I have worked at several steak restaurants, if you order a steak well done, it is never going to taste good. At Outback they would weight it until it was a hockey-puck, or butterfly it and weight it until it was a hockey puck. Worked a small local restaurant for a while, that would first deep fry it and then grill it for a few minutes for grill marks. Steak-out would use weights and spray veg oil, but because of 30 minute delivery times, nothing was delivered below medium, because by the time it made it to the house it had been sitting in a hot bag too long.
Also take into account if someone in your party orders a well done steak, the rest of the steaks will be overdone, because they sat in the window waiting.
I chose Medium Rare, but my favorite is Pittsburgh Style, Crispy Burnt on the outside, Rare-Medium-Rare on the inside, probably increases my cancer risk a bit, but you only live once.