AI Asian Parent GPT: Why Practice Scales Capacity
Lesson 12 of 25 from podcast conversations with leaders who leave the world better than they found it
Brandon Lee told me something that made me laugh and then think hard about how we prepare for difficult conversations.
He built a GPT—a custom AI chatbot—that mimicked his mother's communication style.
"I figured rather than wait to interact with my mom, I'll just create a GPT that acts like her and learn to lean into the discomfort," he said.
He knew certain conversations with his mother were difficult. He knew the patterns—the questions she'd ask, the dynamics that would emerge, the exact phrases that would trip him up.
So he created a way to practice those conversations before having them.
Genius.
And while the AI angle is novel, the principle isn't. Athletes visualize performance. Actors rehearse scenes. Musicians practice difficult passages.
We understand intuitively that practice matters for physical performance. We forget it matters just as much for conversational performance.
Why We Don't Practice Hard Conversations
Most of us walk into high-stakes conversations unprepared.
The board meeting where you need to ask for something difficult. The funder conversation where you need to explain why the program pivoted. The staff discussion where you need to address performance concerns.
We might think about these conversations in advance. We might worry about them. But we rarely practice them.
Why?
It feels artificial. Role-playing feels forced. You're not really talking to your board chair, you're talking to your colleague pretending to be your board chair. It doesn't feel real.
It feels uncomfortable. Practicing means rehearsing the parts of the conversation that might go badly. That's unpleasant. Easier to just hope it goes well.
It feels like avoidance. Shouldn't we just have the conversation? Isn't practicing just procrastinating?
We think we can wing it. We're smart. We know what we need to say. We'll figure it out in the moment.
But here's what happens when we don't practice: we walk into difficult conversations reactive instead of prepared. We get defensive when challenged. We forget key points we wanted to make. We let the conversation go directions we didn't intend.
And we walk out wishing we'd handled it differently.
What Practice Actually Does
Brandon's GPT approach shows what practice makes possible:
It surfaces the difficult moments. When you practice, you encounter the questions that will trip you up. The challenges that will make you defensive. The dynamics that will throw you off.
In practice, those moments are low-stakes. You can fumble, recover, try again. By the time you're in the real conversation, you've already worked through the difficulty.
It reveals gaps in your thinking. Sometimes you think you have a clear answer until someone asks you a hard question. Practice surfaces those gaps while there's still time to think them through.
It builds muscle memory. The more you practice staying calm when challenged, the easier it becomes to actually stay calm when challenged for real.
It reduces anxiety. Much of conversation anxiety comes from uncertainty about what might happen. Practice removes some of that uncertainty. You've already been through versions of this. You know you can handle it.
How To Practice Without AI
You don't need custom AI to practice difficult conversations. You just need:
Someone willing to role-play. A colleague. A coach. A friend. Someone who can take on the other person's perspective.
Clarity about what makes this conversation difficult. What are you worried about? What questions do you dread? What dynamics concern you?
Permission to make it realistic. The role-play only helps if it's challenging. Tell your practice partner to actually push back, not just lob softballs.
Time to try multiple approaches. Practice the conversation more than once. Try different ways of framing your points. See what lands.
Reflection on what worked. After each practice run, pause. What felt good? What didn't? What would you adjust?
Here's a simple structure:
Brief your practice partner. "You're my board chair. You're skeptical about this pivot. You're worried we're mission-drifting. Here are the questions you might ask..."
Run the conversation. For real. Not just talking about it—actually have the conversation. Let your partner challenge you.
Pause and reflect. What worked? What didn't? What got hard?
Adjust and try again. Same conversation, but apply what you learned.
Practice the hardest moments. Once you've identified what trips you up, practice those moments specifically until they feel more manageable.
Fifteen minutes of this kind of practice changes how you show up to the real conversation.
The High-Stakes Conversation Prep Exercise
Here's something you can do before your next difficult conversation:
List the five hardest questions or challenges you might face.
Not the questions you hope they'll ask. The questions you're dreading. The challenges that will make you most uncomfortable.
For each one, write out:
Your initial reaction (probably defensive)
The response you actually want to give
How you'll stay grounded if the question makes you reactive
Then practice delivering those responses. Out loud. Multiple times. Until they feel natural instead of scripted.
This doesn't mean you'll perfectly execute in the moment. But it means you've already worked through your reactivity in private, which makes it less likely to hijack you in public.
Why This Matters For Organizational Capacity
Organizations make decisions in conversations. Board meetings. Funder calls. Staff discussions. Partner negotiations.
The quality of those conversations determines the quality of organizational decision-making.
And yet most organizations treat high-stakes conversations as something you just wing.
Leaders walk into board meetings without having practiced how they'll respond to likely objections.
Development staff pitch funders without having rehearsed the difficult questions.
Managers have performance conversations without having worked through how to stay non-defensive.
Then they're surprised when these conversations don't go well.
Practice is strategic capacity work.
When your leadership team practices difficult conversations, you build collective capacity to handle them well. You surface assumptions. You identify gaps. You develop shared language. You build confidence.
This isn't "soft skills." This is organizational infrastructure for better decision-making.
What Brandon's GPT Teaches Us
Brandon's approach—creating technology to enable practice—shows something important about preparation.
He didn't avoid the difficult conversation with his mother. He just prepared for it.
He didn't pretend it would be easy. He acknowledged it would be hard and created structure to work through that difficulty in advance.
He treated conversational capacity as something you can build, not something you either have or don't.
And the AI part? That's just a tool. The principle works whether you're using custom GPT, a willing colleague, or just talking to yourself in front of a mirror.
What matters is practicing the difficult parts before you're in the high-stakes moment.
This is lesson 12 in a 25-part series exploring insights from podcast conversations with leaders who leave the world better than they found it.
Subscribe for weekly tools for showing up prepared to difficult moments.
