, I can see now, all seem to lead in impersonal directions. The answers may be interesting, but soon enough, they almost always invite disagreement—even argument. They’re not the kinds of questions that can bring together disparate views to cast things in a whole new light. 

All of which now leaves me wondering: How many times over the years have I and others here fallen into exactly this kind of rut, asking the narrow, controversy-causing “hows” that Block is trying to teach us to avoid? 

By contrast, the questions he suggests in place of the “hows” drive us to dig deeper—to explore our hopes, dreams, fears, and insecurities. In this spirit, he challenges us:

If we could agree that for six months we would not ask How?, something in our lives, our institutions, and our culture might shift for the better. It would force us to engage in conversations about why we do what we do, as individuals and as institutions. It would create the space for longer discussions about purpose, about what is worth doing. It would refocus our attention on deciding what is the right question, rather than what is the right answer.

I can’t help but smile imagining the response I would get if I were to propose that everyone at Zingerman’s avoid the word “how” for half a year! So rather than propose this, I’ll start by practicing it. At the very least, I can explore how well I do with this challenge personally before I try to take it to the next, collective level. The work is about reframing and rethinking—building new intellectual habits and better question-asking discipline.

Writing about his longtime friend Peter Koestenbaum, the business philosopher and writer who died in 2024 at the age of 96, Peter Block says,

It is [his] willingness to reframe, turn, and even invert a question that creates the depth and opening for authentic change. Questions take on an almost sacred dimension when they are valued for their own sake. This is in stark contrast to the common need for answers and quick formulaic action.

Reflecting on all this, I realize that from the get-go back in 1982, we were already asking questions that were quite different from those of the mainstream business community. Looking back, here’s a list of what it seems we were asking of ourselves—and the world—when we were preparing to open the Deli 44 years ago:

• What if we didn’t try to grow our business as large as possible, as fast as possible?
• Why do so many other food businesses assume that customers can’t tell the difference between truly great food and only so-so fare?
• … And what makes them believe that people aren’t willing to pay for higher quality?
• What if, instead of settling for what’s working well enough to get by, we continuously pushed ourselves to make everything better?
• What if we treated everyone with dignity and care, rather than acting as if they’re just another interaction/transaction on the way to making more money?
• What if we committed to creating uniqueness—instead of the replication that has become so common in the Industrial Era? (Or, as Wendell Berry pithily puts it, “plopping a cookie cutter down on dough.”)

As organizations evolve over time, and the greater ecosystem around us does the same, the questions we pose need to evolve as well. Moving into the present moment, I find myself thinking about the questions I and others here have been asking in recent years:

• When it comes time to consider succession planning, what do you do with your business if you want to keep it local and within the community that made it possible for you to stay in operation for so many years? Our answer was to create the Perpetual Purpose Trust.
• Do you have to consolidate ownership the way we read about over and over again in the business pages? Our answer: you don’t. We now have 18 Managing Partners and over 300 staff members who own what we call a “Community Share.”
• Do you need to think and make decisions hierarchically? Our answer, again, is you don’t—hence, we have been running the Zingerman’s Community of Businesses by consensus of our Partners Group for 31 years.
• What if you decided to engage with everyone—regardless of position—as if they were a partner? (This is the idea embedded in Peter Block’s superb Stewardship.)
• What do we do when autocracy is on the rise all around us and we continue to try to be more and more democratic in the way we work? My answer is in the “Why Democracy Matters” pamphlet.

In the coming weeks, I’ll keep reflecting on other questions that have been unconsciously driving our work over the years, while also exploring tools to help us ask better ones. I believe this could become a meaningful part of what we do.

In this context, the work of a leader becomes to help reshape, reframe, and rewrite the suboptimal questions that so many are stuck with. Peter Koestenbaum shares more:

People come to me because they want to make more money. I ask questions like, “Who are you?” “What are you?” Ultimately, the toughest question is, “What kind of a person are you going to be?”

The latter strikes me as a better question to ask in an interview or a performance review—or, really, any difficult conversation—than the more typical, “How do you handle stressful situations?” 

Questions, I’m seeing now, can be a critical means of accessing new insight. When we’re faced with a challenging situation, it’s important to turn away from the anxiety of arriving at quick answers and, instead, to get more curious about the questions themselves. As Ocean Vuong writes,

You’re working on a poem or a story, when you’re hitting a dead end, when it’s not going, take it with you. Get away from the desk. Now you have to work with your body. Maybe there’s questions you’re not asking. 

Jacqueline Rose’s most recent book, On Violence and On Violence Against Women, explores this subject in intriguing ways. In The New York Review of Books, Christine Smallwood writes,

What has the most force in Rose’s thinking are not her conclusions but her questions. “What, in moments of historical crisis, is being passed down from one generation to the next?” she asks in a chapter on Rhodes Must Fall. “What do we not want to know about the past? What do we not want to know about ourselves?” … The question “What do we not want to know about the past?” has no single or definitive answer, and no book can resolve it. But we must keep asking the question.

