If you aren’t certain that you can trust a roofing company that is attempting to sell you a roof, then yes, you should “interview” two, three, or more companies until you find one that is fair and trustworthy. Insurance companies often coach property owners to get three estimates to make sure the owner isn’t taken advantage of by the first salesperson that knocks on the door. However, if you know a roofing company to be trustworthy there is nothing wrong with giving them the responsibility of doing the work.