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Blog Short #186: How to Prepare for a Difficult Conversation

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When you need to have a difficult conversation with someone, what can you do to increase the probability that it will be constructive?

This is a good question to consider, especially when the subject is a hot issue, or you’re afraid it will be poorly received. There are some steps you can take up front that will help reduce the likelihood of emotions getting out of control while also increasing mutual receptivity on everyone’s part, even when you disagree.

Start by prepping yourself before approaching the other person. By doing so, you can get clear on what you need from the conversation and anticipate what could go wrong so you’re ready for that.

From there, we’ll go over how you can structure the conversation.

Your Pre-Conversation Prep

Ask yourself these questions and make some notes so you can refer back to them.

1. What do you hope to accomplish?

In other words, what do you need or want from this conversation?

To answer that you must first clearly define the issue. Is it something practical, like how do we divvy up the household chores with our work schedules? Or maybe it’s an emotional issue, such as feeling disconnected, how you talk to each other, or something related to your kids.

No matter the problem, there’s always an emotional component, and it’s important to know what that is before you start because emotions are where things get complicated.

What feelings do you have about the issue?

After you’ve considered this, write a concise statement that defines the problem and the outcome you want.

A note here: Choose a specific, singular issue. Big global conversations that cover more than one issue easily get out of control. Stick to one thing, and don’t let it evolve into a kitchen sink battle.

2. Why is this issue important? What’s at stake?

On a scale from 1 to 10, how important is the issue to you? How much emotional space is it taking up in your mind? How would a resolution affect and benefit you? How would it benefit the other person? Answer these questions and then list for yourself what you want to say or get across and what solution(s) you have in mind, if any.

3. What are the obstacles you anticipate when talking about this problem?

How much receptivity do you expect from the other person to (1) have this discussion and (2) come to a consensus on how to resolve the problem? What kind of reactions do you foresee, and how will they be expressed? Write these down.

4. What can you do (or both do) to deal with these obstacles?

For this one, get specific. What will you do if the other person becomes angry or attacking? What if there seems to be no interest in negotiating a solution? What if they shut down?

The purpose of this exercise is to think ahead about how you can react to keep the conversation constructive. This is the hardest part of the process.

The Together Prep

Once you’ve thoroughly answered the prep questions and clearly understand what you want to accomplish, approach the other person and let them know you’d like to talk with them.

You might say something like,

“I’d like to talk to you about something, but I’m worried it could be a difficult conversation, and I’d like to make sure we do it in a way that leaves us both feeling good about the outcome. I thought we could do that by setting up some rules to follow so we don’t let things get out of hand. Are you amenable to that?”

If the answer is no, then explore what they’re concerned about or what they would need to make the conversation more palatable and proceed from there. Once you’ve done that, set up some rules together.

Here are some examples of rules you might establish:

  1. No personal attacks, labeling, sarcasm, or hurtful comments.
  2. No blaming or shaming. We’ll both be responsible for our own thoughts, feelings, and actions.
  3. If either of us feels emotionally overwhelmed or too angry to continue, we can take a break and allow each other to recover. But we vow to continue the conversation when we’re both ready.
  4. We can signal that we need a break by raising our hand; the other person must accept that without arguing.

You might come up with other rules or ideas to add, such as when and where you’ll talk or not interrupt each other except to ask questions for clarification, etc.

Add whatever you think will be helpful based on what you know about each other and your previous conversations.

Here’s something that can make things easier.

You Don’t Have to Solve the Issue in One Conversation

If the topic is too volatile, agree to break the discussion into several conversations.

Use the first conversation only to investigate and fully understand each other’s point of view. Don’t try to solve the problem. Don’t even talk about solutions.

Get into the mindset of a curious investigator whose goal is to understand what they’re hearing.

The value of having this kind of conversation first is that it takes the pressure off both of you in several ways:

  • You don’t feel pressured to convince each other of the outcomes you want because you’ve removed that from the discussion.
  • Knowing that going in will help you both keep your emotions in check.
  • You foster mutual understanding and get more insight into what you each need and think about the situation.
  • Doing that creates a connection and gets you both on the same side.

After this first conversation, take a break so you can consider what you’ve learned from each other regarding the issue. Now brainstorm possible win-win solutions. A break can be an hour, a day, or several days. When you’re both ready, come back together and problem-solve.

The Biggest Factor

Staying connected to each other as you proceed is the most critical factor in working through a difficult conversation or issue.

It’s the difference between working as a team so you can find solutions or erecting barriers to put you on opposite sides, leading to mutual frustration and a breakdown of the process.

To stay connected, use the empathetic detective approach, which you can read about here if you haven’t already. It is possible to have diametrically opposing points of view yet maintain respect and consideration for each other.

You must take the time to identify and understand the feelings underneath each other’s assertions and ideas.

Sometimes there are hidden background experiences that are influencing the current situation. It’s good to learn about these. Don’t therapize the other person, but be open to hearing how they’ve arrived at their conclusions and what they feel is at stake in the conversation.

You’ve defined that for yourself while prepping ahead, but you need to understand what the other person wants and needs from the conversation as well. When you successfully do that, you have a much greater chance of finding win-win solutions.

The Timing

Timing is a factor you should consider when choosing when to have a difficult discussion. Too often, people start these kinds of conversations late in the evening when it’s time for bed or in the midst of other stressful events, or because they feel pressure to get something off their chest.

None of those are good ideas. Choose a time when you both can be receptive, free to listen attentively, and are not tired or stressed out.

By all means, don’t have these conversations when drinking any alcohol – not even one drink. Alcohol is an emotional lubricant, and your ability to regulate your emotions decreases as a result.

Remember That . . .

Communicating and problem-solving are skills that take lots of practice to hone and perfect. It feels great when things go well, but don’t be discouraged if they don’t. Review conversations that didn’t go as expected or desired, analyze where things went astray, and try again.

The most essential skill to be successful is to listen with your full attention. If you work at that, all your conversations will improve.

That’s all for today!

Have a great week!

All my best,


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