It's not exactly the simplest thing to explain, but i'll tell you how I would do it...

  • Save questions and answers in files formatted like: question<tab>answer
  • Load the file to a hashtable for quick access.
  • Ask a question in the channel, wait for about a minute and then end the question and ask a new question.
    If the question is answered within the time limit then turn the timer off and ask the next question.