Most great heads knew that they needed some coaching right before they became a head of school, or shortly thereafter but many did not ask for that assistance because they were concerned it might reflect weakness and insecurity.

Interestingly, we have found that seasoned heads and board chairs have asked Littleford & Associates for mentoring and coaching assistance and have not been one bit embarrassed to ask for it. They acknowledge that continuous improvement is something they expect of their employees and must ask the same of themselves. Mark Ulfers, a renowned and experienced former international school head now working in the US State Department overseeing American affiliated international schools, was not wary of coaching for himself.

There is a movement afoot now to build coaching into the DNA of head of school searches to ensure that new heads do not have to ask for it. However, the head should interview a few coaches and should choose one with whom he has a professional and personal rapport. Otherwise, the relationship will not be productive. 

The board should be upfront and clear about rules of coaching:

1. The amount of freedom the head has in choosing that coach. Some boards advocate for people they know form the corporate and HR world and those individuals, while well intentioned, may not understand the pressures and vagaries of the life of a school head. 

2. Is the board asking that the coach have a direct pipeline back to the board chair or leadership of the board to report on progress and outcomes? This is not generally a healthy idea, but if the head agrees to it in advance, the coach/mentor may help shore up support for a head. However, this is a delicate ground to walk and almost all our coaching assignments do not include a direct line of communication back to the board even though the school is paying the fees.

3. How long will the coaching last and what might be the topics? Some might be at the macro level about leadership and some maybe at the micro level of dealing with specific onsite concerns that the head is facing daily.

4. Is there any link of this coaching to the head’s compensation, contract, or evaluation? The answer is probably or should be “no”.

Some boards want coaching because the head is new.  Some boards want it because they are worried about the head’s relationship with various stakeholder groups. Again, while this kind of coaching may be welcomed, and helpful, a board should never force a head into a coaching relationship or treat it as a punishment or condition of employment.