A Holiday Party Primer: Ask Deeper Questions

Photo by Jeremy Bishop via Unsplash

In his December newsletter for The School of Life, Alain de Botton—the beloved British philosopher of everyday relationships, work, art, and meaning—begs his readers to stop asking superficial questions. If someone says they are spending the holidays with their partner and their partner’s family, instead of asking, “Whereabouts do they live?” ask “Do you feel like you might be unconsciously avoiding your own family?” If someone complains of all the stress and holiday multitasking, instead of chatting about meal prep, ask, “Have you always felt pressured to please those around you?” If someone has not figured out what present to buy their father, instead of suggesting a gift certificate, ask, “Do you feel like the two of you struggle to connect as individuals?”

I gulped for air. Not only did those questions sound like a quick way to get the contents of the cut-glass punch bowl dumped on my head, but they took me straight back to adolescence.

My mother would ask anybody anything. “Have you had sex yet?” she would inquire eagerly when a young secretary confided a new romance. A casual acquaintance might be asked, “Do you like your mother? I couldn’t stand mine.” To an anxious neighbor: “Have you tried Xanax? I couldn’t get to the grocery store without it.” My friends (and later, boyfriends) underwent such sweet grillings, they left dazed, having poured out more information than they ever told their own mother.

Nette would have made a hell of a spy, because she asked her questions with such pure sympathy and candor that people blurted the answers in spite of themselves. There was no judgment, and they could sense that. Soon she had a soap opera season’s worth of information about what the person dreamed about, yearned for, regretted.

As a kid, of course, I was mortified. I developed a faraway stare, removing myself from these messy and unpredictable exchanges. She was the extrovert; I was too shy even to raise my hand in class, let alone ask a question.

But then I went to college and found myself majoring in philosophy, which was all about questions. The choice itself proved Nette’s power: I had been pondering the abstract since the day she casually asked, as we carried in groceries, if I believed in fate. Not quite sure what the word meant (I was five years old), I made a valiant stab at an opinion. She listened, then nodded in grave agreement. My first serious opinion validated! I spent the next two decades refining that answer.

In philosophy classes, we asked all sorts of questions, but in a remote and cerebral way, cribbing from Aristotle or Kierkegaard. It was, I had to admit, rather fun. Alas, there are not many career paths in philosophy. So I chose journalism, which had the second-worst job prospects and required entirely different sorts of questions.

As a young reporter, I drafted long lists of questions before each interview, carefully placing the tough questions at the end, and showed up nervous every time. After a few years of this, it began to dawn on me that my mother had been right: People were eager to be asked even the most intimate questions. Asking meant that you thought that person’s experience and opinions—about fate, say, or the future of the country—mattered.

With the last inhibitions cut away, I went deep. What did they simultaneously hope for and fear (a favorite I stole from a Tarot card)? What did they blame their parents for? Who was their first crush and why? What shaped their attitude toward money? What did they believe unshakably? What had they done a 180 on? What was their wildest dream ever?

I might need a shot of Scotch to ask one of De Botton’s questions. I could come close, though. I might muster “Do you feel closer to your partner’s family than your own?” or “What would cut you loose from all that holiday busywork?” or “Are you more like your dad or your mom?”—and let the conversation open from there. The surface is an utterly boring place to stay.

And questions are an art too seldom practiced.

A 2019 study at the University of Pennsylvania found that “individuals avoid asking sensitive questions, because they fear making others uncomfortable—no rocket science there—and because of impression management concerns” (which require jargon to acknowledge). “We demonstrate that this aversion to asking sensitive questions is both costly and misguided,” the authors continued. Conversational partners did not mind being asked sensitive questions; nor did they think less of the questioner.

What matters is not how far you probe, but how you word and intend your question.

The traditional reporter’s wrap-up, “Is there anything else I should have asked?” elicits very little, because people are intrinsically courteous and do not want to criticize you. “Oh, no,” they say, “you were very thorough.” So I have learned to ask, “What else about this topic intrigues you?” or “If you were interviewing yourself, what would you ask?”

A thread on a teacher’s Twitter account offered other suggestions: Instead of asking “Any questions?” after a presentation, ask “What questions do you have for me?” or “What can I clarify?” One teacher had begun asking students “On a scale of one to ten, how comfortable do we feel?” Another threw in a more personal suggestion: If someone is going through a rough time, instead of the obligatory “Is there anything I can do?” ask “How can I help?”

The trick is, you have to want to help. Because when you ask a question the right way, you just might get a real answer.