Discussing Your Career Path with Your Boss: Prepare Yourself with These 5 Questions
Career advancement can be a tricky subject to talk about in the workplace. Dwell on it too much and people will accuse you of being overly ambitious; show too little interest on it and people will think of you as lazy and short-sighted.
This is the reason why a lot of employees are hesitant to talk about their career path with their colleagues, more so with their respective bosses. But when the time comes that you need to eventually discuss your career path with your superior - maybe in your next annual review or during some random one on one discussion - you need to be prepared.
Having a one on one talk with your boss is a great opportunity for you to verbalize your career plans for the future (assuming that you already have some). It’s not often that employees get to talk to their bosses about career advancement. Once given the opportunity to do so, you need to ensure that your discussion becomes a productive one. Doing so entails a lot of preparation on your part.
What follows is a list of important questions you need to ask yourself before discussing your career path with your boss.
1. What have you accomplished so far?
In a general sense, any sensible conversation regarding the future is built upon what has been accomplished in the past. This includes your future plans for your career.
Remember, your career trajectory will always be dictated by what you have accomplished so far. Before you get lost in your deep musings about your future as a successful career person, you have to quantify the things that you have achieved yesterday, in the past year and the entirety of your professional career.
Determining your past accomplishments will provide you with supporting materials to prove to your boss during your one on one that you have what it takes to achieve your career goals.
Top tip: Let your past inspire your future success
Looking back at your accomplishments will give you a more realistic picture of what you can accomplish in the future. While you may have experienced a lot of failures and mistakes in the past, don’t let them dissuade you from planning a bright future for yourself.
In the event that your boss brings up past mistakes or indiscretions during your one on one discussion, make it a point to acknowledge them. Tell him or her that you have learned your lesson and that you are ready to move past it to pursue your desired career path
2. What do you hope to achieve in your career?
This is of course the ‘million dollar question’ that pops up in every conversation about career plans. Too often, people are incapable of answering this question in a concrete and specific way.
Of course it’s perfectly normal not to know what you want. Most people are confused themselves on what they want to achieve. But if you want a productive discussion with your boss regarding your career path then you better give this question a lot of thought. There will be no sense in asking your boss for career advice if you don’t know what you want.
Top tip: Think short-term and long-term
Add in a mid-term goal if you will. The important thing is that you set objectives for yourself. Whatever steps you take towards achieving them will determine your career path. So start planning for your future professional success by setting near-term or short-term goals (i.e. learn a new skill) and medium-term goals (i.e. promotion). More importantly, make sure that these goals will lead you closer to an ultimate goal which can be anything from being a regional manager, a CEO or even an early retiree.
Letting your boss know about these goals during your one on one will help him or her understand what you really want to pursue. It also helps that you’ve thought about your goals ahead of time because if will show that you have a clear grasp of the career path that you want to take.
Also read: Top 7 Personality Test to Help You Determine Your Career Path
3. How do you plan to reach your career goals?
A common mistake that employees make when talking with their bosses about career advancement is making their plans sound more like a destination than an actual journey.
Any objective that you have in mind, regardless if it’s short-term, mid-term or long-term should come with a plan. Yes, you might not know exactly what specific steps you need to take to achieve your plans for now, but who does anyway? What is important is that you have plans that will pave the way towards reaching your goals.
Top tip: Be flexible with your plans
The journey towards success is seldom a narrow and straight path. Plans can change over time. You might deviate here and there and hit a roadblock once in a while. In those times, flexibility will play an important role in achieving your plans.
A productive conversation with your boss will never just be about Plan A. There is a big possibility that your boss will try to broaden your insight when it comes to career development. Show interest and express your openness to his or her views.
4. Am I on the right path?
If you think that you’re currently in the right place and in the right job to pursue your desired career path, then you’re among the lucky ones. But then, there’s also a chance that your current job isn’t really aligned with the career path you want to pursue.
What if you’re simply holding out on your current job and waiting for the right opportunity to pursue the career you want? Should you tell your boss about it? Should you pursue an exit strategy immediately?
Top tip: Determine the level of trust you have towards your boss
The answer depends entirely on you and your situation. You also need to consider the kind of boss that you have and whether he or she can be trusted. If you feel like your boss will be open enough to understand the predicament that you’re in, then feel free to open up. But if you feel like your honesty will compromise your position in the company, then you might want to give your situation some more thought before going on a one on one discussion with your boss.
5. How can my manager or boss help me?
You may be very close to your boss at work but don’t ever expect that he or she will be able to notice everything. Managers are often busy and do not have time to ponder on all your wants and needs. That is why, when anticipating a one on one, figure out in advance how your boss can help you out.
During the discussion, feel free to express to move up the career ladder. Tell your boss what you want and remember to ask for it politely. You can reasonably expect your boss to support you on your career plans. Whether you realize it or not, it is in your boss’ best interest to help you. Your success is also your boss’ success. And in a broader sense, your success will contribute to your company’s success.
Top tip: Sometimes moving up means moving out
Ideally, your boss will be ready to support and even sponsor you to help you pursue the career path you want. But in case he or she is not willing to advocate for you, then moving up the career ladder will most definitely mean that you’ll need to move out of the organization.
Of course, it’s not uncommon for people to leave the companies behind to pursue their professional goals. So don’t ever think that you’ll be the first one to do so.
Conclusion
At the end of your discussion with your boss, you might realize a number of things. There’s the possibility that you’ll realize that you’re in the right path and that you’re perfectly happy with the job you want. Or you might end up realizing that there is a need for you to head out to pursue your desired career path. Regardless, you’ll be very glad that you had a one on one discussion with your boss.
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