Bring a large of water to a boil. Meanwhile, heat oil in a large, deep skillet over medium heat. Add the pancetta and cook, stirring occasionally, until the fat renders and becomes translucent, about 5 minutes.
Add the shallots and cook stirring occasionally, until tender, about 3 minutes. At the same time, generously season the boiling water with salt. Add the pappardelle to the boiling water and cook according to the package's directions for al dente, reserving ½ cup cooking water.
Add the asparagus to the skillet, along with ¼ cup pasta cooking water, and season with salt and pepper. Raise the heat to medium-high and cook, stirring occasionally, until bright green and crisp-tender, about 5 minutes. Turn the heat down to low.
Add the drained pasta, olives, and cheese to the skillet. Toss until the noodles and veggies are evenly coated with the sauce. Add more water if needed.
Divide among serving plates and top with more cheese.