Add garlic, Greek yogurt, Parmesan cheese, Dijon mustard, red wine vinegar, anchovy paste, lemon juice, salt, and pepper into a food processor. Blend until smooth. Slowly stream in olive oil while blending.

Preheat oven to 425°F (220°C). Toss cubed butternut squash with olive oil, salt, pepper, smoked paprika, and garlic powder. Spread on a baking sheet and roast for 18-22 minutes, flipping halfway.

In a large mixing bowl, combine kale and Brussels sprouts. Add a teaspoon of olive oil and massage the greens gently with hands to soften leaves. Let sit while preparing croutons.

In another bowl, mix olive oil and Dijon mustard. Toss sourdough bread cubes to coat, season with salt, and spread on a baking sheet. Bake for 10-12 minutes.

Toss the massaged kale and Brussels sprouts with creamy dressing until well coated. Arrange roasted butternut squash on top and finish with shaved Parmesan cheese and croutons.