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3 questions leaders should ask daily

Effective leadership requires effective question-asking. Sometimes, the job of a leader can feel as if it is infinitely more answer-providing than question-driving. Despite that, the strongest leaders recognize that the questions more than the answers tend to significantly impact the achievement of those they serve. With that in mind, here are three questions that leaders should ask themselves daily. (In complete honesty, I don’t do this as often as I should.)

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Effective leadership requires effective question-asking. Sometimes, the job of a leader can feel as if it is infinitely more answer-providing than question-driving. Despite that, the strongest leaders recognize that the questions more than the answers tend to significantly impact the achievement of those they serve. With that in mind, here are three questions that leaders should ask themselves daily. (In complete honesty, I don’t do this as often as I should.)

What can I do today to help you meet your goals for tomorrow?

This question has the dual benefit of asking people about their hopes and dreams while also making it clear that you, as the leader, are ready to support them. It also emphasizes the leader’s immediate support so that a colleague can grow into the future. An important piece to mention with any of these questions is that if you ask them, you must be willing to hear the answer. A question asked without commitment to connect from the asker will detract from relationships rather than build them up. 

I sometimes get an immediate response when I ask this question or something similar. Those are great situations, because they clarify how I can do a better job supporting the people I work with. Sometimes, though, an answer isn’t clear. And that’s OK, too. This question’s value is both the potential responses it leads to and the open invitation to provide constructive and critical feedback on my work as a support. 

This question is also great because it is reflexive and can be used to prompt reflection. When we turn this question on ourselves, we are checking in on what we can be doing differently today to help us reach future goals. There’s value in that, too.

What’s on your mind?

A much different way of asking, “How are you?” this question pushes others to consider what is occupying their thinking. Because of the level of thought required to answer this, a simple “I’m good” or “Fine, how are you?” won’t work. 

That’s not to say asking, “How are you?” is bad, far from it. I regularly ask people how they are doing. However, I believe that asking people what they are thinking about provides us as leaders with more fuel for the leading and learning fire. Getting a sense of how people are doing is important, as well as getting a sense of what they are thinking about. Sometimes even more important. As a leader, knowing what a colleague is processing helps me understand what I can be thinking about to help them and helps me check my own thinking. 

This question also requires us to be comfortable with wait time. Verbalizing what’s on our mind at any moment doesn’t often come quickly. And, for those who process while they speak (like me), this question can lead to a web of interconnected ideas, requiring the question-asker to help refine details through prompts such as “Tell me more about … or “I think I heard you say . . . “ 

Despite the added work that comes with this question, knowing what, why and how people think prepares a leader to provide appropriate support, adjustments, etc. And, at the core, that is what leadership should be all about.

What surprised you recently?

I don’t ask this question as often as I should. It always leads to interesting responses and new, and often important, questions. Despite what we might think initially, surprises, at their core, are always good. They push us out of our usual patterns of thinking and acting and help us to gain perspective we didn’t have only a few moments before. 

By adding in the “recently,” we get at more relevant and connected surprises, things that have happened to people in the near past that could impact the present and future. 

Some of my most interesting discussions with colleagues came from unexpected happenings. While the result might not be positive at first, I’ve found that these surprises always lead to changes that make our work better and lead to more positive outcomes in the long term. It’s one of the main reasons I’m a fan of surprises. (Although, I sometimes have to allow myself some time to take a step back and look beyond the surprise’s impact on me.)

If we were to ask these three questions daily, I think our roles as leaders would be more beneficial for everyone. Of course, they aren’t the only three questions we should ask people daily. I like these as foundations since they are so focused on getting people to think about their needs and experiences. That is always an important step toward leaders helping systems improve their work. 

This article originally appeared on SmartBrief.

Fred Ende is the director of curriculum and instructional Services for Putnam/Northern Westchester BOCES in Yorktown Heights, N.Y. Ende currently blogs for SmartBrief Education, and his two books, “Professional Development That Sticks,” and “Forces of Influence,” are available from ASCD. Connect with Fred on his website or on X (formerly known as Twitter).


Guest Editor