Preheat your oven to 400°F and prepare a baking sheet with parchment paper.
Trim the woody ends off the asparagus and toss the spears with 0.5 tbsp of olive oil, 0.25 tsp salt, and 0.25 tsp pepper.
Spread the asparagus in a single layer on the baking sheet and roast for 12-15 minutes until tender-crisp.
While the vegetables roast, pat the steak dry and season both sides with the remaining salt and pepper.
Heat the remaining 0.5 tbsp of olive oil in a cast-iron skillet over medium-high heat.
Sear the steak for 4-5 minutes per side for medium-rare, then remove from the pan and let it rest on a plate.
Reduce the skillet heat to medium and add the minced garlic, balsamic vinegar, and honey to the pan drippings.
Whisk the sauce constantly for 2-3 minutes until it reduces and thickens into a glossy glaze.
Slice the steak against the grain and serve immediately with the roasted asparagus, drizzling the warm balsamic glaze over the meat.