Questions designed to trip him up or teach him a lesson are emotionally tempting, but don’t seem very useful to me. Better to ask him how he thinks practical stuff can be improved, or what he thinks particularly big mistakes of GiveWell or other EA orgs were in terms of funding decisions, not broad philosophy (we’ve all heard standard objections to consequentialism before.) I suspect he won’t have any good suggestions, on the EDIT former (originally said “latter” by mistake). but you never know.
Questions designed to trip him up or teach him a lesson are emotionally tempting, but don’t seem very useful to me. Better to ask him how he thinks practical stuff can be improved, or what he thinks particularly big mistakes of GiveWell or other EA orgs were in terms of funding decisions, not broad philosophy (we’ve all heard standard objections to consequentialism before.) I suspect he won’t have any good suggestions, on the EDIT former (originally said “latter” by mistake). but you never know.