Difficult Conversations, You Just Have To Have Them!

Posted on Mar 20, 2023 in Communication,Conflict Resolution . 0 Comments.

Implied or explicit: there is an expectation that you will participate in difficult conversations at work. How do we get that on a billboard???

Sometimes there is a need to go back to basics and state the obvious. Part of being an employee is accepting that from time to time you will be expected to participate in difficult conversations in the workplace. Let me make it clear, I am NOT talking about unsafe ones, but those that are awkward, uncomfortable or strained, where we may not always walk away feeling wonderful. Those uncomfortable or difficult conversations you are expected to have in the workplace include:

  • performance related conversations
  • setting boundaries with colleagues
  • someone raising with you that they don’t like some of your behaviour (within reason)
  • raising concerns even when you know there may be pushback
  • receiving feedback etc.

If I had my way, I would include it in people’s PDAs or KPIs. In fact, I’d make it a part of the bonus structure! I think this implied expectation should be made explicit in the employment contract! Here, I’ll draft the clause “Part of being an employee is accepting that from time to time you will be expected to participate in difficult conversations in the workplace.”


Part of being an employee is accepting that from time to time you will be expected to participate in difficult conversations in the workplace!!!

How do we get that on a bill board? I’d settle for a bumper sticker!


Taking on this mindset helps overcome our innate desire to avoid difficult or uncomfortable situations. A participant from one of our Better Conversation Workshops provided feedback – “Just hearing you say that, that’s all I need to hear. That alone has pushed my thinking and into the room of a conversation I’ve been avoiding”. Sometimes knowing you are expected to do something may just be enough to give you the confidence to step into it, to get over that innate hesitancy.

There are so many environments where we expect people to participate in difficult conversations and I strongly believe the average workplace should be considered one of them, even where discomfort is experienced. Imagine if we told doctors, nurses or other health care professionals they didn’t have to participate in challenging conversations with patients. Or that teachers didn’t have to raise uncomfortable topics with students. Or that insurance agents never had to discuss unpopular outcomes. There are so many places we already expect individuals to participate in tricky conversations. Let’s own our responsibility in the workplace too. It will actually make the workplace better! The benefits of participating in difficult conversations including gaining insight into perspectives, increasing empathy and reducing frustration are well understood and clear.

Obviously, this expectation must be married with the growing understanding of psychological safety and the need for the employer and the employees to play an active role in creating safe dialogue. There is increasing expectation on employers. As individuals we can contribute by making things safe or safer for ourselves and others including managing our own emotions, preparing for conversations, knowing our boundaries and being able to communicate them, sharing preferences for how conversations ideally occur.

PS – If you are in a leadership position, I would suggest there is also an implied or explicit employment expectation that you will initiate a difficult conversation. But that can be covered in a blog and on a billboard another time!

Got a conversation that needs to happen? Perhaps a discussion about how to take on a different mindset would help? Let’s chat about how to make that conversation better! Please just reach

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