Let’s face it. There are some conversations that nobody really wants to have– from confronting an employee at work to talking to a parent about his or her unsafe driving, and everything in between.
Although many of us try to avoid these difficult conversations, doing so can have a negative impact on ourselves, the other person, our teams, our families, the public, and anyone else who is affected by the issue.
If it’s time to have that difficult conversation, a little planning and preparation can go a long way toward a better outcome.
However, before you start that conversation you’ve been 
avoiding, you need to take some time to think about the issue and prepare for the conversation. You need to know:
• What the real issue is
• Why the issue needs to be addressed
• What “resolution” would look and sound like
Here are some questions to help you get started.
1. What is the issue or concern that needs to be addressed?
Be able to describe it SPECIFICALLY, FACTUALLY, and as NEUTRALLY as possible. If you can’t identify it, you’re not going to be able to address it, NOR will the other person be able to help you fix it.
2. Why is it difficult for you to have this conversation?
What are you afraid of? Maybe you’re worried the other person will blow up, break down, shut down, or run the conversation off track? Maybe you’re worried about keeping control of your own emotions? Identifying your fears and potential barriers can help you plan to overcome them.
3. What is the cost of not having the conversation- the impact on you and others?
Knowing the cost provides both you and the other party with motivation for having the conversation and fixing the problem.
4. What part of the situation can you own?
What role have you played in causing or perpetuating the problem? What haven’t you done thus far to make it better? People are more likely to be open to “owning up” to their roles, responsibilities, wrongdoings, or shortcomings if you admit yours first.
5. What is your purpose in having the conversation? If you’re having the conversation for any other reason than to fix a problem and/or improve a relationship, you should inspect your motives. If your goal is to punish, humiliate, degrade, or “put them in their place,” you should not have the conversation.
6. What are some possible solutions to the situation? You don’t want to inundate others with a long list of solutions, including your advice on how they can fix themselves. However, you should come to the table prepared to contribute well-thought-out ideas for possible solutions.
7. What’s the worst thing that could happen if you do have this conversation? Some people create worst-case scenarios that are very unlikely to happen, but cause them not to have difficult conversations. “My boss is going to fire me!” “My mother will never speak to me again!” Lay out your worst-case scenarios and look at them rationally. If they’re truly likely to occur, then prepare for them accordingly. If they’re just exaggerations, identify them as such and move on.
