How to Have a Difficult Conversation with your Boss

Having a tough conversation with a superior at work is something that can make almost anyone feel nervous, particularly if there are strong feelings involved.

Follow these steps to have a successful exchange:

  1. Use “I” statements rather than “you” statements. With any sensitive conversation, it’s always important to be conscious of the words you choose. It’s easy for others to feel defensive when receiving feedback, and language can make a big difference in how your comments are received. Use statements like “I need”, “I’ve noticed”, “It’s important to me that…” and so on. Avoid making statements that start with the word “you”. They can often sound accusatory.

  2. Provide facts to support your point. If you are trying to make an argument to support what you’re saying, it’s important that you have facts to back it up. Be prepared with specific examples, data or other information that can support your point.

  3. Avoid the statement “I feel”. Difficult conversations can bring out all kinds of emotions. In order to keep things professional and prevent the conversation from getting personal or going off-track, avoid discussing how you feel. Stick with the facts.

  4. Be clear on what you want from the conversation. Before entering in to any type of difficult conversation, it’s important that you are clear about your intended outcome. This should help inform how you approach the issue. You may be hoping to receive feedback, reassurance, or some kind of specific change in your circumstances. Be clear on what you are hoping to come away from the conversation with and make sure that your boss is also clear on your request.

  5. Keep it brief. When we’re uncomfortable, it can be easy to become long-winded. As in many situations, less is more. Be direct, say your piece and stop talking. It can prevent you from making unnecessary comments that you may regret later.

Assertive conversations are difficult for many people. For some, this leads to passivity and rarely results in getting our needs met. If you have a hard time speaking up and advocating for yourself, therapy can help to learn these skills and manage related discomfort. Make an appointment with me today.