5 Questions You Can (and Should!) Ask Your Boss

Leading employees is a two-way street. Leaders share information, and employees who are engaged ask questions. Here are five questions that will elevate engagement, involvement and respect for your efforts.

What Are Your Expectations?

Leaders who are newly promoted or haven’t developed this habit sometimes forget to share their expectations out loud. Unless telepathy was on your resume, that doesn’t bode well for your understanding of what needs to be done, how, and in what time frame. If the leader hasn’t given this much thought, the question will prompt the discussion and provide value for you both.

How Can I Help?

When your boss is clearly overwhelmed, an offer to help take some of those things off his list will be well received. However, asking this question before taking the initiative to simply do some of things on his list will also prevent double work and leave you perceived as a valuable resource.

Which One Comes First?

If your boss is a stereotypical “Type A” over-achiever, she may overload your plate without even thinking or knowing it’s been done. A well-timed question to clarify priorities will prevent a miscalculated choice and the ensuing consequences. The question might sound like this: “Thank you for these projects. I will add them to the ones you shared yesterday. Just so I’m clear, which one takes priority?”

How Far Can I Take This?

Most bosses crave employee initiative and yet, if you’re new to the team, or new to your boss’s style, or they’re new to you, probe for more information before you step on toes. Asking how far you can go before checking back in will also prevent finding out later what it looks like when their inner control freak comes out.

What Drives You Nutty?

Finding out what drives your boss nutty is the same as asking for their pet peeves. Consider these the ditches on the side of the high performance road. You wouldn’t drive off into the ditch on purpose, but when working with your boss, if you don’t ask where they are, you might not even see them and find yourself there having to ask for help or apologize.

Employees who assert themselves with their boss often build exponentially greater amounts of respect and rapport. In each question, maintain a tone of sincere interest and curiosity. After all, the goal is to truly find out the information, not challenge the way in which it was delivered or what was delivered, and this information will then increase the strength of your relationship and the team.

Monica Wofford, CSP, is CEO of Contagious Companies, Inc. and a leadership development expert who training, coaching, consulting, and assessments for managers who’ve been promoted, but may not have been prepared. She is the author of Contagious Leadership and Make Difficult People Disappear and may be reached at www.ContagiousCompanies.com.

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