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8 Tips to Successfully Handle a Difficult Conversation

Everyone dreads difficult conversations. Having to deliver unpleasant news, discussing a delicate subject, or talking about a situation that was offensive or hurtful can be daunting. You may be uncomfortable with setting limits or worry about how the other person will react. 

While all of that is completely natural and normal, these conversations cannot be avoided altogether. In fact, putting them off for too long can potentially let the issue grow worse. Discussing difficult matters in a respectful way is an immensely important part of any healthy relationship, whether it’s a friend, an employee, a relative, or a significant other. 

Approaching difficult conversations correctly will not only raise the chances for a positive outcome, but it will also make you feel more at ease before and during the talk. Here are some essential tips from mental health and communication experts to keep in mind. 


1. Prepare ahead and be as clear as possibleTips for Handling a Difficult Conversation, woman thinking

To prepare for the conversation, you need to first identify the problem you are about to raise. To do so, ask yourself the following questions:

  • What exactly is the behavior that is causing the problem?
  • What impact does that behavior have on you (or the group/organization)?
  • What do you want to accomplish by having this conversation?

It’s important that you maintain clarity for yourself so that you’re able to articulate the issue concisely to the other side. Confusion or hesitation could make the situation more awkward, and derail the conversation in a direction you didn’t plan on and that isn’t productive in solving the problem at hand. 

Use specific examples for your concerns and the things you’d like to happen differently. Avoid words like ‘always’, ‘never’, ‘everything’ or ‘nothing’. These words may express your frustration, but they overgeneralize and aren’t helpful in the communication process. 

2. Don’t wait too longTips for Handling a Difficult Conversation men arguing

When a friend or a relative does something that offends you, it’s best to discuss the challenging issue as it comes up or soon thereafter. It’s never helpful to hold onto feelings of anger, frustration or resentments for days or weeks, and then unleashing them on another person all at once. Discussing an issue when it’s still fresh in your mind will usually make for a calmer, more grounded conversation. 

3. Manage the emotionsTips for Handling a Difficult Conversation woman crying during conversation

As we mentioned, you might be coming to the conversation with a bag of emotions like anger or frustration. It’s important that you express how you feel, but try not to fixate on these emotions and let them run the show. Speak as calmly in a matter-of-fact tone as possible.

That being said, don’t block emotions completely out of the conversation. If the other person seems annoyed, saddened, or even starts to cry, these emotions should be acknowledged and respected, not ignored.

Related: These 8 Mistakes Are the Biggest Conversation Killers

4. Don't be afraid of silencesTips for Handling a Difficult Conversation couple sitting in silence

There will be moments in the conversation when silence occurs. Don’t let it faze you and don’t rush to fill it in with words. These silences are helpful; they allow us to really hear what was said and let the messages sink in.

Some people are uncomfortable with silences and that is understandable, but it’s important to be prepared for them when approaching a sensitive conversation. A constant flow of words can come across as steamrolling or overbeating. A pause also has calming effects and allowing these moments is likely to lead to a better outcome. 

5. Give the other person your full attentionTips for Handling a Difficult Conversation active listening

When the other person is speaking, consciously listen to what they are saying, with the intent of hearing them. That is very different from waiting for the other person to finish speaking so you can respond.

To achieve this, you must approach the conversation with a genuine interest in solving the problem, rather than prioritizing the need to be “right”. If you see the conversation as a competition where you need to be right, it means the other person must necessarily be ‘wrong’. This kind of either-or mentality makes reaching a mutual understating much less likely. 

If you are not sure what the other person said or meant, ask for clarification before you respond. For example,  “I’m not sure what you mean. Can you please help me better understand?” Making the other person feel heard will prevent the conversation from turning into an argument

6. Choose your time and placeTips for Handling a Difficult Conversation setting time

We already established that if you need to have a challenging conversation with someone, it’s best to plan it out rather than just walking into it spontaneously. The time and place can make a big difference in the other side’s willingness to accept and hear what you are saying. Choose a relaxed location and a time that suits both of you, so no one is under any external stress.

For example, if you approach the other person right before they have to meet an important deadline, the additional stress they are under can affect their reaction negatively. Telling someone “we need to talk” helps to signal that time needs to be set aside to have the conversation.

Related: 9 Habits All Assertive People Share

7. Give it timeTips for Handling a Difficult Conversation time

Keep in mind change doesn’t happen overnight. You might reach a big breakthrough during the conversation, or have an eye-opening moment, but chances are both parties will need time to digest and reflect. So give each other the space needed for that. Don’t be discouraged if you don’t feel like everything is perfect right away. What’s important is that both of you expressed how you feel respectfully, and are on the same page. 

8. Drop your assumptions

Tips for Handling a Difficult Conversation hand on table

Even if you know someone through and through, it doesn’t mean you can always predict what they are feeling and thinking. Ultimately, you can’t control how the other person will react to your effort to engage them in a challenging conversation. 

People grow and change, and their needs and expectations change over time too and need to be renegotiated. So it’s best to drop any assumptions before walking into the conversation in order to be truly open-minded and accept the outcome. 

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