When could asking personal questions come across as nosy and intrusive … and when could it take conversations into richer territory? Nobody wants to ask questions that could upset or offend a conversational partner. But because we don’t always know what those questions might be, any social interaction contains a bit of risk.
Still, if we asked only about the weather or bus departure times, there’d be no potential for friendships or intimacy. If our intention is to connect with others so that we may know them better, asking personal questions from a place of curiosity and care, is the way to go.
Most of the 84 stories in my book The Big Ask focus on asking for things like opportunities, permission, clarity, and truth. The story ahead, however, is one of the few about asking personal questions — those questions so essential to connecting with and understanding the people in our lives.
The storyteller is Jeffrey Saver, a musical director and conductor on Broadway, Off-Broadway, and in regional theaters.
Jeffrey’s Story
When you work with people you admire but never thought you’d have the opportunity to work with, you find out just how human, how vulnerable they are.
One night in 1991, at the Arena Stage in Washington D.C., I was sitting with Stephen Sondheim as he gave me notes after a performance of his and George Furth’s show Merrily We Roll Along.
I was the music director/conductor. There was nobody there in the back of the theatre but us and it was quiet.
When he’d finished giving his notes, he asked me about my family, and I started talking about my parents a bit, that I was excited they were coming to see the show.
I didn’t know anything about his personal life at that point. He started asking me more probing questions about my parents and said, “It sounds like you have a great relationship with your mom.”
And I said, “Yes, I have great relationships with both my parents. Do you have a good relationship with your mom?”
At that point he was facing straight ahead, not looking at me, and said, “My mother was in the hospital for an operation several years ago. And just before she went into surgery, she said to me, ‘The only mistake I ever made’—Sondheim turned his head to face me—‘was having you.'”
I wanted to disappear.
I wanted to sink down into Middle Earth!
I felt like I had asked the worst possible question.
Also, I couldn’t even take in the information. What kind of parent would say that to their own child?
I somehow changed the subject and then walked him back to his hotel.
Upon arriving back in New York, I immediately called [composer] John Kander and told him about that conversation. And he said, “You asked him WHAT? Everybody knows that story about his mother, and that he had a f’d-up childhood!” Well, I didn’t know.
Sometimes asking questions takes courage, and I suppose to have that courage you have to feel it’s safe to communicate. You’ve got to trust that the person senses that your interest in them is genuine, and that the choice to respond is always theirs.
(The conversation Jeffrey Saver and Stephen Sondheim began that night was the first of many the two would enjoy in a friendship that flourished until Sondheim’s passing in 2021.)
Jeffrey Saver’s question wasn’t remarkable; it merely followed the casual thread of conversation. But as he found, even the simplest questions can open the door to deeper conversations if not surprising revelations. They can reveal commonalities, invite reciprocal sharing, and build rapport with our conversational partners.
So, what to do if we’re concerned that the personal question we’re considering could be perceived as off-limits? we might first check our motives:
Am I asking so that I can somehow use the person’s disclosure against them?
Do I feel I’m owed an answer?
Am I willing to be as vulnerable if asked a personal question?
Am I asking in a spirit of genuine curiosity, caring, or willingness to help?
If the person is uncomfortable answering the question, they’ll say so (or simply avoid responding). But in the best cases they’ll sense our positive intention. They’ll accept our invitation to engage, connect, and—even if it’s only for the duration of the conversation—be known.
Jeffrey Saver’s story is excerpted from Paul Quinn’s book, The Big Ask: Unlock the Possibilities in Your Work, Life & Dreams with Courageous Requests.
Cover photo of Stephen Sondheim and Jeffrey Saver (1991) by Joan Marcus.
Closing photo of Jeffrey Saver by Grace Rainer Long.