Preheat oven to 375 degrees. Toss the diced butternut squash with the olive oil, 1 tsp kosher salt and a few turns of the pepper mill.
Lay the butternut squash out on a sheet pan lined with parchment paper in a single layer and roast in the oven for about 20 - 25 minutes until very tender and slightly caramelized.
While the squash is roasting, heat the chicken stock in a saucepan. Leave it on low heat, it needs to stay warm as you add it to the rice.
In a heavy-bottomed pot, melt the butter and saute the shallots on low - medium heat for about 10 minutes until the shallots are translucent. Add the sage and let it perfume the butter. Add the rice and stir to slick the grains of rice with the butter.
Add the wine and cook for 2 -3 minutes, then add 2 ladles of simmering stock to the pot. Season again with a little salt & pepper. We're building flavor here, so we need to season as we go...
Give it a good stir, let it simmer and keep stirring until stock is absorbed, about 5 - 10 minutes.
Check on the squash - rotate your sheet pan if necessary, remove from oven when done and set aside.
When stock has been absorbed, add in 2 more ladles and stir frequently until the stock is absorbed and rice is cooked through, but still al dente. (rice will take about 30 minutes TOTAL).
Remove from heat, add Parmesan cheese and 3/4 of the roasted squash. Stir to combine, place remaining cubes of squash on top and serve.
Garnish with fried sage leaves and extra cubed butternut, if desired.