Jim has generally been clear about being at the center of a position he has to take. Eg. If it’s a tax optimization strategy, the questions are clear:
1) are we within the bounds of tax code
2) is this something that most companies do - are there precedents
3) what’s the gain from this, a likelihood of litigation and impact if it is litigated.
If we are in the center (or close to), wherein the rewards are commensurate with the probability of risk materializing, and we are within the law, it’s a reasonable risk (even if litigated). The answer is not always clear, but general philosophy is to try and seek clarity.
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