While remote and hybrid work indisputably offer amazing benefits for both employers and employees, it’s recently occurred to me that they can also make one aspect of work particularly challenging: having difficult conversations.

Whether it’s addressing performance concerns, navigating disagreements, or providing constructive feedback, these conversations can feel more complicated when colleagues aren’t sitting across the table from one another.

In a traditional office, people have countless opportunities to connect informally. A quick chat before a meeting, a hallway conversation, or even casual small talk can help build trust and strengthen relationships. Those everyday interactions often create a foundation that makes difficult conversations easier when they do arise.

In remote environments, however, communication is often more scheduled and transactional. Without the benefit of body language, facial expressions, and other nonverbal cues, misunderstandings can happen more easily. An email intended to be straightforward may come across as harsh. A brief Slack message may be interpreted as frustration when none was intended.

On top of that, many managers and employees may postpone an awkward or uncomfortable conversation because they figure, “Well, I don’t see that person every day.” But unresolved issues rarely disappear on their own—in fact, they often grow more complicated over time, making it just as important to address concerns promptly, just as you would in a traditional office environment.

To that end, I’ve come up with a couple best practices for engaging in these important dialogues in a predominatly remote environment, such as:

• Choose the right communication channel. If a conversation involves sensitive feedback, conflict resolution, or an important disagreement, and an in-person conversation is impossible, resist the urge to handle it through email or chat. Whenever possible, opt for a video call. Seeing one another face-to-face—even virtually—can add context, empathy, and clarity.
• Prepare. Before entering a difficult conversation, take time to gather facts, define the issue, and focus on solutions rather than blame. Similarly, employees should approach these discussions with curiosity and an open mind. The goal shouldn’t be to “win” the conversation, but to reach a better understanding.
• Be an active listener. Ask questions, avoid interrupting, and take a moment to confirm what you’ve heard before responding. Small habits like these can significantly reduce misunderstandings and help people feel heard and respected.
• Finally, don’t wait until there’s a problem to communicate. Frequent check-ins, regular feedback, and consistent recognition help build trust over time. When employees and managers communicate openly on a regular basis, difficult conversations become less intimidating and more productive.

The reality is that tough conversations are part of every workplace—remote or otherwise. But with empathy, transparency, and intentional communication, they can become opportunities for growth rather than sources of tension. How has your organization handled difficult conversations in a remote-work environment? What strategies have helped your organization foster productive dialogue and maintain strong working relationships?