After completing (or failing) the quest Roadside Chatter, the player will receive a miscellaneous objective to check in with Valerine.
When they ask her about more Emissary work, she will start this quest.
The player will be tasked with acting as a mediator to settle an inheritence dispute. The client the player needs to meet with is waiting for them near the Whiterun Stables.
From this Emissary mission onward, the player does not get second chances like the first two - though a common thread among these quests is that there isn't a hard failure point that would block off the Emissary jobs. Failing will simply cause Valerine to not pay, and belittle the player for their failures.
The client is Sha'khar, a member of the East Empire Trading Company. He will explain that he is trying to see a family of cattle farmers that are famous for their high-quality meat resolve their differences (so that he may start selling their meat on behalf of the East Empire Company).
Players with the East Empire Expansion installed who have already worked with Sha'khar in that questline will receive acknowledgement that he knows them.
The player will be sent to speak to Malana and Ennbjof, who will be waiting in the Bannered Mare in Whiterun. When the player arrives, they can speak to each to get more information.
They will then be given the objective to sit in a particular chair when they are ready to begin.
The goal is to keep both of them even, in other words not appearing to take sides with either of them. The two have opposite likes and dislikes, so any option that satisfies one will upset the other.
Ennbjof responds best to Dramatic, while Malana responds best to Enigmatic. So long as the player chooses two of each of these options, they will succeed, as the end result will leave them feeling even.
There are other combinations that will succeed or end in a neutral ending, as in addition to the strong reactions mentioned previously, Malana will respond slighlty positively to Heartening, and Ennbjof will respond slightly positively to Whimsical. So long as neither is left feeling extremely underrepresented, the player should still succeed.
If the player ends the discussion with one sibling feeling considerably more positive, they will fail the negotiation and the two will end the talk seeming just as angry at one another as they started.
Whatever the result, the player will need to report to Sha'khar, and then to Valerine.
Valerine will reward the player with 500 gold if they reconciled things, and 250 gold if they received a neutral ending with the siblings at least agreeing to stop fighting.
The next mission will become available a short while after this is finished. The player will be prompted with a miscellaneous objective to remind them to speak to Valerine again.