5 Tough Conversations to Have with Your Boss and How to Have Them

TSP • @myTSPnet


For most employees, conversations with the boss can be daunting. But, there are some topics that can be harder to navigate than others. Maybe you’re unhappy at work or you feel like you’re being underpaid, but regardless of your specific situation, your boss is there to help.

The first step in approaching a tough conversation is to set up a meeting with your boss. Send over a quick note asking for 30 minutes to go over some things. This will allow your boss to give you his or her full, undivided attention during your meeting. Here are some tough conversation topics to have with your employer and how to appropriately handle them.

You’ve put in the work, done research and contributed to some great company wins! These are perfect examples of things that constitute to a raise. Asking for more money is a difficult conversation, but if you have the work to show for it and the right attitude, there is nothing to fear!

Before your meeting, determine your ideal new salary and make sure it aligns with similar job titles in your industry. Discuss reasons why you deserve a raise, but keep in mind the conversation should never turn to why you need a raise. Also be ready to be willing to take on more responsibility in your company. Highlight some key wins in your current role and talk about your future with your current company, because no one wants to give more money to someone who plans on leaving in the short run.

You must be prepared to hear a no, as there are a number of reasons you might not receive a raise, for including a tight company budget or a company need for other positions. Whatever the reason may be, asking for a raise teaches you to advocate for yourself and maybe even get you a boost in income!

Most companies offer quarterly, semi-annual or annual performance reviews, but for some employees, hearing that you're on the right track can help motivate you to work harder. Start by sending your employer an emailing letting them know you would like to discuss your recent performance. Be proactive about any feedback you receive, positive or negative, and take a notebook and jot down notes from your meeting.

The most important part of receiving feedback is ensuring you put into practice the areas you need improvement in. There is nothing more frustrating to an employer than an employee asking for ways to improve and that person never putting feedback into practice. If you really are committed to being a better employee, make performance reviews a regular for you and your employer.

Asking for benefits is an intimidating conversation, especially for recent graduates entering into the workforce, but it is not something anyone should skip over. Benefits include sign-on bonuses, health insurance, time off and much more. Often times, people underestimate the power of asking for something, but the worst you will ever hear is a “no.”

The best way to go into this discussion is to evaluate your compensation package entirely and address it before accepting a job because you do not want to have to come back to the hiring manager with new requests. Keep in mind that the best time to bring up benefit packages is during the hiring process, but if you’re a seasoned employee with your company it is okay to revisit your current package. All in all, you never get what you don’t ask for.

Sometimes jobs can be difficult, or your co-workers can be hard to work with. It is important to remember that everyone is unique and perceives things differently than you. Don’t be afraid to have those uncomfortable conversations with your co-workers or your direct supervisor to discuss any issues. Odds are, your up line may be unaware of the issue or the co-worker may not even know what they said or did to upset you. You should never let things go without addressing them, and this can prevent future occurrences from repeating themselves and it gives both parties the space to communicate everything on your mind.

Many times your supervisor does not need to be included in the conversation, but if you are dealing with an employee who you are having frequent issues with, it might be best to include them. Be sure to approach your employer with solutions to your problem at an appropriate time. Your supervisor is a great person to ask for guidance.

Unfortunately, workplace harassment and bullying are a regular occurrences in many jobs. But it is important to know how to identify it. Many employees report feeling uncomfortable about approaching HR or a supervisor, but that does not mean that these toxic habits should continue in the workplace.

Whatever the difficult conversation you need to have with your boss may be, remember that he or she is there to help. Approach your conversation from a kind, professional place, never positioning yourself as the victim or bashing your co-workers. If you enter the conversation in the right way, your boss will respect your confidence and you might even make a friend along the way!