Thinking about questions to ask your boss can feel pretty intimidating. That being said, asking specific questions to your boss can be extremely valuable and provide great learning experiences. These experiences allow you to progress in your career while finding your time at work more enriching. A one on one meeting is the perfect opportunity for you to prepare some questions to ask your boss. Make sure that you engage in good meeting etiquette by preparing the questions for your meeting, by engaging in strong non-verbal communication and of course, by taking notes. 

Because it’s so important to ask your manager questions when you get the opportunity, this article is going to outline 12 important questions to ask your boss along with some points on how to prepare for the meeting

12 Important questions to ask your boss

1 What are your expectations of me as an employee in this position? 

This is an important question because if you don’t understand what is expected of you in your job, you will lack focus and therefore it will take you longer to complete your responsibilities. Even when you do complete your responsibilities, if the expectations are not clear, you may worry about whether you have completed your work properly. It’s helpful to both you and to your relationship with your boss because when expectations are clearly set, you can accomplish your work more efficiently, effectively and productively. 

2 How can we create an ideal workflow? 

When you ask your boss how you can create an ideal workflow, you show initiative, curiosity and commitment. This question asks your boss what kind of management style they prefer to engage with and allows you to establish a style of communicating at work as well. It’s important to gain an understanding of the way in which you will work together to achieve your goals, which makes the outcome of this question useful for both you and your boss. Once that understanding is established, you will feel confident in the way in which you go about your projects. 

3 What performance goals should I be setting? 

Asking about what kinds of performance goals you should be setting shows your boss that you’re thinking about your own development and that you want to continue to learn and grow in your position. This is in line with asking about expectations, except it’s slightly more specific in that it’s about your own career growth. When you ask this question to your boss, you show them that you are committed, eager to learn and determined to achieve your goals. This is going to be mutually beneficial, as you work towards your goals and you strengthen or acquire even more skills and competencies. 

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4 What career achievements are you most proud of? 

When you ask your boss what career achievements they are most proud of, it demonstrates a personal interest in your boss’s opinions and insights. This highlights that you would like to learn from them and use any advice or guidance that they have in order to work on your own career. Not only is this question somewhat flattering, but it shows that you intend to achieve career goals that you, yourself are proud of. This is helpful to you as you gain some insight from someone who has more career experience than you and it is helpful to your boss in that you will likely share what kinds of career achievements you would like to attain as well. The hope is that your boss will guide you to get there. 

5 What advice would you give me at this point in my career? 

Asking about what kind of advice your boss would give to you considering your current position and stage of your career is also going to give you some great insight and a valuable learning experience. Because this is a fairly generic and open-ended question, it gives your boss some space to really be honest with you and share whatever they believe will be the most helpful to you. This question demonstrates interest, eagerness and shows your boss that their opinion and advice truly matters to you. This kind of inquiry is beneficial to you because it’s an opportunity to learn from someone who has likely gone through a similar career path. 

6 What is your personal definition of success? 

When you ask your boss what their personal definition of success is, you open the floor to all kinds of valuable advice. It’s likely that your boss’s personal definition of success is quite different to your own, which is actually what makes it so beneficial to you. Taking the time to listen to someone else’s opinions, insights and beliefs is enriching to both your personal and professional life. Being open to your boss’s perspective may actually contribute to your own ideas and the way in which you define success. This can be helpful to your career and it shows your boss that you are interested in their beliefs and how they may shape your own successes. 

7 What kind of skills and training should I seek out? 

This is a great question to ask your boss because it shows that you want to learn more, grow more and develop more in order to be the best that you can be in your current position. It demonstrates great initiative and tells your boss that you feel ready to acquire or strengthen skills and competencies that are valuable to the job. This is beneficial to both you and your boss because as you gain more training, you are going to feel more confident and more effective in your position. This also questions if the company has the appropriate training opportunities for you to succeed. 

8 How can I help you do your job better? 

Asking your boss how you can do your job better demonstrates great interest and initiative in helping the organization succeed in achieving its goals. This question shows selflessness, seeing as you are concerned with how you may be able to better support your boss and their own pressing demands. When you ask such a direct question, it makes your boss truly consider which areas of the business require more attention and where support is needed. Not only does this show initiative but it shows your boss that you are committed to your role and to the organization as a whole. 

9 What’s the best way that I can offer feedback or ideas? 

If you ask your boss what the best way is for you to share your ideas and feedback, you show your boss that you have insightful and valuable ideas that you would like to share. This not only demonstrates confidence but it opens an opportunity for you to be better seen and heard within the company. This also makes your boss consider the organization’s feedback model and evaluate if it is effective. Therefore, this becomes helpful to both you and your manager, because together, you are establishing a way for the voices of employees to be shared and considered in a way that works for management. 

10 What can I improve on to take me to the next level? 

Asking about what kinds of improvements you can make in your current role shows a huge interest in learning and growing with the company. By asking what can take you to the next level within the organization, you tell your boss that you want to remain with the company and continue to support the larger, overarching goals that the company is aiming to achieve. This asks your boss to consider different career paths that you may be able to take from your current role and it helps create a performance development plan that you can follow up with and track. This is helpful to both you and your boss as you work on areas that need improvement to take you to where you want to be. 

11 How would you have approached this project or situation? 

When you ask your boss about how they may have approached a particular project or position, it demonstrates that you value their opinion and value the way in which they tend to handle business. Asking this question shows that you are eager to learn from your boss and that their approach to work is respected by you. This is a great learning opportunity but it will also strengthen your relationship with your boss as you continue to show an interest in their opinions and insights. This question affirms that you respect and value the career experience that your boss holds and that you want to learn from it so that you can perform to the best of your ability. 

12 What’s your preference when it comes to communication?

Being specific about what kind of communication your boss feels will be the most beneficial to your relationship and to the work that you do is extremely important. Establishing exactly what kinds of communication and how frequently to communicate is going to allow you to be much more productive and effective in your job. It shows your boss that you understand how important communication in the workplace is and that you’d like to approach it in the most effective way possible. This is going to be mutually beneficial and create a strong synergy between you and your boss, including the way you execute tasks and achieve your goals.  

How to prepare for a meeting with your boss

Prepare the questions

Begin with preparing your questions. Chances are when you draft them, you’ll be able to see how effective they’ll be. Another tip is to try it before you ask, e.g., if your question is for assistance, try to perform the task you need help with first and go from there. 

Ask directly and politely

Ask your questions as directly and as politely as possible. Having good etiquette and showing respect will ensure that you get the most out of your conversation with your boss. 

Practice in advance to avoid feeling nervous

Find that inner confidence and let it shine! While it can be intimidating to ask these kinds of questions to your boss, you have a positive intent, which is to enrich and improve your career. That is something to commend, not something to be nervous about. 

Other questions to ask your boss

  • Can you recommend any books or media?
  • How often should we schedule one-on-ones?
  • What is your least favorite part of the job?
  • What type of training would you recommend?
  • Where can I improve?

Parting advice

It can seem daunting to compile valuable questions to ask your boss, but with a little confidence and direction, you’ll get the most out of your one-on-one meetings with your manager. Try out these questions and document the answers in Fellow to easily review your notes at your convenience.