Today, management and tuning questions are approached using if… then… rules of thumb. This reactive approach requires expertise regarding system behavior, making it difficult to deal with unforeseen uses of a system’s resources and leading to system unpredictability and large system management overheads. We propose a What…if… approach that allows interactive exploration of the effects of system changes, thus converting complex tuning problem into simpler search problems. Through two concrete management problems, automating system upgrades and deciding on service migrations, we identify system design changes that enable a system to answer What…if… questions about itself.