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The essential questions we must constantly ask ourselves and each other

“Be a good listener,” Dale Carnegie advised in How to Win Friends and Influence People. “Ask questions that promote conversations. Ask questions the other person will enjoy answering. Ask questions so you can listen and learn.”

Whether you’re trying to get to know somebody, or trying to solve a problem, the art of asking good questions is one to cultivate.

Why do we fail to ask the right question or enough questions? There are a number of reasons.

We are often egocentric—eager to impress others with our own thoughts, stories, and ideas (and not even think to ask questions). Sometimes we are apathetic—we don’t care enough to ask, or anticipate being bored by the answers we’d hear.

We may be overconfident and think we already know the answers. Or perhaps we worry that we’ll ask the wrong question and be viewed as rude or incompetent.

But the biggest inhibitor most often is that most of us just don’t understand how beneficial good questioning can be.

Cultivating the art of asking good questions may very well be the sleeper secret to success and happiness.

That’s the claim by James Ryan, the dean of the Harvard Graduate School of Education, who delivered a popular commencement address nearly six years ago on the subject titled “Good Questions.”

Ryan says there are five truly essential questions that we should regularly ask ourselves and others:

“Wait, what?”
This is an effective way of asking for clarification, which is crucial to understanding. “Wait” is also a good reminder to slow down.

“I wonder why/if…?”
Asking “I wonder why” is the way to remain curious about the world, and asking “I wonder if” is the way to start thinking about how you might improve the world.

“Couldn’t we at least…?”
This question helps you get unstuck and moving forward. It’s a way to get started even if you don’t know where you’ll end up.

“How can I help?”
This offer is at the base of all good relationships. “How” is a humble way to ask for direction and recognize that others are experts in their own lives.

“What truly matters?”
This question gets to the heart of life. This forces you to catalog your core values and convictions.

Of course, these aren’t the only questions to ask. But they are good ones to keep handy to ensure understanding, move past old and easy answers, open up new possibilities, and remain focused on what’s genuinely important.

Have a great week.

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