Today’s question comes from a busy professional:

What are the questions you should always ask your boss? What do you need to find out, or clarify? And why?

  1. What questions should people always ask their boss, and why
    are they important to ask?
  2. Is it okay to ask your boss questions? Why might it be
    important to do so?

A company executive speaks with a woman during a business meeting.

Yes.  It is not only “okay” to ask your boss questions, it’s very important to ask your boss questions.  Questions show that you are taking control of your own career and professional development.  You are not waiting to be told the information; you are initiating and guiding the conversation with your questions.

The reason it’s important to ask questions is that you want to be able to

  • Understand what your manager expects of you
  • Be able to better anticipate his/her requests.

While these are very good questions, another important aspect is “when” to ask these questions.

Questions to ask

One of the scariest (and most important) questions to ask is “How am I doing?”  Because it’s the most difficult question to ask, we often postpone asking or avoid it altogether.  The risk of never asking this question is that (even though you may feel that you are doing a great job), your manager may feel that you are missing your mark in a few areas.

When to ask

If the only time we have a one-on-one meeting with our manager is when something goes wrong or at our performance review, we are going to be uncomfortable talking to him or her.  The more performance-related conversations you initiate, the easier the interchange will be.

Therefore, setup frequent one-on-one meetings with your manager. I recommend at least twice a month or weekly meetings.

Use these regular meetings to review status, upcoming projects, your career goals and career roadmap.

Schedule the topics

Once you have your one-on-one meetings schedule, take control of the agenda by proposing the various topics.


Topics Frequency
Status of current projects Weekly/every meeting
Current issues or challenges Weekly/every meeting
How am I doing?

·         What should I start doing?

·         What should I stop doing?

·         What should I continue doing that I do well?


Monthly/Every other month
What’s your biggest problem — and how can I help you solve it?


Share your career goals and ask advice on how to accomplish

·         I’d love to oversee _________ in the next six months.

·         What do I need to accomplish to achieve that goal?




I know your situation is different.  If you would like additional information on this topic, please contact

I am a business coach and this is what I do professionally.  It’s easy to sign up for a complementary one-on-one coaching call, just use this link


With enough notice, it would be my honor to guest-speak at no cost to your group organization.


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