This study documents trends in the number and quality of applicants for superintendency over time and the success rate of female applicants throughout the search process. Substantial data indicate a gender bias in selecting superintendents. Data collected in New York in 1999 were compared to 1995 data to determine if the size and quality of the applicant pool is changing, ascertain factors that correlate to pool size, reveal percentages of women candidates, document evidence of gender bias, and learn if recruitment strategies change to address projected shortages. The data indicate both the quality and size of the applicant pool continues to decline. Women comprise only 21% of the pool and minorities average less than one applicant per search. Once in the applicant pool, women are slightly more likely to be hired than are men. Salary and socioeconomic status are important factors making superintendency attractive to applicants. Recruiters are becoming more aggressive, but this approach may be counterproductive, unless definitions of professional experience and competence are broadened, because searches will focus on professional qualities likely held only by traditional candidates, and neglect nontraditional applicants. (Contains 29 references.)(TEJ)