Get the Glossary

Glossary Paragraph


Resource Center / Teams

5 Tips for Managing Difficult Conversations with Employees

It’s delicate to tackle difficult conversations and sensitive topics with employees, but these tips can help you better manage such situations.

Moses, Certified HR Consultant
Moses Balian
Apr 13, 20207 minutes

As a business owner or manager, there have always been times when you’ve had to tackle sensitive topics with employees. Today, those conversations are more crucial, and more nuanced, than ever.

Hosting a difficult or uncomfortable conversation via video chat is probably the last thing you want to do, but it might be necessary for the overall health of your company. One employee’s disruptive behavior or absenteeism can often impact your whole team in negative ways, and addressing it head-on is often the best way to reach a resolution.

Difficult Conversations While WFH

There are a number of behavioral issues that an employee might display that may require your attention. These issues can impact other members of your team or disrupt the office environment, and lower productivity within the company.

Some examples of potential behavioral issues include:

  • Absenteeism

  • Decreased collaboration due to lack of physical presence

  • Constantly offering unconstructive criticism with no suggested solutions

  • Using offensive language

  • Acting rudely or mean to colleagues, especially on Slack

  • Poor hygiene as observed on video chat

  • Inappropriate dress

As uncomfortable as it may be to broach topics like these, there are ways you can prepare yourself for managing difficult conversations should they arise.

A Guide To Remote Employees Ebook

Get tips for hiring and managing your remote workforce.

Thanks for downloading!

If the requested file does not load in a new window, click here.

Download Your eBook Today


1. Build Trust Early

Tackling sensitive issues at the workplace starts from the ground up. A culture of trust and transparency within your company is an important building block that sets you up for success when talking to your employees.

According to the 2016 Edelman Trust Barometer, only 65% of employees surveyed said they trust the company they work for. That’s important because employees can be your business’ biggest advocates. Employees who trust in leadership are more likely to advocate for their company and its products and services.

When employees know you have their back, sensitive conversations become easier.

Not only that, but when employees know you have their back, sensitive conversations become easier. If employees feel they can trust you as their employer or manager, they are more likely to feel you have good intentions in approaching difficult conversations at work.

Leverage the trust that you developed in person before COVID-19 compelled us to work from home. Employees will increasingly draw on their memory when anticipating your expectations or reaction to a particular situation.

Maybe you have employees that started in the world of work from home. Take extra care to give these folks a warm welcome, touch base often, and carve out the time for candor in addition to communicating workflow objectives.

Related Article: 10 Affordable Ways to Improve Team Morale at Your Company

2. Check in with HR

Before you schedule a meeting, talk to your HR person to help ensure that you’re approaching the conversation in a way that follows company policies, and is sensitive of any issues the employee might be facing. Be conscious of your words to avoid saying anything that may be discriminatory, and keep in mind that different cultures may have different norms or standards.

For example, what you regarded as absenteeism may in fact have been an excused absence for observance of a religious holiday. Perhaps your employee shared (only with HR) that a family member of theirs recently passed away, and they're having trouble focusing on work as a result.

If you don’t have an HR department — or you wear the HR hat yourself — you can seek guidance from other sources. Justworks customers can contact our HR support team, who will provide tips and advice, or flag considerations you might not have been aware of. If you want to make sure your bases are covered in terms of legal issues, particularly regarding discrimination, consult with an attorney when necessary.

Related Article: Make Effective Company Policies and Procedures With This New Guide

3. Bring it Back to Business

Always make sure you tie the personal or behavioral issue back to a business or performance concern. After all, you’re not having a difficult conversation just to meddle in someone’s personal life. You’re bringing up the issue because it directly impacts the individual's or other employees’ ability to perform their jobs.

For example, absenteeism in the age of coronavirus might have uniquely devastating effects on team members who are coping with a disrupted workplace while picking up their colleague’s slack.

The drastically altered work environment has changed the means by which people communicate professionally and, in turn, the etiquette associated with these platforms. For example, employees might not give as careful consideration to their chats as to in-person conversations. Behavior like swearing or snide remarks to a colleague probably isn’t grounds for a harassment claim. However, it likely violates your company’s core values. Emphasize to the employee that they aren’t representing the values of the organization, and that this is a key part of being on your team.

It’s also important to avoid conjecture or assumptions. Focus on objective observations, then follow up with a question to clarify. For example, "I noticed you’ve sounded really distracted in our team video chats lately. I brought this up because our team values having you present and contributing.” This opens up the conversation to them being able to discuss the stressors of their childcare obligations.

Or, “You let your beard grow out and always seem to be wearing the same clothes when we talk. How are you adjusting to this new work from home environment, and is there anything I can help you out with?" This might be the invitation they need to open up about their mental health challenges during these unsettling times.

Focus on a job-related consequence, and work with the employee to brainstorm a plan to address it. Allowing the employee to come up with possible solutions to the problem is a good way to help them feel heard, rather than feeling chastised or talked down to.

4. Show Sensitivity

Everyone handles stress and change differently, and some employees and their families might be more personally affected by COVID-19 than others. At the end of the day, cheesy as it may sound, think of the golden rule. How would you like to be treated if you were on the other side of the conversation? Try to put yourself in the employee’s shoes and imagine how you’d want your boss to talk to you about a sensitive or personal issue.

How would you like to be treated if you were on the other side of the conversation?

For example, allude to the fact that this will be a serious conversation by way of an email or calendar invite. This will allow the employee to choose a private place in their home to meet with you, in order to engage in the conversation candidly without being overheard by their family or roommates or distracted by their child. Aim to be respectful and compassionate, but at the same time, direct. Don’t leave room for misinterpretation. Use specific language as much as you can so the employee doesn’t feel attacked.

Some communicators swear by “I” statements. “When you do X, I feel Y,” or, “it imposes Z dynamic on the team.” This way, the criticism isn’t received as an affront to someone’s character, but rather focuses on the behavior itself and what might be problematic about it.

Related Article: 10 Ways to Reduce Workplace Stress

5. Set Clear Expectations

It’s also important to be transparent about what your expectations are for the outcome of the conversation. If the issue goes beyond a personal concern and directly relates to poor job performance, make that very clear.

Consider actionable steps the employee can take to improve, or provide specific guidance for what enforcement mechanisms can be put in place. From that point, you may need to consider what disciplinary actions your company policy outlines, should the problem persist. If the employee doesn’t take steps toward the solution you agree upon, what will the consequences be?

Managing difficult conversations with employees is never easy. But by being clear, compassionate, and direct, you can help to ensure that everyone is on the same page and moving toward a solution.