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Turn Difficult Conversations into Win-Win Conversations

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Communication - Difficult Conversations


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Difficult conversations usually mean bad news for at least one person, and they affect both the teller and the receiver of the news. Difficult conversations are best held in person or if necessary, through video conferencing. When the conversation affects an entire group, the group should be broken up into as small units as possible to allow time for the group to react to the news together. 

But it is possible to turn a difficult conversation into a win-win conversation if you follow these rules.

Know Your Goal

Before you begin a difficult conversation, make sure you are clear in your own mind why the conversation is necessary and what you hope to accomplish. Sometimes a difficult conversation means conceding points along the way; but if you keep your goal in mind, those compromises will be easier.

Know Your Facts 

For example, if you speak to your boss about getting a raise, you should make the case based on facts, such as your contribution to the company, the current industry standard for pay, and the current income of your peers in the company. If you are giving negative feedback to someone who reports to you, come prepared with specific instances and examples of the behavior you would like the person to change and reasons why the current behavior isn’t working.

Arguments based in fact are more likely to succeed than emotional appeals or vague complaints.

Be Respectful and Straightforward

You may need to rehearse the words you will use to be sure that you are using respectful language to describe the situation that led to the conversation. You may also want to rehearse your body language and gestures. 

Hedging around a topic often causes the other person to imagine something worse or to lose patience before you start. Therefore, let the other person know the topic of the conversation right at the beginning.


There are at least two people in any difficult conservation; if you want it to become a win-win conversation, you have to be prepared to listen. New information may emerge that changes the direction of the conversation. Express a willingness to find a mutual solution, if one is possible. 

Pay attention to body language and use your emotional intelligence to help you understand what the other person is saying. Summarize what the other person says and ask questions to make sure you understand their viewpoint before replying. 

Look for Solutions

Turning a difficult conversation into a win-win requires that both parties treat the situation as a problem that is capable of solution. Solutions may not always be possible—for example, if you are laying someone off. However, even then, you can suggest resources or write a recommendation if appropriate. 

End Politely

Ending a difficult conversation politely and professionally helps to turn it into a win-win conversation. If the other person resists ending the conversation, avoid phrases like “I refuse to talk about this further” and instead suggest coming back to the issue later when you’ve both had more time to think. If the other person resists continuing the conversation, you may have to give them time to settle. Whether you gain your point or not, thank the person for listening.

You may want to send an email summarizing the conversation, the next steps that both parties agreed to, and any timeline.

Provide Time

Sometimes one or more persons in a difficult conversation may have difficulty expressing their reaction in the moment or at all. They may feel a need to revisit the conversation and that should be allowed when appropriate.

Key Takeaways

A difficult conversation becomes a win-win conversation when it has a clear goal, concentrates on facts, is respectful and straightforward, demonstrates active listening, includes a search for solutions, ends mutually, and is capable of being revisited at a later time.

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