Rose’s question regarding what we don’t want to know about the past seems apt on many levels—certainly in the context of the vulnerability I wrote about last week, and my own understanding of the way my personal past influences how I show up in the world every day. It’s also vitally relevant for all of us in this country. Until we can come to agreement on what happened in the past, it’s hard to imagine being able to effectively move forward together into a positive future.

It comes as no coincidence that the most creative people—the people I’ve learned the most from over the years—are those who are themselves asking better questions. One of them is On Being’s Krista Tippett, who has been doing this for decades now on her award-winning podcast, and who offers some great insights into the power and significance of asking better questions:

I also find a question to be a mighty form of words, and I have learned a few things about questions. I have learned that questions elicit answers in their likeness—that answers rise or fall to the questions they meet. We’ve all seen this. We’ve all experienced it. It’s very hard to respond to a combative question with anything but a combative answer. It’s almost impossible to transcend a simplistic question with anything but a simplistic answer. But the opposite is also true: it’s hard to resist a generous question. This is a skill that needs relearning, but I believe that we all have it in us to ask questions that invite, that draw forth searching in dignity and revelation. There is something redemptive and lifegiving about asking a better question.

Better questions, I’m realizing, create more authentic engagement and more thoughtful answers. They call for the kind of purposeful reflection Peter Block believes is possible, rather than the rushed action of simply pushing for an answer. Exploring the ethics of a situation becomes more important than mere effectiveness. Block reiterates his core point here:

The right questions are about values, purpose, aesthetics, human connection, and deeper philosophical inquiry. To experience the fullness of working and living, we need to be willing to address questions that we know have no answer. When we ask How? we limit ourselves to questions for which there is likely to be an answer, and this has major implications for all that we care about. The goal is to balance a life that works with a life that counts. The challenge is to acknowledge that just because something works, it doesn’t mean that it matters.

If “how” has such a narrowing effect, then what word opens us up to new possibilities? Block says,

Yes is the answer—if not the antithesis—to How? Yes expresses our willingness to claim our freedom and use it to discover the real meaning of commitment, which is to say Yes to causes that make no clear offer of a return, to say Yes when we do not have the mastery, or the methodology, to know how to get where we want to go. Yes affirms the value of participation, of being a player instead of a spectator to our own experience. Yes affirms the existence of a destination beyond material gain, for organizations as well as individuals.

A poem I love by singer-songwriter Carrie Newcomer offers an artistic perspective on all this. These are the opening lines (and you can read the whole piece here):

“A Box with No Sides”

I have never written a song because
I had an answer.
I write songs because I have questions.
I write questions because
An answer presumes an ending,
This is this and that is that.
An answer alone has very few open spaces
With no room for returning to the well
For checking the map
Maybe retracing my steps
To walk the same path
But to see with new eyes …

Newcomer’s framing is, indeed, aligned with this exploration—and also, I recognize now, with my two most recent pamphlets. Both are based on, and built out of, questions that were very close to my heart—questions that pushed me to research and reflect for months and years before arriving at enough clarity to put something in print. “A Revolution of Dignity in the Twenty-First Century Workplace” emerged from a question that was essentially, “How do I deal with despair over the violent, heartless act of an authoritarian leader over whom I have no influence?” Similarly, “Why Democracy Matters” arose from my struggle to deal with the coming apart of the rule of law and the democratic constructs that I, for one, have taken for granted for far too long in our civic life. I can say now that although there was no clear answer to either question up front, over many months of study and reflection, I truly learned a lot. Those learnings have already influenced my own thinking enormously, and they’ve begun to sink roots into our organizational culture as well as the keynotes and training work I do through ZingTrain. 

I’ll close with the beautiful, inspiring words of the Austrian poet Rainer Maria Rilke, from his Letters to a Young Poet, written in the early 20th century. I’ve read this passage countless times before, but in the context of all I’ve gleaned working on this week’s essay, I see it now in a much deeper and more meaningful light. 

Be patient towards all that is unsolved in your heart and try to love the questions themselves as if they were locked rooms or books written in a very foreign language. Don’t search for the answers, which could not be given to you now because you would not be able to live them. And the point is to live everything. Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer.

It’s clear I have many new questions to consider throughout my days, and I will need to remind myself regularly to stop stressing out when I don’t have an immediate answer. (To the eight-year-old, answer-focused child in me, I offer Peter Block’s sage words: “There is always something that cannot be explained.”) Instead, I will lean lovingly and gently into the questions, and I look forward to all the compelling, curiosity-driven learning to come. 

Lean in. Live the questions. See what comes of it. Let me know what you learn!

Find some answers

P.S. All this reminds me now of a framework I developed for helping new leaders to succeed. It’s called “Twenty Questions for Managers.” I haven’t used it in ages, but now I’m wondering if I ought to bring it back! Email me at [email protected] if you’d like a copy.