Working Conversations Episode 8:

7 Steps to Have Difficult Conversations Remotely

Ever been on the receiving end of difficult feedback – that came as email?  I’ll be that once you first read it, you didn’t want to open again after reading it the first time!

It might be a message about your work performance or a difficult conversation from your manager that took you by surprise.

Holding a difficult conversation can be hard enough as it is. But the remote work environment can make it even more challenging.

And I’m here in this episode to explain exactly why holding difficult conversations on email DOES NOT work.

With so many people working from home these days, we have become even more reliant on email than ever before. And even when we are trying to move things out of our inbox and onto other platforms, those platforms – like Slack and Channels on Microsoft Teams – are still text-based, where we don’t have the additional social cues that tone of voice and body language afford us.

So in this episode, I walk you through a seven-step process to make even the most difficult conversation flow smoothly when working remotely.

This is basically the same model that I teach in my course Holding Difficult Conversations and the process I outline in my book “How to Approach Difficult Conversations Directly.”

Listen here or wherever you get your podcasts. Go on, be a courageous boss, coworker, spouse or friend and share the constructive feedback with the person using this model. It will get result all while preserving the relationship.


  1. Set up a time to meet, either by phone or by videochat.
  2. Ask for their permission.
  3. Start with something you both agree on that is related to the situation.
  4. Lay out a set of facts that moves you from the starting point (the thing you said that they agree with), using a neutral tone, and that arrives at the organizational impact of their behavior.
  5. Now it is their turn to talk. Invite them to take a turn.
  6. Once you’ve heard them out, co-construct the next steps or the solution together.
  7. Lastly, send a meeting invitation for however much time you agreed on for seeing results or changed behavior.




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