How To Have Your Next Difficult Conversation By Practicing With AI

How To Have Your Next Difficult Conversation By Practicing With AI

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You can spend years building credibility at work and still feel unprepared for the moment you need to say something uncomfortable. That one difficult conversation you wish you could avoid often turns out to be the one that matters most. These situations are hard to face because emotions can cloud your thinking. That is why preparation is often the most important part of communication. Jeff Wetzler recently shared in Harvard Business Review that successful conversations begin with what he calls a Curiosity Check. He shared that before you walk into a high-stakes conversation, ask yourself if you are truly open to learning something new. That pause can create space for clarity, empathy, and better decisions. What many people still overlook is how much more effective this pause can become when you practice with a quick AI simulation. A short role-play can help you rehearse what to say, how to say it, and what to expect when the other person responds.

Why Difficult Conversations Fail Without Preparation

Most people think they will know what to say in the moment, but then something gets triggered and the conversation shifts. The message gets buried under tension or misunderstood entirely. You may feel clear on your intention, but the words come out different than planned. This is why writing out what you want to say ahead of time makes such a difference. It helps to get all your thoughts out first, even the parts you would never actually say. I like to do this to get my thoughts and emotions out of my head, to vent, so I can see what I really want to communicate. It is important not to send that draft, though, because it can be very blunt. You can re-read the message a few times until you land on the wording that gets your point across in a way that really matters. This step alone can lower your stress before anything is said out loud.

How AI Can Support A Difficult Conversation Before It Happens

After writing your thoughts down, the next step is to run a practice round with an AI tool. You can use a simple prompt like, “Pretend you are my coworker. I am about to give you this feedback. Tell me how you would respond.” What comes back might surprise you. You can take that feedback and rewrite your approach. Look for areas where the AI questions your tone, asks for clarification, or misunderstands your meaning. These types of responses can show you where your message may be too vague, too harsh, or missing context. That kind of feedback is helpful because it points to areas where a real person might also get confused, defensive, or disengaged. Ask the AI to improve your language or tone. Try out different ways to open the conversation. AI likes to tell you what you want to hear, so I often ask it to respond to me as if I were wrong. That kind of prompt is especially helpful because people rarely see themselves as wrong. If you only ask it to respond, it may give you polite agreement, which does not help you improve. The tool can give you an instant preview of how your words might be received if you tell it to respond in multiple ways like positive agreement, argumentative, etc., which means you walk into the real conversation better prepared.

What Happens When You Practice Both Sides Of A Difficult Conversation

There is even more value when you go one step further. Ask the AI to now act as you, and then you take the other person’s perspective. Allow it to question your own message. Ask questions like, “Why are you bringing this up now?” or “Have you considered my side?” When you play both parts, you build awareness about what the other person might be feeling or needing. That allows you to stop rehearsing a speech and start preparing for a two-way conversation. Most people expect to deliver a message instead of having an exchange, which rarely happens. Practicing with AI shows you how quickly things can shift once the other person speaks. It also helps you prepare follow-up questions that keep the conversation constructive.

How AI Practice Helps You Recover If It Becomes A Difficult Conversation

Even with preparation, conversations sometimes still take a turn. You might get interrupted, the other person may become emotional, or you might forget what you wanted to say. Practicing with AI can also help you recover in those moments. During your role-play, ask the AI to interrupt you mid-conversation or push back in a way that catches you off guard. Then practice how you would respond. You can test ways to redirect the conversation without losing momentum or sounding defensive. Try prompts like, “What can I say if I lose my train of thought?” or “How do I respond if the other person gets upset?” These simulations prepare you to stay calm even when things feel unpredictable. That way, if the conversation veers off course, you will have already practiced what to do next.

Using AI To Reduce The Emotional Impact Of A Difficult Conversation

What makes this method so helpful is that the conversation starts to feel like something you have already experienced. That familiarity gives you confidence. When you reach the moment that might have triggered a reactive response, you pause instead, because you know how to steer in a positive direction. You already know the questions that help clarify issues. You start thinking less about proving a point and more about communicating effectively.

Building A New Habit Around Difficult Conversations With AI

The best part is that this does not have to take much time. In fact, most people find that just five to ten minutes of AI practice gives them exactly what they need to feel more confident. Once you do it a few times, it becomes a habit. You catch yourself before sending that rushed message or making the phone call you will regret. You take a few minutes to write, pause, and simulate the conversation. That extra layer of preparation saves time in the long run. It helps you avoid miscommunication, awkward follow-ups, and the kind of tension that lingers after things go unsaid or poorly said.

Making Space For Curiosity In Difficult Conversations With AI

When you use AI in this way, you are preparing your mindset. That is where Jeff Wetzler’s idea fits so well. A Curiosity Check is a reminder that even when you think you are right, there is always more to learn. Practicing with AI gives you a chance to ask questions before the conversation even starts. You can test your own assumptions and find language that avoids resistance. Most of all, you give yourself time to cool off, think clearly, and walk into the moment well-prepared.

How Practicing With AI Can Improve Every Difficult Conversation You Have

Preparing for a difficult conversation is a small step that helps you find the words you need and the tone that fits. It keeps you calm in the moments that used to trigger defensiveness. It builds your ability to listen, adjust, and stay focused on what matters. Difficult conversations will always be part of the workplace. What changes is how you prepare for them. When you write first, rehearse with AI, and consider your mindset, you avoid a lot of conflict and confusion, which helps build stronger work relationships.