Allow me to generalize for a moment: there seems to be a constant tension, especially in the public school systems, of teachers versus administration. Often teachers feel stifled by bureaucratic measures or undermined by central office edicts. Given my belief in the tie between entrepreneurialism and teaching, this is no surprise.
Entrepreneurs are people who reject the corporate culture in order to implement their own vision in their own way. Corporate bureaucracy drives entrepreneurs mad because when they see problems or opportunities, the process to act on them is often cumbersome and slow (or even more likely: outside of their job description). Being entrepreneurial means working with a persistent sense of urgency that demands quick action. It is not difficult for someone thinking entrepreneurially to see the ‘big picture’ and strategize ways to improve a situation. Working alone, or running a small business, allows entrepreneurial people to make the best use of their skills and somewhat idiosyncratic penchants.
However, so does teaching in your classroom. That is what makes good teachers entrepreneurial (see Manifesto). The problem arises, however, when teachers step outside the classroom and become employees of their school and/or district. This entrepreneurial freedom and penchant becomes a source of tension and frustration. It is not teachers being obstinate or insubordinate; it is simply teachers manifesting the same characteristics that make them amazing educators. Imagine being a complete entrepreneur at one moment (in your class) and then having to step out and instantly be part of a bureaucratic machine (say in your staff meeting). Yet despite these dichotomous realms, teachers are forced (and expected) to shift gears seamlessly.
This may sound like I am coming to a gloomy conclusion. In fact, I do believe that as long as schools hire good (entrepreneurial) teachers, there will be tension between this cohort and the administration. I do not see this, however, as a hopeless conclusion. Rather, I believe these two constituencies can easily improve schools by learning to understand and embrace these differences. If administrators viewed faculty as a cohort of hundreds of mini-entrepreneurs, they could adjust their approach and even leverage the expertise of this skilled group.