Every large urban school system has one school where the principalship is seen as a career-ending appointment. In 2005, Portland Public Schools in Oregon was having a particularly challenging time finding the right principal for one such school—Roosevelt High. As you might guess, Roosevelt wasn't an affluent school where all the kids were above average and white picket fences abounded. Student achievement scores were in the dumps, with only 2 of 10 students reaching grade-level benchmarks. The community was disenfranchised from the school. There was no parent–teacher association or active parent groups. The school was truly multicultural but was in a gang-impacted, isolated part of town, and 72 percent of its students lived in poverty. Incredibly, it had had 34 administrators in the previous 15 years.

Although administrative openings in Portland's high-prestige high schools regularly receive at least 75 applications, Roosevelt received only a handful for this opening, most of them from administrators applying for their first principalship. As the human resources administrator in charge of filling this position, I knew within a week of posting the opening that the search was in trouble. Our superintendent used her considerable national network to bring qualified candidates to our area. But none of the candidates accepted the opportunity.