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How to Talk to Your Manager About Career Development

Updated: Mar 2, 2022

Following a difficult period, many employees are looking at next steps for their careers. Throughout the pandemic, companies have had to quickly pivot their operations, leaving many other things, such as career growth, on the sidelines. The topic of career development and advancement is a key topic to discuss with your manager, as it is one of the first steps in reaching your full potential as an employee. Not sure where to start first? Keep reading to learn more about some tips and tricks on how to advance your career growth.

People In A Meeting

Be Prepared

Before you approach the conversation, ensure that you conduct some research first. Creating an action plan along with a series of steps will not only help you track your progress, but it will also create checkpoints to receive feedback. That is why communication with your manager is essential, and alerting them of your action plan is key in order to maximize your growth. Throughout the process, it is key for employees to initiate conversations with their managers and have these conversations on an ongoing, frequent basis.

It is also important for employees to first conduct a self-evaluation and consider what their objectives are. For instance, ask yourself:

  • “Are you happy with the progress you have made in your career so far? Why or why not?”

  • “What are your strengths? What skills set you apart from others?”

  • “What are some valuable experiences you have had in your career and why?”

  • “If you could add or take away a responsibility from your position, what would it be?”

  • “What accomplishment(s) are you most proud of and why?”

  • “What new skills would you like to learn and why?”

  • “Are you aware of your developmental gaps? Are these gaps currently standing between you and your future role?”

  • “Do you have any mentors that you can rely on for support?”

  • “Where do I see myself in the next 5 years?”

Once you have conducted some research and have determined the answers to some of these preliminary questions, it is time to put the first phase of the plan into action. The next step is to determine a good time to speak with your manager. According to expert Joseph Weintraub, while it is important to be mindful of timing, keep in mind that there will never be the perfect opportunity to have this sort of conversation (Knight 2018). There will always be a million reasons not to do or pursue something, so in most cases, you will need to initiate and lead the conversation.

When the meeting is set-up, now it is the time to gear questions toward your manager. One of the best ways to begin the conversation about career development is to ask questions. Gauge what their thoughts are and use this meeting as an opportunity to figure out next steps in achieving your goal. What is their opinion on your proposition? What do they suggest you do to advance your career? These are all questions you must contemplate after the discussion, as a basis for determining next steps. Once you get an idea of what is feasible and what is not, you can plan the next phase of your plan.

Executing Your Action Plan

This may be one of the most difficult parts of the plan, because it will take the most time and energy. Finding a mentor and doing frequent check-ins with your manager on your progress is key to ensuring you are on the right track. That is why it is important to stay committed to your goals and don’t be afraid to open yourself up to feedback. Feedback is the backbone of how people improve and in something as important as career development, it is paramount to improving and achieving your goals.

This is where we can help. Retainify offers a 360 development tool for both employers and employees, and can help to provide you with useful insights that can help you determine areas of strength and improvement that will help advance your career. Click here to learn more about our 360 Development Tool.

Once you receive feedback, it is time to act on it. This is where you should revisit your action plan and make necessary changes as needed. Consider the following:

  • “What do I need to work on and how can I implement this into my action plan?”

  • “How can I use feedback to improve my performance?”

Keep in mind that career development is a marathon, not a sprint, and you will likely need to make frequent revisions to your action plan.

Advance Your Skills

Another great way to fasttrack your career is to advance your learnings and knowledge. It is never too late to learn something new, and with the world constantly evolving, there is never a shortage of skills to acquire. Many companies offer training reimbursement programs, so consult with your manager to determine what your options are.

Throughout the course of the pandemic, there has also been a revolution in how information is transferred and learned. With the large shift to digital platforms, now more than ever there is a plethora of resources that are readily accessible through the Internet. Many websites and businesses have also created online workshops, classes, and webinars, all of which can be done at your own pace, and at any time, anywhere.

Long-Term Process

Remember, career growth and promotions won’t happen overnight. This is a long-term process, one that will always be ongoing throughout your career. Keep in mind that this likely will not just be a one-off meeting and that you are likely to have more in the future. These meetings will be the key to recognizing what opportunities lie ahead, how you can improve, and your progress toward achieving your career goals. However, it is also alright to realize that perhaps your growth potential may lie outside of your current company, and that other external opportunities may be better suited for you. Therefore, keep an open mind and don’t be afraid to embrace new opportunities when you encounter them!

Questions or Feedback?



  1. Knight, R. (2018, January 29). How to ask for a promotion. Retrieved July 9th, 2021, from

  2. Loades, R. (2020, February 18). How to talk to your boss about your career. Retrieved July 9th, 2021, from

  3. Mendoza, N.F. (200, September 17). The covid-19 effect on career development: forward , backward, or stalled? Retrieved July 9, 2021, from

  4. Shambaugh, R. (2015, November 20). Having the here’s-what-I-want conversation with your boss. Retrieved July 9, 2021, from

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