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How to discuss difficult subjects with your boss

Difficult subjects

When it comes to challenging conversations, it might seem like it’s easier to talk to almost anyone other than your boss. But sometimes you must approach your supervisor about a tough subject, such as asking for a raise or requesting time off to handle a personal issue.

“Although it can feel extremely difficult to broach sensitive topics with your manager, you will feel better after you’ve been honest and gotten the topic off your chest,” says Gwendolyn Jones, MA, area chair of organizational behavior and development and an instructor in the human resource program at the University of Phoenix Cincinnati Campus.

Jones, a veteran in human resource management, offers five tips for talking to your boss about a difficult situation:

Make an appointment.

“Schedule a time in advance,” Jones says, “and let [your manager] know you have something you need to discuss that requires an appointment.” Doing this, she adds, will give you “a much better chance of getting your boss’s full attention.”

Prepare for the conversation.

No matter the topic, it’s key to write bullet points on what you plan to say, Jones emphasizes. “Try to second-guess your boss’s response so that you are ready to address any questions,” she advises.

Jones suggests role-playing the conversation with a friend or family member because another person might come up with responses you hadn’t considered.

Don’t make it one-sided.

If your conversation involves asking your boss for a favor, you want to balance it by offering something in return, Jones explains. For example, she says, “if you’re having trouble getting to work on time because of a personal issue, be honest with your manager but also be willing to give back time to the company so that you aren’t putting him in a bind.

“By offering to stay late several days a week or working on a Saturday,” Jones points out, “your manager will see that you are thoughtfully considering the needs of the company.”

Neutralize your emotions.

If what you need to discuss upsets you, it’s important to put your emotions aside before meeting with your boss, Jones explains.

“You want to keep your demeanor professional and stick to the facts of the situation rather than venting or getting emotional,” Jones stresses. Practice what you plan to say and take slow, deep breaths for two minutes before your conversation to help you control your feelings.


Be assertive.

“If you have something pressing to discuss that’s affecting your ability to do your work, don’t procrastinate,” Jones urges, recalling a previous job at a bank, where she sat next to a co-worker with terrible body odor. After several weeks of suffering in silence, Jones decided to talk to her boss about it.

“I was so glad I forced myself to have that difficult conversation,” Jones says, “because right after I spoke to my manager, the situation was resolved and I could go back to concentrating on my work.”