There’s no perfect time for an important conversation.
Of course, there are bad times to attempt an important conversation. For example, launching into a performance discussion as someone is racing to their next meeting. Or raising a relationship problem just as the lights dim at the theatre. (I’m sure there are examples you’ve experienced along the way!)
We have all carried conversations around with us. It’s most often a conversation we know we need to have, but haven’t. We think about it while driving, drinking coffee, before we fall asleep. We rehearse it in our minds, imagine the other person’s responses, worry. And then we decide we’ll deal with it next week. And the next. And the next.
This important conversation becomes a burden, a distraction, a stress. And we make having the conversation a bigger, heavier, more anxiety-filled event. Sometimes this results in our becoming silent and even avoiding the other person.
In other words, we damage the relationship while we spend time talking to ourselves.
Waiting for the perfect moment is one reason that, in our 2026 Real-Time Business Conversation Index, 98% of business leaders shared their belief that real-time conversations are critical to their business success, while only 11% believe they happen exceptionally well.
Replace Procrastination with Preparation
Like anything we procrastinate on, we have plenty of reasons to embrace the delay. We tell ourselves things like: “I’ll talk to her when things settle down,” or “I’ll bring it up at our next meeting,” or “I need to think about it a little more,” or “I’m sure they’re too busy to have this conversation right now.”
Of course, these statements can be true – sometimes. But often the real truth is we don’t want to have the conversation yet. The issue is that our “yet” can become weeks, months or even years. And this has a cost, one we may not be able to surmount.
Reasons for an important conversation do not remain frozen in time. If it’s a performance conversation, the behaviour continues. If it’s a client concern, dissatisfaction builds. If it’s a team conversation, the concern keeps spreading to other people. And in personal relationships, resentment starts to accumulate.
One way to avoid these situations is to replace procrastination with preparation. We don’t want to be one of those people who blurts things out whenever they occur to us, but we do want to inspire important conversations.
When we find ourselves carrying an important conversation, running through scenarios over and over again in our mind, we can shift to asking ourselves some questions such as:
- What exactly needs to be understood?
- What are the facts that are important for this conversation?
- What is the hoped-for outcome?
- What questions are valuable to ask?
- When and where can this conversation receive the appropriate attention?
Scheduling the conversation, like scheduling other tasks we want to complete, ends the procrastination cycle.
Mindset Shift
Stop waiting until you feel ready. Get ready enough to begin.
Try This This Week
Think about one conversation you’ve been delaying and acknowledge why you’ve been waiting. Perhaps it’s because you want more confidence, more certainty, the perfect words, or a better opportunity.
Then ask yourself: “What will happen if I don’t have this conversation?” Honestly recognizing the consequences will help you move forward. You’ll be able to make the call, schedule the meeting, knock on the door.
Meaningful conversations rarely happen at the perfect time. They happen because someone decides they’re important enough to begin.
