Here’s a question for you: what’s your favorite question? (This is one of my favorite questions.)

I’m admittedly obsessed with questions, mostly because I know that the right answer to the wrong question is not really an answer at all. 

I’ve also come to see that the art of asking the right question, in the right way, at the right time, might be the most undervalued leadership skill of all. 

Two books in particular have informed my thinking – and fueled my curiosity – about questions: The Book of Beautiful Questions, by self-described “questionologist” Warren Berger, and Humble Inquiry, by the late organizational psychologist Edgar Schein.

From Warren Berger, I’ve learned that a “beautiful question” is a question that “shift[s] the current thinking, open[s] up new possibilities, and ultimately [leads] to a breakthrough.” Beautiful questions help us grow, make better decisions, think more creatively, build more intimate connections with others, and lead teams more effectively. 

Appropriately enough, Berger poses several questions we can ask ourselves to see if we qualify as “beautiful questioners”:

·       Am I willing to be seen as naïve?
·       Am I comfortable raising questions with no immediate answers?
·       Am I willing to move away from what I know?
·       Am I open to admitting I might be wrong?
·       Am I willing to slow down and consider?

From Edgar Schein, I’ve learned the concept of Humble Inquiry, “the fine art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on curiosity and interest in another person.” Schein wisely observes that we live today in a “do-and-tell culture,” in which we feel the need to tell everyone we know everything we know, every chance we get. Working and living in such a culture, it’s easy to lose touch with the fine art of asking thoughtful questions. 

The result? Many of the questions we ask turn out to be nothing more than thinly disguised statements seeking validation and confirmation. 

Am I right? 

Not all questions are meant to be answered, at least not right away. They need time to simmer, like a good stew. 

In his Letters to a Young Poet, Rainer Maria Rilke encourages his correspondent, a depressed young Prussian military cadet longing to live the life of a poet, to “love the questions” of life rather than always searching for answers. “Live the questions now,” he writes. “Perhaps you will then gradually, without noticing it, live some distant day into the answer.”

I took Rilke’s advice several years ago and adopted my own question to live into, courtesy of Elizabeth Mattis-Namgel’s slender, beautiful volume The Power of an Open Question.

“’How do we live a life we can’t hold on to? How do we live with the fact that the moment we’re born, we move closer to death; when we fall in love, we sign up for grief? How do we reconcile that gain always ends in loss; gathering, in separation?” 

Any questions?