7 Difficult But Important Topics to Discuss With Your Boss

Making small talk at the coffee machine or discussing a project in a meeting are relatively painless, but broaching a more serious conversation with your boss can be daunting. In fact, you might be tempted to take the easy way out and avoid potentially difficult discussions at all costs—but that won’t do your career any favors. Clear and open dialogue is essential to boosting productivity and morale in the workplace, especially in sensitive circumstances.

If you’re faced with one of these challenging situations, it’s important to keep the lines of communication open with your manager or supervisor.

Sexual Harassment

If you are a target or witness of sexual harassment in the workplace, you should consider it your right and responsibility to report it, says Nina LaRosa, marketing director of Moxie Media, a workplace safety, health and HR online training company.

"Although it may be difficult, preventing and addressing sexual harassment issues is critical for maintaining a safe, healthy and positive work environment," she says. "Creating a culture based on respect is important, because it can help prevent accidents and injuries, increase retention, improve productivity and avoid legal action."

Before bringing the issue to your boss’ attention, LaRosa says it’s important to document the details of the incident while they are still fresh in your mind. When reporting the issue, be direct and professional. If you are feeling anxious, try meditating, picturing yourself in a comforting place and taking a few slow, deep breaths beforehand.


Telling your boss that you are leaving your job can be nerve-wracking—especially if you have a good relationship and they value your contributions. Schedule a private, face-to-face meeting as soon as you’ve made your decision, and before telling any co-workers. Prepare a letter of resignation to hand in along with your verbal announcement.

"To ensure a soft landing, tell your boss how great they have been, thank them for their support and then deliver the news that you are leaving," suggests Chris Chancey, a career expert and professional recruiter. "Of course, let them know how you will help to make the transition as smooth as possible."

Avoid dwelling on any negative aspects of the job, but do share the reason for your decision and be open to your supervisor’s feedback.


We all have blunders now and then, but they can be especially embarrassing in the workplace. As Chancey points out, few people are happy to admit they made a mistake. Usually, the first instinct is to blame others or keep things under wraps and hope the boss doesn’t find out about the faux pas.

"Chances are good that your boss will be more understanding if you immediately own up to a mistake and offer solid solutions on how to solve the problem at hand and how to prevent it from happening in the future," he said.

Salary Concerns

Even for employees who know they deserve it, asking the boss for a raise can be terrifying, notes Chancey. However, he believes this is an important conversation to have—particularly for female workers, who are generally underpaid compared to their male counterparts. Also, requesting an increase shows that you are aware of the value you bring to the company.

"Come to the table with solid evidence of the value you bring to the company—such as your accomplishments, results, contributions and wins—to argue your case for a raise," he recommends.

Although you might have a number in mind, Chancey says it’s best to be open to negotiation. And if you don’t get a "yes," ask your boss when you can revisit the issue.

Personal Issues

When we aren’t thriving personally, we can’t fully thrive professionally, notes Samantha Crowe, PhD, ICF-ACC, founder and CEO of Evalia Consulting LLC. Yet, we tend to avoid conversations with our bosses when our personal lives interfere with our job performance. "When we sit in silence, all others see are our absences, moods, behavioral changes and performance misses," Crowe notes.

Whatever challenge you’re facing—perhaps a major life change or loss, physical ailments or mental health issues—it’s important to have a conversation about what’s happening and how it’s affecting your work. "This will allow you to find out what possibilities exist for support from your boss, team or organization," Crowe says.

Set your intent and key talking points for the meeting. You don’t have to disclose all the details of your struggles, but Crowe suggests saying something like, "I have some personal matters (or personal growth opportunities) that may affect my work if I don’t get support. I’d like to get your ideas on how we can work together to reach our shared objectives."

Inclusion and Diversity

In a culture where growing emphasis is placed on diversity and equality in the workplace, it’s important to speak up if you have questions or concerns about how your company handles inclusion efforts.

"There’s been a lot of effort to build more diversity in the workplace, especially since it’s been proven that more diverse teams lead to more innovation and profitability, but inclusion is something that is often a struggle," notes Kira Nurieli, organizational psychologist, mediator and conflict coach with Harmony Strategies.

Once minority employees are invited to work at the company, how are they treated and encouraged to equally participate? What efforts are made to include those with disabilities? What efforts are made to ensure that all voices are heard? "Many companies shy away from these topics, but these very issues will create a culture of inclusion that drives profits, employee engagement and satisfaction," says Nurieli.

Mental Health

In today’s fast-paced and hyper-connected society, many employees work well past the standard eight-hour workday, which can take a mental and emotional toll. Even so, many employees may avoid broaching the topic of mental health with their bosses, perhaps afraid they will come across as "weak or whiny," says entrepreneur Matthew Ross, co-owner and COO of a sleep and mattress review website.

At his company, Ross has policies in place to prevent burnout and to protect employees’ mental health. They have instituted an open-door policy where employees can come to their supervisors if they are starting to feel overwhelmed or stressed. In fact, Ross sometimes offers paid time off to allow workers to regroup and recharge.

"Having employees who are mentally burned out hurts the company from both an efficiency and morale standpoint, so it's important to get it squared away before it becomes a larger issue," said Ross.