Preheat oven to 400 degrees. Coat a large baking sheet with olive oil and set aside. (I like to place a Silpat mat on top of the tray and just coat the mat with oil.) Place the diced potatoes in a large bowl and drizzle generously with olive oil. Sprinkle with kosher salt and fresh pepper. Toss with hands to combine thoroughly and ensure that all pieces are coated in oil and spices. Spread potatoes across the oiled baking sheet.
Bake for 30 minutes, then remove from oven and turn potatoes over on the tray. Bake 15 minutes longer until tender and slightly crisp on the edges. Remove from the oven and cool potatoes completely.
Place 6 eggs in a small sauce pan and cover with water. Cook covered over medium high heat until the water begins to boil. Reduce heat to medium low and uncover. After ten minutes, remove from heat and run underneath cold water until eggs are cool.
Place the cooled potatoes in a large bowl and set aside. Peel the eggs and roughly chop. Drain the olives and roughly chop. Add the eggs and olives to the potatoes and toss gently.
Combine the dressing ingredients in a small bowl and taste. Adjust seasonings accordingly. If you prefer a stronger pickle flavor, add more relish or additional pickle juice.
One spoonful at a time, add the dressing to the potatoes and toss gently to coat. I usually have 2-4 tablespoons of leftover dressing. I like to make a bit more than what I need, just in case I have more potatoes than I expect. It's always nicer to have a little extra instead of not quite enough when it comes to dressings.
When the salad is combined thoroughly, sprinkle the dried dill or parsley on top just before serving. Enjoy!