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Ideas Made to Matter


How leaders can get the most out of asking questions


Before you judge someone, walk a mile in their shoes. Drive a couple hundred miles in their car, and it turns out you also can learn a lot. In the fall of 2022, Uber CEO Dara Khosrowshahi slid behind the wheel and experienced firsthand what it was like to be a driver for the ride-hailing platform — traffic and all.

“The insights gained to make that driver experience better for Uber were exponential in nature and size and impact, because the CEO of Uber actually put himself in conditions where he was wrong and he was uncomfortable, and he was very reflective about it,” said MIT Sloan senior lecturer “And then he did something about the new questions that were emerging.”

There’s power in putting ourselves in a situation that provokes questions we normally wouldn’t ask, Gregersen said during a recent MIT Sloan Executive Education webinar. Among Gregersen’s research focus is the power of questions. He coined the terms “question burst” and “catalytic questioning” and is the author of the book “Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life.” 

In Khosrowshahi’s case, the executive didn’t know about some of the struggles drivers faced while using the app until he’d experienced them himself. Getting involved and asking questions became a tool for navigating the unknown.

In the webinar, Gregersen and Peter Åberg, managing director of duct manufacturer Nordfab, shared tips for how leaders can get the most out of asking questions.

“Helping others, I think, is the best lesson of life: How can I help you? How can I help my team?” Åberg said. “Questions are the answers.”

What to ask and when to listen

Leaders don’t have to ask complicated or even company-focused questions to break down barriers with employees.

Åberg said he began asking himself how he could help improve the lives of the people who reported to him. Focusing only on “me, me, me” can create a toxic team environment, he said. Instead, leaders should be learning about their workers’ lives, and their ups and downs.

Interacting with employees and being visible in their workspaces — rather than hiding in a C-suite office — helps create a trusting environment where workers feel comfortable raising their hands, particularly when something isn’t working. Relatedly, leaders must develop the ability to accept input and criticism and to listen and without interrupting when someone is sharing something.

Try question bursts and question audits

Even if a leader builds a trusting environment for asking questions, a team can get stuck on a problem. When this happens, Gregersen recommends trying a question burst — the process of asking enough questions at a rapid pace to become uncomfortable enough to generate fresh ideas.

The question burst process helps participants — particularly leaders, who are paid to answer questions — by forcing them to stop talking and just listen.

Gregersen has previously said that people usually experience one of three outcomes after participating in a question burst: a more positive state of mind about their challenge that leads to new, valuable ideas; a feeling that the problem is much bigger than they expected; or a realization that they are themselves part of the problem.

Not only do question bursts help reframe a challenge and generate at least one new idea Gregersen said, but “the act of doing it actually increases human connection and increases a sense of psychological safety.”

Question audits are another tool available to leaders. This involves writing down every question they’re asked in a day — the questions other people ask, and the questions in their heads that don’t get asked. Those internal questions can veer into the “energy-sucking” kind, Gregersen warned, such as “Will I ever measure up and matter? How can I avoid getting hurt? Will I ever get it all done?”

“Those kinds of questions are not really helpful,” Gregersen said. A more constructive question would be, “What could I do right now to make positive progress on this project?”

Teams can also conduct question audits. Consider recording a conversation with your team or having someone audit the conversation and capture the questions that are asked.

Asking questions in a team setting and learning the peaks and valleys of everyone’s lives, their values, and how they overcome mistakes helps build knowledge about how each person acts in positive or stressful situations, Åberg said.

“Asking questions is an individual effort and a team effort, on a private and on a professional level,” Åberg said. “Every question is a good question; dare to ask them.”

For more info Meredith Somers News Writer (617) 715-4216