3. Meet with your boss and ask him questions: Remember to sit down with your boss for at least half an hour on the very first day of work. Likewise, you should be equipped with all kinds of possible questions about your job that you wish to ask him on your first day. Asking such questions as in what you specifically need to do in your job is sure to make your task easy and manageable in the long run, says Sara Ferraioli, partner in the HR Contracts division of Massachusetts-based staffing firm Winter, Wyman.