If you do something in a calculated way, you've given it quite a bit of thought beforehand, and you're very deliberate in the way you do it.
Sometimes calculated can have a positive meaning, like when you plan ahead and are thoughtful about something. A good electrician takes a calculated approach to wiring a new house. On the other hand, a "calculated remark" could be one that's hurtful or manipulative and was made deliberately by the speaker to get a particular reaction or result.