The ChatGPT Experiment – Ep 88: The Near Future Of Conversational Technology

Host: Cary Weston
Date: September 30, 2025

Episode Overview

In this episode, host Cary Weston explores the imminent transformation of how we interact with technology—moving from click-driven interfaces to true conversational experiences. He emphasizes how conversational technology, particularly tools like ChatGPT, will soon be omnipresent in our daily lives, fundamentally changing platforms like Netflix, Amazon, and travel apps. Cary shares thoughtful perspectives on preparing for this shift and demystifies the process, inviting listeners to use ChatGPT as a safe practice ground for the coming two-way conversations with technology.

Key Discussion Points & Insights

1. The Big Shift: Conversational Technology is Coming

• Cary opens by expressing excitement (and urgency) about the near future:

  “Something that I think is going to fundamentally change, or I know it's going to fundamentally change how we interact with technology and tools... Your apps are about to start talking back, and ChatGPT is your practice space for that conversation.”
  (01:16)

• Examples of Potential Changes:

  • Streaming (e.g., Netflix): Apps might begin asking about your current mood or context instead of relying solely on algorithms.
  • Online Shopping: Envisioning a virtual personal shopper that considers real human dimensions and feedback—conversing about fit, styles, and even analyzing real-user reviews.
  • Travel Tools: Travel planning made less risky and more personal, by apps asking about your family’s preferences and travel anxieties.

2. From Clicks and Filters to Conversations

• “We're shifting from this click-driven, this filter sort kind of thing to conversation driven technology. And I know it might sound a lot like tech speak, but stay with me here for a second.”
  (05:54)

• Cary encourages listeners to imagine technology not as a cold, automated series of menus, but as a tool that interacts naturally—asking follow-up questions and responding to your answers.

3. Why Now? The Technology is Already Here (Just Not Everywhere)

• The power for such two-way interfaces exists, but hasn’t been rolled into the most common consumer apps yet.

  “This isn't science fiction. This technology exists. It just hasn't been woven into the everyday apps that we use yet. But it's coming, coming fast.”
  (07:30)

4. Changing Mindsets: ChatGPT is Your “Amazing Intern”

• Cary reframes AI as a helpful assistant, not just “intelligence”:

  “I've started calling ChatGPT an amazing intern... I see people relax, their shoulders drop. They stop worrying about the perfect prompts, and they start thinking about how to talk to it and work with it.”
  (08:00)

• Key Practice: Don’t overthink prompts—focus on communicating clearly, providing context, and being open to follow-up questions.

5. Practical Guidance: How to Practice Conversational Skills with ChatGPT

• Cary suggests using ChatGPT to hone your skills for the future:

  “ChatGPT isn't a perfect tool, but it's a fast, capable assistant. It can be incredibly helpful if you give it context, direction, space to ask questions, right?”
  (09:10)

• He references his prior “four part formula” for enhancing AI responses (see previous episodes).
• Example: Instead of “best family places in Italy,” share your concerns (nervous about driving, picky eaters) and let ChatGPT ask more questions, co-creating your plan collaboratively.

6. The Core Lesson: Don’t Wait—Start Practicing Now

• Cary urges immediate, low-pressure practice:

  “You can wait until every app starts talking to you and figure it out then, or... You can get comfortable with it now. And there's no pressure.... just have the conversation like you would somebody that's eager to help you, right?”
  (10:45)

• Key Point: Every conversation with ChatGPT is “practice for a world that's coming and it's coming fast.”
  (11:27)

7. No One is Behind—Join the Experiment

• Cary reassures listeners:

  “Are you behind? Should you have figured this out already? Absolutely not. No. No one's behind. This is real time, right? We're all right on time.”
  (11:46)

Notable Quotes & Memorable Moments

• On the Relatable Struggles of Today’s Apps:

  “Netflix doesn't know if you're watching alone tonight or with your whole family. It doesn't know if you've had a terrible day or just want something light.... 30 minutes later, you're either suffering through it or you just give up, right?"
  (02:20)

• On Personalization in Shopping:

  “I'm 6'3” 250... and everything these days is not built for me. So I have to go on this exploration, this safari of trying to buy and return because I don't know if the sizes are real anymore, right?”
  (03:24)

• On Tech Anxiety:

  “This tech thing is real, this anxiety thing is real. Being frozen with tech is real."
  (08:57)

• Reframing Website History as a Precedent for ChatGPT:

  "But a website isn't a computer problem, is it? It's a sales tool, it's a conversation tool, it's a marketing tool.... Well, the same thing is happening now with ChatGPT."
  (09:30)

• On the Importance of Curiosity:

  “The most important thing I always share is your curiosity. So go have some fun. Be curious. You can't break it. Talk to it. See what happens, right?”
  (11:53)

Timestamps for Major Segments

• 00:00 – 01:16: Cary introduces the episode’s focus on conversational tech and the coming changes.
• 01:17 – 04:56: Real-life frustrations with current streaming, shopping, and travel apps.
• 04:57 – 07:29: Vision for apps starting to have real conversations; "this tech already exists."
• 07:30 – 09:10: Introducing ChatGPT as an “amazing intern;” reducing tech friction.
• 09:11 – 10:45: Practical tips to practice with ChatGPT: focus on conversation, not prompts.
• 10:46 – 11:46: Why to start practicing now; reassurance about “not being behind.”
• 11:47 – 11:58: Closing encouragements and call to stay curious.

Resources & Further Exploration

• Cary highlights his four-part formula for context-rich prompts in a previous episode.
• Additional articles and in-depth content available at chatgptexperiment.com.

Final Note from Cary:

“The shift to conversational technology—it’s here. It’s here in small doses... Practice with it. Don’t just use ChatGPT like Google or give it simple tasks. Don’t treat it like software, right? Start practicing the conversation. Because soon, more tools that you use every day... are going to be ready to have a conversation with you. And I want you to be ready.”
(11:34)

Stay Curious, Practice Conversational AI—It’s Your Advantage for the Near Future.