How to Talk to Your Boss About Your Career Development

Author: Antoinette Oglethorpe

Some people enter the workforce thinking their manager is responsible for their career development. They work hard, deliver results, and wait to be promoted.

Unfortunately, this strategy rarely works.

What no one has told them is: Your career development starts with you—and is amplified by the support of your manager. To advance in any role, you need to proactively initiate a career-planning conversation with your boss. This is a meeting you can use to discuss your interest in growth opportunities, ensure that your individual goals are aligned with the mission of the organization, and develop a longer-term plan to set you up for success.

If this sounds like a lot of work to you, you’re correct. Career conversations take significant planning and preparation, but in the end, you will walk away with a better idea of how to advance. Here is a step-by-step guide to help you get proactive about your growth and set up a productive career conversation with your boss.

Ahead of the Meeting

Start by reflecting on what you want

Before approaching your boss, you need to have a clear understanding of where you are right now and where you want to be in a few years. This will help you verbalize your professional goals and create a development plan in service of them. Set aside some time in your schedule to reflect on your status and your future goals. Ask yourself the following questions:

Where are you now? Think about the tasks you do on a daily basis as well as any projects or priorities on your plate. Which aspects of this work do you find energizing versus draining? Which areas do you consistently feel confident in and which do you consistently struggle with?

Take stock of whether you have mastered the skills needed to succeed at your current level. Gaining this clarity will allow you to more intentionally seek out opportunities where you can leverage your strengths and also identify stretch projects you can use for growth and improvement.

Also seek feedback from peers. Does your analysis of your strengths and weaknesses match theirs? What, in their eyes, sets you apart from others?

What’s important to you in the long term? The goal of this question is to help you identify your values and how they fit into your work. You need to understand this to create a development plan that will help you build a fulfilling career.

Think about what you want to do next. What kind of role do you see yourself in two years from now? When you imagine this dream job, what are you willing to compromise on and what is nonnegotiable?

Recall the tasks that you found most energizing. For example, you might realize that administrative tasks drain you and interacting with clients energizes you. How does this fit into your image of the future? How does it fit into your next role at your current organization? Perhaps being promoted into a role that includes more face time with clients is a nonnegotiable, whereas administrative work is something you will need to negotiate or compromise on. This information will be valuable during your career conversation with your boss.

Before moving on, as a last consideration, think about how your ambitions align with the mission or goals of your team and organization. If you can connect your future goals back to the goals of the company, you can present your manager with a more convincing argument for your growth.

What does success look like to you? Success means different things to different people—an upward trajectory is just one version. Maybe, upon reflection, you’ve realized that you don’t want to take on more responsibility or become a people manager. Maybe, to you, success involves more work-life balance and heads-down creative work. Define your version of success so that your manager understands your ambitions and can help you reach them.

Request a meeting with your manager

A career conversation should not be folded into your weekly one-on-one or tagged onto your performance review. It should be a separate meeting specifically focused on discussing career growth. The frequency of these conversations will vary, but ideally your manager should be open to holding them several times a year to allow for ongoing feedback, goal setting and alignment, and discussion of new or upcoming career development opportunities. It’s usually best to have them shortly after an annual or semiannual performance review—when you’ve already spent time reflecting on your past work—and can now develop a forward-looking plan.

When requesting a career conversation, be clear about the purpose of the meeting. Email your manager and suggest meeting at their convenience within the next week, giving them time to prepare.

During the Meeting

Start on a positive note

Begin the conversation by expressing gratitude for the opportunity. You could say, “Thank you so much for meeting with me today—I really appreciate it. I’d like to use this time to discuss my career aspirations and, hopefully, come up with a development plan that will help me align my goals with our larger team goals and the goals of the company.”

Next, clearly articulate your insights from your self-reflection time. Explain where you see yourself currently, including the aspects of your role that you find fulfilling and those you would like to grow in, change, or develop in new ways. For instance, you might say, “I feel most fulfilled when I’m working with clients and think that my welcoming and clear communication style is a strength that sets me apart on the team.”

