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9 Crucial Questions for your Boss

Rachel Zupek, writer

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There are certain things you probably shouldn't ask your boss:

"Are you an idiot?"

"Who actually pays you to do this?"

"How much did you spend on that bad toupee?"

But what about the things you should ask your boss? In today's turbulent job market especially, it's important to ask important questions and be on your boss's radar (and not because you asked him if he showers daily).

Some job seekers and employees mistakenly think asking questions shows lack of intelligence, says Caroline Ceniza-Levine, partner at SixFigureStart, a career coaching firm. On the contrary, it's worse to think of questions later and then have to go back and get them answered. It's even worse to not ask questions at all and find out you misunderstood or left something out.

"Thoughtful questions show professional maturity; clarification questions show that you are actively listening and thinking of the details," Ceniza-Levine says. "If you are just asking the boss to repeat herself, then you show you are not paying attention.  If you ask a question that deepens and expands the discussion then you demonstrate that you are paying attention, reflecting on what is said and adding to this." 

Here are nine questions to ask your boss that can help boost your career:

1. How will we gauge my success in three, six or 12 months?
It's important to know the metrics of how you and your boss will gauge your success, and to have a working timeframe, Ceniza-Levine says. You need to know that you are working on what matters and aiming for results that will be measured. The less subjective you can make your work, the better it will be for you come bonus or promotion time.

2. How do you prefer to communicate and how often?
It's important to talk to your boss formally for things like performance evaluations, but it's also imperative to know how to get feedback on an everyday basis, Ceniza-Levine says. Does the boss want you to check-in every day, every week or only when a specific project is happening?  Do they want you to swing by unannounced, make an appointment, send an e-mail or call first? 

"People have different expectations in terms of frequency and method of communication, so ask how your boss likes to communicate and adjust accordingly.  If you need more or less feedback, this will be something you need to communicate," she says.

3. What does my career path look like at this company?
This is a tricky one. On one hand, asking this question shows that you are focused on making a long-term career at the company. On the other hand, you have to be careful not to appear as if you are constantly looking outside, Ceniza-Levine says. Ask this question after you know that your boss is happy with you in your current job and then you can decide what your next move is.

4. What areas do I need to develop to advance my career?
This shows your manager that you're being proactive in making something happen for yourself. You're trying to get explicit direction regarding advancement, and asking for specific feedback shows that you aren't assuming what your weaknesses are. 

"You don't want to assume that you need more strategic planning or more analytical skills," Ceniza-Levine says. "Maybe they really value relationship building and the time you spend in front of the computer is time better spent meeting people in other departments."

5. What's our top priority?
Oftentimes, bosses assign employees more work than they realize. Asking him or her upfront what takes precedence makes your boss choose among the many projects you may have been assigned, Ceniza-Levine says. This is important so you know how to budget your time. You want to know the top priorities and save your best work for these. 

6. Let me see if I understand this correctly ... am I missing anything?
After your boss has explained something to you, it's beneficial to summarize what you've heard so that the boss knows what information you retained and can fill in the details where you may have missed something, Ceniza-Levine says. Repeat what your boss says so that you are on the same page about next steps, otherwise you're in for a rude awakening when the due date comes around.

7. What are my strengths?
You want to know your strengths so you can build on these to advance your career down the line.

"Sometimes people value things that you don't realize; it might be so natural to you that it is unnoticeable," Ceniza-Levine says.  "Now that you know your boss notices and likes this strength, you can find a way to incorporate more of it into what you do." 

8. What can I do to help you?
Asking how you can help is important because it shows you are willing to go above and beyond, Ceniza-Levine says. Make sure you've completed everything already asked of you, otherwise it might seem like you're angling for something other than your current job.

9. I'm working on projects X, Y and Z -- do you think I can handle this task?
As mentioned earlier, managers don't always know if you have too much on your plate. If you ask before committing to a new task, your boss's priorities will dictate your choices -- not your personal preference, Ceniza-Levine says. By listing what you already have going on but offering to do more, you come across as willing to go the distance.  

Rachel Zupek is a writer and blogger for and its job blog, The Work Buzz. She researches and writes about job search strategy, career management, hiring trends and workplace issues.

Last Updated: 11/05/2009 - 1:41 PM

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