Eight Tips For Approaching Your Boss With A Difficult Conversation


No one enjoys having difficult conversations—especially with their boss. However, whether it’s about a problem with a co-worker, a mistake that’s been made or a disagreement on a project, difficult conversations are often necessary in the workplace and can help you and anyone else involved move forward and grow as a professional. But, that doesn’t make approaching your boss with a problem any easier.

To help you learn how to do it right, eight leaders from Young Entrepreneur Council offer their advice. Here, they share tips from a leadership perspective for how to approach your manager or boss with a difficult conversation in a way that reduces your anxiety and allows you to succeed.

1. Write It Out First

If you aren’t sure how to broach a subject, it can help to write it out as a letter first. That way you can organize your thoughts and order them by which one you most want to communicate. If you’re concerned you’ll have trouble communicating your needs in a meeting, you can just turn the letter into points and send them within the email requesting the personal meeting. – Matt Doyle, 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 is better to express how the problem affects the work or the team and propose a solution. It can also be helpful to have an objective, third-party perspective, if possible, to provide a different view of the situation. It’s also important to be open to feedback. – Kazi Mamun, CANSOFT

3. Stay Calm And Composed

Maintain composure and remain calm when approaching your boss with a difficult conversation. That’s all there is to it. Respecting your manager or reporting authority is a good thing, but that doesn’t mean that you should be intimidated by them. Just stick to the agenda and be transparent with what you say. Recommending potential solutions that can fix the concern under discussion would be great. – Stephanie Wells, Formidable Forms

4. Come Prepared

These conversations can be challenging, but they are a necessary part of any successful working relationship. Employees should prepare ahead, schedule a meeting, be specific and respectful, focus on finding solutions, listen actively and follow up after the conversation. Approaching tough conversations in a prepared manner helps alleviate anxiety so you and your boss can process effectively. – John Rampton, Calendar

5. Be Direct And Succinct

Be direct and to the point with just the specific information that the conversation needs when you communicate with your boss or manager. Learn to value the time you are investing in that conversation. Being a leader, I always hate difficult conversations with my employees. But, I always like a genuine conversation that is essential for both my employees and me. – Kelly Richardson, Infobrandz

6. Leverage The STAR Method

When approaching your manager or boss with a difficult conversation, try the STAR (Situation, Task, Action and Result) method for a positive outcome. First, discuss the situation followed by facts. Second, describe your role in the scenario or how the situation affects you. Third, come up with suitable recommendations to address the situation. Fourth, share expected results. – Jared Atchison, WPForms

7. Stick To The Facts

It’s critical to avoid blaming others or being defensive. Instead, prepare yourself in advance and figure out what you want to say. When it’s time to have the difficult conversation, talk about facts rather than highly charged emotions. It is possible to express discomfort without being hostile. By staying positive, you can also win your boss’s trust and have a productive conversation. – Syed Balkhi, WPBeginner

8. Admit Your Discomfort

Try to focus on the reality of the situation and what you hope to achieve from it. If you’re nervous or angry, this will only make it harder to communicate clearly. If you’re feeling stressed about an issue, you could start the conversation by admitting your discomfort. Your boss is human and has had similar feelings, so they will be more likely to empathize if you’re up front about it. – Kalin Kassabov, ProTexting



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