5 Conversations You Shouldn’t Be Afraid To Have With Your Boss

Career News

by William Arruda, Contributor,

You’re an employee, not a robot. That means you shouldn’t expect to merely acquiesce. In fact, the workers who move up the corporate ladder fastest are the ones who advocate for their own needs and build a solid, differentiated brand.

Sound scary or uncomfortable? To be sure, making a request of your boss can feel a little off-putting. Rest assured, in a healthy organization, making a request is perfectly acceptable behavior. A bonus benefit is that it pushes you outside of your norm, which can be good for your future. As Vicki Walia, chief talent and capability officer at Prudential, writes, “Don’t wait for your career to come to you—you need to take ownership of your own growth.” Good advice from someone who’s been there, done that.

Take raises, for instance. After at least a year of putting your best foot forward and excelling, you should be perfectly poised to ask for more money. You’re not being greedy, and most managers won’t think you’re uncouth by making the case for why you’re worth a bump in salary. Just make sure it’s in line with competitive rates for what you do and where you work.

Of course, money isn’t the only thing you’ll want to talk to your boss about. A Glassdoor survey revealed that most benefits and compensation matter less to professionals than other workplace factors, anyway. Consequently, your ask may be unrelated to finances and more attuned to some other personal or professional need.

Below are five conversations, beyond asking for a raise, that you should never be afraid to have with your supervisor or employer.

1. Advocate for flexibility.

Life doesn’t follow a neat little continuum, allowing you to be available to work from precisely 9 a.m. to 5 p.m. every day. More than likely, you’ll occasionally need to head out to pick up the kids from school, help a parent get to medical appointments, or take your ailing dog to the vet. Or you might just need time to get your hair cut. When you realize that sitting at a desk for eight hours at a stretch isn’t necessary for your particular job, you may want to ask for some schedule flexibility.

The key to making your case involves anticipating your manager’s biggest concerns, such as how you’ll get work done, stay in touch with the rest of the team, and prove that you’re really putting in those hours when you’re off site. Outline some methods to successfully work remotely or come in at different times. If you bring a few creative plans, you will take the onus off the boss to come up with a solution. And you’ll be much closer to hearing, “OK, we can try that for a few weeks to see if it plays out well.”

2. Discuss your plans to use your paid time off.

Are you afraid to take your paid time off (PTO) because you fear being vacation-shamed by colleagues? Or do you relish being seen as a work martyr, like nearly half of Millennial employees, according to figures from the U.S. Travel Association? If so, you’re doing yourself and your company a huge, costly disservice. After all, Harvard Business School research suggests that burnout takes a nearly $190 billion toll on the economy each year. And burnout is just one outcome of never taking “me time.”

Even if you’re sitting at your desk, you’re not necessarily adding value. As Srini Pillay, M.D., CEO of consulting firm NeuroBusiness Group and an award-winning author, notes: “Just because you show up at work doesn’t mean you’re saving the company money. Many people show up with their bodies, but their minds are either fried or somewhere else.” Leaving PTO on the table makes no sense from a practical standpoint. Ask for time to get out of Dodge. You’ll come back refreshed and ready to conquer that to-do list, and you might set a positive new trend if your organization is overpopulated by martyrs. Besides, you’ve earned it!

3. Request frequent, personalized feedback.

Do you wait until your annual performance review to get feedback from the boss? You probably want to know how you’re doing much more often—and you deserve frequent assessments. PwC research reveals that anywhere from 60% to 72% of employees crave feedback at least weekly. However, you probably won’t get what you need until you talk to your direct supervisor.

Set up a time to meet when your boss isn’t under tremendous stress. Explain that you want to do your best work, and you would like regular check-ins to ensure that you’re performing at your highest levels. Most managers will be pleased by your willingness to improve, and they’ll arrange to give you constructive feedback. Just make sure you’re prepared to put that feedback into action.

4. Lobby for a mentorship program.

Behind every successful businessperson is a line of insightful mentors. Yet finding a mentor can be tough. While you shouldn’t ask your manager to become your mentor (it can produce conflicts of interest), ask whether the company can help you find one. Your request could be the springboard your organization needs to create a formal arrangement between mentors and mentees.

Many companies are starting to recognize how valuable mentorship programs can be for their team members, especially future superstars just starting out. Data from PwC indicates that 65% of Millennial professionals want to develop themselves on the job, and mentorship falls into that category. Want examples of brands getting mentoring right? PayPal gets top ratings, according to data from InHerSight, by offering mentorship to build team members’ acumen. Likewise, LinkedIn woos top talent with mentoring.

5. Ask for stretch assignments.

Do you consistently get overlooked to lead projects? The next time a team assignment is on the horizon, ask to own it. If you get any flak, be prepared to explain why you think you’ll do well at the task. Don’t be afraid to raise your hand to oversee assignments that might be a stretch based on your current title or duties. As long as you believe you have the skills to do well, put in your request.

And when you get the go-ahead from the head honcho? Really kick your abilities into high gear and leave nothing undone that you can conceivably do to make the project a success. If you excel at the role, you will almost certainly get more chances to show off your leadership chops. Over time, this will help you prove that you’re a strong candidate for promotions.

In most organizations, it’s not risky to ask for what you need. Indeed, it can be riskier to remain silent. Discover your voice at work and make sure you’re heard by your supervisor. You might not be the boss yet, but at least no one will mistake you for a robot.

William Arruda is the cofounder of CareerBlast and creator of the complete LinkedIn quiz that helps you evaluate your LinkedIn profile and networking strategy.