Remove leaves from cauliflower head, core, and cut into bite-sized florets. Bring a small pot with cauliflower and enough lightly salted water to cover to a boil. Cook until tender, about 12 minutes. Stem Swiss chard. Cut stems into 1/4” slices and coarsely chop leaves. Coarsely chop dried cherries. Rinse steaks, pat dry, and season with a pinch of salt and pepper.

Lightly coat two small (or one medium) casserole dishes with cooking spray. Any small, oven-safe dish will work. Drain cauliflower in colander, return to pot, and, using a potato masher or fork, mash with sour cream, half the butter, and half the Asiago cheese. Season to taste with salt and pepper, transfer to casserole dishes, and top with remaining Asiago cheese. Place on prepared baking sheet and bake until browned, about 20 minutes.

Heat a medium pan over medium-high heat. Add 2 tsp. olive oil and steaks to hot pan and cook 4-6 minutes on each side, or until steaks reach a minimum internal temperature of 145 degrees. Transfer to a plate, loosely cover with foil, and return pan to medium-high heat (no need to wipe pan clean).

Add demi-glace, red cooking wine, dried cherries, and 2 Tbsp. water to pan used to cook steaks and cook 2 minutes, or until slightly thickened. Remove from heat, swirl in remaining butter, and season to taste with salt and pepper. Adding butter after pan has been removed from heat enriches sauce without separating.

Rinse pot used for cauliflower and set over medium-high heat. Add 1 tsp. olive oil and chard stems to hot pot and cook 3 minutes, or until tender. Add leaves and cook for 2 more minutes, or until just wilted. Season to taste with salt and pepper.

Serve gratin directly in casserole dish. Spoon sauce next to gratin and place a steak over sauce. Place chard next to steak and serve.