IES 05.22.19

Briefing:  Wednesday, 22 May 2019

Inside the Executive Suite

(Tips, Tricks, and Techniques used by the Nation’s top Executives… to get things done.)

What Questions Do You Have?

If you haven’t noticed, we love excellent questions.

They boost creative thinking and lead to better results.

This fascination with questions is why we frequently feature lists of them within Inside the Executive Suite.

We’ve seen that in answering better questions, people uncover new insights and shine a light on overlooked opportunities.

In a recent article for The Wall Street Journal, MIT’s Dr. Hal Gregersen recounted six tactics from his book Questions Are the Answer for creating an environment where great questions, and the answers they generate, are quick to flourish:

  • Pick the right question types to generate creative ideas
  • Make it a habit to ask questions
  • Expand the range of questions you use
  • As a boss, don’t supply the immediate answer to questions
  • Before imagining answers, imagine questions
  • Make it attractive to ask you (the boss) questions
  1. Picking the Right Questions

All questions are not created equal. For the highest-impact questions, Gregersen recommends ensuring they comprise five characteristics:

  • Reframe: Offer a new thinking perspective
  • Intrigue: Capture attention and trigger creativity
  • Invite: Others are drawn to participate through answering
  • Open up space: Suggest many possibilities because there is no one right answer
  • Are nonaggressive: Nobody is targeted for derision or discomfort through the question

Our Suggestion for #1:

Gregersen’s tip is to keep a daily log of questions you use that meet all five criteria. We want to suggest a twist on the concept, one we use: as you develop lists of questions that you like, monitor how they perform on each of the five areas. This qualitative assessment is helpful in guiding future situations.

From a professional standpoint, we consider high-performing questions to be those that trigger lots of productive conversation, new ideas, and fully engage a group. On a more personal level, we see questions that definitively get people to participate, even in challenging situations, as highly productive.

  • Habitually Asking Questions

The classic profile of a boss is of someone that tells others what to do, and not someone who asks for input and ideas before acting. Gregersen suggests that many executives are under-using their intellectual and humility muscles for asking inviting questions. His recommendation, in the early days of trying to adapt your style, is to copy questions from other sources, including management experts. Additionally, he suggests taking the organization’s strategic priorities and turning those into frequently asked questions. For instance, if innovation is one of your organization’s strategic priorities, pepper daily conversations with questions that lead employees to keep innovation top-of-mind and to routinely identify ways to improve products and processes.

Our Suggestion for #2:

Asking questions that provide strategic focus and invite daily thinking about strategies is a good way to stimulate implementation on your strategies. While you will want some variety in questions, returning to just a couple of core questions every day makes them routine. In this case, routine is good, because employees and project teams will better understand the most important expectations. They will also begin to use those same questions in their work. This will help them make sure they are exploring on-target possibilities and delivering on management expectations. They’ll also more efficiently and effectively be able to consider routine questions to prepare for what they know they’ll be asked.

  • Growing the Variety of Questions

As in so many of life’s situations, the best answer is, Yes and, rather than simply yes or no. While routine, familiar questions are tremendously productive, Gregersen recommends continually adding to your go-to questions list, with questions that add variety, accommodate new business areas, and deepen your command at using questions as a learning and outreach method.

Whenever you see something new or different, he says, ask questions of someone else about it instead of commenting. Engaging others for their perspectives will yield deeper insights than if an executive simply goes around making declarative statements about changes within the business.

Our Suggestion for #3:

If you are intent on developing new questions all the time, we recommend reading as many case studies as possible. Explore these two areas:

  • Questions the leaders and organization’s in the case study specifically ask.
  • Questions that you can imagine these same leaders asking, even if they are not noted in the case study.

This is our favorite source for developing new questions. When you see a company that’s on a smart path and making moves that could apply to your own, it’s hugely productive to point their questions at your organization. You’ll see a variety of new ideas emerge. If the detail is provided, also take note of what types of people the case study companies involve in developing their strategies. Are you involving individuals with the same responsibilities in developing your strategies?

  • Stop Answering First

This strategy goes hand-in-hand with the second one. As you cultivate an environment where people are asking questions more frequently, don’t, as the boss, jump in to answer. Instead, respond by asking questions in return, focused specifically on prompting others to share more of what they know, think, and imagine.

This entails asking how team members considered objectives in forming ideas, suggestions for implementation opportunities and paths, and who else to involve in further ideation or implementation.

Our Suggestion for #4:

When someone asks a question, it’s a challenge to not start firing off ideas and/or recommendations. One way to counteract this is to devise informal meeting and interaction rules of engagement that create room for others to share. One simple strategy is to ask, as often as possible, “Can you tell me more?” Another one that we’ve mentioned previously in this column came from a senior executive who always started by asking the most junior team members for their thoughts. This gave them freedom to share their thinking without influence from the boss.

  • Many Questions in a Little Time

Dr. Gregersen suggests approaching a challenge by thinking through all the questions you can ask about it. He suggests taking four minutes right away and applying a brainstorming approach to quickly come up with15-20 new questions. He reports stronger insights, increased group energy, and new possible solutions emerging from this exercise.

Our Suggestion for #5:

This is definitely a novel idea. We always try to brainstorm and test the questions upfront that we use with any group. This is driven by the desire to have the group find success right away with questions that we’ve at least imagined working. Dr. Gregersen’s technique is so intriguing that we plan to use it as a group exercise this week and see what happens. We suggest you find an opportunity to do the same.

  • Inviting and Rewarding

The final strategy emphasizes the importance of making team members comfortable in asking challenging questions of you. That requires an executive to embrace humility, openness, and the understanding that everyone has a lesson to teach you. The questions and productive conversations that this approach generates are a fruitful way to practice these business virtues.

Our Suggestion for #6:

Relative to rewarding your team for asking questions, pay attention to what they prize. Then make that part of the associated reward. Maybe team members who ask the best questions are assigned more leadership roles or are invited to senior leadership meetings to actively participate. Maybe money is the thing, and you can have them select a list of great questions that the team has used for the month. Let them vote on their favorites and award gift cards to the individuals who asked the questions.


No one, not even seasoned executives, learns while talking. Active learning comes through asking questions of others and engaging them in productive conversations to improve the diversity, soundness, and actionability of the team’s thinking.

Link: The Wall Street Journal – To Be a Better Leader, Ask Better Questions by Dr. Hal Gregersen

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