The best conversations I had with the worst people stemmed from me not even telling them my opinion at all. I just asked them to explain theirs to me and asked the questions that occured to me in a respectful manner. Leaving them in healthy confusion and doubt afterwards (and learning a thing or two about them on the way) is more rewarding than winning a debate with them. Sometimes those people really surprise you as well, because they hold a combination of opinions that seem incompatible to you.
I absolutely agree with you that the best conversations tends to come from the latter approach you describe. Unfortunately, it can often be difficult and take some skill to avoid pushing the other person into "debate mode" by making them feel like they're losing. Especially if there's an audience, however small.
What people often don't realize is that winning a debate doesn't necessarily mean you side with the truth. A debate is aimed at winning on your existing opinions and the other losing. It is not aimed at discovery, validation or learning. Victory is more important than truth, and a lot of 'good moves' in a debate actually bring you further away from the truth.
If you engage in a conversation where you are both curious and submit to what's true (whatever that means), this conversation will rarely be a debate.
If a debate is in public between skilled debaters who show sportsmanship, then I think the public can gain a lot because a debate forces you to be very on point.
That's true of the sort of debate that's practiced competitively by "debating teams", but I don't think it's always true of debate as the word is used in an everyday context. A debate can also be more like a dialectic.
That's the problem with how we see a debate. It's just about that. There's no need to present your position in a compelling way or find common grounds with whoever you're debating.
If you read any books by professional negotiators - you'll notice that they conduct themselves very differently than you would in a debate.
Getting to Yes and Getting Past No have been eye opening to me. I no longer feel like I even need to "win an argument".
> the public can gain a lot because a debate forces you to be very on point
I recall reading some articles stating, that debates fail to convince anyone of anything. Public debates only encourage tribalism, IMO. If you watch a presidential debate - no amount of "winning" changed people's opinions.
I can even argue, that just hearing "X won the debate" will cause more impact; compared to listening to them.
Most people aren't debating you on purpose so there's no point as they continue to rubber duck (and maybe even thank you later). In case they really are in it for a debate, then by all means proceed.
While in reality for many things there are judgement calls, trade-offs, unknowns and basically "it depends". In software, POCs, trial&error, R&D, etc help you test out the options.
Many would do better to frame a discussion as surfacing the risks, trade-offs, potential pitfalls, and benefits of different answers such that the "bad answer" is avoided, more than "the one right answer" is somehow discovered.