Special offer 

Jumpstart your hiring with a $75 credit to sponsor your first job.*

Sponsored Jobs posted directly on Indeed with Urgently Hiring make a hire 5 days faster than non-sponsored jobs**
  • Visibility for hard-to-fill roles through branding and urgently hiring
  • Instantly source candidates through matching to expedite your hiring
  • Access skilled candidates to cut down on mismatched hires
Our mission

Indeed’s Employer Resource Library helps businesses grow and manage their workforce. With over 15,000 articles in 6 languages, we offer tactical advice, how-tos and best practices to help businesses hire and retain great employees.

Read our editorial guidelines
7 min read

Awkward conversations at work are bound to happen eventually, especially for leaders. From inappropriate comments to personal discussions to conversations about poor performance, your composure may be tested in many ways. Luckily, there are some things that you can do to reduce discomfort for yourself and your team the next time you encounter an awkward conversation.

Ready to get started?

Post a Job

Ready to get started?

Post a Job

13 tips for handling an awkward conversation at work

The good news is that you aren’t powerless against awkward or uncomfortable moments. There are plenty of things you can do as a leader to lessen the strain of an uncomfortable topic. Here are 13 strategies to use the next time a conversation veers off course.

1. Choose a private place

In some cases, you may need to initiate an awkward conversation yourself. This may include discussions regarding employee disputes or worker performance. For topics that are sensitive, having an audience only adds more discomfort.

Before initiating an awkward conversation, choose a private place away from the rest of the team. Doing so not only shows an employee that you’re serious about the discussion but also gives them space to speak freely. This can reduce awkwardness and help facilitate a productive interaction.

Additionally, suggesting a private setting can diffuse an inappropriate comment before it becomes a full-blown situation. When someone brings up a sensitive topic, try saying something like, “Let’s discuss this in my office” or “Why don’t we talk about this one-on-one” to move the conversation away from unwanted audiences.

2. Manage your anxiety

Awkward conversations can lead to anxiety and discomfort. As a leader, you aren’t prepared to deal with the situation if you’re struggling to control your own response. To perform your best, learning how to manage anxiety is essential.

Fortunately, there are plenty of ways for employers to manage stress at work. These include keeping a journal and practicing relaxation techniques, such as meditation and deep breathing. Finding a new hobby can help you de-stress at home so that you’re ready to take on the next day at work.

Improving the workplace environment is another way to keep stress levels low for your whole team. This can mean implementing health-centered initiatives or simply getting to know your employees better. Brushing up on conflict resolution skills can also boost your confidence in tricky situations.

3. Keep the conversation flowing

In one 2011 study, psychologists found that a four-second lull in a conversation was long enough to cause a major increase in the participants’ anxiety, giving new meaning to the phrase awkward silence. Once an uncomfortable phrase is spoken, it can be hard not to react with quiet shock.

Moving the conversation along can minimize awkwardness. By not giving the comment time to sink in, you can reduce its ability to cause damage. The next time a team member makes an awkward or overly personal statement, don’t give it any attention. Try jumping in with an observation of your own to draw attention away from the misstep.

4. Be transparent

When you need to initiate an awkward conversation with a team member, it’s tempting to try to save face. However, in most cases, your audience will quickly sense your reluctance. Suppressing your obvious discomfort could come across as disingenuous.

Sometimes, one of the best things you can do is acknowledge the awkwardness. Offering a quick explanation, such as “This is slightly awkward, but I think it’s important we have a conversation regarding …” is an easy way to recognize discomfort without letting it overtake the situation.

This can also ease the nerves of the team member you’re speaking to, who was likely just as anxious as you. With the discomfort acknowledged, you can then move the conversation forward more effectively.

5. Listen actively

Whether you’re breaking bad news to an employee or confronting them about a difficult subject, listen closely to their response. Practicing good listening skills can help you understand their perspective despite the awkwardness of the situation.

One of the most useful ways to listen actively is to paraphrase the other person’s words after they speak. Not only does this ensure that you understand their message, but it also shows that you’re serious about hearing them. This can help diffuse the awkwardness of the situation by showing the employee that you’re on their side.

