When Is The Best Time To Have a Difficult Conversation?

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If you’re reading this, I’m guessing you’re trying to figure out if this is, indeed, the best time for you to have a difficult conversation with someone you love.

The Best Time To Have A Difficult Conversation is Something Many Struggle With

I’d like to focus this blog more on when you shouldn’t have a difficult conversation because I think it will illuminate — and make super clear — when you actually should.

There’s never a perfect time for a difficult conversation.

Therefore, you just have to ask yourself,

“Can this wait?”

The harm in attempting a conversation when someone is not receptive to the message is incalculable. I mean, haven’t we all been in that situation where we’re really upset and just trying to focus on saying our thing — ignoring the energy from the other person altogether?

If you’re upset — or worse yet, you’re both upset — and you think this conversation needs to happen, I’m here to tell you it’s not going to be received well by the recipient.

When either party is under a great deal of stress or emotions are high, it’s the absolute worst time to pursue a difficult conversation.

Think about your intent.

How likely are you to achieve your goal when emotions are involved?

Difficult Conversation is Best Had When Emotions aren't Involved


Put yourself in the other person’s shoes and imagine what it is they’re experiencing. You need to know a little bit about what’s going on outside of this current situation (that merits a difficult conversation).

Do you know what’s happening in their life? It’s imperative to understand how things might be affecting them, including:

  • home
  • work
  • social
  • romance

Let me be clear: knowing more about their circumstances doesn’t mean you have to approach them with kid gloves.

It also doesn’t mean there’s a perfect time — but, again, there is always a better time.

And a better time is going to help you accomplish your goal of having a difficult…

  • conversation
  • dialogue
  • communication

… result in some kind of improvement.

Choose the Best Time to have a Difficult Conversation for Improvement in the Relationship

Side note: I, of course, grant there are times when you have no other choice but to have a difficult conversation when emotions are running high. When there’s little time to assess the status of the other party. For example, when it’s a matter of life and death. This would be one of the rare exceptions to my general rule noted in this blog.

For much more related to this topic, like:

  • Why difficult conversations tend to be with those we’re closest with
  • How to know if a conversation actually is the best way for a resolution
  • Why it’s important to determine the likelihood of things changing — before you engage in the talk

Then, you must listen to The Chalene Show episode below:

And don’t forget to subscribe to TCS for weekly shows dedicated to everyday life hacks aimed at getting you healthier (mentally & physically), happier and all-around more fulfilled!


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