EQ WORKOUT #80 How to Start a Difficult Conversation with an Employee


Most people don’t like having difficult conversations. Just the thought of it makes most people feel a sense of dread! This aversion to difficult conversations is so prevalent that 36% of people have put off a difficult conversation in the past month and 24% have put it off for more than a year!

And yet, it’s often important and necessary to have a difficult conversation. These strategies will help you be more thoughtful and proactive in having these conversations, which ultimately will help save your energy and come through it positively on the other side.

Pre-Conversation Preparation

Pre-Conversation Preparation

We often don’t put a lot of thought into what the conversation will be like. But preparing for a difficult conversation can significantly impact the outcome of that conversation. Instead of going in blind, you are prepared and ready to address the situation.

Here are three areas to think about before your conversation:

1. Goals


Why are you having the conversation? What are the goals and desired outcomes? Thinking about the desired outcome will help clarify your approach to the conversation and give you direction. It also means you can keep the conversation more succinct and to the point because you know where you’re going with it!

2. Emotions


Emotions are normal in any conversation, but especially a difficult one. Spend some time thinking about what might be involved so you are more to manage them when you’re in the conversation. Consider these questions:

  • What is your emotion about the topic (i.e., angry, regretful, shameful)?
  • What are your emotions about the person or people you speak about?
  • How do I feel about the emotions that are likely to come up?

3. Bias


We all have some bias and some pre-judgment. Bring that to light so you are familiar with what your biases are. Take a step back and acknowledge your bias and judgments so that you can be as neutral as possible when in the conversation. Without doing this, you may let your biases cloud your judgment and make a poor decision.

Conversational Awareness

After doing some pre-conversation work, it’s also important to be mindful of the conversation itself. Here are three areas to focus on:

1. Where and when

The environment you choose can dramatically impact your difficult conversation’s outcome. Think about where to have it, making privacy a top consideration. The time of day also matters as you want everyone to be as alert and engaged as possible. Difficult conversations drain energy, so it’s important to put some thought into the environment you choose.  

2. Emotions… again.

Ideally, you have prepared already and know what kind of emotions may come up. But when you’re in the moment, you need to practice self-awareness and tap into how you are feeling in the moment. Then you can use practices like deep breathing or taking a break to manage your emotions during the conversation.

3. Body language

We often practice and think about what we’re going to say, but do we ever think about what our body language is? An open stance—i.e., open torso, smiling, nodding—can help set the tone of the conversation. Our emotions often impact our body language, so make sure you are aware of how you’re showing up.

The final piece of advice for preparing for a difficult conversation is to rehearse. You know what they say—practice makes perfect! It can really be a powerful tool to practice a difficult conversation with someone else so you can test what you might say, your body language, and the emotions that will come up.

We might not like it, but difficult conversations are part of life… and definitely part of the workplace! But if you can invest some time into the preparation and planning for a difficult conversation, you will find that it pays off in a big way. Do your pre-conversation mindset work and practice self-awareness while you are in the conversation. If you are intentional about approaching a difficult conversation, you can move through it and achieve your desired outcome.