So we know that many smart people make stupid (at least in retrospect) decisions. What these people seem to be lacking, at least at the moment they make a poor decision, is wisdom ("judicious application of knowledge"). More from Wikipedia:
It is a deep understanding and realization of people, things, events or situations, resulting in the ability to apply perceptions, judgements and actions in keeping with this understanding. It often requires control of one's emotional reactions (the "passions") so that universal principles, reason and knowledge prevail to determine one's actions.
From Psychology Today:
It can be difficult to define Wisdom, but people generally recognize it when they encounter it. Psychologists pretty much agree it involves an integration of knowledge, experience, and deep understanding that incorporates tolerance for the uncertainties of life as well as its ups and downs. There's an awareness of how things play out over time, and it confers a sense of balance.
Wise people generally share an optimism that life's problems can be solved and experience a certain amount of calm in facing difficult decisions. Intelligence—if only anyone could figure out exactly what it is—may be necessary for wisdom, but it definitely isn't sufficient; an ability to see the big picture, a sense of proportion, and considerable introspection also contribute to its development.
From SEP:
(1) wisdom as epistemic humility, (2) wisdom as epistemic accuracy, (3) wisdom as knowledge, and (4) wisdom as knowledge and action.
Clearly, if one created a human-level AI, one would want it to "choose wisely". However, as human examples show, wisdom does not come for free with intelligence. Actually, we usually don't trust intelligent people nearly as much as we trust wise ones (or appearing to be wise, at any rate). We don't trust them to make good decisions, because they might be too smart for their own good. Speaking of artificial intelligence, one (informal) quality we'd expect an FAI to have is that of wisdom.
So, how would one measure wisdom? Converting the above description ("ability to apply perceptions, judgements and actions in keeping with this understanding") into a more technical form, one can interpret wisdom, in part, as understanding one's own limitations ("running on corrupt hardware", in the local parlance) and calibrating one's actions accordingly. For example, of two people of the same knowledge and intelligence level (as determined by your favorite intelligence test), how do you tell which one is wiser? You look at how the outcomes of their actions measure up against what they predicted. The good news is that you can practice and test your calibration (and, by extension, your wisdom), by playing with the PredictionBook.
For example, Aaron Swartz was clearly very smart, but was it wise of him to act they way he did, gambling on one big thing after another, without a clear sense of what is likely to happen and at what odds? On the other end of the spectrum, you can often see wise people of average intelligence (or lower) recognizing their limitations and sticking with "what works".
Now, this quantification is clearly not exhaustive. Even when perfectly calibrated, how do you quantify being appropriately cautious when making drastic choices and appropriately bold when making minor ones? What algorithms/decision theories make someone wiser? Bayesianism can surely help, but it relies on decent priors and does not compel one to act. Would someone implementing TDT or UDT to the best of their ability maximize their wisdom for a given intelligence/knowledge level? Is this even a meaningful question to ask?
EDIT: fixed fonts (hopefully).
Thinking about the wise(1) people know (real people, not fictional), the property they seem to have in common that others lack is that they habitually reason with all of the data available to them, which includes data about their own habitual behavior and reasoning processes. They rarely if ever seem to have that experience of suddenly realizing that they've been doing or believing something which they already knew was the wrong thing to do or believe, but somehow that didn't seem to matter. That's not to say that they're always right, but when they're wrong it's easy to identify what data they're missing, and when that data is supplied they self-correct quickly.
Wisdom, in this sense, is "seeing the forest despite the trees." It relates to having a well-integrated mind.
By contrast, I seem to class as merely "intelligent" people who are able to reason effectively from a set of data to a justified conclusion, even if they have a habit of neglecting vast chunks of the data they have available. I know lots of intelligent people who apply their intelligence differentially to different domains -- who are brilliant at math, for example, but hopeless at working machinery, or skilled engineers who can't seem to figure out what pisses off their colleagues, or brilliant at developing working models of other people's motivations but unable to make sense of a stock prospectus, etc. (The example of creationist scientists gets used a lot on this site as well.)
I suspect that wisdom in this sense is distinct from intelligence (EDIT: as an attribute of humans), but that I'm less likely to notice wisdom in an unintelligent person because there are so many implications of the data they have which are obvious to me but not them that it's easy to assume they aren't attending to that data in the first place. That's just speculation, though. It's true that the people who strike me as wise often also strike me as intelligent.
If I wanted to build a system that demonstrated wisdom in this sense, I don't think I would do anything special... it's likely to come for free as an emergent property of a well-designed intelligence. I suspect that "lack of wisdom" in humans is an artifact of our jury-rigged, evolved, confluence-of-a-million-special-purpose-hacks brains.
Conversely, if I wanted to increase wisdom (in this sense) in humans, I would probably focus my attention on attention. It seems to be associated with diffuse focus of attention. Which is consistent with my experience that fear, anxiety, obsession, addiction, and other cognitive patterns that focus attention tend to inhibit wisdom.
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1 - When I talk about people being wise here, I'm referring to those I intuitively class that way, and then reasoning backwards from that set to get at what the element that leads me to class them that way is. This is, of course, just an element of my own intuitive classification, I don't mean to present it as some kind of universal definition for "wise" or anything like that. If it reflects your own use of the word as well, great; if not, that's OK too.