How to Start a Difficult Conversation

Putting off that awkward conversation because you hate conflict? Many of us will go out of our way to avoid difficult conversations with loved ones, because we worry about making the situation worse. In reality, ignoring a troublesome situation will almost always make the situation worse. Here are some tips to start tough conversations off on the right foot.

The First Step: Setting Up Tough Conversations

To set up a difficult conversation, you need to approach the other person in a non-threatening way. Handle this with grace and humor, as you would an invitation. Remember: What affects you negatively is also having an impact on them. Find a way to bring up the fact that you are both stuck in a pattern that isn’t working, and ask if they would sit down with you for a few short conversations to explore ways you might tackle the problem together. Make it clear you are not looking to solve the problem right away, but rather to establish a framework for talking about it.

Do Something—and Establish Ground Rules

For your first meeting, it’s often good to agree on a simple activity together, like a meal or a walk. If things are so tense that it seems unnatural to spend time together, consider asking a third party to help you get together and facilitate your meeting. Make it clear you hope this is the first of many conversations, and ask them to come prepared to set up times for follow-up.

Use email to establish ground rules and ask for input. Some examples:

  • Keep meetings to 30-45 minutes, or another set period of time.
  • Let each person have time to speak uninterrupted.
  • Choose a neutral space – get out of the house and office; consider something less-formal / more friendly.

Before you meet, spend time reviewing and agreeing on guiding principles for the meeting itself, such as:

Connecting

Instead of presenting your case, and potentially making the other person feel attacked, find a way to join with them and open the lines of communication. Consider even sitting on the same side of the table to approach the conversation together. Acknowledge the ways you see the situation hurting both sides, and ask what they think might help. Try to consider their communication style and frame your comments in a way that is compatible to their thinking. For example, some “data” people or “problem solvers” are impatient with small talk. Some people feel most comfortable entering in on small talk (“How was your weekend,” “Boy, it’s foggy today!,” etc.) Speak to your audience.

Thanking

Show appreciation for the other person’s willingness to talk. At the start and end, thank them for having the conversation with you. Make it clear you see this conversation as a joint effort. Show gratitude to people for bringing up the hard stuff instead of punishing them—adopt the attitude of “bring it on.”

Timing

Set a time limit, or appoint a neutral party as a time keeper. Whether you are making great progress or things get really heated, watch the clock to make sure you don’t get exhausted. Thirty to forty-five minutes is usually a reasonable timeframe. It’s great to set several appointments for conversations to continue so both parties know they will have time to be heard.

Listening

Beginning a conversation about a tough topic is more about the process of talking to each other honestly than it is about what actually gets accomplished. Opening up this conversation is going to be tough, because our communication “muscles” can become weak with lack of use, and past memories of fighting and avoidance can make the situation fraught. Practice reflecting what you hear the other person saying and ask them to do the same for you. This builds trust on both sides.

Taking Turns

Agree to an agenda in which each party gets to speak their piece uninterrupted. Consider making lists of your questions, but don’t insist they all be covered at once. Having things on paper can reduce your anxiety that your concerns might get lost. Have a neutral party monitor that each side gets to speak.

Keeping it Cool

Both parties probably have strong feelings about the issue at hand. It’s important to be honest and talk from your heart, but not to let your emotions run you. Be prepared to hear things you don’t like or that hurt your feelings. Remember that there will be time to process these things in further conversations if you can just get the ball rolling today. Try to avoid blaming or starting sentences with “you” or “you always,” and instead use “I feel” or “I have noticed.” Avoid “conversation killers,” such as “You always,” “You never,” and “Just forget it.” Avoid blame.

Celebrating and Contracting

At the conversation’s end, review what you have accomplished and what you have decided to do (even if it’s only that you made it this far and you agree to continue talking – that’s progress!) Agree on a format and time for the next conversation.

Having difficult conversations is challenging for everybody, but with time, willingness, and practice anyone can master the art of tackling conflict before it builds momentum. Trust yourself and use these strategies to get past the initial fear and awkwardness, and you can take pride in knowing that once you have gotten your issues on the table, you have taken the first step to making things better.


Continuity helps families turn difficult conversations into productive outcomes. Learn more about Continuity’s expert meeting or retreat facilitation or contact us.

Trying to move on from past conflict? Read more about releasing blame and moving forward.

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