How asking the right questions can shape your career


For many high-achieving people, goal setting is a familiar process. Decide what you want to accomplish, then make the goal SMART–that is, “specific, measurable, attainable, relevant, and timely.” Break it up into steps, then get to work.

But, innovation expert Hal Gregersen, executive director of the MIT Leadership Center and a senior lecturer at MIT’s Sloan School of Management, says there’s a better way: ditch the goals, and get to work on a list of compelling questions.

At first, the thought that questions can replace goals seems unlikely. After all, a goal is a declaration of what is to be achieved; it’s specific, and we can measure progress toward achieving it. But in his interviews with more than 200 leaders for his book, Questions are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life, Gregersen says that turning those statements into questions creates more engagement and helps us think about our goals in new ways.

“The bottom line is that question-based goals deliver more than statement-based goals,” he says. “We’re programmed to start solving.”


Questions have a curious power to unlock new and positive behavior changes in every part of our lives, he says. He points to the company Patagonia, which recently changed its mission statement to “Patagonia is in business to save our home planet.” Regardless of your role in the company, your job, in part, is to translate that goal into the question, “How can we save our home planet?” Gregersen says. The question immediately begins yielding answers that are key to success in the role.

The answers can then be posed as new questions: How can I do that? How quickly can we make that happen? What’s standing in the way? What can we do about that? These additional layers help individuals and organizations get past superficial niceties and dig into the real challenges they face. That’s more effective than trying to struggle through obstacles within a stated goal, Gregersen says.

One of the key ingredients for this approach to goal setting to work is psychological safety, he adds. To feel comfortable asking tough questions and discussing answers, you as an individual or your employees need to feel as though they can share honestly without being ridiculed, admonished, or otherwise punished. This also allows people to explore questions that others may be afraid to ask.


Gregersen says this type of achievement-related work is best done in small groups—perhaps two to four people. Start with the issue you want to address or the achievement on which you want to make progress. Then, set the ground rules: no answers to the questions, simply brainstorm 15 to 20 questions related to the issue.

One example Gregersen shares is Salesforce. More than 20 years ago, Mark Benioff, cofounder of Salesforce, asked, “How might we sell large enterprise level software off the internet?” The cloud didn’t exist then. Had he not spent 15 years selling large enterprise software, having hundreds of conversations and interactions, he may not have reflected on what he was doing and questioned how to find a better way, Gregersen says. “There’s something where the fundamental assumption got challenged and it was false and it energized us to do something about it,” he says.

How does this relate to individuals? It’s time to start posing tough questions about what you want. For example, if you are trying to figure out how to get started on the book you want to write, your questions might be:

What’s getting in my way?

How can I make more time to write?

Are there creative solutions that can help me? What are they?

Then, dig deeper. Are there fears or some other obstacles stopping you? What can you do about that? Review your questions regularly to see if the answers have led to new questions–or if you need to change the basis of the questions entirely.

The way you engage with those questions immediately begins a process of finding answers, Gregersen says. Operating at the edge of uncertainty, trying to figure out a better question, is far more productive than trying to figure out a better goal. The right questions can surface a false assumption and give us energy to do something about it.


Gwen Moran writes about business, money and assorted other topics for leading publications and websites. She was named a Small Business Influencer Awards Top 100 Champion in 2015, 2014, and 2012 and is the co-author of The Complete Idiot's Guide to Business Plans (Alpha, 2010), and several other books

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