Season pork medallions with half of the salt and pepper. Heat 1½ tablespoons oil in a large sauté pan over medium-high heat and cook medallions until just barely pink in the center, about 3-4 minutes per side. Transfer meat to a plate and tent with foil.

Add remaining olive oil to the pan. Add cauliflower florets to the pan and season with remaining salt and pepper. Toss to coat. Cook for 10-12 minutes, until fork-tender but not mushy. Stir as the cauliflower browns.

Add shallots during the last two minutes of cooking the cauliflower and reduce heat to medium. Sauté until shallots just begin to soften. Deglaze the pan with chicken broth, scraping up any brown bits. Add wine and dried cherries and cook until liquid is reduced by half, about 4 minutes. Season with additional salt and pepper, if needed. Add pork medallions back to the pan to re-warm and coat with sauce. Garnish with fresh chives. If desired, serve with salad and potatoes.