How to Approach a Difficult Conversation

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How to Approach a Difficult Conversation

Difficult conversations only feel difficult if you don’t have the skills to navigate them expertly. Much like a negotiation, you should always prepare for any difficult conversation. You want to be heard, so you will also need to understand a bit of strategy. First, you should think about what you want out of the situation. How would you like it to be resolved? Are there multiple scenarios to this situation? If so, make sure you consider them all. How do you want each of them to play out? What kind of leverage do you have? Prepare, prepare, prepare.

Two-step conversation

Whenever you need to have a difficult conversation with someone, you need to prep them. So you should have an initial conversation to schedule the more difficult conversation. First, let them know that you would like to discuss this. Then, find out when would be a good time for them to meet with you. It would be best to give them an idea of how long you expect the conversation to last. If possible, share with them information about what the discussion will be about.

Ground Rules

Set some ground rules before you begin when you meet for the difficult conversation. Let the other person know that you want to have a productive discussion where everyone is heard. The ground rules should have no interrupting, no raising of voices, or name-calling. It should also have some general guidelines such as, each person should be brief and not talk longer than 5 or 10 minutes without allowing the other person to respond. Each side should take notes if they have the urge to interrupt. Finally, each side is allowed to take a break if they feel too upset or triggered to continue with the conversation.


Practice active listening when it is not your turn to speak. Listen carefully to what the other side is saying. You want to be able to repeat back what you heard. When the other side has completed what they want to say, you should mirror back to them by saying, “I want to make sure I understand what you are saying. Are you saying that…” or “What I am hearing from you is that…” If the other person was angry when speaking, you would visually see the temperature of the room decrease.

Reading Between the Lines

Reading between the lines means understanding what is not being said. First, you must try to understand what is going on emotionally. You should use neutral statements which remove both parties. These statements sound like, “It seems like,” “It looks like,” and “It sounds like.” Then you go on to state what you think might be happening. For example: “It sounds like you are frustrated that I don’t take your ideas seriously.” Then give the other person a chance to respond. They will either give you more information, confirm what you are saying or refute it. Even if you did not read between the lines accurately, the other person can correct you and clear up any potential misunderstanding.


Finally, once you come to an agreement, it is always good to verbally recap the conversation and e-mail a summary. It is too easy for people to forget the nuances of the conversation later. Therefore, it is very effective to write it down to capture all the details of the conversation. Once you can smoothly get through these steps, you will realize that difficult conversations are not anything to be afraid of. On the contrary, they help resolve issues and create a clear path to move forward in a positive manner.

By Alice Shikina

Alice Shikina is an international speaker, author of “Negotiating with Your Kids,” mediator, and negotiation coach. She lives in Oakland, CA, with her two boys.

How to Approach a Difficult Conversation

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