Disclaimer: I have disagreeable tendencies, working on it but biased. I think you're getting at something useful, even if most people are somewhere in the middle. I think we should care most about the outliers on both sides because they could be extremely powerful when working together.
I want to add some **speculations** on these roles in the context of the level at which we're trying to achieve something: individual or collective.
When no single agent can understand reality well enough to be a good principal, it seems most beneficial for the collective to consist of modestly polarized agents (this seems true from most of the literature on group decision-making and policy processes, e.g. Adaptive Rationality, Garbage Cans, and the Policy Process | Emerald Insight).
This means that the EA network should want people who are confident enough in their own world views to explore them properly, who are happy to generate new ideas through epistemic trespassing, and to explore outside of the Overton window etc. Unless your social environment productively reframes what is currently perceived as "failure", overconfidence seems basically required to keep going as a disagreeable.
By nature, overconfidence gets punished in communities that value calibration and clear metrics of success. Disagreeables become poisonous as they feel misunderstood and good assessors become increasingly conservative. The succesful ones of the two characters build up different communities in which they are high status and extremize one another.
To succeed altogether, we need to walk the very fine line between productive epistemic trespassing and conserving what we have.
Disagreeables can quickly lose status with assessors because they seem insufficiently epistemically humble or outright nuts. Making your case against a local consensus costs you points. Not being well calibrated on what reality looks like costs you points.
If we are in a sub-optimal reality, however, effort needs to be put into defying the odds and change reality. To have the chutzpah to change a system, it helps to ignore parts of reality at times. It helps to believe that you can have sufficient power to change it. If you're convinced enough of those beliefs, they often confer power on you in and of themselves.
Incrementally assessing baseline and then betting on the most plausible outcomes also deepens the tracks we find ourselves on. It is the safe thing to do and stabilizes society. Stability is needed if you want to make sure coordination happens. Thus, assessors rightly gain status for predicting correctly. Yet, they also reinforce existing narratives and create consensus about what the future could be like.
Consensus about the median outcome can make it harder to break out of existing dynamics because the barrier to coordinating such a break-out is even higher when everyone knows the expected outcome (e.g. odds of success of major change are low).
In a world where ground truth doesn't matter much, the power of disagreeables is to create a mob that isn't anchored in reality but that achieves the coordination to break out of local realities.
Unfortunately, to us who have insufficient capabilities to achieve their aims - to change not just our local social reality but the human condition - creating a cult just isn't helpful. None of us have sufficient data or compute to do it alone.
To achieve our mission, we will need constant error correction. Plus, the universe is so large that information won't always travel fast enough, even if there was a sufficiently swift processor. So we need to compute decentrally and somehow still coordinate.
It seems hard for single brains to be both explorers and stabilizers simultaneously, however. So as a collective, we need to appropriately value both and insure one another. Maybe we can help each other switch roles to make it easier to understand both. Instead of drawing conclusions for action at our individual levels, we need to aggregate our insights and decide on action as a collective.
As of right now, only very high status or privileged people really say what they think and most others defer to the authorities to ensure their social survival. At an individual level, that's the right thing to do. But as a collective, we would all benefit if we enabled more value-aligned people to explore, fail and yet survive comfortably enough to be able to feed their learnings back into the collective.
This is of course not just a norms questions, but also a question of infrastructure and psychology.
I agree with the general point that idea generators are often overconfident and poorly calibrated, but I'm not super excited about conflating that with being disagreeable. There's something there, in that being impatient with the failings of others can be a good impetus to create something better, but I think there are also plenty of generators who aren't highly disagreeable, and if that's the case it seems bad for the dichotomy as formulated here to catch on.
One example archetype of a generator who isn't disagreeable is someone who is both very intelligent and very enthusiastic/excitable. This person will generate lots of cool new ideas they're super excited about, and will likely still be overconfident and poorly calibrated, without feeling particularly motivated to yell about other people's bad ideas.
This clustering is based on anecdotal data; I wouldn't be too surprised if it were wrong. I'd be extremely curious for someone to do a cluster analysis here and see if there are any real clusters here.
I feel like I've noticed a distinct cluster of generators who are disagreeable, and have a hard time thinking of many who are agreeable. Maybe you could give some examples that come to mind to you? Anders Sandberg comes to my mind, and maybe some futurists and religious people.
My hunch is that few top intellectuals (that I respect) would score in the 70th percentile or above on the big 5 agreeableness chart, but I'm not sure. It's an empirical question.
I don't remember hearing about a generators/evaluators dichotomy before, that you & Stefan mention. I like that dichotomy too, it's quite possible it's better than the one I raise here.
Spencer Greenberg also comes to mind; he once noted that his agreeableness is in the 77th percentile. I'd consider him a generator.
At the very least I think we can be more confident in the generators/evaluators (or /assessors) dichotomy, than in the further claim that the former tend to be disagreeable.
I'm coming at this from science, where lot of top generators have a strong "this is so cool!" sort of vibe to them – they have a thousand ideas and can't wait to try them out. Don't get me wrong, I think disagreeable generators play an important role in science too, but it's not my go-to image of a generator in that space.
[Wild speculation] It's plausible to me that this varies by field, based on the degree to which that field tends to strike out into new frontiers of knowledge vs generate new theories for things that are already well-studied. In the latter case, in order for new ideas to be useful, the previous work on the topic needs to be wrong in some way – and if the people who did the previous work are still around they'll probably want to fight you. So if you want to propose really new ideas in those sorts of fields you'll need to get into fights – and so generators in these fields will be disproportionately disagreeable. Whereas if everyone agrees that there are oodles of things in the field that are criminally understudied, you can potentially get quite a long way as a generator before you need to start knocking down other people's work.
Obviously if this theory I just made up has any validity, it will be more of a spectrum than a binary. But this sort of dynamic might be at play here.
Dr. Greger from NutritionFacts.org also seems like an agreeable generator. Actually he may be disagreeable in that he's not shy about pointing out flaws in studies and others' conceptions, but he does it in an enthusiastic, silly and not particularly abrasive way.
It's interesting that some people may still disagree often but not be doing it in a disagreeable manner.
Albert Einstein also comes to mind as an agreeable generator. I haven't read his biography or anything, but based on the collage of stories I've heard about him, he never seemed like a very disagreeable person but obviously generated important new ideas.