Using a small, sharp knife, cut between the membranes of the orange, releasing the segments into a small bowl. Over a large bowl, squeeze the remaining membranes to release 1 to 2 tablespoons juice; whisk in 2 tablespoons olive oil and the honey. Add the fennel and toss to coat; season with salt and pepper.
Preheat a cast-iron skillet over medium-high heat. Rub the steak with the remaining 1 1/2 teaspoons olive oil and season with salt and pepper. Add to the skillet and cook, turning once, for 7 to 10 minutes for medium-rare. Transfer to a cutting board and let rest for 5 minutes before thinly slicing on an angle against the grain.
Meanwhile, in a large skillet of boiling, salted water, cook the asparagus until crisp-tender, 1 to 2 minutes; drain. Thinly slice crosswise and stir into the fennel mixture. Add the romaine and the orange segments and toss. Divide the salad among 4 plates and top with the steak.