Have the Conversation You Have Been Avoiding
You know you need to have it. You have been putting it off for weeks. The longer you wait, the harder it gets. Practice it first, then have it for real.
What Is Actually at Stake
Relationships
Unspoken issues fester. Resentment builds. A conversation handled well can save a relationship. Handled poorly, it ends one.
Team Performance
The underperformer everyone ignores drags down the whole team. Addressing it early is a kindness to everyone.
Your Peace of Mind
Avoiding the conversation does not make it go away. It just takes up mental space until you deal with it.
Why Traditional Approaches Fail
Scripting what you will say
You write it down, but the other person does not follow your script. When they push back, you are unprepared.
Rehearsing in your head
Mental rehearsal helps, but it is not the same as saying the words out loud under pressure.
Asking a friend to role-play
Friends do not get angry. They do not cry. They do not respond the way the actual person will.
Just winging it
Emotions run high. You say something you regret. The conversation derails. Now you have a bigger problem.
The DebateClub Approach
Describe the Situation
What is the conversation? Who is the other person? What is their likely reaction? The AI becomes them.
Have the Conversation
Say what you need to say. The AI responds as the other person would. Handle their defensiveness, their questions, their emotions.
Refine Your Approach
See where you lost them. Get suggestions for better phrasing. Try again until it feels natural.
Conversations You Can Practice
Performance Feedback
"Your work has been slipping. Here's what I need to see..." Be direct without being cruel. Set expectations clearly.
Asking for a Raise
"Based on my contributions, I'd like to discuss my compensation..." State your case confidently. Handle pushback.
Conflict Resolution
"I want to address what happened in the meeting..." Navigate disagreements without escalation.
Setting Boundaries
"I can't take on that project..." Say no without damaging the relationship.
Delivering Bad News
"The project is being cancelled..." Be honest and empathetic. Handle the emotional response.
Resigning Gracefully
"I've decided to move on..." Leave on good terms. Handle counteroffers and emotional reactions.
Techniques for Difficult Conversations
From the 12 core techniques, these four matter most here:
Before and After Practice
- Keep putting it off
- Lose sleep thinking about it
- Say the wrong thing in the moment
- Make the situation worse
- Schedule it and do it
- Walk in with practiced language
- Stay composed when they react
- Reach resolution
Stop Avoiding. Start Practicing.
Describe the conversation. Practice it. Have it for real.