How to Have a Difficult Conversation

You’re here, so you’ve taken the first step: acknowledging that you need to have a difficult conversation! In this post, I’ll walk you through the steps to prepare, practice for, and have the conversation.

how to have difficult conversations

What makes difficult conversations so… difficult?

Difficult conversations are personal. They are hard to have because we have to deal with our feelings, our identity and our values. Difficult conversations can force us to face our insecurities. They can push us to confront our biases, judgements and assumptions. They are just uncomfortable.

But they are also an opportunity for so much growth and learning. On the other side of a difficult conversation could be a transformed relationship with a coworker, a new perspective, or a surprising solution to a problem.

So, how do you push past the discomfort and fear and actually have an effective, meaningful conversation?

Before we get into how to have difficult conversations, side note on when to have them (really when NOT to have them).

I do not recommend jumping into a difficult conversation in the heat of the moment. That is actually the worst time to have one. It is harder to see things objectively or from one another’s perspective when you haven’t had any space to reflect. If you’re in an emotionally escalating situation, it is okay to say, “I’d like to pause this conversation and come back to it at a later time.”

How to Have a Difficult Conversation

Executing an effective difficult conversation requires reflection, planning and practice. Follow these 4 steps to prepare for and execute that difficult conversation you’ve been avoiding!

1. Reflect

Start by scheduling time for yourself to reflect on the situation. Give yourself 10-15 uninterrupted minutes to think about what happened.

Here are some examples of questions to ask yourself. Write down your answers.

  • What are the facts? (Try to distinguish your story about what happened from what actually happened.)
  • How did it make me feel?
  • What impact did it have on me/ my ability to do my job?
  • What would I like to be different as a result of having this conversation?
  • Why does having this conversation matter?

Wait until you can clearly answer these questions before moving on to step 2.

2. Plan

Use your reflection answers to help plan out the structure of your conversation. Being prepared is the best way to effectively communicate, especially when one or both parties are being vulnerable.

  • Actually write out what you will say. This should include your experience of what happened, the impact it had on you and your goal for talking about it now. What do you want to be different as a result of this conversation?
  • Is the purpose to rebuild trust? (It often is!)
  • Or is the purpose to give difficult feedback?

3. Practice

Role play the conversation with someone you trust. Pay attention to any points where you stray from your plan and start getting absorbed in your story.

Ask your trusted companion for feedback.

  • Were you clear about how the situation impacted you?
  • Were you clear about your request?
  • Did you listen well? Did you interrupt?
  • What was your body language and tone like?

If it feels challenging to practice this conversation, practice it again. And again! If it is a conversation worth having, it is worth the time to get it right. If you don’t feel comfortable role playing, you certainly won’t feel comfortable doing the real thing.

There will always be some discomfort and fear that won’t go away, no matter how much you practice. Because you have to be vulnerable and honest and there is no way to know how the other party will react. So just practice enough until you feel 70% comfortable 🙂

4. Have the conversation

You’ve reflected, you’ve planned, you’ve practiced. Now it is time to actually have the conversation! Don’t turn back now. You have to go through the muck to move past it. You can do this.

When scheduling a time to speak with the other party, consider some conditions:

  • Time of day (what time works best for you both/ don’t schedule back to back with another meeting so you have time to process after)
  • Location (privacy, neutral ground, comfortable)
  • It’s okay to bring your notes/ plan! And it is okay to let the other person know you may reference them because you want to make sure you’re communicating intentionally.
  • Listen as much as you speak. It is a conversation, not a speech you’re delivering to them uninterrupted. Pause and make sure they have time to respond.
  • Ask clarifying questions. Make sure you understand them, too.
  • Remember to breathe!

You did it!

Maybe it went really well and you and your coworker had a breakthrough.

Maybe it went okay: you understand each other better now, but you may need to have further conversations to really rebuild trust.

Maybe it did not go as you’d hoped. Not at all. That’s okay! Reflect on how it went. Regardless of how it went. There is so much to learn about yourself, how you communicate and the conditions you need to thrive in the workplace.

I’d love to hear from you. Where are you in your “having difficult conversations journey?” What resources do you need?

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