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Fair point. I don't think downshifts are the problem here. A well designed/custom ring will have pins and ramps that extend deeper towards the ring centre that will assist large upshifts, but I cbf googling to see what brand chainring he was running. Still, you would need damn near perfect FD alignment to do it.
Only if you shift at an exact point in the crank rotation - the same for upshifts.
That's still a massive jump. Pro mechanics have special powers.