How to Have a Career Development Discussion With Your Boss

The purpose of having a career development discussion with your boss is to help you grow and develop to your optimal capability over time. It isn’t asking co-worker Alice for career advice in the lunchroom.

Most employees want what they do for a living to serve a greater purpose for both personal and professional growth. Not just something to do to fill time and earn money.

Career Development is a Key to Employee Engagement

Over the past two decades much work has been done to understand what causes some employees to have high engagement with their employer – actively realizing personal and professional growth – while other staff members are disengaged and feel tired, stagnant, and disinterested in their work.

One the findings in the studies done by the Gallup Organization and others is that employees dramatically increase their levels of engagement when their boss shows concern for their progress at work. In his iconic book First Break All the Rules, Marcus Buckingham outlines twelve top indicators that translate to employee engagement. Aspects of career development are present in over half of the factors.

Who Owns Career Development?

Each person is responsible for his or her own career development. No one else is. Others can help, but ownership rests with the employee. Others can be your thinking partner and your accountability partner, but it must be your plan and your work.

One of the best ways to engage your boss in your own career development is to request he or she meet with you to discuss your career progress. While many managers may initiate a career development discussions with their staff members, most are not trained in how to optimize the process. That is why you, the owner of your own career development, need to be prepared to drive the process. And you can.

Preparing for a Career Development Discussion

Since you own the process, you’ll want to precede a discussion with your supervisor with some solid planning. Here are some strong preparatory steps to take:

1. List the steps you have already taken to establish career goals, and review whether they are they realistic given your skills, aptitude, and realistic given your skills, aptitude, and how your employer defines an “ideal employee.” This step requires total honesty.

2. Review your last performance evaluation to see how you are currently doing. This requires some critical assessment of yourself.

1. Were there any improvements required since the last performance progress meeting, and if so, how has your work been?

2. Consider how long you have been performing at your current level in months or years.

3. Evaluate how you have responded to work requests and the suggestions your boss has made.

3. Build a list of questions to ask your manager – what do you want to learn about as a result of meeting with him or her?

4. Investigate the tools that your employer provides to help you develop in your career, such as offering training or a tuition assistance benefit.

5. Identify the things you’d like to do in your current job that would stretch you.

6. Are there other responsibilities at work you could take on?

7. Provide an agenda (a list of points you want to discuss with your manager). An agenda will allow both you and your manager to think about the topic in advance.

Initiate the Discussion if Your Manager Doesn’t

Because you own your own career development, don’t wait for your manager to suggest a career development discussion. Initiate the discussion. Look to find an opening on your manager’s calendar for a week to ten days out and ask if you could meet with him or her to discuss your career progress. Indicate that you would appreciate his or her perspective and guidance. You could provide the agenda to allow him or her to prepare.

Good Questions Can Open Your Discussion

In general, you’ll want to develop five to seven really good general questions to kick off the discussion. Here are five questions that you might want to use and build upon:

1. “What opportunities are there here for someone like me?”

2. “Where do you see my career path lying, based on what you know about me and the company?”

3. “What skills gaps do you think I have (for current/future role)? How long do you think it will take me to learn and master those skills?”

4. “What do I need to do in order to get promoted or assigned new responsibilities?”

5. “Are there any special development opportunities ahead you think would benefit me?”

These are just the opening questions. Ask follow-up questions based on the answers you receive in order to drill down to the details. Make sure you fully understand the answers.

Bring an Open Mind and a Notebook

An open mind is essential. Recognize that your boss sees you differently than you see yourself. He or she has seen your work, knows some of your strengths and shortcomings, and has a perspective of where your employer is going. It is quite likely that he or she will make observations, offer suggestions, and go in directions that you didn’t expect. Yet he or she has your best interests at heart so you need to be open to what he or she says.

One of the ways you demonstrate your commitment to the process is to take notes during the meeting. Notes suggest that you will take action (which you will absolutely need to do). They also assure that you don’t forget something that was said during your meeting.

Close the Meeting, Build Your Plan

Summarize the actions you plan to take as a result of the meeting. Thank your boss for his or her time and guidance. And if you believe you will be ready to do so, ask your boss to meet with you to review your plan (and schedule this meeting).

Your plan should be in writing. Anything less is just a fuzzy dream or wish. Written plans demand commitment and follow-through. A lack of a written plan tells your boss that you are not really serious about your career, and that he or she only had a nice, not-going-anywhere chat instead of a career development discussion.

Your plan should set forth your specific goals and objectives for a time frame of one to two years out, and contain action steps that will move you from where current are to where you want to go. It does not have to be War and Peace, but it needs some detail. You may want to vet your plan with others as well as your boss.

Bottom Line

You own your own career development. Part of that ownership is reaching out to people who can help you develop your plan, offer appropriate guidance, and serve as both a thinking partner and an accountability partner. One of the very best people to engage in this process is your boss.

This article was in part excerpted from the seventh edition of the textbook included with the Job Search Readiness Assessment.

I help job seekers, higher ed, and employment services connect people to better jobs faster. My company’s acclaimed career development tools, the Job Search Readiness Assessment for experienced professionals/skilled workers and Graduate Employment Preparedness Assessment for students/recent grads both assess and explain over 3,000 career and job search best practices. I also work with some of the world’s top employers by helping them get the most out of their talented people. My company’s extensive leadership development course catalog provides effective skills-building for everyone in the organization, from the new / developing leader to the seasoned C-level executive. My company’s coaching programs produce significant results in compressed periods of time. To find out more, please visit us at, email us at, or call us at 215-942-0982.


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