How Asking Questions Can Help Your Career

Dr. Rodger Dean Duncan is a bestselling author of LeaderSHOP: Workplace, Career, and Life Advice From Today’s Top Thought Leaders. In addition to his work in government, he has taught at three major universities and was head of global communication at Campbell Soup Company.

Early in my career, I was an advisor to cabinet officers in two White House administrations. I then worked for several members of the U.S. Senate. Although this was my only experience in government work, it gave me a good taste for career management. After all, in those posts, I was a political appointee with virtually zero job security beyond my own competence. On any given day I could have been fired for wearing the wrong tie to work.

In the private sector, I later discovered—again—that the trajectory of my career was largely up to me and no one else. Although I certainly had a few good mentors and a lot of helpful colleagues, I and I alone was in charge of the direction my career would take.

So I learned to ask questions. Lots of questions. When I saw someone succeed in a particular job, even a job that I knew would never interest me, I inquired about the needed skills, how the skills were acquired, and how that job intersected with similar work. When someone seemed to manage a tough workplace situation, I asked about relationship building and trust building. When someone experienced a job failure, I tactfully requested a briefing on what went wrong and what might have helped avert the misstep.

In other words, I was a constant learner. I still am. I frequently seek out people who have interesting insights into the world of work and careers. I ask them a lot of questions. And they’re usually generous with their time in responding. (For examples of these highly-informative conversations, see my book LeaderSHOP: Workplace, Career, and Life Advice From Today’s Top Thought Leaders.)

Here are three of the many career questions I’ve pondered over the years, along with some helpful insights from people whose opinions are well worth considering.

My grandfather had an expression for that approach: “Yard-by-yard it’s hard, but inch-by-inch it’s a cinch.”

RODGER DEAN DUNCAN

How can I best prepare for my “dream job” if I’m not happy with my current position?

Jon Acuff, author of Quitter: Closing the Gap Between Your Day Job & Your Dream Job, advises people to “fall in like” with the job they don’t love.

“People who are miserable all week have a hard time hustling on the weekend,” he says. “If you’re going to spend 40-50 hours a week doing a job, you set yourself up for failure if you refuse to make it as good as it can be while you’re there. It’s not about falling in love with it. It might always be a job you only like. That’s okay. But don’t accept ‘misery’ as the only option you have until you find your dream job.

Sometimes, he says, adjusting your attitude and expectations about your current job can even help you discover a dream job hidden at the place where you already work.

What are some good ways to deal with a boss who’s incompetent?

You don’t have to let a poor boss derail your career. Mary Abbajay, author of Managing Up, offers the following approaches:

  • De-escalate your anger. “Having an incompetent boss can be infuriating,” she says. But anger and resentment can cloud you from making smart and strategic choices. “Let go of the anger and replace it with empathy, compassion, or even humor,” she advises.
  • Diagnose the incompetence. Does your boss lack experience? Have poor emotional intelligence? Make poor decisions? Fail to hold people accountable? Is this really incompetence, or just someone who does things differently than you?
  • Compensate and cover. After you pinpoint the major deficiencies, devise and deploy strategies to compensate. “Is this fair? No,” Abbajay says. “But letting an incompetent boss derail your career isn’t fair either. Look for opportunities to shine by doing great work and becoming your boss’s biggest asset.”
  • Take the long view. Don’t fret if your boss gets the credit for your successful projects. Success eventually gets noticed. Besides, Abbajay says, a lot of people likely already know that “you are the success engine behind your incompetent boss.”
  • Learn what you can. If your boss has technical skills, make the time to learn about that expertise. Regardless of the situation, there are likely many things you can learn—even if it’s how not to do some things.

Is goal-setting a good idea, or does it get in the way of success?

In a world where goal-setting is at the core of everything from sports to academia to business to personal fitness, even asking the question may seem heretical. But Jeff Haden, author of The Motivation Myth, says the real value of a goal is now it informs the process you create to achieve it.

“Most high achievers instinctively create processes that focus on the day-to-day and not the end result,” Haden says. “If you focus solely on your goal, you realize just how great the distance is between where you’re starting and where you hope to someday be. Then that gap is so wide that it’s incredibly demotivating. If you want to run a marathon and today you can run only a mile, thinking about someday needing to run 26 miles is hugely daunting. Think about just how far you need to be able to run and you’ll quit.”

My grandfather had an expression for that approach: “Yard-by-yard it’s hard, but inch-by-inch it’s a cinch.” It applies to managing your career, too.

Dr. Rodger Dean Duncan is the bestselling author of LeaderSHOP: Workplace, Career, and Life Advice From Today’s Top Thought Leaders. In addition to his work in government, he has taught at three major universities and was head of global communication at Campbell Soup Company.

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