10 Career Development Questions to Ask Your Boss

Looking to advance your career? Start by asking your boss these 10 career development questions.

Posted April 11, 2024

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Your boss is one of the most important people in terms of your career development. No one has as much insight into your daily work life, and if they are on your team, they can be powerful advocates and mentors who can help you grow professionally and personally.

To create buy-in from your manager and set yourself up for career success, asking a set of preliminary questions can be a great place to start and will potentially spark a longer conversation about your trajectory and goals. In this article, we will cover ten of those questions. Factors like your industry, stage, team dynamic, and others can affect the relevancy of these questions – we highly recommend altering them to make sense for your circumstances and supplementing with questions outside of this list. With that, let’s dive in.

Why You Should Talk to Your Boss About Your Career Development

As we’ve already alluded, there are many, many reasons to loop your boss into your career development. The better they know what your goals are, the more that they will be able to help. If they feel like they’re on your “team,” they’ll be more comfortable and willing to advocate for you, help you grow, challenge you, etc.

Other benefits of talking to your boss about your personal career development include:

  • They can help you identify areas of improvement or skill gaps.
  • They can work with you to break down goals into tangible, obtainable steps.
  • Depending on the company, they may be able to help you get into specific training, mentorship, or leadership programs.
  • It shows that you are proactive and motivated which may help you stand out when promotions or raises come around.
  • It can help you build a great relationship with your supervisor and demonstrate your value to the company.
  • … and many more!

How to Approach Your Boss About Career Development

We get it – talking to your boss, especially if it’s a new one or traditionally a more distant relationship, can be scary. The trick is going in with the right intentions and having a game plan. Here are some best practices, whether it’s your first time discussing your career or the nth time.

1. Schedule the meeting in advance.

And, either in the meeting invite or in person-to-person communication beforehand, mention that you want to talk about your career development and would love any guidance that they have to offer. This gives both of you time to prepare and shows that you’re taking it seriously.

2. Know what you want to talk about.

You don’t have to have every second planned, but have a couple of core things that you want to discuss and core objectives that you want to get out of the call. You’re inviting your manager to the call – they are probably expecting you to lead it (and even if they’re not, you should lead it). It will be the most productive and effective for you if you have a clear idea of what you want accomplished.

3. Keep an open mind.

It is important to remember that your boss may not have all the answers or solutions to your career development. However, they can provide guidance and support in helping you achieve your goals. Be open to feedback and suggestions, and be willing to take on new challenges and responsibilities.

4. Show your appreciation.

Remember to follow up with your boss after the meeting to show your appreciation and keep them updated on your progress. They are taking time and energy to help you – be grateful, and show your gratitude. Taking them out to lunch or buying them a coffee afterward doesn’t hurt either.

5. Keep the right attitude.

Go into these conversations with a mindset of humility and determination, and a willingness to learn. Show that you genuinely care about your career development and want your manager’s help. The right intentions and clear communication will go a long way toward helping you succeed.

What to Expect

After asking your boss about your career development, you should expect some form of feedback. Whatever form the feedback takes, make sure to be appreciative. In almost every case, it is coming from a place of trying to help you. If it’s negative, or primarily involves areas of improvement, take it as an opportunity to reflect and think about what you feel like you can do to improve. You will know yourself best, but feedback can give you a window into how others, especially leadership, see you and your work.

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10 Essential Career Development Questions to Ask Your Boss

Now, here is our curated list of 10 essential career development questions designed to spark insightful conversations and pave the way for advancement. From clarifying expectations to identifying opportunities for growth, these questions will empower you to take charge of your career trajectory and cultivate a path towards success.

  1. What do you see as some of my strengths, and how do you think I can best leverage them (in this role and in my career in general)?
  2. What skills should I develop further to be an asset to this team and the company?
  3. How can I better contribute to my team's overall success?
  4. Are there any expectations for this role that I am not meeting, and if so, how can I do better?
  5. What are some specific goals that I could set within this role to set myself up for success later in my career?
  6. Are there any opportunities available for professional growth within the company that I could take advantage of?
  7. What are the main factors that you’re considering for promotions and raises?
  8. What qualities do the most successful employees on the team and at the company possess?
  9. Is there anything I can do to make your job easier?
  10. Do you have any advice for [x goal]?

How Often Should You Ask Your Boss About Career Development?

There is no hard and fast rule regarding how often you should ask your boss about career development. However, you should have regular check-ins, preferably every six months to a year. Additionally, if you experience significant changes in your job role or responsibilities, it's a good idea to discuss how this impacts your career growth. Remember, demonstrating a proactive approach to your career shows your employer that you are invested in the company and your professional development.

It’s important to note that not every manager is created equal – you may have a great relationship with some that is naturally conducive to mentoring. With others, it may be a bit more distant or they may not be as willing to be involved. Take the information that is the most helpful for your situation, but make sure to adapt things for your relationship and goals.

5 Mistakes to Avoid When Asking Career Development Questions

Asking career development questions is critical, but it's important to avoid certain missteps. Don't be too aggressive or pushy when asking your boss about your career growth, as this can be perceived negatively. Additionally, don't get defensive if you receive negative feedback. Instead, be open to learning, and ask for clarification if necessary. Be flexible in your approach and willing to pivot your goals as necessary.

When asking career development questions, it's essential to approach the conversation thoughtfully and strategically. Here are five common mistakes to avoid:

  1. Vagueness: Asking overly broad or vague questions can lead to unclear or unhelpful answers. Instead, be specific and targeted in your inquiries, focusing on particular aspects of career development that are relevant to your goals and aspirations.
  2. Lack of Preparation: Failing to prepare adequately for the conversation can undermine its effectiveness. Before meeting with your supervisor or mentor, take the time to reflect on your career goals, identify areas for growth, and formulate specific questions that you'd like to discuss.
  3. Overlooking Opportunities for Feedback: Career development conversations provide valuable opportunities to receive feedback on your performance, strengths, and areas for improvement. Don't shy away from seeking constructive feedback from your supervisor or mentor, as it can help you identify areas to focus on and grow professionally.
  4. Neglecting to Listen: Effective communication is a two-way street, and it's crucial to actively listen to the responses and insights provided during career development discussions. Avoid the mistake of dominating the conversation or dismissing feedback, and instead, engage in active listening to fully understand and absorb the information shared.
  5. Failing to Follow Up: Career development is an ongoing process, and it's essential to follow up on the insights and action items discussed during the conversation. Take proactive steps to implement any recommendations or strategies identified, and schedule regular check-ins to review progress and adjust your approach as needed.

By avoiding these common mistakes and approaching career development conversations with intentionality and preparation, you can maximize the value of the discussion and make meaningful progress towards your professional goals.

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