you could do this any number of ways really...

on *:JOIN:#HelpChannel:{
//msg $nick Questionone
//set %awaitresponse <awaiting this response>
}
on *:TEXT:*:?:{
if (%awaitresponse != $null) {
if ($1- == %awaitreponse) {
//msg $nick Questiontwo
}
}
}

or do it with aliases if you dont want to stack the if's.