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Career Growth Questions to Ask Your Manager

Posted on May 19, 2022
Set of colorful tiles all with a question mark piled up in a fanned-out presentation - as if stacked on top of one another.

It seems that recently, I have had a number of conversations with former colleagues and students about career growth and how to navigate a path forward. It involves a strategic approach that pulls together networking, professional development, reflection, skill attainment, and a packaging of everything to present your best self. It also involves support from your current manager or supervisor. You should be meeting with your manager on a regular basis to discuss daily operations, challenges, achievements, etc. It is preferable that YOU run these meetings, i.e., you create the agenda (not to say your manager won’t have topics to discuss). An important part of these touchpoint or 1:1 meetings is to also discuss your career growth.

A good manager will understand that while they hired you for a specific role, part of their job is to help facilitate your growth into other more senior roles. But they can’t, and shouldn’t, do that in a vacuum. As an employee, you are responsible for your career trajectory and need to play the biggest role in growing your skills and experience, so you can move up. A key way to do this is by asking your manager, in your 1:1 meetings, the following questions:

Where do you see my areas of strength? This is a great question to help you gauge how your manager sees you. Often, others see strengths we don’t, and it can help you think more about your trajectory and how you can capitalize on those strengths. It is also good to ask for examples, which can be added into a resume and provide good information to be shared in an interview.

What skill gaps do I have? No one should take a job where they start with 100% of the skills or experience laid out in a job posting. You want to have room for growth. Generally speaking, you should understand where your skill gaps are when you begin a position, but as time passes, your ability to see your skill gaps, unless they are causing issues, may be more challenging. And again, your manager’s 360-degree view is valuable. For example, you may be writing great reports, but your manager sees a deficit in your ability to convey data visually. With this information, you can self-teach or you can ask to attend a class on data visualization.

Where do you see me in 3 years? This is a great question because it will give you insight into how your manager thinks about you and your trajectory. If a manager is not thinking about when you might leave – then, “Houston, there is a problem.” You want your manager to envision growth for you because that indicates they will support you in your goal to grow. Without that support, it can become more challenging to grow, get the recognition needed to get promoted, etc. The worst managers either are indifferent and don’t view your career growth as part of their responsibilities as a leader and others might actually put-up barriers to growth. In either of these cases, you might need to consider an external move to find a more supportive manager.

I’ve noticed that Joan is asked to work on interesting and challenging projects, what can I do to take on to be asked to participate in these? This aligns with the skills gap question, but it also shows initiative. You are asking for an opportunity to take on more challenging roles, while recognizing there may be some steps you need to take to get there. You may not have a skill gap; it could be that Joan asked previously and so the manager often just passes them along to Joan. If there are skill gaps, then your manager can share those with you or ask that you partner with Joan, so you can learn.

Can you talk more about your career trajectory and goals? Showing an interest in your manager’s career path not only helps to create a stronger bond between the two of you, but it allows you to see how easy or challenging their trajectory was. It also can provide you with a potential map, especially if their career growth has occurred within the same company or within the same industry. Understanding your boss moved from Associate to Senior Associate to Assistant Director to Director to Managing Director, shows you a potential growth path for you. It also gives you the opportunity to discuss how they learned the skills necessary or gained the experience needed for those promotions.

How have my skills evolved over the past year? I have spoken and written a great deal about reflection. My students know the value I place on this practice. However, the art of reflection is to take the deep dive while also pulling in observations of others and then reflecting more – for reflection to truly benefit you, you must seek input from others. Therefore, asking your manager how your skills have evolved over time is a great question to tease out your progress. Most companies and employees don’t approach performance reviews the right way, where time is taken to help the person grow and provide clear and attainable benchmarks. This often happens only when a Performance Improvement Plan (PIP) is put in place, which is used when an employee is not performing up to expectation. So, asking your manager about your skills and how they have evolved is a great way to get a sense for whether you are meeting your manager’s expectations. Also, it opens the door to asking for assistance in developing skills or asking for more responsibility.

Have you noticed any habits that might hinder me from getting promoted? Let’s be honest – we all have bad habits! Some bad habits are not going to hinder us, while others might. For example, if you are a procrastinator, but your procrastination only impacts you, you are not leaving others constantly waiting, etc., then while it is a bad habit, it likely won’t have any impact on your career trajectory. If, however, you are moody and when under pressure, you snap at your colleagues, that might very well become an impediment. So, asking your manager if there are bad habits that are, or could be, hindering you, gives you some time and space to work on those bad habits before they become viewed as part of your persona.

Do you anticipate opportunities for growth in the department in the next 18 months? By asking this question, you are opening the conversation up to more specific growth opportunities. If your manager says, “No,” you can ask when they might. You can also ask if they believe there may be growth opportunities in other departments. You do want to be careful not to imply that if there aren’t growth opportunities, then you will be leaving the company. There is a balance you need to maintain to ensure your manager supports you in your growth and pursuing external opportunities. If you are viewed as someone who is just chomping at the bit to move on and move out, you may miss out on internal opportunities that are brewing or have not been publicized. That is not to say, when you believe you are ready for a promotion or a move that you should not pursue any, and all, opportunities, you just need to keep your cards a little closer to the chest when considering outside positions. A good manager will support you if you become a strong contender for an external position.

The more you can create a dialogue – not at every 1:1 meeting – but provide space and time to have these conversations around your growth, the more you will understand what kind of support you can expect from your manager. A manager who is not interested in the conversation about your career, your growth, etc., is one who ultimately won’t support you in your achieving your goals, so you will need to find a mentor who can assist you. And if your manager actively tries to derail or put barriers in place, making it difficult to grow and get promoted, then you need to consider a move sooner rather than later, which might have to be a lateral move. On the other hand, a manager who is willing and wanting to engage in these conversations with you, is one who will support you as you grow and help you grow to best position yourself to achieve your goals. You may not always like what you hear, but when a manager wants you to succeed and has demonstrated that, you need to listen and ask for their support in helping you obtain the skills and experience you need.

As I mentioned at the opening of this post, planning your career trajectory must be a strategic exercise. There not one element, but rather a series of moves, like on a chessboard, that you need to control and maneuver to achieve your goals. Seeking the support and guidance from your manager is only one, but an important one.


Anne Converse Willkomm
Assistant Dean, Graduate College
Assistant Clinical Professor, Goodwin College
Drexel University
Posted in professional-development-career-tips, leadership-management-skills