The Ryan Leak Podcast - What ChatGPT Taught Me About Self-awareness

Episode Date: June 2, 2025

In this episode, I did something I’ve never done before.I asked ChatGPT to give me feedback—not just a one-time evaluation, but based on hundreds of prompts and conversations we’ve had over time.I asked:“What’s it like to be on the other side of me?”“How can I get better?”“What’s the thing I need to hear that I probably wouldn’t want to hear?”The answers were honest.Insightful.And a little uncomfortable—in the best way.We talk about the gift of feedback, how even AI can hold up a mirror, and how blind spots get smaller when you’re brave enough to ask better questions.If you’re willing to grow, this one’s for you.

Hey, welcome to the Ryan League podcast where we keep things short and sweet to add value to your life in very, very practical ways. Today's episode is a little bit different and it perhaps is one of the most important episodes that I have recorded. There is a question that I use all the time in my personal life and in my professional life, whether I'm sitting with friends or talking with executives from a Fortune 100 company, health care teams, HR leaders, professional sports. teams, I always end up talking about a particular question that points us towards self-awareness. And it is this question, what's it like to be on the other side of me? Do you have any idea what on earth it is like to be on the other side of you, on the other side of a meeting with you, on the other side of a reply all from you, on the other side of being your family member,

your brother, your sister, your parent, do you know what it's like to be led by you, hired by you, fired by you? I just know so many people that live and work decades of their life and they never pause to consider what on earth it is like to be on the other side of them.

I think it's a very, very powerful question. It's a very, very powerful tool that I think when we really consider that there is often a gap between how we think other people experience us versus how they actually experience us. And we will never know the truth until we're willing to ask the question, what's it like to be on the other side of me to somebody that is actually on the other side of us. Now, this is a question that I've asked many people in my life. And it's

always interesting to get different answers. But recently, I basically got a new employee that is very, very, very smart. And no, I did not hire a person. I started using chat GPT. like the rest of the world. And I started using this tool like a team member, because let's be real, it's that good. I mean, it helps me do so many things. It helps me plan. It helps me organize. It helps me create. It helps me communicate. And it just saves me so much time, especially time that I get to reinvest into my family and my own health and things that I value the most. And so I figured, why not ask my newest employee, the same question that I ask. ask everyone else. So I went to chat GPD and did a sort of a what's it like to be on the other side

of me exercise and I gave it four prompts and I'm going to take you through what those four prompts were. The first prompt was I asked chat GPT how it would describe my leadership style. Now here's what chat GPT told me. Now you're going to understand chat GPT has gotten thousands of prompts from me from helping me craft emails or social media content whatnot. So this entity, this intelligence knows me very well. Here's what it said. It said, hey, Ryan, you are a visionary leader, driven, clear, focused, and intentional. It also said that I lead with strategy, communicate directly, and have high expectations. It also said that I move fast, execute efficiently, and care about impact, that I empower people without micromanaging, and I create momentum for those

around me. But it also said that my speed and high standards might overwhelm some people and that if they're not keeping up, they might feel lost. If they're not used to clarity and drive, they might feel like I'm already five steps ahead. Basically, it told me I'm inspiring, but also intense. So I thought that that was pretty accurate. The second prompt I asked, which takes us a little bit deeper, I asked, well, how can I get better? And it told me, well, here's a deal. You could be a little bit more clear about the depth that I want. So whenever I'm making a request, sometimes I'll do like a really quick prompt. But it said, hey, you're not going that deep, which a lot of people would tell me. So they said, hey, oh, when you give me a request, Chad GPT is saying this, tell me the tone

that you're looking for. Is it funny, casual, professional, or clean? And, utilize me to be able to help you brainstorm things. A lot of times I come to chat GPT with my ideas already cooked and saying, hey, can you refine this? But this is saying, no, like, let me actually help you. And when you're actually clear and give a little bit more depth about what you want, the more depth and clarity I can give you. And I just thought in that moment, man, that's a lesson for leadership, parenting, marriage,

perhaps for every area of our life. People can't win with us if we don't often show them how. The third prompt that I put in was that exact question that is kind of the whole point of this exercise, which I just asked the question, hey, well, you just tell me, Chad GPT, what is it like to be on the other side of me? And let me just tell you what GPT did not hesitate to say.

You guessed it. I'll give you one guess what Chad GPT said it was like on the other side of me. I'll wait. I'll wait. Just take a guess. It said, ding, ding, ding, ding, it's complicated. It said people around me probably feel challenged, inspired, stretched, and motivated.

That I can bring some clarity, and I can also bring some momentum, that I make people better by sometimes simply being in the room. But it also said that it can feel like a whirlwind, that my pace, my expectations, and my directness can feel like a lot. that not everyone can thrive under the pressure, especially if they don't feel seen or supported. And I think that's the tension for a lot of us. We want to lead well. We want to help others grow, but we have to remember that growth is hard and leadership isn't always easy to receive, even when it's well intentioned. Then I asked Chad GPT a very, very important fourth prompt.

And again, I'll put all of these in the show notes so that you can, go through a similar exercise if you leverage chat gpti as well i'm here here was a fourth prompt i said hey chat gpti what's the thing i need to hear that i may not want to hear what's the thing that i need to hear that i may not want to hear here here's what it told me it says you may need to slow down for others to catch up not because they're incapable but because greatness doesn't always move at the speed of your ideas. You might think speed is a gift, and it is, but patience. Patience might be the gift that makes your speed sustainable for others. Not everyone needs you to be faster. They need you to be present. What? That one got me, because it's true. Speed has always been my superpower, but if I'm not

careful, it can also become my kryptonite. What good is a vision if no one can keep up with it? What good is momentum if no one has time to process it? So here's the truth. You don't have to be a CEO to ask this question. You don't have to be in leadership. You can be a parent, a spouse, a friend, a coworker, a student. And you can still go decades, decade without ever considering what it's like to be on the other side.

of you. And here's the deal. I love asking people how work is going or how marriage is going. And you know what most people say, it's good. Yeah, yeah, yeah, yeah, it's good. And then I just, I love following up with it and saying, but how do you know? Because there's no way for you to really know unless you're asking the question what's like to be on the other side of you, because the truth is we'll often say everything's going good according to our vantage point, according to our perception. But the only way for you to know if your perception is an actual reality is if you're willing to ask the people who live and work

on the other side of you. I love Ken Blanchard, author of the One Minute Manager. He says this, feedback is the breakfast of champions. I love that. Feedback is the breakfast of champions. But the problem is, most of us treat feedback like Brussels sprouts. We avoid it. We dodge it. We pretend we're fine without it.

But if you want to grow, if you want to take your life to the next level, you have got to get comfortable at the feedback table. Because people who ask for feedback aren't weak. They're just hungry for growth. So here's your challenge. I want you to reach out to three to five people in your life. It could be friends, could be colleagues, could be family members. And I want you to ask them, hey, what's it like to be?

on the other side of me. You don't have to be perfect. You just have to be curious, curious enough to grow. And if you interact with AI like I do, go ahead and ask it too. You might be surprised by what it has to say. Because becoming a better version of you

doesn't start with proving that you're right. It starts with being willing to listen. Thank you, my friends, for joining me on the Ryan League podcast. If today's episode spoke to you, inspired you, added value to your life, I would invite you to share it with a friend. And I would love it if you would rate, review, and subscribe. Your support helps keep these short and sweet episodes going

and it helps us reach even more people with practical inspiration. Thank you so much for being a part of the journey, and we will see you next time.