Yeah works that way, because you have to get past the monster anyway to talk with Cleofas in the Cathedral. Just don't talk with Redento until Cleofas jumps down.
Btw this was the last cheevo I got (only recently), because at day1 it wasn't known what has to be done and I couldn't figure this out back then.
Yes, but I screwed my quest anyway, I talked with the guy at the church and he gave me the item to bring back to Cleofas. I couldn't make Cleofas jump, I will try now in NG+, second run haha. Thank you!
Yeah I know that can happen, it happened to me twice, because I'm quite a completionist and I always talk with everyone... this time it was detrimental though, lol. I think I got the achievement on my 3rd attempt or something, because once I mistakenly released the lady of pain and afterwards it all got messed up for me (but that was on the previous version, maybe it works differently now).
At least there are NG+ and more content now, though kinda bummer that they didn't add dlc/expansion related cheevos too. Would have been interesting to get them imo. Anyway, good luck dude, you can do it!