5 Questions Leaders Should Be Asking All the Time

The best teachers all have at least one thing in common: they ask great questions.

Leaders should ask these questions both on a daily basis and during critical moments. Of course, these aren’t the only questions to ask; context certainly matters. But I have found these five to be a very practical and useful way to ensure understanding, generate new ideas, inspire progress, encourage responsibility, and remain focused on what is genuinely important.


The best teachers all have at least one thing in common: they ask great questions.  They ask questions that force students to move beyond simple answers, that test their reasoning, that spark curiosity, and that generate new insights. They ask questions that inspire students to think, and to think deeply.

As a business leader, you might have years of experience and the confidence of your organization behind you, so it may be tempting to think that your job is to always have the right answers. But great leaders have to inspire the same curiosity, creativity, and deeper thinking in their employees that great teachers inspire in their students – and that starts with asking the right questions. Any answer is only as good as the question asked.

As a dean, I find it useful to remember the statement often (perhaps spuriously) attributed to Albert Einstein that if he had an hour to solve a problem, and his life depended on it, he would spend the first fifty-five minutes determining the proper question to ask.

Yet asking a good question is not an easy task.  It requires us to look beyond simple solutions and to encourage colleagues to do the same.  It requires courage and tact, to generate hard questions without sparking defensiveness, as well as being open to new ideas and to questioning untested assumptions. It requires being willing to listen and follow up.

I believe there are some essential questions that are useful across a variety of contexts, including, and perhaps especially, the workplace. In fact, I gave a commencement speech last year on this topic, suggesting to students from the Harvard Graduate School of Education that there are really only five essential questions in life. Although the audience was future educators, I believe these questions are equally valuable for anyone in a position to lead or influence others.

“Wait, What?”

Too often, we jump to conclusions without having enough information. We listen just long enough to form a quick opinion, and then we either endorse or oppose what has been said.  This puts us at risk of making faulty judgments, leaving key assumptions untested, and missing out on potential opportunities.

Leaders (as well as their employees) need to be able to ask colleagues and direct reports to slow down and explain in more detail what is being proposed, especially if something doesn’t quite sound right or seems too easy to be a lasting solution. Asking “Wait, what?” is an exercise in understanding, which is critical to making informed judgments and decisions—whether in the office or the boardroom.

“I wonder why …?”  or “I wonder if …?”

“Couldn’t we at least…?”

“How can I help?”

“What truly matters?”

Read More