Security Reminder: Tandym may send job opportunities to contacts by text message, but we will never ask you for personal information, passwords, account details, or financial details over text; we’ll never charge you money for applying for a job with Tandym; we’ll never ask you to install software; we’ll never ask you to switch to a different messaging platform like WhatsApp. If you receive any additional messages that look suspicious, please call our corporate headquarters at (212) 922-1001.
March 01, 2021 | 5 min read
How To Have Difficult Workplace Conversations Virtually


Difficult conversations are just that, difficult. This is especially true in the workplace where inevitable conflicts may arise. While “difficult” is subjective, if you are having an issue with a colleague, expressing concerns about your work environment or role, or resigning—the tone of the discussion is a serious one. While it is usually a best practice to have conversations such as these in person, it is not always possible, especially with hybrid and remote work arrangements. If you find yourself anticipating a serious on-screen chat, here are six tips for gearing up for difficult workplace conversations.

Schedule the meeting ahead of time

Similar to an in-office environment, you’ll want to give all people involved in the meeting time to prepare. That being said, you should try to schedule the conversation at least a few days in advance if possible. You’ll also want to provide as much detail as you can so that there are no surprises as to the type of meeting it is. While you might not want to outright describe in writing what the purpose of the conversation is, you can set the tone by mentioning you have some important news to share and that you’d like to sit down in private and discuss. You can do this by either sending an email ahead of your calendar invite, or including details within the meeting invitation.

Read Also: How To Quit Your Job The Right Way

Think about your talking points

Virtual or not, it is always best to come prepared. To make the best use of your time, write down talking points ahead of your call and practice the points you want to touch upon. For example, if you are meeting to talk about a conflict with a co-worker, perhaps write down examples and specific situations where the conflict arose and how it may have hindered your work. If you are proposing a change to your role or work environment, think about points for why this would make sense and how it would both benefit you and/or the company in the long run.

Test your tech

Technical glitches do happen, but you’ll want to do your best to mitigate the chances of them happening while on an important call. In advance of your meeting, be sure to test your wifi connection, camera, and platform you will be using for the meeting. This will give you time to troubleshoot any problems that might arise either yourself or with IT, and will help you feel confident you can carry out your difficult workplace conversation without any disruptions.

Dress up

A virtual office has made workplace attire less formal. However, when gearing up for a difficult workplace conversation, you’ll want to make sure you’re dressed the part. Be sure to dress as if you were attending an interview at your company—you want to be taken as seriously as possible.

Acknowledge the situation

While a remote office environment is nothing new, having difficult workplace conversations may still feel unnatural via video call. That being said, there is nothing wrong with addressing the situation. If it feels right take a quick second at the beginning of the call to mention that you would’ve felt more comfortable having a conversation such as the one you’re having in person, however due to the circumstances it wasn’t feasible.

Use verbal and non-verbal active listening

Social cues are harder to pick up on when you’re virtual. By listening carefully, maintaining eye contact, and avoiding distracting movements—you can ensure you’re taken seriously, that your responses are thoughtful and that your difficult workplace conversation emulates a face-to-face in-person interaction as best as possible.

Subscribe to the Tandym blog

Get our latest job search and career insights delivered straight to your inbox

Related Resources