How to Handle Difficult Conversations



Some workplace conversations are just hard to have.

Like telling two of three applicants for a promotion that they won’t be getting one. Or speaking frankly about how unproductive your company’s meetings are.

Andrea Lee, CEO of Thought Partners International and author of We Need to Talk: Your Guide to Challenging Business Conversations (Thought Partners International, 2015), said the first step to having such discussions is to acknowledge that they can be awkward and even painful. She approaches difficult conversations by first asking herself three questions:

  • Where are we now?
  • Where are we going?
  • How would we like to get there?

These questions “can be a game changer,” Lee said. “Without them, there are a lot of assumptions that can be made on both sides, sometimes because of the flavor [workplace] relationships have taken over the years.”

For example, take the tricky task of picking only one of several applicants for a promotion that means more money, more power and more prestige. Lee suggested that the conversation go like this...

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