Leading with Questions

"Questions can elicit information, of course, but they can do much more.  Astute leaders use questions to encourage full participation and teamwork, to spur innovation and outside the box thinking, to empower others, to build relationships with customers, to solve problems and more."

- Leading with Questions, page 1

The book covers the power of questions, how to ask questions effectively, and provides a guide for leaders. While the topic can be of use for anyone who uses conversation to further projects and relationships, there’s a specific focus on how leaders can use questions and in particular, how they create a questioning culture.

Questions are not only helpful on a one-to-one basis, but can help a team move forward, or help an organization to:

  • Become more adaptable and ready for change
  • Share responsibility
  • Encourage learning


The Big Idea

The Big Idea: The biggest takeaway from the book

Ask questions, even if it scares you

"Great leaders are humbled by the realization of all they do not know."
- Leading with Questions, page 46

What’s in the way of leaders asking more and better questions, right now?

  • We’re protecting ourselves – we look smarter if we don’t ask!
  • We’re too busy
  • We may lack skills in asking great questions
  • We may work in environments that discourage questions

Corporate cultures can discourage questions. As leaders, we’re supposed to know everything. We may be afraid to admit we don’t know everything. But, if we’re afraid to ask questions, how will we learn what others can share in terms of new market information, fresh perspectives, or innovative ideas?

Insight #1

An actionable way to implement the Big Idea into your life

Better questions, better thinking

"Questioning leaders are confident and willing to challenge beliefs and assumptions."
- Leading with Questions, page 59

As an extravert and a people person, I’m always willing to share my story, my ideas, and my perspective (perhaps a little too willing at times!). This book made me realize that not everyone feels the way I do.   Some people are waiting to be asked for their ideas. Cindy Stewart, a former factory worker, shares a story of overhearing the management team discussing a bottleneck problem on the factory floor. As they wrestled with solutions, Cindy thought “I wish they would ask me.” Imagine what a difference it would have made if they had asked. Cindy’s managers missed an opportunity to learn, to empower a staff member, and to quickly find a workable solution.

By asking great questions, leaders can develop their team members and:

  • Cause people to focus or stretch, for example: “What are you trying to accomplish?”
  • Create deep reflection, for example: “How is this supported by our core values?”
  • Challenge taken for granted assumptions, for example: “Why do we do it this way?”
  • Generate positive and powerful action, for example: “How can you take a leadership role in resolving this issue?”

What questions could you ask, that will take the conversation beyond the routine? Consider your next opportunity to take the conversation to a new level during you next meetings or telephone call.

Insight #2

An actionable way to implement the Big Idea into your life

The art of questions

"The search for great questions is never completed."
- Leading with Questions, page 76

Here’s the action: keep looking for questions that will open doors, challenge assumptions, and promote creative thinking. So, what makes a great question?

Start with asking open-ended questions that allow others to tell their story.  Questions that elicit a short response, like yes or no, give others limited room to share their perspective.  Open-ended questions on the other hand help to establish, gather information, and expand understanding.

Asking open-ended questions is natural for children, who love to ask: “Why?”  Let’s take a leaf out of our own childhood books and ask that question. As leaders, when we ask why, it forces people to look at cause and effect.  Continuing to ask the question allows us to dig deeper into the layers of the situation and generate insights.

When using questions to open doors, it’s important that your team feels it’s safe to answer. Here’s where mindset comes in. Do you have a learner mindset or a judger mindset?

The learner mindset tends to be optimistic and presupposes new possibilities, a hopeful future, and sufficient resources. The learner mindset asks: What’s good or useful about this? How can we stay on track?

Conversely, the judger mindset focuses on the past to apportion praise or, more likely, blame. The judger mindset asks: Whose fault is it? Why can’t you get it right?

Considering the need to ask questions that are open and have the learner mindset, here are some examples of questions you might use:

  • What other options can we think of?
  • How do you feel the project is going?
  • Tell me more about…
  • What resources have we never used?
  • Can you elaborate on why this is happening?
  • What would success look like?

Questions can empower or constrain. Questions can open up or shut down conversations. You can use questions to create a culture of learning or a culture of defensiveness. As a leader, the questions you ask can not only create benefits for you, but for your whole team and for your organization.

What are some examples of great questions you’re planning to ask in your business or organization?

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Susan Gregory

ABOUT Susan Gregory

I am fascinated by what motivates people, how we communicate with each other and we can perform at our best. As a corporate trainer, I love to learn and share techniques to help people to build skills in communicating effectively, managing work and priorities, and thinking creatively...
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