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Do's and Don'ts of Having Difficult Conversations With Employees

By Christopher Coble, Esq. | Last updated on
As a small business owner, you have to focus on the health and success of your business. When an employee's behavior or conduct threatens the business' success or reputation, you have to lay down the law.

While you can't always be your employees' best friend, you don't necessarily want to be hated as the mean boss, or be sued for something you said.

So, here are some do's and don'ts for having an effective and legal difficult conversation:


  1. Don't be angry. You want to conduct these conversations with a clear head. Don't rush in angry. You're more likely to say something you will regret later on if you have a difficult conversation while angry. Take a deep breath and a few minutes to calm down. Step back and take a second look at the problem.
  2. Don't say anything harassing or discriminatory. Stick to the facts because one of the things you will definitely regret is saying something harassing or discriminatory. Comments like "Old people are such slackers!" can get you sued.
  3. Don't rush to conclusions. Things may not always be as they seem. Again, marshal your facts: Do you know for sure what the problem is, who caused it, and what the mitigating circumstances may be? While you may not get sued if you accuse the wrong person, you will lose a lot of credibility among your employees.


  1. Do self-evaluate. Before you start a difficult or uncomfortable conversation, ask yourself, "What is the point of this conversation? What do I want to accomplish?" Are you trying to get an employee to confess to wrongdoing? Are you trying to teach a lesson? Are you trying to enforce a rule? If you have a clear understanding about what you want to communicate, it will be easier for your employee to understand and absorb what you need to say.
  2. Do seek answers, and listen to them. Along the same lines of not rushing to conclusions, ask questions. Let your employee explain her side of the story. Did the employee make a mistake in production? Let her explain why that mistake happen. There may be a systemic error that you overlooked because you were to hasty to pass judgment.
  3. Do be direct. Don't beat around the bush when giving feedback. Say it directly, respectfully, and simply. Statements like, "It can be difficult for company productivity when certain distractions in the work environment affect workers' focus," can go right over your employee's head. From this statement, I don't know what the problem is or what the solution should be. Just keep it simple.

Difficult conversations with employees are just another part of being a boss. Just follow these tips to help you address problems in a positive and legal way.

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