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For many people, work is more than just a paycheck—it’s about fulfillment, striving for a higher purpose, or reaching new heights in personal development.
If you’re not advancing in your career the way you envision, discussing your feelings with your boss might feel uncomfortable—nobody wants to appear discontent or unappreciative. However, if your manager genuinely cares for their team, sitting down to discuss your five-year aspirations could benefit both of you. Not only will it clarify your path, but your employer is likely to appreciate your ambition and desire for growth.
This conversation will require some self-reflection and strategizing, but it doesn’t have to be awkward or intimidating. Below are some useful pointers.
Clarify Your Goals
Before meeting with your boss, it’s essential to have a clear understanding of your plan and prepare what you want to say. Amy Gallo provides helpful steps in the Harvard Business Review. Though these steps are intended for answering the classic interview question “Where do you see yourself in five years?”, they are also highly relevant for this situation:
Reflect deeply: To discover the right career direction, be honest about your strengths, weaknesses, values, and how you want to spend your time. Ask yourself: What values guide me? What goals do I have? What am I willing to do to reach them? Consider performing a life audit to better understand your aspirations.
Be honest if you’re unsure: It’s perfectly fine not to have everything figured out. However, if you’re uncertain, it’s a good idea to address this before arranging a conversation with your employer.
Prioritize learning and growth: There’s always room to grow. What skills do you want to acquire, or in what areas could you become an expert to improve yourself, your employer, or your industry?
Reframe the question: Five years is a long period, especially in industries like technology and media that evolve rapidly. It’s likely that new and exciting jobs that you can’t even envision will exist in five years. So, instead of focusing on what you want to achieve in five years, shift your focus to two or three years. What will it take to reach that milestone?
This blog, from Boyer Management Group, a company that specializes in employee management, provides even more practical advice on preparing. This includes outlining the steps you’ve already taken toward your goals and evaluating whether your ambitions are “realistic given your skills [and] aptitude.” Furthermore,
Create a list of questions to ask your manager—what do you hope to learn from your discussion with them?
Look into the resources your employer provides to support your professional growth, such as training opportunities or tuition assistance benefits.
Determine the tasks in your current role that would challenge you and help you grow.
Prepare an agenda (a list of topics you’d like to cover with your manager). Having an agenda gives both you and your manager time to think about the conversation ahead of time.
Once you’re ready, approach your boss or manager with confidence to discuss your career growth and how they can support your goals.
Share Your Aspirations with Your Boss
Career development plays a crucial role in keeping employees engaged and satisfied with their work. A great manager is invested in their team’s growth, and they want to see their employees succeed in the way that matters most to them. The only way for them to know what that looks like for you is if you communicate it to them.
“Make it a point to share your overall career goals with your manager at least once a year,” advises career coach Sabina Nawaz in the Harvard Business Review. “Be clear about your plan so your manager understands your strategy.”
This is especially crucial if you’re striving for a promotion or considering a different career path. “Communicate the full range of experience you want to gain so decision-makers can consider you for a broader set of opportunities,” Nawaz suggests. “This could also involve sharing your flexibility regarding location or other logistical factors.”
This doesn’t necessarily mean you’ll be asking for something in this particular conversation, but it can set the stage for future requests. When the time comes, your boss won’t be surprised because she’ll already know your ambitions.
It doesn’t have to be a grand gesture. Here’s what The Muse recommends:
Begin by mentioning where you see yourself in the future: “I’d love to take on a management role one day.” If your manager responds positively, then you can discuss the specific steps needed to achieve those goals—even if that requires transitioning to a different department or company down the road.
This is also a chance to gain feedback from your boss. Here are four questions Forbes suggests asking during your meeting:
Are my objectives achievable?
Would you suggest a different approach?
What steps should I take to qualify for future roles?
Are there any unique development opportunities coming up this year?
You don’t have to follow all of their suggestions, but getting a second opinion can be valuable, especially if you have a positive working relationship and trust their perspective.
The ideal time to discuss your career development might be during your annual review, or perhaps in a casual lunch or coffee meeting you set up. Don’t forget to bring a notebook for jotting down important points, and give them a heads-up that the discussion will focus on your growth so they can prepare accordingly.
Hopefully, discussing your career goals with your boss will show them that you value their support and guidance. They may be able to point you toward helpful programs within or outside the company that can improve your skills or suggest other ways to enhance your performance.
What’s more, this can strengthen the trust between you and your boss. You’ll feel empowered by the support you're receiving to grow in your career, and your boss will benefit from having an engaged employee who is enhancing their skills. It’s a win for everyone involved.
