Very interesting. I'm going to try my hand at a short summary:
Assume that you have a number of different options you can choose, that you want to estimate the value of each option and you have to make your best guess as to which option is most valuable. In step one, you generate individual estimates using whatever procedure you think is best. In step 2 you make the final decision, by choosing the option that had the highest estimate in step one.
The point is: even if you have unbiased procedures for creating the individual estimates in step one (ie procedures that are equally likely to overestimate as to underestimate) biases will still be introduced in step 2, when you're looking at the list of all the different estimates. Specifically, the biases are that the highest estimate(s) are more likely to be overestimates, and the lowest estimate(s) are more likely to be underestimates.
The best laid schemes of mice and men
Go often askew,
And leave us nothing but grief and pain,
For promised joy!
- Robert Burns (translated)
Consider the following question:
Or, suppose Holden Karnofsky of charity-evaluator GiveWell has been presented with a complex analysis of why an intervention that reduces existential risks from artificial intelligence has astronomical expected value and is therefore the type of intervention that should receive marginal philanthropic dollars. Holden feels skeptical about this 'explicit estimated expected value' approach; is his skepticism justified?
Suppose you're a business executive considering n alternatives whose 'true' expected values are μ1, ..., μn. By 'true' expected value I mean the expected value you would calculate if you could devote unlimited time, money, and computational resources to making the expected value calculation.2 But you only have three months and $50,000 with which to produce the estimate, and this limited study produces estimated expected values for the alternatives V1, ..., Vn.
Of course, you choose the alternative i* that has the highest estimated expected value Vi*. You implement the chosen alternative, and get the realized value xi*.
Let's call the difference xi* - Vi* the 'postdecision surprise'.3 A positive surprise means your option brought about more value than your analysis predicted; a negative surprise means you were disappointed.
Assume, too kindly, that your estimates are unbiased. And suppose you use this decision procedure many times, for many different decisions, and your estimates are unbiased. It seems reasonable to expect that on average you will receive the estimated expected value of each decision you make in this way. Sometimes you'll be positively surprised, sometimes negatively surprised, but on average you should get the estimated expected value for each decision.
Alas, this is not so; your outcome will usually be worse than what you predicted, even if your estimate was unbiased!
Why?
This is "the optimizer's curse." See Smith & Winkler (2006) for the proof.
The Solution
The solution to the optimizer's curse is rather straightforward.
To return to our original question: Yes, some skepticism is justified when considering the option before you with the highest expected value. To minimize your prediction error, treat the results of your decision analysis as uncertain and use Bayes' Theorem to combine its results with an appropriate prior.
Notes
1 Smith & Winkler (2006).
2 Lindley et al. (1979) and Lindley (1986) talk about 'true' expected values in this way.
3 Following Harrison & March (1984).
4 Quote and (adapted) image from Russell & Norvig (2009), pp. 618-619.
5 Smith & Winkler (2006).
References
Harrison & March (1984). Decision making and postdecision surprises. Administrative Science Quarterly, 29: 26–42.
Lindley, Tversky, & Brown. 1979. On the reconciliation of probability assessments. Journal of the Royal Statistical Society, Series A, 142: 146–180.
Lindley (1986). The reconciliation of decision analyses. Operations Research, 34: 289–295.
Russell & Norvig (2009). Artificial Intelligence: A Modern Approach, Third Edition. Prentice Hall.
Smith & Winkler (2006). The optimizer's curse: Skepticism and postdecision surprise in decision analysis. Management Science, 52: 311-322.