NOTE: this is not site policy, just my personal suggestion
Being a newcomer and having your post downvoted can be very discouraging. This isn't necessarily a bad thing—obviously we want to discourage people from posting things that are not worth our time to read—but it doesn't provide much feedback other than "something about this post/comment/question/answer makes it undesirable to have on LessWrong". So here's my idea:
If you downvote something that isn't obvious spam, you should comment the reason why. This will nudge the newcomer in the direction of "people don't like this particular quality of my post/comment/question/answer" rather than "people don't like my post/comment/question/answer." So as to avoid flooding bad content with comments, simply upvote any comment that states a reason for the undesirability of the post/comment/question/answer instead. Hopefully this helps the newcomer get feedback about what they should change, rather than just blindly guessing.
This post is definitely not site policy, and at least I as the site admin disagree with any kind of "should" here.
People are already too hesitant to downvote content on the site. Explaining your downvote is good, but do not feel any obligation to do so. The voting system is anonymous for a reason. Use it for expressing what your values are, approximately whatever they may be, even if you cannot put them into words.
Whether upvotes need to be explained overall is not relevant to my comment, as I'm talking about the specific considerations named by Noah Birnbaum.