Move on to recapping your achievements and highlight how they have contributed to the success of your team or company. This will not only demonstrate your value but also provide a foundation for the conversation around your growth. You could say: “Over the past year, I successfully led the X project, which resulted in a Y% increase in client engagement—contributing to the organizational goal of increasing client engagement by Z%. I believe this shows my potential to take on more challenging client-facing roles on our team and coach others on how to successfully do the same.”

Follow up by sharing what’s important to you in the next stage of your career and how you see those changes contributing to your long-term growth: “As I grow at the company, I’d love to continue taking on more client-facing projects and eventually leading them. I see this as a way to further develop my communication skills and evolve as a people leader, which is a role I want to grow into.”

Finally, if there are development areas you want to acknowledge, don’t ignore them. Instead, connect them back to the vision of the organization. You could add, “I know I still have more to learn about project management, and taking on more initiatives will allow me to do this. The company wants to increase our client outreach this year, so my growth would help contribute to that goal.” Remember, your career goals should create a win-win situation for both you and the organization.

Identify next steps

You’ve just given your manager a lot to think about, and it may take them some time to consider before responding. After making your case, follow up with something like, “I’m curious to hear your thoughts and feedback.”

In some cases, your manager may thank you for opening up the discussion and ask to revisit the conversation in a week—giving them more time to process and come up with a plan. In the best-case scenario, your manager will have come more prepared, with their own ideas about where they can see you growing. In this case, you can work together to develop next steps.

Start by discussing the following areas:

• Understanding the opportunities available to you. Ask your manager what opportunities are available to you given your goals and aspirations. Do you need to learn new skills before moving up the ladder? If so, what are they and how can you better demonstrate them? Do they feel you are ready to take on a stretch project? If there are no opportunities on your team, is there another team you could work with in order to grow?

• Navigating the processes and politics of the organization. Your manager is not the sole decision-maker in most cases, especially when it comes to promotions. You need to understand how the organization works, including both processes and tactics; who the key influencers are; and how to raise your profile and be more visible to key people. Ask your boss, “Are there other people in the organization whose work I should be observing more closely? I would love to speak with them and learn how they’ve become successful here. How would you suggest I make my work and myself more visible?”

• Identifying and evaluating different options and opportunities. It’s unlikely that you and your manager will put together an elaborate plan in this first meeting. Once your manager presents you with options, thank them for their insights. Then let them know that you will think about what you discussed. Ask if you can take some time to outline a more tangible plan for them to review in a follow-up meeting. This will give you the space you need to reflect on the pros and cons of your discussion and propose a few solid next steps.

After the Meeting

Draft a development plan

Take what you’ve learned and put together a plan that outlines next steps, including any new skills you need to acquire, any projects you’ve agreed to take on, and any important stakeholders you want to begin building relationships with.

Remember, the best plans are both ambitious and realistic, pushing your boundaries while still being achievable. Use SMART (specific, measurable, achievable, relevant, time-bound) goals so you can monitor your progress over time. While there will always be factors that are out of your control, it’s useful to structure your plan using concrete milestones (even if they are subject to change). For instance, setting a goal like “finishing the leadership training program within six months” or “increasing client engagement by 10% in Q2” are more feasible than something unpredictable like “be promoted to people leader by fall of 2024.”

Follow up

Once you’ve outlined your goals and milestones, set up some time to review your plan with your manager. Try to do this no later than a week after that first meeting so that the conversation is still top of mind. It can be helpful to send your manager your plan prior to your discussion to give them time to review it thoughtfully beforehand.

Use your follow-up meeting to gather their feedback, make adjustments, and ensure that you’re both aligned. Then ask if you can check in on how things are progressing—either in additional follow-up meetings or during your regular check-ins throughout the year.

Career conversations are vital to your professional growth. By initiating them, you make your ambitions known, gain valuable feedback, and pave the way for a fulfilling career path. Prepare well, communicate clearly, and always be open to feedback. In doing so, you’ll empower yourself to move forward, secure the knowledge you need to grow, and give your manager an opportunity to fully understand and support you on your journey.