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?

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

The Power of Stories

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

My client was nervous. He was embarking on a strategic planning effort for his agency’s child abuse/neglect program. I asked about his anxieties. “Our staff are used to doing what they’ve always done, but we need to take a fresh look at how we do our work. I’ve got an idea about a new approach, but some of them may not like it.”

I asked about his idea. He said that they should focus more resources on prevention, rather than only work with children who’d already been abused or neglected. He cited statistics showing the benefits of a prevention-oriented program. I said that the numbers were impressive, but I doubted that most staff would be persuaded by data alone. “Could you tell me in a few words what the new direction is all about and why it’s needed?”

His eyes got wide and he leaned forward. “It’s like this. For years we’ve been going down to the river to pull struggling kids out of the water. But we need to go upstream and figure out how to prevent them from falling into the river in the first place.”

That was a powerful explanation: short, clear, easy to visualize. Stop the harm before it happens. After a few meetings, most of the staff welcomed the change and they started to make real gains as they went “upstream.”

When we’re trying to influence people about a change, demonstrating that we know the facts may (or may not) help get us in the door. But a short, compelling story can create meaning out of the facts. It can connect to people’s interests and values. A compelling story can clinch the deal. How?

Compelling stories usually trump facts.

Stories can build rapport. Say you’re listening to someone tell a story about her grandmother. What comes to your mind? If you grew up knowing a grandmother, you’ll probably think about her and start connecting with the storyteller. In addition, stories stick. People remember them. Memorable stories spread, as people repeat them to others. Perhaps one of the most useful benefits is that a compelling story helps people focus on one key idea, and not get lost in the details. That was the beauty of my client’s story. Here’s another example of focusing people’s attention:

On April 19, 1995, two men blew up the Alfred P. Murrah Federal Building in Oklahoma City. 168 were killed, hundreds more injured. It was horrific, a shock to the entire country. As prosecutors prepared their case they waded through thousands of pages of evidence. Merrick Garland, the chief prosecutor on the case (and later President Biden’s Attorney General) worried the jury would get lost in the thousands of pages of evidence his team could present to them. So, when he huddled with the attorneys who would argue the case in court, he gave them one simple message: “Do not bury the crime in the clutter!”

He told them to describe the families and children lost, the first responders who put their own lives at risk by rushing in to save others, the massive damage done. Present the bombers’ confession. Keep it simple, focus on the crime. Prosecutors followed his lead, telling a powerful, emotional, accurate story. The man who planned the attack received the death sentence; his accomplice is in prison with no possibility of parole.

Our brains are more receptive to stories than to numbers and statistics. I’m convinced that’s one reason why the Bible has been read by countless millions; it’s a collection of wonderful stories about human beings with great strengths and no shortage of flaws, people we can relate to. And stories help create meaning.

There are, of course, many people who are quite logical and need to make decisions based on hard data. That said, trial attorneys sometimes remind each other that “the person in court with the best story usually wins.” And when you think of superior speakers you’ve seen, or leaders you admired, chances are they excelled as story tellers.

Trial lawyers say, “The person in court with the best story usually wins.”

Finally, stories can provide compelling metaphors. I once heard a fundraiser tell this story about two bodies of water in Israel.

“The Sea of Galilee is beautiful. Its water is deep blue, it’s full of fauna and flora. Life exists. The Sea of Galilee is fed by the Jordan River on the north. The Jordan continues flowing south from the Sea of Galilee and ends in the Dead Sea. The Dead 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? For every drop of water flowing 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, most of us quickly took out our checkbooks or credit cards!

Stories can touch our emotions and connect to our values. They help people imagine possibilities. The next time you’re trying to persuade someone to consider a new idea, try letting go of your left brain and identify a story that captures your message. If you don’t think you have a talent for this (many of us don’t), no problem. There are excellent books about the creative use of stories. One of the best is The Story Factor by Annette Simmons. She identifies six types of stories, how they connect to people, with numerous examples of each.

What’s your story?

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Leading by Indirection

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

I love to sail. As any decent sailor knows, you can’t sail directly into the wind, even if that’s where your ultimate destination lies. But you can usually get there by “tacking” back and forth, learning how to read the currents and breezes, keeping a firm hand on the tiller and paying attention to timing.

