A case study on technology implementation

I am a regular reader and fan of Chris Dawson's ZDNet blog, Education IT. He is opinionated, seems well-informed and is a real, live school technology director, not just a pundit. But he doesn't often write about his day-to-day challenges. On Monday he did - and it really made me think. (I know, it's dangerous.)
In My LMS debacle, Chris laments that his district (he, specifically) has not yet created a "learning management system," that includes a portal to the student information system that allows parents and students access to grades, homework, attendance, etc.
A number of things Chris wrote about concern me and I thought Chris's blog post might make an interesting "case study" for discussion. As with all situations, I am fully aware that I know but a small piece of the realities of Chris's district and it is always easy to Monday morning quarterback any situation. Given than caveat, here goes...
This [implementing the Learning Management System] also happens to be one of the most fervently requested items in our recent meetings with community members to review progress on our strategic plan. So it has come from upon high (i.e., the superintendent, aka, my boss) that this shall be done. Quite frankly, it’s about time that it percolated to the top of my priority list anyway since so many school districts already offer everything from Moodle to parent access to their SIS.
OK, who died and left the superintendent Chris's boss. Oh, right, most tech directors do have supervisors who help them set priorities. And Chris's super is channeling the public's wishes. Where had Chris been getting his priorities prior to this? Where should all us be getting our direction? From our supervisor? From our advisory committees? From teachers? From watching what neighboring districts are doing? From reading the latest professional journals or blog entries? Yes. But the key, I believe to a successful technology (and library) program is that its focus is on helping others meet their goals - and not having some separate agenda.
Right now, many teachers use blogs, Google Sites, Quia, and wikis to publish course information, assignments, documents, etc. We’ve been fairly laissez-faire about the whole thing and teachers have adopted web-based tools as they felt the need. Plenty still haven’t.
I've felt guilty about not pushing Web2.0 tools more fervently in our district, but with Chris's comments I feel a small breeze of redemption. While never trying to squash our early adaptors' innovative urges (and keeping all Web.0 tools unblocked), I have been reluctant to encourage teachers to use even the free tools until we could adopt a standardized version of the tool. So far our teachers have access, training and support in our website (a content management system) that allows the creation of pages, galleries, drop boxes, discussions, etc. Wiki and blog capacity are coming soon. We've just now adopted GoogleApps for education. But we aren't exactly pushing the envelope here.
The logic of my approach is that my departmen has the resources to train and support our staff on only so many tools. And the more teachers using the same tool, the more peer-to-peer support. It's dull, perhaps, but the slow, deliberate, planned rollout of such tools has a more comprehensive and lasting impact than simply boosting the early adopters.
...we haven’t rolled out this so-called “parent/student portal” because it requires fairly spotless family management or, in a basic implementations, a login for every student in a family.
Fairly spotless family management? Is the daily attendance this system tracks "fairly spotless?" I hope so if Chris's state like ours wants accurate attendance data on which to base school aid payments. Again, as dull as it may be, data integrity and completeness are hugely important qualities that good tech departments have to deal with. Sorry.
About half of our teachers use the full functionality of the gradebook (required to communicate useful information about assignments to parents) while the other half only submit their term and final grades through the system, preferring to maintain their individual assignment records elsewhere. More and more are adopting the SIS as their gradebooks, but it’s a slow process.
Why have no common expectations for gradebook/SIS use been set for Chris's teachers? Do soldiers get their choice of weapons? Do bank tellers get to choose whether to use the bank's computer system? Do physicians get to choose not to use the CAT scan if so inclined? If the parents in Chris's district have indicated that better access to their children's progress metrics are important to them, why have the administrators in Chris's district simply not said "Using the SIS gradebook is a basic job expectation, just like taking roll or giving grades or having PT conferences. Do it." We've done it here.
My sense is that Chris comes from the "visionary/leadership" school of training technology directors. I've said it before and I'll say it again - having a vision ain't worth squat if you don't have those plodding old management and administrative skills needed to put that vision in place.
Good luck with the LMS, Chris. You are more than welcome to set me straight on everthing I am clueless about here.