Preparing for a Tough Talk

Last Reviewed: October, 2023 Reviewed by: JES

Sometimes to settle a dispute our first and best option is to have a conversation with the other person even when we know it is going to be tough. Perhaps we have had a conflict with our boss but nothing has been resolved. Maybe our cell phone provider is overcharging what it promised. Or maybe the property manager of our apartment building isn’t making the repairs he agreed to. Whatever the issue, it is usually a good idea to negotiate face to face to settle a dispute. The key to having a successful conversation, though, is to be well prepared.


Weigh the Risks and Benefits

It does not always seem worth it to negotiate a resolution to a dispute. Maybe you have already tried talking to the other person and the situation seems hopeless. You do not know if you want to take the risk to bring up the subject again. On the other hand, the risk of not having the conversation may also be costly.

Here is a good exercise that will help you decide whether you should have that difficult conversation:

Sort facts from fears exercise:

  1. Take a sheet of paper and divide it into two columns.
  2. On one side, list the potential risks of bringing up the issue.
  3. On the other side, list the potential benefits of doing so. You may see benefits you had not thought of before.

If you list that you are uncomfortable about having the tough talk, ask yourself whether it’s because you know the conversation is going to be difficult (in which case you can prepare), or whether it’s because you feel unsafe around the other person. If talking to the other person is going to make you feel uncomfortable, consider how you might be able to increase your safety. This might be meeting in a public place, having the conversation virtually, or using a third party to resolve the dispute.


If you fear for your safety contacting them may not be advisable and a formal dispute resolution process may be better. Go to Get Help to find out what kind of resources and support are available.

You should also ask yourself what might happen if you do not try to settle your dispute through negotiation. The answer may make your situation clearer and provide you with the motivation you need to work things out. If you have decided that it is worth having the discussion you will want to make sure you truly understand what you hope to accomplish.


Know What You Hope to Accomplish

Take some time to check in with yourself about your motivations for talking with the other person and what you hope to get out of it. Here are some steps to help you clarify your intentions for the meeting:

  1. On a piece of paper, create three columns:
    • In the first column, write down what you hope to accomplish for you.
    • In the second, write down your guess about what the other person hopes to accomplish (what is “in it” for them).
    • In the last column, write down what might be your common goals. (Keep in mind that it can be dangerous to assume you know what is going on in the head of another person.)
  2. Think about what you would reasonably consider the best outcome of the process.
  3. Think about what you would consider the worst outcome of the process, and how you should prepare for it.
  4. Ask yourself if you are more upset than the situation necessitates. Consider how you may have contributed to the problem, and likewise, how the other person may have. Is there something in your personal history that is being triggered?
  5. Check your attitude towards the meeting. If you think the conversation is going to be horrible, it probably will be. If you believe that no matter what happens some good will come of it that will likely be the case.

Once you are clear about what you hope to get from the meeting, take some time to plan for it.

Plan for the Meeting

It is important to plan for a meeting where you will try to settle a dispute. Here are some ideas for how to prepare:

  • Write description: Prepare a description of the events that led to the conflict: include a timeline of dates, behaviours, who said what, and how each side reacted. It might also be helpful to refer back to original documents, financial statements, invoices, and photographs so that you are clear on the facts from your point of view.
  • Your concerns: Consider what you are most concerned about and what the other person can do to respond to those concerns. Identify areas of agreement between you and the other party.
  • Their concerns: Consider what the other person is most concerned about and what you can do to respond to those concerns. Sometimes the dispute is not about money and a sincere apology will resolve matters.
  • List discussion topics: Identify and list everything that needs to be discussed. Try to look beyond the obvious. List the items in order of importance to you. Are there items that you would consider letting go of?
  • Prepare questions: Decide what questions you need to ask the other person. Think about the information you need to gather from them. Consider what questions they might ask you and how you are going to answer them.
  • Consider options: Ask yourself what is your best option if you cannot reach an agreement with the other person. Can you get your needs met in some other way? With at least one other option in mind for solving the problem, you will feel less pressure if the negotiation goes sideways.
  • Practice: Plan what you want to say ahead of time so that you will be able to express yourself clearly. You might try practicing in front of someone else and getting their feedback on what you said. Or practice it out loud to yourself. Do not memorize your message; just get comfortable with delivering it.
  • Listen: Remind yourself that you will need to listen to the other side and respond respectfully.

You are now ready to request a meeting.


Request a Meeting

Many of us begin a tough conversation by blurting out what’s on our mind. We do not think about whether it’s the right time or place. But there is. Here are some tips on how to request a meeting to have a tough conversation:

  • Make your request for the meeting in private. Do not ask in front of others.
  • Suggest a neutral setting if possible. Where would the two of you feel most comfortable having the conversation?
  • Ask the person when it is a good time to talk. Choosing the right time of day is important. If you have a history with the person, you may know when they are usually in a better mood.
  • Let the person know what you want to talk to them about. You do not need to get into details, but at least give them the “agenda” topics. You may want to tell them that the conversation could be tough. This will not work for everyone, but it may help prevent some awkwardness if the other person thinks the topic is going to be a happy one.

You are all set to go, or are you? Maybe the other person makes you angry or you get defensive too easily. Being relaxed and in control of your emotions will help you feel more confident.

Manage your Emotions

Before you head into your meeting with the other person you will want to manage your emotions. Sounds obvious, but our emotions are often managing us. To get emotionally prepared, consider using one or more of the following calming strategies:

  • Stop and take another look: Often called “reappraisal,” this technique involves thinking about the emotional situation in a way that reduces its negative meaning. Ask yourself: “Why would a reasonable, rational, and decent person act this way?” Allow a reasonable, rational, and decent answer to arise. This will help you reframe the situation that got you upset and reduce the tendency to think the other person is motivated by negative intentions.
  • Coping self-talk: Ask yourself what annoys you about the other person’s approach to the subject. Once you identify what your body and mind does when you think about that behaviour, pick a cue word or phrase that is the opposite of that reaction. For example, if you feel tight when you feel an emotion like anger, then your cue word could be “open.” Or if you recognize that you feel angry, your cue phrase might be “cool it.”
  • Deep breathing: Deep breathing is a simple, but very effective, method of relaxation. It is for good reason that it is the basis of so many calming approaches. All you have to do is take a number of deep breaths and relax your body further with each breath.
  • Progressive muscle relaxation: In this technique, you slowly tense and relax each muscle group, starting with the muscles in your toes and working your way up to your neck and head, or starting with your head and neck and working your way down to your toes. Tense up each group of muscles so that they are as tight as possible and hold for at least five seconds, then relax them for 30 seconds, and repeat.
  • Visualization: By forming peaceful mental images, you will take a visual trip to a more calming place or situation. During visualization, try to use as many senses as you can, including smell, sight, sound, and touch. A common image is relaxing by the ocean. In this case, you might think about the smell of salt water, the sound of crashing waves, and the warmth of the sun on your body. You may also want to close your eyes for a moment.

Make a conscious effort to practice one of these relaxation techniques as soon as you recognize that you are responding emotionally in a conflict. Remember that all techniques take practice. If one does not work for you, try another. Now that you have prepared for your tough talk, you are ready to negotiate. See Negotiating a Solution.

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