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How to Talk to Your Boss About Your Career Path

July 14, 2016
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As a recent college graduate, I know (just like many of my cohorts) that adapting to the working world is at times an uncomfortable situation in its own right. Pair that with the innate pressure of consistently wondering what your long-term role at that company will look like, and you’ve got all the early makings of an inevitable stress-induced meltdown. The way to combat this seems easy in theory, right? Just talk to your boss about your future or path, and see what they have in mind.

But in reality it’s not that simple. Why is that?

There’s a widespread discomfort in asking or conversing about this kind of stuff, specifically with today’s young professionals who are new to the workforce. We want to be assertive but not presumptuous, show our ambition without stepping on too many toes, yet still get some kind of bearing on where our life is headed if we stay on the path we’re currently taking.

Talking to your boss can be a daunting (and at times straight up intimidating) prospect, no matter what business or industry you’re in – and even more so when something as important as your career path is the topic of discussion. Something thing that I’ve learned firsthand in my time as an intern, then part-time employee, and now full-time employee; is that there is most certainly a right way to talk to your boss or employer about your career path.

Through my experience, I have found that there are 3 main things to remember in effectively talking to your boss about your career path:

Before You Meet, Take The Time To Mentally Prepare

The whole point of talking to your boss about where they see you going in the years to come is to make sure it aligns with the goals you have for yourself. The only real way to make sure of this is to take some time to sit down and reflect on where you see yourself going. I know this sounds extremely remedial, but you would be surprised at the number of people who go into conversations like this with no game plan, and no real sense of where they even see themselves going.

Think about it; how is your boss supposed to know where you want to go if YOU don’t?


Once you have a solid concept of where you see yourself and what your professional aspirations are, write it down. That way, when you get into that meeting you are fully equipped to answer any kind of “where do you see yourself in 5 years?” questions.

The most important thing this accomplishes, aside from providing a framework to base your professional expectations on, is communicate to your boss that you truly care about the conversation you’re about to have, and your career. Employers want to know that if they are going to try to help you progress your career forward, you are willing to put in the time to make it happen, and whether you care enough to prepare for a meeting is oftentimes a good indicator of that. Otherwise, the whole endeavor would simply be a waste of not only their time, but your own. It’s your career and your livelihood – take the time to think it out and set yourself up to get what you deserve.

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Be Realistic In Your Expectations (By Being Objective)

On that same note of taking the time to think through what you want for yourself, don’t set your goals so high that your boss or employer brushes them off as unrealistic or reaching.

When you think about your professional and personal aspirations, try to be as objective as possible in assessing your capabilities and your projected path. You also need to take into account your experience level, and gauge how far along your skillset is.

Being realistic here is the key to building out a career path with your boss that you two can agree on supporting together. It also demonstrates to them that you are able to think critically about not only yourself, but your capabilities too. While maintaining a positive and ambitious mindset is crucial for success, another huge aspect of creating success for yourself is being able to accurately assess where you’re currently at.

When you’re speaking with your boss, they won’t want to listen to your dreams and aspirations for yourself if they are indicative of overly-wishful thinking. Make your goals and path as rational in nature as possible while still ambitious, because that is what will help you the most, and is the type of language your boss will likely be the most receptive to in supporting your professional ambitions.

Build Out A Roadmap

Once you and your employer are in the midst of conversation and seem to be on the same general page about where you’re headed at whatever company it may be, break down that path into smaller timelines. One great way to do this (and something your boss will likely appreciate) is to build out a “roadmap” of sorts.


When I built out my roadmap, I broke my long-term path down into a 30-day lookout, 90-day lookout, and 1 year lookout, highlighting what progress I aim to make by those time deadlines. This gave me a great visual representation of what smaller wins I would need to make in order to get where my employer and I see myself going in the future. It also makes the whole nature of a “career path” seem way less daunting – because even though my goals seem far off, I can see tangible things to put into practice today that will help me get closer to them.

Aside from breaking down those big-picture goals into more achievable mini-wins, it acts as a huge motivator and keeps you oriented and focused. It’s always easy to say you want to reach your professional ambitions (I mean, who doesn’t want to reach them!?), but I’ve always been taught that the difference between those that realize their potential and those that don’t is personal accountability, and this is a great method to hold yourself accountable for your own successes!

Wrapping Up

Look, I know that all of this is way easier said – or I guess in this case “written” – than done. Talking to your boss is always a bit intimidating, even if they are the nicest and most understanding person on the planet, simply by virtue of the fact that you work for them. But, that doesn’t mean that you should shy away from a conversation that can truly help you in the long run because it’s nerve-wracking.

Think hard about what you want, show your boss that you truly care about your career, think critically and objectively about where you stand now, and build out a plan with your boss to get where you want to go.

At the end of the day, it’s your career; make sure you get the most out of it that you possibly can. Don’t hesitate to reach out with any further questions about talking to your boss about your future. I’d be happy to help out in any way I can. Just shoot me an email at pat@powerdigitalmarketing.com.


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