In order to trigger the quest for this achievement, you have to complete "The Fate of the Skaal" quest, which comes after you complete "The Temple of Miraak". When you complete the Skaal Village quest, you have to teleport back to Skyrim, and then come back to Solstheim.
Then teleport to Skall Village and you will see 2 NPCs talking with each other, dont interrupt their conversation, and then speak with the man in order to the quest for this achievement begins, or else it will become unobtainable.