The Power of Probing Questions

In 1983 Apple Computers was looking for a new CEO. Steve Jobs was brilliant when it came to new products, but he was a terrible manager. So, the board asked Jobs to find a promising CEO. After interviewing 20 candidates, Jobs decided that Pepsi executive John Sculley was his choice. When Jobs asked him to lead Apple, Sculley said no. He didn’t want to leave Pepsi. Jobs kept asking, Scully kept declining.

Jobs made a final pitch. He asked Sculley one question: “Do you want to sell sugar water to teenagers for the rest of your life, or come to Appel and change the world?” Sculley said the question landed like “a punch to the gut.” He took the job. Years later Sculley reflected on his decision: “I came out of the world of corporate combat. If Pepsi went up, Coke had to go down. It was a zero-sum game. These guys [at Apple] were talking about a ‘noble cause.’ I had never heard those words before. It stuck with me.”

Sometimes the best way to get someone to change is to take the direct route; say what you want and give them a reason. But that often doesn’t work. If you want your spouse/partner, your adolescent kid or a subordinate to change a habit, it can get complicated. There’s a back story; you need to think about timing and whether it’ll just make person defensive; about your ongoing relationship. Rather than telling the person you want them to change something, what if you were to ask this person what I call a probing question? Here’s an example:

When I started writing a new book in 2019, I asked Warren Blank and two others to read and critique drafts of the manuscript. Warren is a gifted instructor and author. After he read the book’s Introduction, I learned that he’s also a skillful coach. When I asked him a few questions about the Intro, Warren said, “Actually, Russ, I wanted to start by asking you a question. If you had to summarize what your book is about in 30 seconds, what would you say?”

After I talked for a couple of minutes, I laughed. Then Warren joined in. It became clear that I couldn’t state the book’s overriding purpose in a few words. Warren had asked one simple (and fundamental) question. He didn’t have an answer in mind. He thought that the Intro was fuzzy, but rather than say so he asked his question.

Asking a probing question – one that asks the person to reflect on what they’re doing or how they’re thinking – has many advantages. It’s an invitation, not a demand. The person is free to think without pressure. It helps the person reflect on their assumptions and beliefs. Sometimes, it leads to enormous change. For instance:

In 1988, when leadership expert Jim Collins was in his first year on the Stanford University faculty, he wanted feedback on his teaching. So, he asked an older colleague, John Gardner, for his thoughts. Gardner, former Sec. of Health, Education and Welfare and founder of Common Cause, knew the power of probing questions. He made it brief: “Jim, it occurs to me that you spend too much time trying to be interesting. Why don’t you invest more time being interested?” Later, Collins reported that this one question changed his life. He needed to become an active learner and stop trying so hard to impress others.

When a probing question is part of a story, one that grabs us, it can be especially effective. That happened at a fund raiser I attended. The attendees had all decided to donate, the only question was, how much? When the leader made his pitch, he ended with this story:

“The Sea of Galilee is beautiful. Its water is deep blue, it is full of fauna and flora. Life exists. Trees line its banks. The Jordan River feeds the sea, coming down from the north. The Jordan continues flowing south from the Sea of Galilee. and ends in the Dead Sea. This sea is well named. There are no fish, no birds above, no trees along its banks. Nobody would ever drink its water.”

What makes this enormous difference? The Jordan River? The soil? The people? No. So, what is the difference?

“For every drop that flows into the Sea of Galilee, another drop flows out. The Sea of Galilee gives as it receives. But the Dead Sea only keeps. It has no outlet. Every drop stays there. The Sea of Galilee gives, lives, and flourishes. The Dead Sea keeps everything, shares nothing and is dead. Which kind of sea do you want to be?”

As you can guess, I donated more than I’d expected! I’m sure many others did the same.
Sometimes a probing question can be used to reframe a conversation when it’s not going the way you want. Here’s a great example:

A musician named Calvin Earl was trying to line up support for a Congressional resolution to ‘Recognize the African American Spiritual as a National Treasure and honor the enslaved Africans for their gifts and contributions to our Nation.’ When he asked one Congressman to sign on as a co-sponsor, the man answered, “We’ve never had slaves in America, and I don’t know what a spiritual is!” Calvin described what happened next:
“I just took a deep breath, understanding that his intention was to be demeaning to me. I explained that a spiritual was an original song created by the enslaved Africans here in America. Then I said, ‘Did your grandmother sing one of the spirituals to you as a young boy?’ At that point I began singing the African American spiritual ‘Swing Low Sweet Chariot.’ After I sang a few bars of the song, he asked me to hand him the legislation and he signed on as a co-sponsor.”

A changed heart? Of course not. That wasn’t Calvin’s goal. Rather than take the bait when the man said, “We’ve never had slaves in America,” he reframed this as a part of the man’s memory. He changed it from the political to the personal.

Finally, the Torah includes several probing questions. One occurs near the beginning, after Adam and Eve eat the forbidden fruit, become frightened and try to hide from God. God calls out, “Where are you?” It’s a rhetorical question; God obviously knows where they are. What did the question mean? Some religious commentators suggest that God is asking something specific: now that you have disobeyed me, have you changed your mind? Do you regret your act? Others believe that “Where are you?” is far broader. It is God’s question to us all: Where are you in the world? What have you accomplished?

So … where are you? What probing questions have helped you rethink something important about your life? Is there a probing question you want to ask someone else?

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Adapted from Russ’ new book: Loss and Discovery: What the Torah Can Teach Us about Leading Change. [more info]