Well, in a sense the pond will be "cycled" as soon as you put the media in, just for a much lower bioload than you probably intend. So if you took out 20% of the filter media you'd probably be completely cycled for something like 15% of the bioload in the 55 gallon (a guess), assuming the change in water temp/chemistry doesn't kill off too many. The bacteria would then be playing catch up for any fish waste beyond that.
I don't think I'd pull more than 20% of the filter media at a time, and even with that I'd be sure to replace it with fresh media and monitor water parameters in case of a mini-cycle in the established tank.
If the fish you're putting in are much smaller than the expected adult size even that may be enough to keep from having an ammonia spike, but I think it's more likely you'd want to add a smaller initial batch of fish to the pond and then keep adding more until you reach final stocking.