How to Have a Difficult Conversation with an Employee

Here's what to do before, during and after to make the talk easier and more effective.
When having a difficult conversation with an employee, make sure to set clear expectations moving forward. (Photo: akov Filimonov/Shutterstock)

As a small business owner, at some point you’ll probably have to have a tough conversation with one of your employees. Whether you have to give negative feedback about job performance, manage a conflict with another employee, deal with a dress code or attitude problem or even address a personal hygiene issue, discussions like these are difficult and stressful for everyone involved.

NCR Silver asked two human resources experts to share their advice on how to approach them.

Related: Why Job Performance Reviews Are Important for Your Small Business


“Everyone has a different method for maintaining a positive attitude. Do what works best for you.” -Samantha Cortez (Photo: Samantha Cortez)

Don’t procrastinate

According to Samantha Cortez, HR manager for digital healthcare startup DrFelix, the time to confront an employee on an issue is when it starts to get in the way of their work performance or affect your company’s culture. Or if a situation has the potential to quickly get out of hand by causing gossip among staff — “that’s also grounds for a talk,” she said.

Noted Jana Tulloch, who manages HR at technical training firm DevelopIntelligence, “We all procrastinate on things we don’t want to do, hoping they may go away on their own,” but sometimes an issue needs to be nipped in the bud. Even if the behavior didn’t cause an immediate problem, it should be addressed to avoid the risk of a problem in the future, and to help the employee learn what is appropriate in the workplace and what isn’t.

As soon as you realize an issue needs to be addressed, advised Cortez, schedule a time and place for a discussion. “This locks you into a commitment and shows your team that you’ve officially acknowledged there’s an issue that requires attention.”

Go in with a neutral mental state

Scheduling the conversation also gives you time to mentally prepare. An angry or accusatory attitude won’t help anyone or anything.


Try scheduling difficult conversations immediately after a meditation session in order to confront the issue with a positive attitude. (Photo: Dragon Images/Shutterstock)

Cortez advised scheduling the meeting for early in the day, after a balanced breakfast and short meditation or yoga session. “This puts you in a neutral mental state and prepares you for what’s ahead.” If you’re not into yoga or meditation, try a different approach. “Everyone has a different method for maintaining a positive attitude. Do what works best for you.”

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Stick to the facts

During the meeting, stick to the issue at hand, the impact it’s having and your expectations moving forward. As much as possible, focus on the behaviors and not the person, said Tulloch.

Give the other person space to explain his or her side of the story, Cortez advised. That opens up the floor and allows you to get a fuller picture of the situation.

Watch your body language

“Regardless of the situation, refrain from reacting defensively,” warned Cortez. “People react to gestures, tones and body language. Keep a cool composure, with your hands together on your lap and eyes focused on theirs.” Staying calm and collected will help the discussion go more smoothly and help you achieve the desired results.

“Acknowledge that it is not an easy discussion, but they need to be clear that there is an issue that needs to be addressed.” -Jana Tulloch (Photo: Jana Tulloch)

Expect a range of responses

“You’re working with a range of personalities, so not every approach works with each employee,” said Cortez. If you have to play “bad cop” and lay down the law, “let them know that you’re not against them, but if their behavior or the situation continues, you’ll have to take affirmative action.”

In some cases, said Tulloch, the employee may become defensive, deny the problem or deflect. “Acknowledge that it is not an easy discussion, but they need to be clear that there is an issue that needs to be addressed. If the meeting becomes too emotional, cut it short and reschedule for the following day.”

Create a plan for improvement

After the issue has been discussed, set clear expectations about what changes in behavior you expect, and offer any training or support the person may need to help fix the problem, Tulloch said.

“After any type of meeting where expectations are set, document it. Sometimes an email follow-up is sufficient, other times a formal letter would be more suitable. Recap the issue, the impact it’s having, your expectations and any timelines that may have been established.”

Related: How to Fire Someone When it’s Time to Terminate

Consider bringing in backup

If the issue escalates, consider if you need to bring in a third party for support. “A mediator might be good in cases where the employee is extremely angry or unapproachable, or when there is an issue between staff that you have been unsuccessful in resolving,” said Tulloch.

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