Questions and Resolutions

Questolutions2016ArtWe’re coming up on a new year and that means it will soon be time, once again, for New Year’s resolutions.  As someone who believes questioning is a tool that can and should be applied to almost any challenge, it should come as no surprise that I recommend applying basic Why/What if/How questioning to potential New Year’s resolutions. And I suggest doing this early, as you’re starting to think about your list of possible challenges.

So what questions should you ask? For me, good questioning often seems to start with Why, and as you’re first considering a possible New Year’s resolution, here are two particularly important “Why” questions worth asking. First, Why is this resolution important to me? And second, if it’s so important, Why haven’t I done this already?

The first question will help clarify the reasons you should be doing this thing—and that’s important for building up motivation. It’s one thing to say to yourself,“I really should exercise more;” but when you dig into that and think about the various worthwhile benefits that could come out of it, it becomes more compelling.

That second Why question (Why haven’t I done this already?) can help you take stock of obstacles you may have to overcome. If you’ve tried to do this thing before and failed, you need to think about why you might have failed, so you can take those factors into account this time around.

Once you’ve asked your “Why” questions, here’s a great “What If” question to ask: What if I start small? I wrote in “Want to change your life? Start with one small question” about how resolutions often fail because we try to do too much, too soon (the author Caroline Arnold has an excellent book on this subject, Small Move, Big Change: Using Microresolutions to Transform Your Life Permanently). So it’s often wise to consider whether you can take a big, difficult resolution and make it more do-able (and more specific) by starting with a modest goal. Hence, the resolution to “exercise more” might work better as a modest and specific goal of taking a 20-minute walk every day.

Perhaps the most important question to ask, when it comes to resolutions, is “How”—as in, How the heck am I ever going to do this difficult thing? But let me suggest a better way to phrase that: as a “How Might I” question. Readers of this blog will know that I love “How Might I” questions (or, for groups of people, “How Might We” questions). Questions that start with the words “How might…” tend to be motivating and they seem to encourage creative thinking, which is why it’s a preferred form of inquiry at innovation firms like IDEO. You may need both motivation and creativity to tackle next year’s challenges, so I recommend that you actually phrase a New Year’s resolution as a “How Might I” question. Instead of declaring, “I will exercise more!” pose the question, “How might I exercise more?

By posing your resolution in the form of a question, you invite your brain to start working on this challenge right away. The question is apt to spark ideas and get you thinking about potential strategies for getting the job done. Questions are also a little less intimidating than grand pronouncements. They’re more open-ended, which allows for flexibility. And they tend to be more shareable; tell a friend you’re working on the question How might I exercise more? and it invites that person to offer ideas and support.

For more on this subject:

» Previous article: The Power of Questions to Get Things Done

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About the Author

Journalist and speaker Warren Berger realized that the majority of successful creatives and entrepreneurs he was interviewing over the years were great questioners. His wondering about "How can we all learn to do what they do?” led to this website and the writing of his latest book, A MORE BEAUTIFUL QUESTION. Follow him on Twitter at @GlimmerGuy and subscribe to his blog posts here.

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