What should you ask your boss to improve your chances for success?

While you are in your role, receiving feedback is important — “no news is good news” doesn’t always apply. Often, “no news” means that a manager is too busy and, as such, has difficulty finding the time to provide feedback. Or, your boss might prefer to “let things slide” rather than confront a tough situation.

While a good boss will provide you with constructive feedback on regular basis and encourage you to ask questions, it’s ultimately up to you to manage your career. Communication is a two-way street. If you have questions, ask. It has multiple benefits including helping you ensure that what you do is what is expected. Doing so might present you with a perspective you hadn’t considered, provide valuable career guidance, and show your manager that you’re interested in your professional development. So here is my take on the questions you should ask!

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. And well, the CEO has to answer to the board nevertheless. 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. “What are the three must-win battles for our division (company, team) this year?”
We all have limited time in the day. Knowing what your senior managers view as key priorities for the company should help you align goals and measurable outcomes at your level as well.

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.

There is definitely an tinge of fear to ask but hey, give it a try. As you build that rapport, you’ll focus on how to work together towards mutual success.

Check out my related post: How to tell our boss you are bored at work?

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