10 ‘Beautiful’ Questions to Ask at a Career Crossroads

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Whether in the classroom, laboratory, or conference room, higher education professionals know how good questions can induce learning, innovation, and problem-solving. But when it comes to our own career development, we sometimes need a reminder that asking the right questions can help us invent or reinvent the work we do or make better job decisions, rather than relying on our instincts, biases, and assumptions.

Self-described questionologist Warren Berger provides such a reminder as author of “The Book of Beautiful Questions.”

“Through questioning, we can more accurately assess risks, overcome irrational fears, and figure out what’s in our long-term best interests,” Berger writes. “We can begin to clarify what matters most to us and identify passions to pursue. We can do all that by making better decisions, and we can do that by first asking better questions about those decisions.”

There are more than 400 questions in his book (yes, he indexed them), but for this article we are going to examine the 10 best questions to help people at a career crossroads, that is, deciding to apply for a job or accept a job offer. (In a future HigherEdJobs articlewe will tackle the 10 best questions to help professionals perform better in their existing jobs.)

10. What would I try if I knew I could not fail?
Fear is an enemy of questioning, and it can be rational for you to fear the unknown of a new job by leaving the safety of your existing job — or perhaps you prefer the devil you know over the devil you don’t know. You might also fear rejection: the invested cost of time, money and dignity from chasing a job that you either won’t get or you’ll take and then not succeed. Removing this fear of failure and envisioning hypothetical success can provide clarity for your motivations.

9. When you have failed, how did you respond?
“What’s the worst that could happen?” is also a contender for this list, but to avoid your imagination running wild, a better question to mitigate fear is to consider how you’ve already overcome failure. How many times in your career has a mistake provided an opportunity for redress or strengthened your ability to adapt? Honor your struggles and reflect on past failures to guide your decision.

8. Can I have influence in this organization?
Berger offers several questions to ask before taking a job — related to promotion, acquiring skills, and connecting with coworkers from cross-functional areas — but making a difference within the institution or department is just as important as climbing the ladder.

7. Which option will allow me to evolve and flourish?
Long-term decision making is challenging, according to Berger, because people underestimate how much they will change in the next 10 years. Remember that you are a work in progress and, as Berger writes, “If we think about this question in terms of, say, joining a new company, it encourages looking beyond the more immediate incentives (such as a pay hike) in order to consider growth opportunities and other future benefits.”

6. Will I enjoy the “small pleasures” of my daily routine?
While it’s important to acknowledge that “future you” may be different, there’s also a bias that what you care about in the present won’t be as important in the future. Berger cites research from Ayelet Fishbach, professor of behavioral science at the University of Chicago, which maintains that people tend to think about the future in overly realistic terms. For example, right now they might prefer doing interesting work or spending time with people they like, but they expect to make the tradeoff for a boring but well-paying job in the future. Don’t underestimate the “small pleasures” that create job satisfaction.

5. What if I already had this job in that location and was offered a chance to move back closer to home — but with a pay cut? Would I accept that?
Deciding to relocate for a better paying job often vexes people at a career crossroads. Berger tackles the quandary by providing this question suggested by Julia Galef of the Center for Rational Thinking. Reframe the question in reverse to remove your biases towards risk aversion.

4. What are you trying to get better at?
Strip away the fancy titles, the name of the institution and perks, like your commute or even your budget, and think about why you set out for a career in higher education. Process matters. Choose a job for what you get to do, not who you’ll be.

3. What have I gone out of my way to defend?
Think about a time in your career when you’ve taken a principled stand. Or notice if you ever think about a problem for college students or an institution and insist, ‘Someone should do something about that.’ These reactions can help you choose an option that aligns with your values ​​and brings your best self to your work.

2. What is my tennis ball?
Drew Houston, cofounder of the tech startup Dropbox, told Berger that successful people remind him of a dog chasing a tennis ball by how obsessed they are to solve a problem. Identify what holds your single-minded attention, so much that you lose track of time and forget to eat. Don’t resist the pull; let it guide your decisions and increase your chances for happiness and success.

1. What is my sentence?
An approach suggested by author Daniel Pink in Berger’s book, is to come up with a single sentence that sums up who you are and what, above all, you aim to achieve. This personal mission statement will help you succinctly define your purpose and provide clarity, hopefully first for a hiring committee that offers you a job, and then for you to make the right choice.

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