University of Wisconsin–Madison

Career Conversations

Having career conversations with your manager outside of review time is critical to success. Additionally, career conversations enable managers to support their employees’ professional development, and is one of the ways to develop an engaged and skilled workforce. These types of conversations can be difficult to have, but with thought and preparation, it doesn’t have to be that way, and you can have an honest and authentic dialog.

Types of Career Conversations

What is expected of me?

At some point, this question must have come up, but roles evolve, and organizational needs change. Therefore, it is important to ask this question every now and again to ensure that your goals and aspirations align with those of the organization. To succeed in any role, you have to know and understand what is expected of you, what you are responsible for, how your work is measured and evaluated, so you can perform well in the role. Let your manager know what resources you need to perform your job well. Work with your manager to set career goals with attached timelines, clarify what needs to get done, and discuss how you will be rewarded and recognized for the work you do.

How am I doing?

You need to know how you are doing so you can course correct if needed. You want to be on meaningful projects that make an impact. Take the opportunity to find out from your boss how others perceive you. Solicit feedback whenever you need it, and do not wait for performance review time.

What’s next for me?

It makes sense to map out your career path so you have a sense of where you want to go next. During this type of career conversation, share your career map/plan, and ask about opportunities and the organizational landscape. This conversation will allow you to make changes to your career map/plan and find out how each choice will impact your career.

What and how should I develop?

If you do not have a coach or a mentor, chances are you will need guidance to help you develop your career. Although you are going to talk about employee development with your manager, think about what you want professionally, and not leave it entirely up to him/her. Think about possible gaps in your skills, and how you might fill them. Although you have done some work prior to the career conversation, listen to what your manager has to say about your development needs, and the best ways to develop them because he/she will have an entirely different perspective from you.

Adapted from “Career Conversations to Have With Your Manager” by Right Management

Tips for Initiating a career conversation with your manager

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/his 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 skills
  • 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!

Adapted from Right Management

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My career discussions began subtly and progressed over time. In the beginning, I took advantage of the simple questions, like “How are things going?” or “What do you think you’re doing well?”. It is easy to respond with a few word answer and move on. But I chose to be forthcoming about exactly how I felt I was progressing, especially with areas where I needed more support. I think that honesty ignited a trusting relationship. My supervisor knew I cared about doing well and I knew that she cared about my well-being. That made opening up feel natural when she asked more pointed questions about my career aspirations. Now I feel comfortable discussing anything career-related with my supervisor, from my desire to join a certain committee or attend professional development workshops to my interest in taking on additional job responsibilities.

Kate Miller, Payroll Services, Office of Human Resources