How to Have a Difficult Conversation at Work

How to Have a Difficult Conversation at Work — An Employer’s Guide

There are some conversations that are more difficult than others to have in the workplace. Whether you’re sitting down with an employee to discuss inappropriate behavior, an error, or a failure to pull their own weight, knowing how to have a difficult conversation at work is crucial. Studies show that the cost of a failed work conversation can be as high as $7,500.

Follow our suggestions for making the most of an unpleasant yet unavoidable conversation with an employee.


Plan what you can and act swiftly

When having a difficult conversation at work, you want to avoid flying blindly into the situation. While you can’t control an employee’s response, you can set the tone by choosing an appropriate setting.

For example, the middle of the break room probably isn’t the best choice. But planning a meeting in a closed office or private conference room will ensure that the discussion remains confidential.

It’s also important to act swiftly. Many put off difficult conversations because they’re hard to take on. But if you put off a conversation for too long, it may no longer be relevant. An employee deserves to know if they’re underperforming and the company as a whole deserves a solution sooner than later.

Be specific and focused

Every difficult work conversation has two sides. When you’re the one initiating the conversation, you may feel as if you need to steer the entire discussion. While you don’t want to lose control of the situation, you should allow the other party to respond and have the ability to ask questions.

If they need some time to process the information, briefly step away. However, always give the other party your full attention as they voice their opinions and concerns without letting the conversation go off track. This includes:

  • Looking directly at the employee
  • Simply listening and not planning a response
  • Eliminating distractions, like outside conversations and smartphone notifications
  • Paying attention to body language

Offer a solution

When learning how to have a difficult conversation at work, coming up with solutions is part of the process. This type of brainstorming should be done before the conversation takes place, though the final solution may change once the employee has had a chance to respond.

For example, if you’re discussing an error an employee made that damaged the relationship with a client, you may want to assign a new team member to the account. But the employee may have a way to repair the relationship on their own.


Be Firm Yet Encouraging

It’s important to note that at the end of your conversation, an employee should know:

  • What they did wrong
  • How their actions affected the company or their coworkers
  • What needs to change moving forward


As their employer, provide them with a few next steps they can take to prevent the same mistakes in the future. This will also show that you’re committed to their future with the company.

Being firm throughout a difficult work conversation is important. But that doesn’t mean it has to end on a sour note. If you’ve done your best to plan the interaction, provided plenty of time for equal discussion, and suggested potential solutions, you’ve hopefully been able to keep the overall tone of the meeting professional and productive.


Bonus tips on how to have a difficult conversation at work

No two conversations will play out the same way. Here are a few bonus tips to keep in mind when preparing for one.


  • While you can (and should) be empathetic towards an employee, don’t let your emotions take over.
  • Keep discussions short and to the point. There’s no benefit to drawing out difficult conversations, especially if you’re up against an emotional employee.
  • Safety should always be your top priority. If you’re terminating an employee or have reason to believe a discussion could take a violent turn, read our tips for staying safe.


Knowing how to have a difficult conversation at work can make all the difference. Put some thought into the conversation before it takes place, let the other party have their share of the floor, and provide support as required. With a little prep work, even the most difficult work conversation can go off without a hitch.


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