by Dennis Gershowitz
Date Published June 10, 2024 - Last Updated June 10, 2024

I read an article in the May-June issue of HBR titled “The Art of Asking Smarter Questions. In this article, the authors (Arnaud Chevallier, Frederic Dalsace, and Jean-Louis Barsoux) discuss “that business professionals are not formally trained on what kinds of questions to ask when approaching a problem.

They went on to explain the five types of questions to ask during strategic decision-making: investigative (these aim to gather facts and data), speculative (these encourage creative thinking and exploration of possibilities), productive (these focus on action and solution), interpretive (these delve into meaning and context), and subjective (these explore personal perspectives and emotions).”

Jeff Wetzler, author of Ask: Tap into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life, says people do not often ask enough questions, “The biggest reason is that we don’t realize the question that needs to be asked in the first place,” he says. “We size up situations so quickly and jump to conclusions. We feel that those conclusions are reality, and it doesn’t occur to us there is something we don’t know. If you feel certain about something, it’s logical that you wouldn’t ask questions.”Another reason people hold back from asking a question is that they overestimate how the other person is going to feel about being asked, says Wetzler. “We think the other person is not going to want to be put on the spot, but research shows that people actually appreciate being asked questions to express who they are and what they’re going through.”

I began to reflect on the valuable points these authors made and came to realize that there is likely a lot we can all do to improve how we ask questions. I strongly agree with the authors that in these turbulent, ever-changing, and agility-requiring times, we can all benefit from being able to ask smarter questions. Considering this, I chose to add thoughts from my experience on additional steps we should take:

  • Before any meeting or discussion, we should prepare by researching the topic and understanding the context. We will then be able to dig deeper into the subject matter. We must understand clearly what we are expecting from the question(s). John Maxwell continually points out the value of preparedness and that there are no shortcuts to success. In fact, he often quotes Henry Ford, “Before everything else, getting ready is the secret of success.” Talent and preparation often lead to success.

  • One of the cardinal rules of conversation (questioning) is to be an Active Listener. This requires that we listen attentively to the conversation and responses. This means we manage our personal biases, facilitate an open exchange, pay attention to body language and emotions, and acknowledge and look for feedback. We should actively engage with the answers we receive, ask follow-up questions to clarify or expand upon points of interest, and ensure that all involved understand we have listened to them, and they are heard. 

  • We must be articulate, clear and concise All involved need to understand the questions we ask. There is no room for jargon, complex words, etc. I also suggest that open-ended questions encourage more responsiveness and often a livelier discussion. 

  • It is imperative that we create an environment in which all feel comfortable asking questions and participating

  • It is important for us to use empathy and to consider the perspectives and feelings of others in the questions we ask. This demonstrates we value the experiences of others. I find this will often lead to a more meaningful exchange.

  • We must be strategic. Asking smart questions will be strategic and we will be successful in uncovering underlying assumptions, identifying potential risks, exploring alternative solutions, and hopefully engaging all

Over time, by asking smarter questions, we will see how they uncover opportunities, can be triggers to the next level of thinking, can be a tool for engaging the team, and will often lead to collaboration among team members. Incorporate the strategy of asking smarter questions as you look for better outcomes for your team and your business. Think about beginning with “What can I do as a leader to ask smarter questions?”

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