For this achievement you will have to travel to Riften
.You will be soon approached by Brynjolf
and he will offer to let you in on a job which he's working. Accept and do his quest. Then he will direct you to the The Ratway
, an underground tunnel system underneath Riften,there is a tavern there called The Ragged Flagon
, and when you get there you can join his organization. If the you fail to plant the ring, you will still be asked to go to the Ragged Flagon
and join the Guild.
Go there and he will then give you a quest Taking Care of Business
. Keerava has a soft spot for family, Bersi has a priceless - and fragile - urn, and Haelga has her devotion to Dibella, goddess of beauty.
The debts may be collected in any order you choose, but keep in mind that after you have two debtors in line, the last - whomever that may be - will cave immediately, having heard how you dealt with the others.
Return to him and this will end Taking Care of Business
rewarding you the achievement.
Have in mind that if you have not travel in Riften yet you can use Bjorlam's carriage
outside of Whiterun Stables
to travel there for a small fee.
Good luck and enjoy Skyrim on the One