Place sweet potato fries into a large bowl, drizzle with 1/4 cup olive oil, and toss to coat. Mix steak seasoning, black pepper, garlic powder, salt, and paprika in a separate small bowl until thoroughly combined. Use your left hand to toss fries with olive oil as you sprinkle the seasoning mixture over them with your right hand.
Heat 1 tablespoon olive oil in a large skillet over medium heat and place sweet potato pieces into the hot oil. Cover skillet, pan-fry for 5 minutes; uncover and turn fries. Place cover back over fries and cook 5 more minutes; continue turning fries and covering until sweet potatoes are tender, about 10 more minutes.