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 | By Dan Cellucci

The art of asking questions

Recently, a new colleague shyly raised her hand on a team Zoom call and confessed that she felt like all she was doing was asking questions: “How do you know when you’re asking too many questions?” The old saying goes, “There is no such thing as a stupid question, only stupid people who don’t ask them.” As a raging extrovert, I am not embarrassed to raise my hand. After a decade in executive leadership, I can attest to people struggling more because they are unwilling to ask questions. However, not all questions are created equally, and there are three things we can do to ensure we are posing the best inquiries possible at work.


Play back specific words

Often, we can be casual with our language. While we know what we mean, our diction might create confusion with our intended audience. If we hear our supervisor or colleague explain something, but we are not sure what they meant, it helps to play back the specific words you heard and ask, “Can you explain that part to me more” or “Could you say that part differently?” Simply playing back what we hear helps our colleagues clarify their own thinking and correct any unintended miscommunication that has occurred. It also gives us a chance to confirm what we think we are hearing before jumping to conclusions.

Go backward before going forward

Sometimes the issue is not what was shared, but what wasn’t shared. We all benefit from context, yet some of us are better at sharing it than others. Particularly when hearing about a change or a new assignment, it can be helpful to ask questions such as, “Could you share with us a little more about the history of this?” or “I would love hearing a little more about the background on this.” Frequently, this is not confidential information, but it may prove consequential in everyone’s understanding and ability to fully execute the next steps.

Drive to clarity with forced choices

Colleagues can have amazing brainstorming sessions only for the momentum to sometimes die because there was no clarity in next steps. We can bring substantial value by driving to clarity with questions that set up forced choices. It might seem abrasive at first, but done with the right tone, asking questions such as, “Is Dan going to do that or is Emily?” or “Do I need to do this step first or after that step?” creates the opportunity for our colleagues to provide better direction and everyone to leave knowing the who, what, when and how with an extra degree of confidence.

By asking not only more questions but also more effective questions, we can often take our contributions to the team and to our organizations’ culture to the next level.

Dan Cellucci is the CEO of the Catholic Leadership Institute.

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