How to Prepare for a Difficult Conversation

This is intended to assist you in preparing for and initiating a difficult conversation. This will help you look past your own position and look toward an agreeable resolution.

Giving a difficult performance review. Saying “no” to someone. Acknowledging and confronting tension in a working relationship. These can all be difficult conversations that managers and team members need to have and we all sometimes avoid for a variety of reasons.

Unfortunately, avoiding these conversations can have a negative effect on you and your team. Difficult conversations avoided are like the elephant in the corner of the room that no one wants to acknowledge is there. If you don’t have the conversation it is still showing up in your relationship and can affect the productivity and morale of your team. Putting this conversation on the bottom of the to-do list everyday does not usually miraculously solve the problem. On the other hand, taking some time and the following steps will prepare you for the conversation and make it easier.

Step 1: Preparation Work

Questions to ask yourself to prepare for the conversation:

  • What is the issue that needs to be addressed?
  • Why is it difficult for me to have this conversation?
  • What am I afraid of? The potential impact of the conversation on the relationship, perhaps loss of an employee or client, or simply the unknown?
  • What is the worst that could happen if you have the conversation?
  • What is the cost of not having it and the impact on you and the rest of the team?
  • What is your contribution to the situation? Be honest with yourself
  • What are the facts of the situation? When you look at the simple facts as a neutral observer would describe them you may find your perspective changing
  • What is the purpose of the conversation?
  • What does resolution look like?
  • What are the possibilities?
  • Don’t be afraid to ask the other person “What would you like to do here?”

Step 2: Initiating The Conversation

Setting The Stage

  • Choose the right time and place. Think of the balance of power and choose a neutral location and a time when you will not be disturbed
  • Invite the other person to discuss the topic and let them know its OK to ask for time to prepare
  • Set ground rules at the beginning of the conversation, such as keeping the conversation on topic and giving each other feedback if the conversation starts getting defensive

Starting the Discussion

  • Open with a statement to help remind you both that you have a working relationship based on a shared goal. This helps each person let go of their own position for a moment and start the conversation.
  • For example: “I know our work and mission here is very important to both of us. That’s why I want to sit down with you and discuss this situation” or “I really value our relationship and know there is some tension right now. How can we resolve this?”

Review Both Sides

  • Ask for help to understand their situation and interests. Asking for help to understand will reduce the tension between you and also helps you keep an open mind while listening to their story and perspective.
  • Acknowledge your contribution to the situation. Discuss what you did right and what you could have done differently.

Seek Shared Responsibility for a Creative Solution

  • Look for directions or alternatives you are both willing to consider
  • Remember the shared goal that gave you a common perspective at the beginning of the conversation and seek to find a solution that meets your shared goals and values
  • Be willing to accept that the mutually acceptable solution may be a significant change in the relationship or perhaps a parting of ways
  • If you are going to walk away from this meeting agreeing to disagree make sure you know why. In addition, explain what concerns are not met by the rejected solutions.

It’s not always easy to keep your composure and remember the big picture during a difficult conversation. Try not to let the conversation turn to blame and defending.

No matter the outcome, if the conversation is managed well you have cleared the air and raised the relationship to a new level. Both parties and your team will be in a better position to move forward towards your goals.