How to Have Great Career Conversations with Your Manager

There is a natural desire to take your career to a higher level when you get more experienced at your job. At the same time, most organizations look to keep their best talents instead of recruiting and training new employees over and over. To take advantage of this situation, actively discussing your vision and desires with your manager is of paramount importance.

“To advance in your career, you’ll need to learn to advocate for yourself. You can’t assume that the organization will take care of you just because you do a good job.”

– Joseph Weintraub, founder of Babson Coaching for Leadership and Teamwork Program

Leaving your career development talk with your boss till the end of the year is not the best thing to do. As with the ever-changing nature of professions in today’s society, growth opportunities can appear within a short window. To maximize these opportunities and constantly improve as an employee, there is no better time to schedule that career discussion with your boss than now.

And with the importance of such conversions, it is better to get it right the first time. To this end, we have prepared everything you need to have an excellent career conversation with your manager in this guide.

What is a career development discussion?

A career conversation is a purposeful chat between an employee and a third party, often a manager, to discuss the employee’s career aspirations and development path.

Such a conversation allows employees to check if their professional goals and ambitions fit with the organization and vice versa. This discussion should provoke strategic thought about their particular career path and make way for possible career advancement.

Why should we have career conversations with managers?

There are various reasons why you should have a career development discussion with your manager. It could be due to a lack of progression and growth in recent years or a perceived upcoming opportunity you would like to seize.

We will detail the benefits of this discussion in this section to help you know what you stand to gain.

1. Get a clear direction: When your supervisor knows your short-term and long-term goals, they can help provide valuable insights and necessary training. Also, after an open and honest discussion, you will see if you should stay and pursue your career goals in the company or go somewhere else where you can achieve them.  

2. Increase alignment with the company: There is no better way to know if your vision and goals align with the organization than to have a career development conversation with your manager. This also shows your loyalty to the company as you seek to know how you can improve and help the company get better while attaining your goals in the long term.

3. Advance individual and professional growth: Potential opportunities might appear during a career talk. You also get feedback on where you can improve, what are your strengths and weaknesses that you may not have noticed before, and from whom you can learn. This can act as a catalyst to speed up your professional growth.

4. Boost motivation: Natural negativity comes with the uncertainty of not knowing what the future holds in your career. Once you are sure there is a path to fulfill your potential and you see the opportunities and what to do to get them, there will be a remarkable upturn in motivation and focus. A motivated employee with a clear path to success will always be productive. 

How to Have a Successful Career Development Talk

You risk things going south if you mess up the career development discussion with your manager. The tips below will walk you through how to plan and execute the conversation efficiently.

1. Prepare yourself before the discussion

Since this conversation is about the employee, you need to take the lead. Hence, you must enhance your chances by gathering the right information before the discussion.

Before the conversation, you should:

• Know your current positions and the company's hierarchy.

• Collect data to prove your working abilities and achievements and understand what’s your competitive advantage.

• Review your qualifications for any promotional opportunities within the organization. 

• Some questions to ask managers about careers - we have listed them below, don’t worry.

With these preparations done, you can now request a meeting with your manager.

2. Choose the right time

The best time to have a career conversation is not in the middle of a hallway discussion or other impromptu update session but when career development is the only topic on the schedule, and there are no distractions. Therefore, try requesting a one-on-one meeting to talk about career development.

There are a few ways to ask for a meeting with your manager. You can ask in person, via a message, or more formally, by sending a meeting invitation email to explain your purpose clearly.

Pro tips for choosing the right time to have a career meeting:

• Check your manager’s calendar and pick an available time. 

• You don’t want to schedule a meeting at a time like the end of the month or year when everybody has targets to meet.

• The meeting should be at a time when things are going well for the company.

3. Stay positive

Talking about careers might go in unpredictable ways. Your request for an honest evaluation of your abilities can result in negative comments, or the supervisor might not think your career aspirations are achievable. 

Maintaining a positive attitude is essential in these circumstances. Don’t feel devastated; instead, seek advice on how to advance and get better. Tell your manager you want to bring value to the department and cherish your current role. 

If you disagree with what the manager said, gently express your opinion with evidence, but never argue or criticize your manager, which can be detrimental to future career discussions.

4. Describe your successes in detail

Nothing does more harm to your chances of success than underselling yourself. Keep track of your strengths and how they can help you succeed in your next job. 

