Many present-day employees complain about similar issues they face at work. It’s not that today’s workforce is filled with slow, untalented, and unmotivated employees, it’s usually the lack of communication between managers and direct reports. Employees in this situation end up knowing very little about their boss’ expectations and how to work with their manager effectively. 

Some will even make assumptions about their manager’s needs and thoughts ─ based only on their observations and not on any clear communication. No wonder they’re struggling!

Having a difficult boss is an obstacle most employees have had to work around to achieve his or her goals. If you’re in this situation, seeing face to face with your manager and initiating a one-on-one meeting to ask these important questions will be helpful. With that, you’ll have a better understanding of your manager’s viewpoints from his or her responses. It will also help the two of you work together effectively and create more opportunities to become successful.

To start, here are some essential questions you can ask your boss:

Why did you hire me?

Asking your manager why you were selected among all other candidates for a new job is very important. While being overly excited, don’t forget to ask your boss. After all, asking will only help you pinpoint what makes your boss believe you’re a good fit for the team’s success and organizational growth.

Well, your manager may say that you showed your ability to present complex data in a simple way better than every other candidate. You should know that this is how your boss expects you to perform in the new role given to you.

If eventually, you perform better than anyone else on the team, then it’s your chance to shine! You could solve any professional relationship problem when you spend more time in your manager’s shoes and ask these questions.

Ultimately, don’t fret, even if it might be intimidating at first. As you build that relationship with your boss, you’ll start seeing him or her as an essential part of your success rather than an obstacle. Why not give it a try today!

What is your biggest goal in your current role?

With this question, you are sure to have insights into the short-term motives of your boss. It will help you define your goals and objectives as an employee to try and make your manager successful.

Unfortunately, many managers don’t always have a clear idea of their employee’s goals and plans. But you have the opportunity to prioritize your responsibilities and position yourself for success before your boss if you know a little more about his or her goals.

Maybe your organization is in an acquisition process, and your manager’s goal is to enable a smooth transition for the newly added department. Your aim should be to help your boss achieve her goal ─ whether by volunteering to assist with training or spending few weeks reinforcing company documentation.

What are your career goals?

Like the first question, the answer you get here will give you insight into the long-term goals of your boss. For example, does she wish to be a VP by age 35 and CEO by 50? Would she like to start her own business anytime soon or one day?

When you know her long-term goals, you’ll understand her intentions for making certain decisions. For instance, your boss volunteers your department for a project that does not seem relevant to you but places her directly in the visibility of top executives, which could, in return, be an opportunity for her promotion.

Having insight into your manager’s goals helps you understand why she manages your team in that manner, instead of doubting her strategies.

What is the most important thing your boss thinks about?

Your boss also reports to a manager, unless you’re working for the CEO. Asking this question helps you understand the expectations of the higher positions in your organization. Knowing the higher-ups’ goals makes you behold the bigger picture you and your team feature. It also helps you have a clearer sense of direction in your role.

In addition, keeping a finger on the pulse of the company’s high-priority projects offers the opportunity to volunteer for new development – which wouldn’t have come to your attention in the first place.

What can I do to make you more successful?

Questioning your boss regularly on how you can make her more successful (whether in a day, week, month, quarter, or year) makes you optimistic in your boss’s eye. It helps remind your boss that you’re truly concerned about her success.

You will be able to use your energy in the right places once you get a direct answer to how you can make your boss more successful. Also, you’ll be able to select the most important tasks.

What’s one thing I could do differently?

This question is a great way to pinpoint whether you have areas for improvement even if it’s not very serious. It also shows that you are open to constructive feedback and want to continue learning.

Let’s say your manager encourages you to engage and contribute more during meetings. In this regard, you should know that he values a collaborative environment of ideas instead of letting him come up with every initiative himself. Understanding those expectations will help you meet your boss’s expectations.

What should I know about your management style?

How does your boss cope with stress? What about emails on weekends ─ does she respond to them? Do you think she expects you to be available at all times?

A micromanager may not readily agree to micromanage, so you may not get all the answers you need when asking this straightforward question. But with a little insight, you’ll instinctively know what to expect and how to handle it effectively.

How do you prefer to get feedback from me?

It’s inevitable that you’ll encounter some points of disagreement with your boss eventually. No matter how you feel, don’t get boiled over because of frustration. Try to present your disagreements in a calm and rational manner to avoid escalation.

Asking how your boss would like to get feedback gets you prepared for an eventual point of contention. If you play by your boss’s rules, you’ll get a much better response. To make it end well, initiate a one-on-one meeting with your boss, rather than summarizing your thoughts in an email or catching him or her off guard in a hallway discussion.

Once you’ve come up with constructive feedback and understand how to deliver it, you’ll be prepared to ask for what you need: do you prefer more frequent updates on deadlines, regular one-on-one conversation, or quick decision-making on projects?

When making these requests, you should remember that your boss should be your biggest advocate after yourself.