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How to Start a Career Conversation With Your Boss


Don't wait until your annual review to review your career goals with your boss. When done right, career conversations are a series of discussions designed to help you address your career development needs. 

Gone are the days when individuals can rely on their employers to provide all the answers. In fact, Right Management research says, 89% of employees believe they are responsible for their own career development. Career conversations are ongoing discussions between you and your employer that identify specific goals and the skills needed to reach those goals.   

Ideally, your manager would initiate these discussions, but the reality is that many just don't know how. So don't wait around. Own your own career success, take the initiative and start the conversation yourself.  

Tips for Initiating A Career Conversation With Your Boss 

  • Schedule the meeting. You will want to have plenty of time set aside to sit with your boss and discuss your career without interruption. The best way to do that is to get time reserved on her calendar.
  • Set an agenda. In the meeting request, include an agenda and your goals for the discussion. If you give your boss a heads up that you're looking for feedback on how to develop your career, they will have time to prepare their feedback and give more thoughtful responses.
  • Prepare for the conversation. Consider the questions you might want to ask you boss, write these down as a way to help navigate the conversation. More importantly, go into the meeting with a goal in mind - and the outcomes you hope to achieve. These might include:
    • An assessment of your skills
    • Advice on how you can develop your skill
    • Feedback around your performance
    • Insights into how your skills and contributions are recognized
    • A review of your career goals
    • Better understanding around your opportunities for career growth
  • Keep the conversation positive. Don't get into an argument with your boss. Your goal is to leave each meeting with honest feedback. Ensure your boss understands you care about your current position and that you are concerned about being of benefit to her, the department she manages, and the organization.
  • Send a recap. If you want to be taken seriously, make sure to takes notes on the suggestions and recommendations your manager makes during each conversation. Be proactive, and follow up on any action items. Don't forget, the most important action item is to schedule the next career conversation with your boss - don't stop at just one!

Ultimately, it is up to you to own your career development. If you don't feel like you're getting the guidance you need from your boss, it might be time to take another look at the organization and the benefits to staying on in your current role. 


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