No one likes to have difficult conversations, especially with their boss. Whether it’s a problem with a colleague, a mistake you made, or a disagreement about a project, difficult conversations are often necessary in the workplace and can help you and everyone else involved move forward and grow as a professional. But that doesn’t make it any easier to approach your boss with a problem.
To help you learn how to do it right, eight leaders from Council for Young Entrepreneurs offer their advice. Here, they share tips from a leadership perspective on how to approach your manager or boss with a difficult conversation in a way that reduces your anxiety and empowers you to succeed.
Members pictured from left to right.
Photos courtesy of the individual members.
Contents
1. Write it down first
If you’re not sure how to broach a subject, it may help to write it down in a letter first. That way you can organize and rank your thoughts according to which you prefer to communicate. If you’re concerned that you’ll have trouble communicating your needs during a meeting, you can simply convert the letter into points and send it in the email requesting the face-to-face meeting. – Matt Doyl, excel builders
2. Focus on the problem and not the person
The most effective way to approach the conversation is to focus on the problem rather than the person. Instead of making it personal, it’s better to express how the problem affects the work or team and propose a solution. It can also be helpful, if possible, to have an objective third-party perspective to provide a different perspective on the situation. It’s also important to be open to feedback. – Kazi Mamun, CANSOFT
3. Keep Calm and Calm
Keep your cool and stay calm when approaching your boss with a difficult conversation. That’s all there is. Respecting your manager or reporting authority is a good thing, but it doesn’t mean you should be intimidated by them. Just stick to the agenda and be transparent in what you say. It would be great to recommend possible solutions that might solve the discussed problem. – Stephanie Wells, Formidable shapes
4. Come prepared
These conversations can be challenging, but they are a necessary part of any successful working relationship. Employees should prepare in advance, schedule a meeting, be specific and respectful, focus on finding solutions, listen actively and follow up after the call. Approaching difficult conversations in a prepared manner helps reduce anxiety so that you and your boss can process effectively. – John Rampton, Calendar
5. Be direct and concise
Be direct and to the point with only the specific information the conversation needs when communicating with your boss or manager. Learn to appreciate the time you invest in that conversation. As a leader, I always hate having difficult conversations with my employees. But I always like a sincere conversation which is essential for both my employees and me. – Kelly Richardson, Infobrandz
6. Use the STAR method
When approaching your manager or boss with a difficult conversation, try the Situation, Task, Action and Result (STAR) method for a positive outcome. Discuss the situation first and then the facts. Second, describe your role in the scenario or how the situation affects you. Third, come up with appropriate recommendations to address the situation. Fourth, share the expected results. – Jared Achison, WPForms
7. Stick to the facts
It is critical not to blame others or be defensive. Instead, prepare ahead of time and think about what you want to say. When it’s time to have the tough conversation, talk about facts rather than loaded emotions. It is possible to express discomfort without being hostile. Staying positive can also help you gain your boss’s trust and have a productive conversation. – Syed Balky, WPB Beginner
8. Admit your discomfort
Try to focus on the reality of the situation and what you hope to achieve from it. Being nervous or angry will only make it more difficult to communicate clearly. If you’re feeling stressed about an issue, you can start the conversation by admitting your discomfort. Your boss is human and has had similar feelings, so they’re more likely to empathize if you’re honest about it. – Kalin Kassabov, ProText
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