What are strawmen and steelwomen?
A strawman is a version of an argument that no one actually believes, but is very easy to dispute.
In contrast, a steelwoman argument (others use steelman, but variety is the spice of life) is the strongest version of an argument, sometimes called the principle of charity. The goal of steelwomanning is to avoid attributing irrationality, logical fallacies or falsehoods to others' statements, when a coherent, rational interpretation of the statements is available.
If you just wanted to win the debate (and annoy the person you’re speaking to), pick a strawman of their argument and burn it to the ground. If, however, you want to actually try to get to the truth, you should consider the strongest possible argument that your opponent could have meant and reply to that.
Examples of strawmen and steelwomen
Brian Caplan invented the Ideological Turing Test to help determine if an ideologue actually understood the ‘steelwomanned’ versions their opponent’s arguments, or merely debated strawmen.
You might have debated a really stupid socialist/ libertarian (or whatever ideology runs contrary to your own beliefs) that one time, but that doesn’t mean there isn’t some grain of truth (or ‘steelwomanned’ version of) to what they believe. Instead of interpreting whether their claim is true or false, try to determine what the smartest person who holds that view would say, and reframe it. See philosopher Daniel Dennett’s (someone who’s no stranger to debates) rules on how to compose a successful critical commentary.