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Advice / Succeeding at Work / Getting Ahead

This Question Will Impress Your Boss (and You've Probably Never Asked It)

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Early in my career, a mistake ended up teaching me one of the most valuable career lessons I’ve ever learned.

I was assigned to a global project with a team based in downtown Chicago. My boss’ boss asked me to attend a large milestone meeting with key stakeholders being held at a suburban location. While my presence was important, the documents I was asked to bring with me were even more so.

I’d never been out that way before, and I’d failed to think ahead and plan for the time it would take to get to the train station in the city. Long story short: I missed my train and although I got there eventually, things got off to a poor start. My leader was not pleased, to say the least.

Later, a senior team member came to me and said, “Here’s the thing: That was a big miss. I recommend you put some thought into what keeps your boss up at night and solve it, and that you don’t let a mistake like that happen again.”

Ouch! Although I didn’t want to admit it, I knew his advice was right. If I’d asked myself what stresses leaders out—such as my boss’ boss—I probably could’ve come up with the response: looking unprepared in front of very important people.

Until that moment, I hadn’t realized the awkward position my poor planning had put her in.

While I couldn’t take back that moment (though I did apologize), I asked the “What keeps you up at night?” question of my new manager when I began my next role. It surprised him a little, but he answered with, “Interesting question! On this project, getting my arms around expense management, before my boss asks me about our margin. Can you help with that?”

That conversation led him to realize that my intentions were to solve problems, not just accomplish tasks. And from there, our relationship flourished. All because I asked one simple question (that no one else ever asks) and used it to help me make decisions throughout our time together.

So, here’s a challenge to you: In your next meeting with your manager, take the time to straight-up ask, “What keeps you up at night?”

The answer may surprise you, or it may just confirm what you already knew. Either way, it just may change the relationship you have with your boss and end up pushing you ahead in your role.