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Advice / Succeeding at Work / Work Relationships

5 Things You Should be Talking to Your Boss About

Going into your boss’s office can often be hot or cold: You could be getting a pat on the back for a job well done—or a tough dose of constructive criticism. Your boss may want to assign you an awesome new project—or ask you for the report that’s due today (wait, what report?).

But how often do you stop by your manager’s office just to chat?

Turns out, there are several things you should be addressing with your boss on a regular basis. When you take the time to talk about these important issues, you’ll find that you’re happier with your career and better positioned in the eyes of your boss, your team, and the company as a whole. So, the next time you pass by your boss’s office, stop in and start talking about these five things.

1. Where You See Yourself in Five Years

Whether you hope to be in a different role or a different department, it’s OK—and it can actually be very beneficial—to talk to your current boss about your career goals. And yes, it can be intimidating to bring this up for the first time (especially if you’re hoping to make a big career switch at some point), but it can actually help create more opportunities for you in the long run.

Why would your boss be open to your ambition to move up or out of your current role? In many cases, he or she truly does want to see you achieve your goals. As a manager myself, I constantly ask my employees “Where do you see yourself in five years?”—because if there’s a way I can help them along, I’ll do it. Whether that means putting in a good word for them in a different department at my current company or assigning them specials projects that will help them build new skill sets for a different role, I want to help.

Of course, there’s definitely a right and wrong way to phrase your goals (i.e., you don’t want to blatantly announce to your boss that you’re hoping to jump ship ASAP or that you want to take over your boss’s position). Start small by mentioning where you see yourself eventually: “I’d love to move up to a management position someday.” If it’s received well, move on to specifically how you can reach those goals—even if it would eventually require a move to a different department or company.


2. Your Ideas for the Company

When you’re entrenched in your work, it’s a common and familiar mumble: “This would be so much easier if we did it my way.” But, how often do you actually present that idea to your boss as a serious solution to a problem?

Discussing your ideas with your boss helps you in several ways. First, you’re showing him or her that you take initiative, that you’re committed to improving the company, and that you truly want to make contributions to the team. Second, you might actually get to see your idea put in action—and assuming it’s as effective and efficient as you think it is, that’s great news for you and your team.

To make the most out of the conversation, come prepared with a plan in mind. Try something like, “I’ve noticed that our new hires aren’t picking up on the new CRM program very easily. I’d love to put together some training documentation to help learn it a little quicker. Here’s a quick outline I threw together—what do you think?”


3. Advice for Tough Work Situations

When you view your boss only as the person who hands out assignments and performance reviews, you’ll miss out on some great advice. Remember, your boss is a boss for a reason—he or she has been around the block a time or two. So, take advantage of that to further your own career.

For example, before my boss was in his current position as a department manager, he was in my position—a team supervisor. So, whenever I come across a challenge that I haven’t faced before, I drop by his office to talk through the situation. Most times, he’s been through a similar situation and is able to give me valuable advice about how he handled it and what he learned to do (and not to do).

No, you shouldn’t lean on your boss for every problem that pops up, but if you can’t figure something out on your own, why not use the valuable resource right in front of you?


4. Company and Industry Insight

Of course your boss has to manage your day-to-day tasks, but he or she can provide insight into a lot more than just your upcoming deadlines and company values—especially if he or she has been with the company or in the industry for several years.

This can range from unfamiliar company processes (“what’s the standard process to change a position title?”) to company history (“what it was like when the company was acquired by an equity firm a few years ago?”) to your overall industry (“how has the healthcare industry changed since you first entered it eight years ago?”).

Whether it stems from pure curiosity or strategizing for the future, don’t be afraid to ask questions about the inner workings of the company or industry as a whole. You’ll gain some valuable information—and prove that you’re there for more than just a paycheck.

5. Your Life Outside of Work

If your boss follows you on social media, you’d probably rather figure out a way for her to know less about your personal life. But, getting a little personal with your boss isn’t a bad thing—in fact, it can help solidify your professional relationship.

So, spill a few details about your family, your childhood, or even just what you did over the weekend—and ask questions about her life in return. You’ll likely find something you have in common, share a laugh, or at the very least relax for a few moments instead of worrying about the status of your current project.

You don’t have to go into any extreme details or spend hours telling each other your life stories, but connecting with your boss on a personal level can help you feel more comfortable coming to him or her about serious issues. You may never hang out outside of work, but that doesn’t mean you have to avoid any sort of personal connection.


It may not feel natural at first, but try striking up a conversation with your boss about these important issues. In the end (when you’re happier in your current job and that much closer to your career goals), I promise, it’ll be worth it.

Photo of boss and employee courtesy of Shutterstock.