How To Have Difficult Conversations With Employees As A Leader

Kevin Ortzman
Kevin Ortzman Publications
2 min readOct 30, 2020

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Being a leader is rewarding, but there are challenging moments as well, and one of those challenges is having difficult conversations with employees. There may be times when a leader has to talk to someone about their performance at work. They might need to tell an employee they did not get a raise or promotion hoped for or even let the employee go. These conversations are never easy, but there are ways to make them less painful for everyone.

Be Direct
The rules of difficult conversations differ somewhat from other types of conversation. When someone is getting bad news, it is best to be direct. The person usually knows that the conversation is not going to be a good one, and it only prolongs their discomfort if there is a lot of chatter at the start, even if it is positive.

Be Specific
Specificity is also important. If the person needs to improve, it is necessary to tell them what they are doing wrong and what they need to change. This makes the criticism constructive, giving the person something concrete to work on and increasing the likelihood that they will be receptive to the critique.

Prepare For The Conversation
These difficult conversations should not be conducted on the fly. They should be planned out ahead of time so that they can be both concise and precise. Using the right language and managing emotions are both important. There should be no room for confusion about the purpose of the conversation. While controlling their emotions, the leader should deliver the news with empathy, and the employee should have the opportunity to ask questions.

Incorporate Positive Feedback
The conversation does not always have to be entirely negative. For example, if the employee needs feedback to improve, the leader can focus on how that improved performance helps the entire team. The conversation should also include potential solutions. If an employee has been passed over for a promotion or a raise, specific information on how to do better next time can be helpful. Even if the employee is being fired, specific pointers may help them in the future.

No one enjoys giving or receiving bad news. However, the process can still represent an opportunity for growth when the critique is presented in a direct, empathetic, and helpful manner.

Originally posted on KevinOrtzman.com.

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Kevin Ortzman
Kevin Ortzman Publications

Kevin Ortzman is a natural-born leader and professional living in Chicago, Illinois & working as the Region President at Caesar’s. Learn more — KevinOrtzman.net