Leaders often face the same dilemma. They may have a clear goal in mind, only to learn that they’re flying into the wind. Powerful constituents oppose you. Perhaps your staff doesn’t buy in, or there’s no funding for the idea. And sometimes the stars seem aligned, and then a major event occurs and everything else is put on the back burner. These speed bumps occur even more often during the kind of disruptive times that we’re experiencing today. There are myriad reasons why change requires leaders to be flexible, think creatively, and seek other ways to achieve their goal. In short, they need to learn the art of “leading by indirection.” Here’s an example:

Karen, a social services manager, led a division that dealt with child sexual abuse. This is a terrible and complex issue, often involving other organizations like police, health departments, and prosecutors. She met with leaders of those agencies and they all agreed they should work more closely together, but nothing was changing. The leaders were focused on other demands. Since her direct approach wasn’t working, Karen took a different route.  

She did her homework and learned of a collaboration model that was working in other communities. It involved co-locating professionals from agencies that spend the most time on child sexual abuse. Housing these professionals in the same space helps build relationships, which leads to much more collaboration and information sharing. Now that she had a proven model to offer, could she convince the agency leaders to try it?

Rather than meet with the agency leaders again, she found middle managers in the three key agencies who worked on child sex abuse issues and shared her concern about the need for more collaboration. They liked the co-location model. Then she learned about a co-location training session being offered in another state. The three managers agreed to attend and planned to meet at the session. Karen suggested they drive there together. “Let’s save some gas, the meals will be on me. It’ll be a fun road trip.” Even though two of the three didn’t know each other, they agreed. That road trip became a team-building activity. They had time to learn about each other outside of their work responsibilities. And the trip back from the training gave them several hours to compare notes on what they’d learned and how to move forward.

Long story short: The middle managers sold their agency directors on the co-location idea, they tried it on a pilot basis, and continued it as they saw success. More information sharing meant more kids were being rescued from terrible situations and more perpetrators getting caught. Karen had learned the art of leading by indirection.


Those who learn how to lead indirectly are usually good at: 

  • Demonstrating situational awareness
  • Being firm on the goal, flexible on the approach
  • Reading people’s readiness
  • Timing, and “ripening”
  • Being pragmatic

When Karen’s initial efforts toward collaboration went nowhere, she considered the situation. The agency directors weren’t responding, so she was flexible and looked for a different strategy. Courting the managers made sense; they were already eager for collaboration and just needed someone to offer a way to get started. Urging the managers to drive together allowed their ideas to “ripen,” which was critical. And Karen was very pragmatic. She’d originally hoped to try the model for one year. When two of the agency directors balked, she suggested they first pilot the idea for several months, and they agreed. Karen understood the importance of timing.

            Karen was a middle manager; she didn’t have the authority to direct the other managers to work with her. But even leaders who have that authority often need to lead indirectly. Here’s an example from the Hebrew Bible:

In the book of Exodus, when the Pharaoh finally allows the enslaved Israelites to leave,  God is ready to bring the people to the promised land. But God doesn’t lead them in that direction. Au contraire, God leads the people south, away from the promised land. Why? The direct route is occupied by a powerful tribe. God says, “The people may have a change of heart when they see war and return to Egypt.” God is reading the situation as well as the people’s readiness for battle. The timing is wrong, God is flexible and changes course.

People trying to speak out against wrongdoing often lead by indirection when the direct route hasn’t worked. A classic example has to do with unidentified flying objects. A small, secret Pentagon office has tracked reported sightings of UFOs since 2007. Numerous sightings were deemed credible, meaning there was video evidence showing the objects moving at remarkable speeds and making sudden changes in ways that had never seen before and couldn’t be explained. The office’s director, Luis Elizondo, studied the videos and interviewed several Navy pilots who’d witnessed these phenomena and were concerned that the government wasn’t doing enough to investigate. He urged his superiors to reveal the office’s existence, arguing that UFOs are real, we’re studying them because they have national security implications, the public and Congress should know. Nobody listened to him.

So in the fall of 2017 he resigned and then told the New York Times about the office and its evidence of UFOs. The Times investigated the allegations and then printed the story. It prompted enormous public interest in the country and on Capitol Hill. The government finally acknowledged the office’s existence, and members of Congress began demanding more information about UFOs. (“60 Minutes” ran a segment about this on May 16, 2021, and the Times story is at

It’s important to note that leading by indirection as I’m describing it isn’t unethical. These leaders weren’t trying to manipulate people, nor were they hiding their true intentions. They had a clear goal and were open about it, the direct path to their goal didn’t work, so like good sailors they tacked.

Let’s take another look at some characteristics of people who lead indirectly. As mentioned above, they are good at: 

  • Demonstrating situational awareness
  • Being firm on the goal, flexible on the approach
  • Reading people’s readiness
  • Timing, and “ripening”
  • Being pragmatic

What about you? How would you assess yourself on these five characteristics? Which ones would you like to improve?

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