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The Elder Scrolls V: Skyrim Hints
Kill the leader of [random bandit lair].
1 of 4: There are three people in this region that you can get this objective from: Brunwulf Free-Winter in Windhelm, Kjar on the largest ship at the Windhelm docks, and Annekke Crag-Jumper in Darkwater Crossing.
2 of 4: Talk to any of them and agree to chase down and kill a certain bandit/brigand.
3 of 4: Go to the randomly chosen bandit lair and fight your way through it to reach the leader, then kill him.
4 of 4: Return to the quest-giver and report success to get your reward. Annekke increases your Light Armor skill and becomes a follower, Brunwulf increases your Heavy Armor skill and gives you some gold, and Kjar will give you quite a bit of gold. (Note that you can do this quest for all three people and get all three rewards.)