(Not a native teacher of English)
My personal comments:
In the first example, "How was it like..." would be safer.
For the second case, "What did he do" is correct but it is also a very broad question whose answers can be "He ran" or "He didn't stay"...either way, if your question concerns about the direction that he was running, "head for" can be a good choice, "Where did he head for at first?". Hope this helps.