5 of the best questions to ask your boss

No matter if you started working with a new boss or you’ve been working with them for a while, these questions can create a mutually-successful dynamic.

Photo: Matt Brown Via Flickr

From the person whose last name you share to the best friend who holds your darkest secrets close to their chest, every relationship serves a different purpose in your life. While you might not consider it an alliance of sorts, the rapport you build with your boss makes a difference in the progression of your career. And it isn’t a one-and-done conversation to have, but rather, frequent check-ins that foster trust and allegiance.

As career expert Jill Tipograph explains, no matter if you started working with a new manager or you have been working with a higher-up for a while, there are many crucial questions that create a mutually-successful dynamic.

How you ask is important and context is vital — you never want to interrogate in the middle of a busy season, after all. “Questions should be phrased so that they are straightforward, easily answered and are linked to the work. You are not interviewing your manager in this situation,” she explains. “You are gathering important information that you need to meet the manager and your team’s needs so that you can both be successful. If you do this right, you are going to feel more comfortable with your relationship and less stressed.”

Here, a few to consider adding to your next one-on-one agenda:

“Where are you from?”

Nope, this isn’t just an icebreaker when you meet someone for the first time, but an appropriate and essential question to discuss with your manager. You don’t need to be completely straightforward with this one, but can express your interest in understanding your manager’s background, while also revealing your own. As Tipograph explains, you may find some shared experiences that help you relate or assist one another.

“If your manager ran a very similar team, in another company, you can help the manager assimilate into the culture and logistics of your firm,” she continues. “Or, if your manager has more experience with your company, but less in this type of team environment, you might find yourself as a guide-on-the-side, training your manager on the team’s area of specialization.”

By proposing this question — which you would likely ask any new coworker — you both receive the benefit of knowing more about one another.

“What do you think I could be doing more productively?”

It might take an ounce of courage to step into this conversation, but chief learning officer at MentorcliQ Paul MacCartney, stresses the importance of this inquiry. While you will probably need to stomach constructive criticism, it will also help you to be more successful within the company.

“Asking this question allows your boss an inroad to address a concern they might have on your performance but have been hesitant to raise,” he explains. “By asking this, you’re showing your willingness to accept criticism and advice.”

This not only proves that you care about your performance, but that you are committed to continuously progressing and improving your skill set.

What would you say are my strengths?

There are always two sides to every coin, and for every area you could be better at, career coach Cheryl Palmer shares there are likely qualities you have that stand out of the pack. Even if they mean to, she notes many bosses forget to take the time to give praise when it is needed. It’s important to know where you shine, not only in your current role but how it could impact future opportunities, too.

“Asking this question will let you know what the boss sees as your positive points. And, this can be of help to you when you interview for other positions and an interviewer asks you, ‘What are your strengths?’ You can then truthfully and objectively talk about what strengths your boss has highlighted,” she explains.

“How do you want me to manage tasks?”

If you’ve been in the working world for a hot second, you know every manager has a preferred method of interacting with their employees. While some are hands-on, others allow for autonomy, and some are a bit OCD with task management.

Instead of running into any miscommunication situations, Tipograph says it’s better to ask your boss’s preferred style. This not only ensures they are kept in the loop of your deliverables, but it illustrates a proactive attitude. And in some specific cases, it could reveal a weakness on their part that you could take on for them.

“If your manager is not thrilled with the prospect of producing tedious budget reports once a month, your background in accounting can help you alleviate that burden by offering to do the initial preparation,” she explains. “If you discover that both of you are not inclined to certain key tasks, your mental bond of mutual dislike, could be turned into setting a goal.

“Agree to get worst-in-class-tasks done first each month; allowing you both to move past it quickly, then turning attention to more interesting aspects of your work.”

“What is your most immediate goal and how can I help you obtain it?”

Notice this isn’t your goal — but your boss’s. Whether it is personal to their own job description or to the productivity of your squad, MacCartney says you’re adopting a team player attitude with this question.

More importantly, it indicates you are mindful of your boss’s progression, and not narrowly focused on your own. When it comes time for review season, it’s likelihood your manager will remember your attention to detail and thoughtfulness.

“By positioning yourself as your boss’s ally, you establish a foundation of trust that will surely enhance your career prospects, now and in the future,” he adds.

Lindsay Tigar|is a seasoned lifestyle and travel writer