Thanks for challenging my thinking, Carl! In writing this reply I run the risk of plagiarizing as I have been reading so many ideas around how education might change in other's blogs or through online presentations. If I do so please forgive me/let me know if an idea was yours originally.
First I need to clarify. By 'senior administration' I mean those administrators we now have as trustees and school board or ministry officials, in other words the hierarchy that is already in place. Every teacher knows that students will live up to our expectations of them. Show them trust and respect and they will respond. When officials block and hamper permissive and informal networked learning they are showing their mistrust of teachers. In effect, telling teachers it's a scary world out there and we don't trust you to safely guide our young people through it. Unfortunately these decisions are often made by those who aren't teachers and are not taking the time to explore the merits of online networked learning for themselves. For them, it's simply easier to block than to put protocols in place and deal with the rare parental complaints.
So how do we 'train' teachers?
One way might be to model good practice. Among others, both Alec Couros (@courosa) and Dean Shareski (@shareski) make good use of social media tools in their pre-service teaching classes. They demonstrate the merits of social media as well as requiring students to participate by using blogs, twitter and other tools.
Another might be to guide teachers through a series of questions or problems based on scenarios using social media tools in the classroom. For example: With the world of knowledge at their fingertips through mobile devices how might you challenge your students to discover their passions while learning to be good communicators, collaborators and contributors? I know that's a mouthful but I hope you get the idea. As a teacher librarian I always pushed teachers who wanted to bring their classes to the library for research by asking them: What skills will your students need to be successful on this assignment? How will we accommodate individual interests or learning styles? How can we encourage students to collaborate? Is there a way to relate this to a more meaningful real world scenario. How can we allow students to demonstrate competency in a variety of ways? Who is working harder on this assignment, you or your students? How can we provide ongoing mentoring and assessment as opposed to waiting until the assignment is in to grade it?
We need to start honouring teachers who say, "I don't know." These are the ones who are willing to learn. If they can say that in teacher training or in the staffroom perhaps it will be easier to say it to their students, "I don't know. How can we find out? What ideas do you have to solve this problem? Let's try..."
Another random thought: I have heard that schools in Japan do not have government mandated universal tests because teachers simply refused to administer them. They still write exams on leaving high school but not at lower grade levels. If this is true it would free teachers up to teach to students' passions and engage them in activities that were meaningful and provided authentic, real world experiences. Oh course getting educators in North America to take such a stand is a whole other issue.