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6 tips to help with difficult conversations

Difficult conversations are, well, difficult. But with the right preparation and perspective, they can be a little bit easier. Here are some tips from Dr. Hayley Lewis.

Remote teams

Last updated

6 Sep 2022
Difficult conversations

“I am not looking forward to this conversation.”

Maybe a project flopped and it’s time to retrospect on what happened. Maybe it’s a meeting with someone you’ve bumped heads with before. Maybe you need to deliver difficult feedback

Difficult conversations are part of life. Knowing how to navigate these conversations is key to building stronger teams, better relationships, and a psychologically safe workspace

In a recent interview, we spoke with Dr. Hayley Lewis about emotional intelligence when giving feedback. She also left us this sketch with tips to help with difficult conversations.

sketch of 6 tips to help you have difficult conversations

We found it useful, so here we’ve unpacked it for you. 

1. Preparation is key

Trying to wing a tough talk is like training for a marathon by walking to your fridge. You’re likely to end up face down, wondering why you tried in the first place. 

Before you enter a difficult conversation, make sure you’re ready. Know what needs to be covered, be empathetic, sideline your emotions, and stay on track. 

Tip from Dr. Lewis:

  • Jot down key points in priority order in advance. You'll be less likely to be thrown off course.

2. Practice makes perfect

Mastering difficult conversations is like bulking up any other skill—it’s about repetition and experience. You don’t need 10,000 hours, but walking through your talking points before the main event goes a long way. 

Tip from Dr. Lewis:

  • Have a dry run with a trusted colleague or your coach. This can help:

    • Reduce your fear

    • Give you feedback on your style 

    • Hone your message

3. Specifics are important

This doesn’t tell me what I need to fix: “Sometimes in meetings, you tend to show frustration in a way that makes others uncomfortable.” 

This does: “In yesterday’s meeting, you slammed your hand on your keyboard. We all get upset, and that’s okay. But that’s not an appropriate way to express your frustration.” 

Tip from Dr. Lewis:

  • Have one or two detailed examples to add weight to the point you're making. These should be recent and first-hand accounts.

4. Environment is important

Introducing yourself to a new colleague with a handshake in the bathroom is, well, a bit awkward. Better to save it for the coffee machine. 

It’s the same with difficult conversations. Don’t do it with your kids playing in the background of a Zoom call. And don’t bring it up in a group if it’s meant for a single person. 

Tip from Dr. Lewis:

  • The type of space you use can have an impact on how the conversation goes. Ideas:

    • Private meeting room

    • Local coffee shop

    • Walk and talk

    • Sit in a local park

5. Silence is golden

Have you ever sat and listened to silence? For most people, it’s mind-numbing. But apart from being a calming mindful practice, it’s also a necessary space for thought and reflection to unfold. Become comfortable with this space, and give people the time they need to process tough talk. 

Tips from Dr. Lewis:

  • When you’ve said your initial piece, stop.

  • Allow the other person to reflect and take it in.

  • If you find it difficult, put a reminder to yourself, such as a post-It with the word ‘Quiet!’

6. Put yourself in their shoes

Empathy. It’s a word you keep hearing in the workplace. It’s also a key component of emotional intelligence. And it’s a reminder that we all have different backgrounds, experiences, and perspectives. Looking through another person’s spectacles helps lay common ground for difficult conversations. 

Tips from Dr. Lewis:

  • How would you feel to hear the feedback you have to give?

  • What would make it easier for you to accept?

  • “Seek to understand in order to be understood.” – Stephen Covey 

Difficult conversations aren’t easy, obviously. But with the right preparation and perspective, they can be a little bit easier.

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