Interested in applying for a senior IT position? How can you determine whether the job is going to be a good fit? What questions should you ask, and how can you negotiate the best deal? From the institution's perspective, the search for senior IT positions is expensive and time consuming. How can the institution improve its chances of getting the best leader for a senior position? The speakers will share strategies for institutions and individual candidates in the professional matchmaking process. This session was featured at the 2002 Seminars on Academic Computing.