In theory, people who hold leadership positions should be able to communicate with anyone. The reality is, many leaders are uncomfortable communicating — especially with their employees. A Harris Poll revealed 69 percent of managers find it difficult giving direct feedback about employee performance. Demonstrating vulnerability, recognizing employee achievements, crediting others, and giving clear direction was also noted.

Companies are more productive and successful when expectations are clear and positive coworker relationships exist. If conversations are not taking place, there’s a culture and productivity killer in the workplace. From giving feedback on the poor quality of work to explaining why a team member is not demonstrating company values, managers — as well as business owners –need to know how to have difficult conversations.

Here’s a guide on how to handle difficult conversations at work;


The more prepared you are, the easier it is to manage your emotions, deliver feedback, and engage in a meaningful conversation.

Sometimes we unintentionally play a part in a misunderstanding, so self-awareness and empathy are key.

    • Fact check your feelings and the story you are telling yourself about the person involved. What assumptions are you making? Are your assumptions valid? What are you hoping to achieve from this conversation?
    • Think about your relationship history with the person and his or her behavior patterns. This helps you to anticipate potential reactions, identify questions they might ask and have answers prepared. Step into their shoes to see things from their perspective.
    • Practice the conversation in your head.
    • Set the emotional tone. Whatever words you decide to use, the tone of your delivery will determine how your words are received. Keep your gestures (e.g., folding arms) non-confrontational. Be assertive without being aggressive or judgmental.

Start the Conversation

Let’s consider two ways you can start a difficult conversation:

1. Lead with curiosity.

A spirit of curiosity may help you uncover something that you were unaware of. First, you begin the conversation by providing context. Then, ask the other person to share their point of view. Next, share your feedback and get agreement on how things should change moving forward. Here are a few conversation starters:

    • I’m curious about…
    • Help me understand…
    • Walk me through how you see things…
    • How do you think you’re doing on the project?

2. Get to the meat of the problem.

Be specific when describing the behavior, and its impact on the team. Then get agreement on how things should change moving forward. For example, instead of saying, “Today, you were rude.” Say, “I noticed you rolled your eyes when I spoke about workflow changes during the meeting; This makes me feel like you don’t respect what I’m saying. Is this something you are aware of? This behavior is counterproductive to our values.”

When discussing the behavior, avoid phrases like, “Why would you?” and “You never, or you should have.” These statements may make the person feel like you’re blaming them and put them in defensive mode.

Exude Confidence

If you want to be taken seriously, avoid passing the buck and take ownership of the problem. Statements like, “I don’t care, but it’s the higher-ups’ decision,” undermine your authority as a leader.

Also, avoid fluff phrases and filler words (e.g., I think, you know what I’m saying) which demonstrates a lack of confidence and may diminish your authority as a leader.

Be Present

There’s nothing worse than pouring your heart out to someone and their busy texting on their phone or typing on their computer. During a conversation, distractions can cause distrust with someone.  So avoid taking notes, texting on your cell phone, or typing on your computer.

Allow the Other Person to Ask Questions

    • Ask them for suggestions for resolving the problem.
    • Respond with empathy by acknowledging their experiences. For instance,  “I do understand what you’re saying. However, have you considered that…,”
    • Listen to what isn’t being said. For instance, if the person starts to cry or fidget in their chair, acknowledge it. “I get the sense you might be uncomfortable with something. I want to make sure you’re comfortable moving forward. What makes you the most upset about what I said?”
    • Instead of saying “You’re wrong,” say “That’s not my experience.”

Summarize Major Discussion Points

Then, thank the person for their time — even if you agree to disagree.  If possible, identify a date to follow up and check on action items.

Remember, preparation breeds confidence. Think about the big picture before having a difficult conversation. That way you can manage emotions and keep the conversation going in a positive direction.