Teachers often ask whether they should move into school administration. My own father held mythic status in my eyes as a math teacher and union activist. He and my uncle authored one of the first collectively bargained teacher contracts in Illinois. Despite being a lifelong teacher and union leader, when it came time for my father to provide career advice, he often recommended administration over teaching. Teachers, especially the good ones, know how schools fail and seek leadership roles to make the system better. Teachers who aspire to be leaders that create sustainable change often miss the significant legal status change one takes when entering the ranks of the administration. 

Teacher tenure is quickly disappearing. Administrators of the past that held in the back of their minds that they can always return to the classroom ought to be less confident, and younger administrators have clear reason for caution. Would-be administrators thinking they will be the exceptional one who survives usually end up on one of two paths, settling for the status quo and being ineffective or challenging the status quo and departing quickly.  Retention rates for administrators are terrible compared to teachers. Even worse, the few studies measuring retention for transformative leaders highlight dismal chances for a long career.

Before making the commitment to leave teaching, every would-be administrative leader is obliged to understand the greatest legal risk, loss of indemnification.

What do CEOs and teachers have in common? Both are effectively indemnified for legal costs when they get in trouble. Indemnification is one of the strongest forms of legal protection. CEOs usually have indemnification agreements. If the CEO gets in trouble with her own company, the agreement kicks in and funds a defense. Teachers are indemnified in a different way. The teachers union funds the teacher’s defense. Administrators? They have to fund their own defense. The public feels that administrators earn enough to fund their own defenses, but comparing legal spending by union and CEOs to public school administrators highlights the paucity of protection enjoyed by administrators.

Transforming education requires empowered leaders. Leaders push harder when insulated from politics. Before considering any career move, teachers need to consider carefully whether and how they would be empowered as administrators. The root of the empowerment is economic, and this article is highlighting one form of economic empowerment, having a strong indemnification agreement. Empowerment is more than economics; it's emotional,  psychological and social. A disempowered school leader facing political headwinds faces not only salary loss but massive bills for funding a defense when political winds shift. And political winds always shift.

It’s risky to move from the relative security of teaching to heightened vulnerability of administration. Few people do it, and the inability of education to attract and retain the best talent is the primary challenge for any industry seeking to improve. Administrators need to have a personal attorney and remember that despite supervisors offering take-it-or-leave-it contracts, there is always room to negotiate.