How to Approach Tough Conversations

"Weigh your words"


December 2, 2022

by Cora Hageman

Addressing a Situation

As a manager, it's important to have difficult conversations with your team members and colleagues in order to address issues and maintain a productive and positive work environment. However, these conversations can be intimidating and stressful, especially if you're not sure how to approach them. Here are some tips for having tough conversations in a way that is effective and respectful:

1. Prepare in advance

  • Think about the specific issue you want to address and the outcome you want to achieve

  • Consider the perspective of the other person and how they may react

  • Have any relevant documents or evidence ready

2. Choose a private and neutral location

  • Avoid having the conversation in a public place or in front of others

  • Find a place where you can both feel comfortable and undisturbed

3. Use "I" statements

  • Instead of saying "You did this wrong," try "I feel frustrated when tasks are not completed on time because it affects the team's progress."

  • This helps to avoid accusations and puts the focus on your own feelings rather than attacking the other person

4. Listen actively

  • Pay attention to what the other person is saying and try to understand their perspective

  • Use questions to clarify any misunderstandings and show that you're open to hearing their side

5. Stay respectful and professional

  • Even if the conversation gets heated, try to maintain a calm and respectful tone

  • Avoid raising your voice or getting overly emotional

Speaking with Superiors

Having tough conversations with people above you in the chain of command can be especially challenging, as you may feel like you're going against their authority or risking your own job. However, it's important to remember that you have a right to express your concerns and ideas, and that open communication is essential for a healthy work environment. Here are some additional tips for having tough conversations with your superiors:

1. Be respectful and professional

  • Remember that your boss is still your boss, and you should approach the conversation with the same level of respect you would any other conversation

  • Avoid accusing or confrontational language

2. Have a clear purpose

  • Know what you want to achieve from the conversation and come prepared with specific examples and solutions

  • Avoid complaining or making generalizations without offering specific solutions

3. Seek feedback and ask for help

  • Ask your boss for their input and advice on the issue you're facing

  • Show that you value their expertise and are willing to work together to find a solution


Ultimately, having tough conversations is a skill that takes practice and patience. By following these tips and being respectful and professional, you can have difficult conversations in a way that is effective and promotes open communication in your workplace.

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