6. Ask questions

Sometimes, comments may seem inappropriate because you don’t have enough information. For this reason, asking questions is a useful way to reduce awkwardness.

Simply asking, “Could you elaborate on that?” gives the other person a chance to explain their position and clear up any misunderstanding. Digging deeper into the subject can enhance your knowledge while normalizing a topic that you once found uncomfortable.

During personal conversations, asking questions can help you get to know the other person better. In these cases, what at first seemed to be an awkward comment could open the door to a stronger professional relationship built on mutual understanding.

7. Redirect the conversation

When there are no questions to ask and the conversation has stopped flowing, changing the subject could be the best course of action. This is especially true during group discussions when it’s necessary to redirect an entire team away from an awkward comment.

To effectively change the subject, turn to a topic that’s relevant to the whole group. This could be recent developments in an ongoing project or upcoming procedural changes. Be confident in your redirection, but avoid drawing attention to the comment that prompted the shift.

8. Find humor in the situation

As a leader, your team may look to you when deciding how to react to a clumsy comment or faux pas. Choosing to see the humor in these situations could reduce or eliminate the awkwardness.

There are several ways you can lighten the mood in the workplace. Making a joke or poking fun at yourself can encourage your employees not to take the situation so seriously, avoiding potential discomfort. Just make sure you aren’t using humor at another’s expense as this could undermine your company culture.

9. Be compassionate

Awkward conversations are tough for everyone involved, so a little compassion can go a long way. This is particularly true during serious discussions, such as those regarding performance or disputes.

Showing compassion for the other person’s perspective can prevent them from feeling attacked or alienated during the conversation. It can also help you establish your position as someone your team can turn to for guidance and support.

Alerting the other person about the upcoming conversation can also reduce awkwardness. That way, they won’t be taken by surprise upon stepping into your office. This can be as simple as saying, “I’d like to have a discussion about your performance later. Is 3pm a good time?”

10. Be assertive

Showing compassion is important, but maintaining your authority is also part of effective leadership. For this reason, being assertive can be useful when managing awkward conversations.

A direct approach is often ideal for delivering difficult news to a team member or confronting them about problematic behavior. It helps get your message across without the confusion that may come from a less assertive delivery. When using this approach, try to remain polite while stating your message clearly and firmly.

11. Offer your help

When it comes to awkward situations, focusing solely on the problem often leads to more discomfort. Take a solution-oriented approach to awkwardness by offering your help.

For example, if a team member’s performance is struggling, offer your help by answering questions or creating employee development opportunities. Or, if an employee comes to you with a personal matter, suggest ways that you can help them temporarily reduce the strain at work.

Looking for solutions can immediately reduce awkwardness by turning an individual’s concern into a group one. Plus, it shows your team that you’re someone they can turn to in times of need.

12. Build openness

To reduce awkwardness before it arises, turn to teamwork. Building a strong team not only enhances productivity but also deepens employee relationships and promotes a sense of openness.

Office-wide openness can prevent awkward conversations in a variety of ways. For one, close-knit team members are likely more familiar with each others’ backgrounds and sense of humor, making misinterpreted comments less common. An environment where employees feel comfortable speaking and being heard is also better equipped to handle awkward situations, meaning they’ll be less damaging to morale.

13. End the conversation respectfully

Uncomfortable conversations often end awkwardly with participants unsure of how to feel. As a leader, you can help provide closure by drawing the discussion to a distinct end.

You can conclude the conversation by summarizing the message and proposing a plan for the future. Suggesting that the group reconvene at a later date can prevent awkwardness from overshadowing the discussion while allowing your team to get back to business.

Recent Leadership and team management articles

See all Leadership and team management articles
Job Description Best Practices
Optimize your new and existing job descriptions to reach more candidates
Get the Guide

Two chefs, one wearing a red headband, review a laptop and take notes at a wooden table in a kitchen setting.

Ready to get started?

Post a Job

Indeed’s Employer Resource Library helps businesses grow and manage their workforce. With over 15,000 articles in 6 languages, we offer tactical advice, how-tos and best practices to help businesses hire and retain great employees.