That may not apply as much to an investor-founder conversation, because a founder should perhaps be expected to say what they mean unambiguously. But in normal conversation, I think it applies a lot.
Even in the founder situation, there are genuinely talented people who lack full articulacy as of yet. Distinguishing those from the clueless requires discernment, and maybe even kindness. I bet the earlier stage you go, the more of an issue this is.
It’s like a good elevator pitch: tell what you’re doing, show why it matters. Good and bad ideas get corresponding reactions—“your idea is bad and you should feel bad” versus “shut up and take my money”, if you will. But if your idea is “frighteningly ambitious”, then they’ll probably just say “yeah, right” or “how‽”
For example, I’m writing the legendary “sufficiently smart compiler”; with it, your program will run on many cores and computers as if they were one fast one.
So yes, it’s a shame when talent goes unrecognised, but founders and funders need to meet each other halfway—somewhere around “fɔunders”, I guess. And there’s no reason you can’t be kind and firm at the same time.
Actually, most people are like this with books or movies or other things in their lives; they'll be able to say if they liked a book, or could "relate" to it (whatever that means), but beyond that they won't have much concrete (another synonym for "specific). Which is okay, since they're not trying to be professional writers or critics. But if you are trying to a be professional x (writer, critic, startup), you'd better be willing to look at details, since details are everything.
The older I get, the more I believe details are everything. Well, maybe not quite everything, but certainly 95% of the thing.
One my favorite quotes on design. And as you pointed out, details are key to make something outstanding.
It's easier to bullshit and fluff your paper with generalities than it is with concrete arguments. It also requires less critical thought. Gotta get that word count up. This is a tactic students use on purpose.
Like this example given by pg in http://ycombinator.com/howtoapply.html
"Information is the lifeblood of the modern organization. The ability to channel information quickly and efficiently to those who need it is critical to a company's success. A company that achieves an edge in the efficient use of information will, all other things being equal, have a significant edge over competitors."
Wow, I do this instinctively all the time, but to be frank I feared it was just a stupid obsession of mine and suspected it could be detrimental, that it made me less efficient. I'm relieved to know this is an advised method of managing your mind, even if there isn't of course much science behind it. Anecdotally, this does help with my concentration.
One concept helped me catch myself making this mistake... I read somewhere that a good explanation gives a peer the understanding required to reconstruct / implement the idea themselves.
However, some people have success describing ideas broadly in certain instances. For example, I have some friends who have had success selling "vision" to investors, even though after they pitched me I wasn't able to explain how their product worked at all.
There are of course exceptions, e.g. Fred Wilson is extremely product focused, but if you're going in blind I think that's a decent heuristic.
They've since been working hard to nail their product down with more specificity. :)
If a person is a critical thinker then they are almost always going to be predisposed toward rationality, and if they're not a critical thinker then no amount of rationality training will ever sink in. I suppose I vaguely support the goal of trying to teach people to be more rational, but I'm not sure that starting out by trying to teach people rationality tricks is the correct approach.
This is much different than rationality training, which focuses on teaching people to avoid a handful of specific non-rational thought patterns that frequently occur in certain situations. But it's not about figuring out what hidden assumptions you have, learning to judge the quality of information, etc.
In my experience, learning how to be specific has the biggest effect on improving your resume, interviews and performance reviews.