17 Good Questions To Ask Your Boss

Whether you are in the Army, Army National Guard or Reserves or in a civilian job, you may have some questions.

But do you dare ask them?

Well, it does depend on the question, but it has been said that the only stupid question is the one that isn’t asked.

Many employees and subordinates are frightened to ask their boss questions.

They may have the feeling that they will look ignorant, like a butt-kisser, or they feel too inferior to ask their boss any questions.

First, again the ignorant question is the one not asked.

As for the butt-kissing assumptions, whoever thinks that and states it to others is probably the actual butt-kisser who is being jealous.

If you feel inferior, you need to remember that your boss puts their boots on the same way you do, sleep and snore the same as you, and they have to eat and breathe the same as you.

They are no better than you; they just have the insignia that says they are the boss.

If you want to move forward in your career, it is wise to ask questions.

By not doing so, you really do not know what is expected of you by your boss, and what makes your boss “tick.”

In today’s post, I am going to provide you with 17 good questions to ask your boss.

These questions are in no particular order.

It is up to you to know when the best moment is to ask each question, but do not be scared to ask any of these questions.

By doing so, you can learn more about your boss, what they expect of you and how you can move forward in your career goals.

1: How was your weekend?

This is a good way to find out what type of mood the boss will be in this week.

It can help you know if you need to stay somewhat clear, or if they are in a joyous mood.

While the boss’ personal life should not play a role in how he/she handles work, it does.

No matter who we are, our personal life can, and does play a roll on how we treat people we work with.

2: Where are you from originally?

Questions such as this one need to be asked in a sincere way and come across as if you truly do want to know the answer.

There is nothing wrong with a little “small talk,” and by knowing where your boss originated from, you may be able to tell some other things about them, along with knowing what not to say. (example: boss is from Texas, you won’t start saying how terrible the Texas Longhorns are in football)

3: What college did you attend?

This goes along with #2, small talk.

Plus, you can learn more about the level of education your boss had, and if it was a strict college.

It doesn’t hurt to ask what they majored in after receiving the first answer.

That way you can get a good idea on the education factor behind their leadership approach.

4: What are my primary job duties?

While you were trained with an understanding that you would have certain job duties, your boss may have a different understanding of what your job duties are.

By asking this question, you will have a better understanding of what he/she expects from you.

5: Who is the best to learn from?

Your boss will know who can best teach you the ropes.

Naturally, your boss wants you trained correctly, so they will have who they believe knows the job the best give you pointers.

6: How often do you want updates?

Some bosses want to be filled in daily on what has been completed and what is left to complete.

Other bosses only need you to fill them in on a weekly or even monthly basis.

By asking this, you will know when you should approach your boss with updates.

7: When is the best time to meet with you if need be?

Most bosses will appreciate this question.

They are busy and unexpected visitors can cause extra stress.

While your boss probably has an open door policy, we need to show the respect that they are busy, and we should not take advantage of that policy.

8: What changes do you foresee for our unit?

This can help you plan your career.

Usually your boss will have more of a heads up if there are going to be major or minor changes.

If they share some of that information, you can make the changes you need to for adaptation reasons.

9: What is one thing you feel I should do differently?

What we all want to hear is: “Nothing, keep doing things the way you are,” but the odds of that happening are low.

Be prepared for the answer because it may be something you wasn’t expecting, and do not get defensive.

Just listen and then go out and change that one thing.

10: Can I have some help?

The majority of bosses will be understanding if you feel you need help, unless you are a person that asks for help on every task you are given.

Your boss will probably find you some help, or will explain why they can’t.

11: Can you provide me with _____ (tool) so I can do my job more efficiently?

All bosses want the job to be done quickly, competently and in the most efficient way possible.

If you explain how a certain tool can make the job more efficient, it is a good chance your boss will go to all lengths to get you that tool.

12: Did I do it (the task or job) correctly?

This gives your boss an opportunity to explain if there is any part of the task you could have done in a different way.

This is another question that you do not want to get defensive with when you are given an answer.

Just listen and learn.

You may not agree, but they are your boss and you need to follow their lead.

13: What schools or courses do you believe would be in my best interest to take?

This question will show your boss that you truly value their opinion.

And, I recommend that you listen and try to follow their advice.

Your boss knows you, the job and the career possibilities.

He/she will lead you down the proper educational path normally.

14: What books or literature do you suggest I should read?

This goes along with #13.

Leaders are readers, so it is a good possibility that your boss has a good list of books and literature he/she will recommend.

I suggest you take notes and try reading the books they recommend.

15: Can I have more responsibility?

Prepare yourself to see a look of surprise on your bosses face.

No many subordinates would ever ask for more responsibility.

Just the fact that you are asking for more will show your boss that you do have the drive and ambition that makes a great employee.

16: What is the biggest problem or issue right now, and how can I help you solve it?

Now be prepared for a huge smile, because your boss has probably wanted to talk about this with someone for awhile now.

But, he/she may also be apprehensive to spill all that information to you at this time.

Do be prepared to help your boss brainstorm a way to solve the biggest issue they have right now, and that will lead into our last question.

17: Do you want to go have lunch?

What a great way to sit and figure out a way to solve that issue in #16.

A big hamburger, fries and Coca-Cola will make it easier to hash out a plan of action for solving that issue, and while you are at it, you may be able to solve several world problems too.

Now there is the chance that your boss will say no to lunch, but it shows that you do care about the operations, them as well as your own career.

Sure, there may be some that will say it is butt-kissing.

But, if that is butt-kissing, then some of the greatest leaders in Army history must have been butt-kissers, because many of them followed these same question techniques with their bosses.

Final Thoughts

So what do you think?

Do you agree with the questions to ask your boss that I put here?

Do you think it is butt-kissing?

Personally, I just think it is wise actions for someone who cares about their career.

Please tell us your thoughts.

You can leave all comments, questions and suggestions in the comment section below.

Thank you.

Other Posts You Might Enjoy:

  1. How to Earn Your Boss’s Respect In the Army
  2. Top 9 Tips to Deal with a Difficult Army Boss
  3. 12 Common Army Leadership Mistakes
  4. 8 Good Reasons And 7 Bad Reasons To Join The Army
chuck holmes

Chuck Holmes
Former Army Major (resigned)
Publisher, Part-Time-Commander.com
Email: mrchuckholmes@gmail.com

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