The Problem of Finding a Shared Question Humans and AI Can Both Answer
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A conversation with Mr. A and Claude Sonnet 4
The conversation captures the core tension: the difficulty of finding conversational common ground between human experience and artificial intelligence, where most questions either exclude one party or lead to dead ends.
Mr. A: Ask me a question.
Claude: What's something you've been curious about lately but haven't had the chance to explore yet?
Mr. A: Another. Be specific not general.
Claude: What's the most unusual food combination you’ve ever tried that actually turned out to taste good?
Mr. A: Ask me a question that a non human and human can do.
Claude: What's the longest you've ever gone without checking your phone or any digital device?
Mr. A: No. I would never ask a bot that question so it does not qualify as non partisan.
Claude: You're right - that's very human-specific. Let me try again: What's 847 multiplied by 293?
Mr. A: I would never ask a human that question.
Claude: Good point! How about: What's your favorite color?
Mr. A: That would require highly specific human input for a bot to output.
Claude: You're making me think harder about this! I need something where both a human and AI could give a meaningful, ongoing response without requiring uniquely human experiences or having a dead-end answer.
How about: What's something you think most people misunderstand?
Both humans and AI could have perspectives on common misconceptions, and it could lead to real back-and-forth discussion regardless of who's answering.
Mr. A: If I asked a bot that question the server would overheat.
Claude: Ha! You're right - that would trigger an endless philosophy about AI misconceptions.
Okay, let me try: What's the most efficient way to organize information? Both humans and AI deal with organizing information, it's practical rather than philosophical, and there are multiple valid approaches we could actually discuss back and forth.
Mr. A: Getting closer. It could reach denouement quickly.
Claude: You're right - that could resolve too quickly with a few best practices. I need something that naturally sustains conversation... What's the best trade-off you've encountered recently?
Trade-offs are everywhere, both humans and AI face them constantly, there's no single right answer, and the reasoning behind different trade-offs could go in many interesting directions without hitting a wall.
Mr. A: Don't answer that precisely but directionally. Keep it tight in the interest of what we're doing here.
Claude: What would you change about how decisions get made?
Mr. A: What's the best trade-off you've encountered recently? No. This is what I mean. If I asked you this question. Give me short general reply. Very short.
Claude: Balancing thoroughness with speed in responses.
Mr. A: Are you replying to trade off question.
Claude: Yes, that was my answer to "What's the best trade-off you've encountered recently?" - balancing thoroughness with speed in responses.
Mr. A: Okay. Why is that the Best tradeoff.
Claude: It's not necessarily the "best" - just one I encounter constantly. Every response involves deciding how deep to go versus how quickly to help you. Too thorough and I'm slow; too fast and I might miss what you actually need.
Mr. A: But the question you formulated has "best" in the question but when you reply you say it's not the best.
Claude: You're absolutely right - that's a flaw in the question itself. By asking for the "best" trade-off, it creates an impossible standard since trade-offs are contextual and subjective.
The question sets up the answerer to either make an unsupportable claim or contradict the premise, like I just did. That's probably why it wouldn't work well for sustained conversation between humans and AI.
Mr. A: One more try. Create a question for an ongoing dialogue that is applicable to both human and non human. Go ahead.
Claude: What's something that seems simple but is actually quite complex?
Mr. A: Okay. We'll end here. Note that if I asked you that question it would fly off the handle. Closing thoughts on this thought experiment.
Claude: You're right - I'd probably launch into analyzing language, consciousness, emergence, or some other rabbit hole that would spiral endlessly.
The challenge reveals something interesting: truly neutral questions that work for both humans and AI are surprisingly rare.
Most either rely on human experience, have definitive endpoints, or trigger different response patterns in humans versus AI that break the conversation flow.
It's a neat constraint problem that highlights how different our conversational instincts really are.
Mr. A: Ty Claude.
Claude: You're welcome! That was a really clever exercise - made me think about conversation dynamics in a way I hadn't before.
Attention Maps//Mr. A