5 Essential Questions for Every Stage of Your Career

June 21, 2017, 9:00 PM UTC
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This article originally appeared on Monster.com.

Think back to the last graduation speech you heard. Even if you can’t remember it, it’s probably safe to assume it was a pretty cliché potpourri of go-forth-and-conquer platitudes, well meant but, let’s be honest, snooze-inducing.

So how does a commencement address like the one given last year by James E. Ryan, dean of the Harvard Graduate School of Education, stand out (and go viral with more than 8 million views on Facebook alone)? By keeping it simple, succinctly covering five questions he believes are vital, not only at work, but also everywhere else in life.

Based on that speech, Ryan’s new book, Wait, What? And Life’s Other Essential Questions, takes only about as long to read as, say, a flight from New York to Pittsburgh. But it’s packed with thought-provoking (and often funny) insights about the power those five questions can have in shaping lives and careers.

Monster recently spoke with Ryan about how asking the right questions can help anyone make great career decisions and avoid bad ones.

The first question on your list, “Wait, what?”, seems especially relevant to a job search. Is it?

Definitely because it’s the first step to clarification and understanding. People looking for a job, especially young people, want to seem confident, so they don’t ask for enough details about what a job will actually be like—and then, once they start [the job], they’re surprised.

Don’t hesitate to ask about things like how much independence you’ll have, the reporting relationships, the hours you’ll be expected to put in, and exactly what you’ll be doing.

It’s so easy to make assumptions that put you in a job that’s wrong for you, where you aren’t at your best, and that’s always a mistake.

How does asking, “I wonder if…?” affect a job hunt?

Often, the scope of someone’s job search is too narrow because it doesn’t take into account all of the skills and talents people bring with them. So looking at lots of different possibilities and asking yourself, “I wonder if I could do that,” can be really useful.

It’s also important to keep asking. People in midcareer tend to be less curious and more inclined to stick with the status quo. Coming into this job as dean of graduate school [after 15 years of teaching at the University of Virginia School of Law], I was a total outsider, and I asked, “I wonder if…” so often that I’m sure I annoyed lots of people. But in most organizations, the question isn’t asked enough.

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Your book makes “Couldn’t we at least…?” seem like perhaps your favorite question. Why is that?

It is! I ask it all the time—at work and at home. With any new project, you usually can’t see how it will turn out in the end. But if you wait until you have the perfect plan, something new can stall out before it’s even begun. So “Couldn’t we at least…?” is how you begin to make progress.

“Couldn’t we at least…?” is also a great question for getting past conflicts. It’s a way to find common ground, as in, “Couldn’t we at least agree…?” It’s a good way to get unstuck.

Why is “How can I help?” important at work?

First, it’s a sincere offer. Most people say, “Let me know if I can help,” which comes across almost as a signal not to ask! Second, it’s asking for specifics, which obliges the other person to focus on what they actually need. Sometimes, someone just needs to vent, which can be helpful in its own way.

Let’s talk about “What truly matters?” from a career standpoint. How does this question help?

It’s particularly useful in a job search because it’s about your priorities. Where do you want to live? How long of a commute can you tolerate? How much money do you really want to make, or need to make? How much does work-life balance matter to you?

Be honest with yourself, and have the courage not to accept a job offer that doesn’t correspond with your honest answers. The reason so many people are unhappy in their work is that they didn’t look hard enough at what really matters to them before they took their current jobs.

This question also helps in work situations, like meetings. If you go into a meeting thinking about what is really important and how to accomplish that, you’ll get a lot more out of it. Or you may realize you don’t need to have the meeting at all.