Prepare the Potatoes: Quarter the potatoes lengthwise into wedges (if your potatoes are larger, cut into sixths so pieces are roughly the same size). Toss on a large 12x17-inch rimmed sheet pan with 1 tablespoon of the olive oil, and ¼ teaspoon of the salt.
I like to roast directly on the sheet pan without any parchment paper or foil liner to get the crispiest results.
Spread the potato wedges in a single layer and roast for 25-30 minutes, flipping at the 20 minute mark, until golden and crispy at the edges (the cut sides should be deeply browned, that's the good stuff!)
Brown the Beef: While the potatoes cook, heat a large skillet over medium-high heat. Add 2 teaspoons of olive oil and the ground beef. Sprinkle with ¼ teaspoon of salt, granulated garlic, onion powder, and black pepper. Cook for 6-8 minutes, until no pink remains and the beef is well browned.
When the meat is browned and just cooked through, add the Worcestershire sauce and cook for 1-2 minutes more until the seasoning coats the beef evenly and everything smells deeply savory, stirring frequently. Remove from heat.
Make the Special Sauce: While the potatoes roast and the meat cooks, whisk together the mayonnaise, ketchup, yellow mustard, pickle relish, and pickle juice in a small bowl until smooth.
Assemble: Divide the shredded iceberg lettuce among four bowls. Top each with a quarter of roasted potatoes and a quarter of the seasoned beef. Add the shredded cheddar on top of the warm meat, then the diced tomato and pickle chips on top. Drizzle generously with the special sauce and serve immediately.
Notes
Assembly: Order matters here! Lettuce on the bottom keeps it crisp, potatoes and beef go on next while still warm, cold toppings last. Don't add the sauce until right before eating.
Leftovers: Store best with each component separate; reheat the beef and potatoes and assemble fresh bowls.
Sauce: Not gonna lie, if you think your family will like the sauce, just double it. Not worth fights at the table, if ya know what I mean.