10 questions you should ask your boss


The employee-boss relationship can be tricky. In some workplaces, you’ll find it’s pretty strict in that the employee arrives at work, performs his tasks, goes home and doesn’t have much freedom to ask the boss many questions — if any at all.

In others though, you’ll find the employee-boss relationship is the opposite, with the boss being completely happy to answer any and all questions their employees have.

But in either case, asking your boss questions is important because they have the knowledge you want to gain and the only way to get it from them, is to ask the following questions (at least):

1. How was your weekend?

While this may not be the most professional question you could ask, it is a great way to start off the working week because your boss may have had a really good or really bad one and want to talk about it.

Asking this question also does not mean your professional relationship will become over-friendly or undermined. It just allows you both to become more comfortable with each other to have these conversations. Plus it is a very polite question to ask.

2. How did you get to where you are today?

Asking this question shows that you want to progress in your career, develop your skills and get to the same level as your boss — if not further.

It is also a great way to get some professional advice and insight on what to do and what not to do in your career.

3. What should I know about your work and management style?

Asking this question shows that you know your boss has a particular work and management style and you want to do your best to work within it.

And don’t worry. Doing this does not mean you can’t bring your own ideas to the table that are a little ‘out of the box’ because doing that will display your creativity and ability to think on your feet.

4. What’s your biggest problem- And how can I help you solve it?

This question tells your boss that you want to help them with anything at all, even if it isn’t within your normal job description — and that you are up to the challenge and extra workload.

The only downfall with asking this question is that your boss may think you don’t have enough of your own work to do.

5. I’m really excited about working on ________ together. Would it be possible to get some feedback from you over the course of the project?

This shows your enthusiasm for your job, working on a project with your boss and that you relish the idea of feedback while you work.

But bear in mind the possibility that they’ll suggest waiting until the end of a project to give you feedback, as they will be informed on the topic then.

6. I really want to nail the ________ assignment. Do you have any templates I could reference, or is there anyone on the team I should speak to who’s done a good job on one recently?

This shows that you want to do a good job on a project and want to have a look at what’s been done before, or talk to someone who has experience with it before getting started yourself.

Doing this could even give you a light-bulb moment to do something a bit differently and really show your boss what you can do — even if it comes from an old idea.

7. I’d love to oversee _________ in the next six months. Could we keep that in mind as projects are being assigned?

This shows that you have ambition and want to take on a leadership role within the company or team you work with and have a time frame in mind to do so.

8. What should I start doing? What should I stop doing? What should I continue doing that I do well?

Having this conversation with your boss about what you do well and what you can start/stop doing is a great way to show how self aware you are and that you want to improve yourself and do a better job in the future.

9. I’m sure that I’ll have some additional thoughts and questions as I digest all this information. Could we schedule a follow-up conversation in a few days?

Doing this can be a great opportunity for you to ask questions you didn’t think of right away at a later date and needed time to think about because it can show how you like to consider things before speaking or acting.

10. What’s one thing I could do differently?

Asking this question shows how aware you are of your flaws, that you’re are not perfect, and that you want to improve yourself and be a better employee and colleague.

But remember, and don’t take this too much to heart — if at all, there may not be one thing you could do differently.

About Rowena Nagy

Rowena Nagy is a Journalist at The Business Woman Media. A graduate in Journalism, Media and Communications, she is passionate about in writing, travel journalism, video journalism and Public Relations.

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