How to Have a Career Conversation with Your Boss Outside of Review Time

Having career conversations with your boss 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.


During the conversation journey, to ensure that it is both productive and positive, focus on your accomplishments, goals and aspirations. But to be able to do that, there are a few things that you have to do first. If possible, set aside three hours of uninterrupted time to reflect on your career journey, and take an inventory of your accomplishments, goals and career aspirations.


Before the Career Conversation


1.  Write down your values and personal mission statement.

2.  Specific questions to answer that will direct the career conversation include:

a.  What are your strengths and what areas do you need to develop?

b.  What are the critical skills in your job and how would you rate your performance?

c.  What are the key issues driving the company? How can you help to solve them?

d.  What are the major trends shaping your industry and how will they affect your job and the organization?

e.  What skills will you need in the future?

f.   What are your short-term and long-term career goals?

g.  Which goal will position you best for the future?

h.  In what ways can you stretch yourself to increase your skills to make you more valuable to yourself and to the organization?

3.  What specific actions are you willing to take in the upcoming year to achieve your career goals? What are some anticipated barriers that will prevent you from achieving your goals? What are some strategies to work around or overcome them.

4.  List your accomplishments in the organization and the impact that they had.

5.  Gather your “fan mail” - communications from clients, customers, and senior level managers, thanking you for the work you do.

6.  What’s your expected outcome of the meeting?

7.  Create an agenda based on your expected outcome from the career conversation with your manager.

8.  Schedule the meeting with your boss and give her a copy of the meeting agenda.

9.  Do a dress rehearsal of your career conversation with your boss before the meeting to help prepare you, trying to anticipate your manager’s responses and reactions based on what you know about her. Practice until you feel confident


During the Career Conversation


Focus on your accomplishments, goals and aspirations to drive the conversation, using the prepared agenda to guide the discussion. Share with your manager what you think your strengths are and see if she agrees with you. Have a discussion around opportunities within the company and determine the level of support you can expect from your manager. In the event that your manager asks you a question that you are unable to answer, be honest, say you do not know the answer, but will get back to her. Additionally, do not make promises that you know you cannot keep - try to stick to your prepared script as much as possible.


Career conversations can open doors for career choices, and build trust with a manager, so do not wait for your annual performance review to talk to your manager, initiate a career conversation soon!