List your significant achievements and, if you can, give specific numbers. Specify the exact accomplishments you have made for the company to prove that you are a qualified candidate for promotion.

Have you closed a particular contract for the company? Did you improve the company's revenue or reach? Did you achieve department goals with your team members?

Document them all!

5. Share your career vision candidly

Where do you want to be in one, three, or five years? Don't get bogged down in specifics like job titles. Know the overall direction you're going in.

Let your manager know your plans for yourself and if the company can help you actualize them. Consider asking yourself the below questions to know yourself better: 

• Do you want to manage people or prefer being an individual contributor?

• Are you looking to expand your horizons or establish yourself as the authority in your current industry?

• What competencies do you hope to acquire?

• What adventures do you long to experience?

• What skills are you hoping to gain, and how does it translate to the company's progress?

• Are you aiming for a promotion, a new job, or a post in a different industry? Make sure your request is explicit.

6. Prepare an agenda

You don’t want to go into one of the most important meetings of your career without preparing potential talking points. Prepare an agenda with a list of subjects to discuss beforehand.

To ensure that your manager is aware of the topics you plan to discuss, include this agenda with your request for the meeting. The following are some possible topics:

• Discuss your professional goals

• A review of your current skills

• Advice on how to broaden your skill set

• Feedback on your overall performances

7. Ask the right questions

It is not a good idea to just list what you want and expect to achieve. Instead, you can mix things up by asking questions about where and how you can improve and help the company to show loyalty.

Also, you can ask tough questions like whether your manager sees a future for you in the company with the goals you have stated. However, you must ensure that your questions align with the agenda you sent to your boss earlier. 

In the next section of this guide, we will list some potential questions you can ask.

8. Follow up

The last stage of this process is to follow up on the meeting. If you were offered a promotion on the spot, you could check back later to know the next line of action.

Also, if your manager promised to get back, you can give them a bit of a breather and do a follow-up after some time. But be sure not to disturb your boss. It is paramount to respect their time, schedule, and privacy.

10 Career Development Questions to Ask Your Manager

There is more to a successful career conversation than having the right plans. You must also pose the right career discussion questions to the manager to make the dialogue worthwhile.

Below is a list of potential questions you can ask your boss:

1. What do you anticipate for me in this role as an employee?

Explicit expectations will clarify and eliminate any uncertainty in the connection between manager and employee.

2. What do you think are my strengths and weaknesses?

If there is one person to evaluate strengths and areas of improvement, it is your manager. Asking this question shows a desire to improve. Also, this can prompt career advice that will stand you in good stead going forward.

3. Could you suggest some books or other learning materials in the industry?

Assess your manager's success by asking this question. Daily reading fosters fresh ideas, enhances memory, and lowers stress, all of which help develop a rewarding profession.

4. What performance objectives ought I to set?

Ask your manager what goals you should set to contribute the most to the company. During employee evaluations, this is a fantastic moment to monitor your success and, if necessary, modify your goals.

5. How can you assist me in achieving my individual goals and objectives?

You can enlist them as mentors by approaching them for guidance on achieving your goals. A mentor might make your path to achieving your professional and personal goals more straightforward.

6. Do you anticipate any upcoming changes in the department that might come with an opportunity?

Knowing of a potential future opportunity allows you to prepare ahead. You know the skills you already have and other things to add to put you in an excellent position to take advantage of the opportunity when it does arrive.

7. Of what accomplishments in your career are you most proud?

You can learn your manager's leadership philosophy by inquiring about past successes. Additionally, it might motivate you to take career-related action.

8. Does my current role have any growth potential in this company?

This question is vital to know if you can achieve the growth you desire from your current role. This will also allow you to draw up plans to achieve them and see what you need to improve.

9. At this phase of my career, what advice would you give me?

You can get a fresh viewpoint by speaking with someone who has previously held the same position. This is especially true for individuals just one or two steps ahead of you in the hierarchy.

10. Who do you think I can emulate to improve going forward?

Your manager is best positioned to suggest a mentor to help you achieve your career goals. To whom you may learn how to improve productivity and build good working habits.

Seek Career Advancement

You'll be better off having gone through this process whether you remain in your current position and move into the next significant role or switch to a new organizational territory. 

So you don't need to delay it further. With a guide such as this, you have everything to take that bold step now.