Preheat oven to 450° F. Toss together squash, shallots, brown sugar, vinegar, Adobo, chopped sage and 2 tablespoons water in 9”x13” baking dish. Cover with foil and bake 20 to 25 minutes. Uncover and bake until tender and liquid has evaporated, 10 minutes more. Coarsely mash with potato masher.
Meanwhile, heat olive oil in small skillet over medium-high heat. Add sage leaves and fry until crisp, about 20 seconds. Transfer sage leaves to paper toweling to drain.
Reduce oven to 400° F. Place baguette slices on baking sheet. Bake just until golden and crisped, 5 to 6 minutes. Top with Manchego, squash mixture and olives.
Bake until warmed and cheese has melted, 8 minutes. Garnish each crostini with half a sage leaf and serve.
We have garnished these with crispy, fried sage leaves. If you're short on time, you can eliminate this step and instead garnish with some fresh chopped sage.