How to Raise a Difficult Issue with Your Boss

Authors: Steven G. Rogelberg and Jon Gray

Gordon was stewing. He needed to share something with his manager about an ongoing conflict between himself and another team member, Ellen, but he was uncertain how to do it. Although he got along well with his boss, he was nervous about how she might respond. He committed to raising the issue at his next one-on-one meeting, but the meeting came and went and he failed to get up the courage to do it—and then he felt that bringing it up at a later date would be odd. Gordon was not only stewing, he was pretty miserable and discontented, which took a toll on his engagement and productivity at work.

Likely all of us have been Gordon at times. (In fact, he’s a composite of employees we’ve studied.) Wanting to raise a difficult or emotional issue to a manager is a common experience, whether it’s about how to tell them that you’re experiencing difficulties with a colleague; that your team is not going to hit a key deadline; that you’re facing health issues; that you made a mistake; or that you have important feedback for them.

Here’s the key to doing it well. In researching his new book Glad We Met: The Art and Science of 1:1 Meetings, one of us (Steven) surveyed and interviewed thousands of employees in a variety of organizations about what made for productive one-on-ones. He found that the most successful meetings are those in which the employee and manager are clear on and focused on the employee’s needs. Here is a process for establishing your goals and keeping your conversation on target.

Step 1: Pick carefully

Overall, it is important to pick your battles wisely. To begin, consider the underlying key drivers of your concerns, rather than just their symptoms; what your manager can actually help with and what type of help might be needed; and priority items versus secondary items that can be discussed later. Also evaluate whether the issue might naturally resolve itself. Finally, consider factors such as the potential costs and benefits to sharing this information, and how your manager typically responds to feedback or difficult conversations.

For example, if Gordon’s issue with his colleague Ellen is annoying but not affecting his work, and the project they’re working on together is about to end, it may not be worth his raising the issue with his manager. But if it’s causing delays in the project or threatens his future work with her, his manager needs to know.

Depending on your relationship, it might also help to let your manager know in advance that you’re going to need their help resolving an issue or that you want to bring up something important or sensitive. This avoids blindsiding them and sets the stage for a constructive meeting.

Step 2: Ready yourself

Write down and practice your talking points in advance to get comfortable with them. Also consider how your manager might receive your comments. How will they react? What will they say? Envision and plan around their possible responses when practicing your talking points. This type of preparation can help you speak clearly and potentially allay nervousness at the time of the actual meeting. Research has shown that performance visualization can help reduce anxiety and improve your delivery.

Step 3: Start well

Start the conversation off on the right foot to ensure that your comments are well received. Try to be upbeat, as mood states can be quite contagious. Positive body language like smiling and soft eye contact can go a long way as well.

Confirm that your manager is willing to hear your feedback (e.g., “Is it still OK if I discuss . . .”) and show gratitude for their willingness to do so (e.g., “Thank you for taking the time to hear about my concern. It really means a lot to me”). These expressions of gratitude are an example of showing deference through your speech, which researchers believe can influence how receptive your manager is to your requests for help.

Step 4: Demonstrate composure, curiosity, and a willingness to adapt

When navigating the conversation, maintain your composure as best you can and share the core need you’ve identified sincerely and in an organized fashion. This is where you make it clear whether you’re requesting your manager’s help or you’re just bringing something important to their attention. Continue to be mindful of your tone.

After sharing your feedback, listen attentively to your manager’s response. Be curious and show your engagement by asking probing and clarifying questions. A great follow-up is simply: “Tell me more. Why do you suggest that?” This can give you clarity behind declarative answers from a boss. Acknowledge your manager’s perspective, even if you might not agree with them. Negative emotions can cause breakdowns in communication, so try to remain positive and focused on working toward a common ground.

If you’ve presented an issue that needs to be resolved, come to the meeting with possible solutions already in mind. Research has shown that workers are viewed as more competent when they have potential solutions prepared at the time of communicating an issue with their manager. Your proposed solutions don’t have to be perfect, but coming prepared with them is a signal of your proactivity and commitment to overcoming presented issues. Psychologists categorize help-seeking into two primary categories: autonomous and dependent. Dependent help-seeking involves looking for someone else to provide a “quick and easy” solution for you, whereas autonomous help-seeking refers to the pursuit of knowledge that empowers individuals to tackle challenges independently and become self-sufficient. That’s what you should aim for; research has shown that autonomous help-seeking behavior was related to positive job performance ratings, whereas dependent help-seeking was related to negative ratings.

If your manager suggests revisions to your proposed solution, be willing to adapt and make reasonable compromises. Patience and persistence throughout this process will lead you and your manager to a mutually desirable resolution.

Step 5: Wrap up while maintaining momentum

When ending the meeting, it’s important to maintain the momentum you’ve built during your discussion. If you requested your manager’s help during the meeting, verify action items that were assigned during the meeting and clarify both of your next steps. For example, as his meeting with his boss was coming to a close, Gordon could summarize: “OK, so I’ll talk to Ellen using the techniques we discussed, and you’ll follow up with some other team members to see if additional issues are at play.” And to end the meeting on a positive note, restate your gratitude for their time and receptiveness to your feedback.

Bringing up challenging topics with your manager involves careful planning and execution. Rest assured, the rewards are well worth the effort. The steps above will prepare you to navigate challenging communication with your manager and work toward desired outcomes. But they do more than that. They show you how to be an advocate for yourself—how you can sustain your independence and growth as you progress through your career.

Steven G. Rogelberg is the Chancellor’s Professor at the University of North Carolina Charlotte for distinguished national, international, and interdisciplinary contributions. He is the author of Glad We Met: The Art and Science of 1:1 Meetings and The Surprising Science of Meetings: How You Can Lead Your Team to Peak Performance. He writes and speaks about leadership, teams, meetings, and engagement. Follow him on LinkedIn or find more information at stevenrogelberg.com.

Jon Gray is an organizational science PhD student at the University of North Carolina Charlotte. He holds a master’s degree in applied research and evaluation, and is a Certified Animal Welfare Administrator (CAWA). His research interests primarily focus on meeting science, as well as occupational stress faced by dirty work and caring professions. Follow him on LinkedIn.