The Power of Asking Good Questions

The best leaders understand the power of asking great questions. We often work with leaders who are under the assumption that they need to have all of the answers. But in today’s rapidly changing world, leaders cannot know everything, and there is a great opportunity to learn from others. That is where the often-overlooked skill of asking thoughtful questions is a missed opportunity. 

Part of our work involves teaching leaders how to be great listeners and even better at asking probing questions to gain deeper insights. During a recent leadership workshop, participants were put into small groups. Two group members were asked to engage in an exercise in which one person interviewed the other, attempting to understand their unique perspectives on a business challenge. The other participants observed and noted whether the interviewer successfully elicited insights. 

After the exercise, the observers identified moments when the conversation could have mined much more meaningful information – but didn’t, because the interviewer either asked a close-ended “yes” or “no” question or didn’t tune in to the speaker’s emotional cues and follow their excitement about a topic. They noted that the interviewers tended to jump to ask leading questions based on the responses they were hoping for, which hindered the deeper understanding they could’ve obtained in these moments. It was an ah-ha moment for the group. 


Asking good questions is an exceptional practice for unlocking value in organizations.


Surprisingly, the group members, all senior leaders, had never thought about or had the training to ask questions and attune to the person speaking. Questioning is an exceptional practice for unlocking value in organizations; however, it requires leaders to unlearn the process of naturally telling or suggesting ideas to pausing and asking a question to learn from others: It sparks learning and ideation, fuels innovation and performance improvement, and builds empathy and trust among team members. And it enables intergenerational learning, which is more important than ever. It's important to be open-minded to ensure leaders understand challenges and opportunities from multiple perspectives. 

For some people, being curious comes easily. Their natural inquisitiveness, emotional intelligence, and ability to read people enable them to ask great questions effortlessly. But most of us aren’t as good as we could be at asking questions. And often, the questions we pose don’t facilitate nuanced understanding.

The good news is that with a bit of practice, we can hone our questioning skills, encouraging rapport, trust, and understanding —a virtuous cycle. It is helpful to draw on insights from behavioral science research to explore how the way we frame questions can dramatically change the conversation. 

To become a better questioner, start asking more questions. And consider how and when posing a question can be most beneficial. 

Ask follow-up questions. 

According to researchers Allison Brooks and Leslie John, follow-up questions signal to your conversation partner that you are listening and want to know more. People interacting with a partner who asks follow-up questions tend to feel valued and understood. And the good news is that follow-up questions don’t require preparation. 

Ask open-ended questions. 

Open-ended questions are the opposite of questions requiring only a “yes” or “no” response. Open-ended questions promote conversation. When asked in a calm, neutral manner, open-ended questions help leaders gather critical information about the challenges and opportunities their direct reports face. Open-ended questions promote confidence and trust in the relationship. The direct report receives an unspoken message that their thoughts are valued and respected. The relationship between the leader and direct report deepens, strengthening workplace creativity and collaboration. 

Five useful open-ended questions to keep in your back pocket:

  • What are you trying to achieve?

  • Where have you seen this before? 

  • How might this impact the situation?

  • When can you do this?

  • Who needs to be involved, and why does this matter?

Ask bold questions.

John Hagel III. The author of The Journey Beyond Fear suggests asking big questions. For example, 

  • What game-changing opportunity could create more value than we have previously delivered?

  • What are some emerging unmet needs of our customers that could provide the foundation for an entirely new business?

  • How could we leverage the resources of third parties to address a broader range of the needs of our customers?

  • How could we harness sensor technology to create more visibility into how our customers use our products and use this information to deliver more value and deepen trust with our customers? 

These broader questions stimulate thinking outside the box. And Hagel suggests you can bolster your credibility by providing evidence of those long-term trends that underlie your question – for example, identifying the emerging technologies that are likely to offer new opportunities or market shifts you can take advantage of. 

By asking questions as a leader, you also communicate that curiosity and inquiry are essential. You inspire people to identify new opportunities and ask for help when needed. These behaviors lead to a culture of learning, which is critical since the institutions that will thrive in the future must encourage everyone to learn and adapt quickly to optimize their effectiveness and value. 

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