8 Questions You Should Be Asking Your Boss

Guest Post by Lea McLeod

Originally posted @ TheMuse.com

When my client Sarah contacted me to work out some issues at her job, I didn’t think it would be a very tough assignment. After all, she was bright, good at what she did, and committed to being successful.

The trouble, she explained, was her difficult boss: She saw him as an obstacle that she had to work around to achieve her goals, rather than an essential part (or, frankly, any part) of her success.

But as I continued to ask questions, I was surprised at how little she really knew about her assignments, her boss’ expectations, and overall, how to work with her manager effectively. In fact, she tended to make assumptions about what her manager needed or thought, based solely on her observations—without any real facts. No wonder she was struggling!

If you’re having similar issues seeing eye-to-eye with your manager, take the advice I gave Sarah, and initiate a one-on-one meeting to ask these eight essential questions. With the answers you receive, you’ll better understand your manager’s point of view, be able to work together more effectively, and, ultimately, create more opportunity for success—for the both of you.

1. “What’s the Most Important Achievement You Hope to Accomplish in Your Current Role?”

This question will give you insight into your manager’s short-term motivation, which will give you a better idea of what your goals and objectives should be.

Managers, unfortunately, aren’t always clear with employees on their goals and plans, but if you understand a bit more about what your boss is focused on, you can better prioritize your own responsibilities and position yourself for success in your boss’ eyes.

For example, perhaps your organization is in the middle of an acquisition and your manager’s goal is to create a smooth transition for the newly merged department. With that information, you should be aiming to help her to succeed in that, whether that means spending a few weeks beefing up company documentation or simply volunteering to assist with training.

2. “What Are Your Career Goals?”

While similar to question number one, the answer to this will give you insight into your manager’s long-term goals. Does she want to be a VP by age 35? CEO by 50? Does she want to start her own business one day? Knowing her long-term plan will help you understand why she might make certain decisions.

For instance, maybe she volunteers your department for a project that doesn’t seem important to you, but it puts her squarely in the visibility of top executives—which could put her in the perfect position for a promotion.

By having insight into her goals, you’ll better understand why she manages your team the way she does, instead of doubting her strategies.

3. “What Is the Most Important Thing Your Boss Cares About?”

Unless you’re working for the CEO, your boss reports to a manager, too. So, asking this question will help you learn more about what the upper level of your organization expects. And finding out these higher-level goals will give you a deeper sense of meaning in your work, since you’ll see exactly how you and your team fit into the bigger picture.

Plus, getting your finger on the pulse of the company’s higher-level projects may give you the opportunity to volunteer for initiatives you otherwise wouldn’t have been aware of.

4. “What Can I Do to Make You More Successful Today (or This Week, Month, Quarter, or Year)?”

This should be a question you ask on a regular basis—because you should always be trying to make your boss as successful as possible.

When you’re able to get a straightforward answer to this, you’ll be able to focus your energy in the right places—because you’ll know exactly what tasks need to take priority.

(And as a bonus, it will also remind your boss that you’re truly invested in his or her success.)

5. “What’s One Thing I Could Do Differently?”

Having clear expectations is the key to delivering winning performance—and this question is a sneaky way to find out those expectations.

For example, if your manager says he’d like you to make more of an effort to actively participate in meetings, you’ll know that he values a collaborative environment of ideas—rather than coming up with every initiative himself. And knowing that can help you perform exactly to his expectations.

6. “What Should I Know About Your Work and Management Style?”

Does your manager expect you to be available 24/7? Respond to emails on weekends? How does he or she handle stress?

Asking this straightforward question may not get you all the answers (for example, a micromanager may not readily admit to micromanaging). But even if you get just a tiny bit of insight, you’ll have a better sense of what to expect and how to handle it.

7. “How Would You Like to Receive Feedback From Me?”

No matter what, you won’t agree with your manager on everything. But, you don’t have to simply simmer in frustration—as long as you know how to present your gripes in the right way.

To prepare yourself for an eventual point of contention, ask how your manager prefers to get feedback—you’ll get a much better response if you play by his or her rules, whether that means scheduling a one-on-one meeting, rather than catching him or her off guard in a hallway conversation or summarizing your thoughts in an email.

Once you know how to deliver your constructive feedback, you’ll be much more prepared to ask for what you need: Whether you’d like more frequent updates on deadlines, regular one-on-one time, or faster decision-making on projects, it’s important to be able to feel comfortable making these requests.

(And if you’re nervous to do it, here’s how to give honest feedback that isn’t scary.)

8. “Why Did You Hire Me?”

When you get a new job, you’re often so excited that you forget to ask why you were selected over all the other candidates. But this is an important question to ask, because it will help you hone in on exactly how your boss believed you would make the team better.

Perhaps your boss will say that you demonstrated your ability to present complex data in a simple way better than any other candidate. And so, now you know that’s a major part of what your boss expects you to deliver. (Plus, since you probably do this better than anyone else on the team, it’s your chance to really shine!)

By spending some time in your manager’s shoes and asking these questions, you’ll be able to smooth out any rough edges of your professional relationship.

OK—it might be a little intimidating at first, but give it a try. As you build that rapport, you’ll stop seeing your manager as an obstacle and start seeing him or her as an essential part of your mutual success.


Lea McLeod


Lea McLeod, M.A. is a coach and consultant who helps you build Confidence and Strategy for your job search, and career.  You can connect with Lea @ LeaMcLeod.com


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