Jane,
I think I like this discussion already. Two things come to my mind immediately.
1. Being less than truthful to students, even with the best of intentions, is usually a very bad idea. Defining "success" with and for your team and dealing with disappointment (and success) "in the moment" are two difficult and exceedingly important tasks for team mentors/leaders to grapple with each year. In many ways I see these tasks as being very pivotal in our overall effort to change the culture.
2. Woodie consistently talks about "hard problems" and the fact that this is not supposed to be "sticky sweet" as well. Sugar coating things too much is clearly not the intention or vision set forth by our best minds.
I could spew for hours, perhaps days on these items, but I'll let it rest with one final thought. I think, in a perfect world, all teams would consider carefully their people/team/community development model. After some training and work a few years ago, I'm a huge advocate of the "restorative" model as set forth by the IIRP here:
http://www.iirp.org/whatisrp.php - pay careful attention to the "social discipline window" in fig 1 and you'll begin to understand how it all fits.
To me guiding principles and philosophies should always determine how we do business/make decisions in life. Carry on all, I'm certainly interested in reading...