How to Navigate Awkward Conversations at Work

Learn valuable strategies for handling uncomfortable workplace discussions with finesse.

Tough Talks at Work – How to Navigate Awkward Conversations with Grace

Let’s face it, navigating awkward conversations at work is a part of life. Whether it’s letting someone go, addressing a micromanaging manager, or handling a delicate conflict, these tricky talks can leave even the most seasoned professional feeling uneasy.

Watch this video to get your toolkit for tackling tough conversations with grace and finesse.


You need to let go of someone at work. You need to tell a manager they’re micromanaging. How do you have an awkward conversation?

  1. Ask for time to talk before the issue becomes urgent. Be transparent about the topic and block enough time on the person’s calendar.
  2. Address the elephant in the room at the outset in a clear, respectful way. “This is going to be a difficult conversation but it’s an important one, so I’m grateful that you gave me this time to talk”
  3. Listen. Pause. Gauge the reaction. Be ready to adjust what to say accordingly. Be ready to be firm but polite.
  4. It’s ok to bring notes with you and refer to them. It shows the other person that you took time to prep beforehand.
  5. Seek a clear way forward. Don’t leave on an ambiguous note or without clear next steps. Offer to email them after the meeting.

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