Having a career conversation with your boss is an inevitable part of your professional growth. Prepare yourself with the tips below and bring a positive attitude to steer this conversation toward your desired outcome.
Whether you want to evolve from your current role, or act on long-term career goals, a good boss should encourage your professional development. Good bosses view this as you taking an active role in managing your position, and they should be supportive. Still, talking to your boss about something like this can be intimidating.
If you want to be a software lead or a department head, you are entitled to work toward your goals. Regardless of how intimidating it might feel, believing in yourself can help you take the next steps. Think of the process as an exciting new journey toward your future (the one you totally deserve).
If you want to grow, there are two scenarios: you either know where you want to grow or you don’t. You’re not going to get immediate results but the point is to agree on action items with your manager and create a roadmap illustrating your desired growth trajectory. This approach will help you make things more transparent and gamify the process.
Preparing for a career discussion with your boss
When preparing for your meeting, you need to consider two key things:
- When to start the discussion
- What options you have
By addressing both, you optimize the opportunity for a productive conversation.
When is the best time to talk about career advancement?
If you want to talk to your boss about advancement, the best times are:
- Outside of significant events or crisis times
- After you’ve demonstrated exceptional performance
- At a scheduled time, for your manager’s convenience
You’ll also want to schedule a follow-up, especially if you have room for improvement in order to meet the demands of your desired role.
Spoiler alert: you will never find the perfect time to talk to your boss. If you are anxious (which is normal), you might find yourself coming up with a truckload of reasons not to take action. It’s important to overcome those doubts.
Be as direct as possible. I have always been an open-minded person who’s never been afraid of facing feedback. So I encourage you to ask your manager to schedule a one-on-one meeting and tell them about your plans and wishes. Your manager will give you a helping hand anyway.
Identifying your career options
Knowing what options are available to you requires you to do two things:
- Identify available career tracks
- Know what you want to do
Both are equally important. Doing a bit of research can help you here. You don’t want to miss out on a career track that might be an excellent fit for your skills and interests just because you don’t know that it exists, or don’t know enough about it to realize what a good fit it could be. Maybe advancing in your current track is not the best choice for you. Perhaps a lateral move in a different direction would suit you best.
If you are not sure what you want to do, ask around. Ask people in positions that seem interesting about their day-to-day operations. If you like what you hear, keep up the pursuit. Otherwise, you might want to research other options.
Let’s say you have the option to choose between an engineering track or a management track. After talking to people from both groups, you might find yourself loving the opportunities for interpersonal interactions; so maybe you’ll lean toward management. On the other hand, you might prefer solving complex technical problems; if so, the engineering track might be for you.
Deciding on the next step in your career path will enable you to better understand where you need to develop. Whether you want to focus on bolstering your strengths, or addressing weaknesses, a discussion with experienced, successful professionals in these positions will help.
How to discuss career development with your boss
Once you get to the discussion step, it’s normal to feel a bit nervous. Having done your homework — knowing your options and picking the best time — you will be starting off on the right foot.
A discussion of this sort typically involves three goals:
- Creating a career development plan
- Setting appropriate follow-ups
- Obtaining your manager’s sponsorship
What is a career development plan?
When your manager sees your desire, potential, and motivation, they can help clarify what it will take to move toward your future career. How you reach that future is by following a career development plan. Your plan should include:
- How you plan to develop the necessary skills to meet the demands of your desired position
- Milestones you need to reach to demonstrate your skills
- The required stepping stones to reach your career end-goal
When considering how to talk to your manager about career development, it comes down to being focused and goal-oriented. You also need feedback. After all, your manager might have a very different vision about your career trajectory. Ensuring that your goals match leadership goals helps to avoid confusion and unproductive effort.
Part of establishing a career development plan also involves setting follow-up meetings. These follow-ups should provide the opportunity to confirm that you are meeting milestones. Your manager can also check in on your skill development. By demonstrating your growth and accomplishments during these meetings, you give your manager reasons to support and advance your goals.
How do you win your manager’s backing?
Sponsorship from management is paramount to growing your career. Getting that support and sponsorship can be tricky. Here are some key things to do:
- Discuss your long-term career trajectory (not a single promotion)
- Focus your discussions on solutions and problems that you want to solve
- Tell your manager how you plan on growing
- Focus on positivity
If you feel you’ve outgrown your role, it’s time to turn to your manager saying “Hey, could you please share what you think of my performance at the moment? Could you please suggest how I could make my delivery more transparent when working on my growth action items?"
For further tips on winning manager sponsorship, check out our complete guide on what you should and should not do. Whether you want to become a senior director of software engineering or a lead systems engineer, good communication skills are imperative.
How to respond to your boss
When having a career discussion with executive personnel or your direct manager, there will always be some trepidation. As a software engineer hungry for growth, your job is to anticipate their reactions and plan your response.
How to respond to objections in career development
In cases where your manager has doubts about your career path, be ready with a plan for that ahead of time. Being prepared will enable you to counter your manager’s points with greater ease.
Whatever happens, try not to take it personally. It can be frustrating to have to overcome objections from your boss, but their concerns may have nothing to do with you as a person.
Your boss might have another idea for your development or might be focused on other things. There is also a fair chance that they’ve already considered someone else for the position you are interested in. Asking what it will take to overcome their doubts is an opportunity for you.
At what point do you move on?
If you want to grow, you should give yourself every opportunity to do that. If your company doesn’t provide an opportunity, you need to set a hard limit on the number of attempts you make. After that, it might be time to recognize that there are better opportunities for you elsewhere.
Don’t think of this as a bad thing; it is a chance to expand your horizons and find a workplace that is a better match for your interests and goals. You might find exciting job opportunities and a work environment that suits your lofty goals elsewhere.