Preheat a grill to high. Whisk the olive oil, vinegar, herbs, honey, ¼ teaspoon salt and a few grinds of pepper in a medium bowl. Reserve ¼ cup of the vinaigrette to a large bowl; set aside. Add the cucumber, tomatoes, red onion, olives and corn to the bowl with the remaining vinaigrette; toss to coat.
Brush the corn with some of the reserved vinaigrette and season with salt and pepper. Grill the corn, turning occasionally, until charred in spots, about 8 minutes. Remove to a cutting board. Meanwhile, season the steaks with salt and pepper. Working in batches if necessary, grill the steaks until charred and cooked to medium-rare, about 2 minutes. Flip and cook until browned on the other side, about 30 seconds. Transfer to the bowl with the reserved vinaigrette; toss to coat.
Cut off the corn kernels and add to the salad. Serve the steak with the corn salad.