I can't count the number of times I've messed up this year

.
I work in a weird position where I basically have to tell people who are above me on the "ladder" what to do. I'm just a teacher, and they're principals, but I'm the district's curriculum specialist in an area (English as a Second Language) with a lot of state/federal requirements. As a result, I have to send e-mails "asking" them to do things. I can't TELL them they have to do it, but... they have to do it, and I'm the one who knows what needs to be done, and when, and how. It leads to awkward moments, and requires a certain degree of finesse that doesn't necessarily come easily to me. Basically, I have to cc THEIR boss (who is also kind of my boss, more like my boss's boss, but I report directly to him on some stuff because it's not really my boss's area) on everything, just so they know that it's "for real"

.
Suffice it to say that more than once, I've been TOO direct, or not direct enough, or a principal has been unhappy or annoyed with me... but whaddaya gonna do? Luckily their boss/my kinda-boss is cool and supportive and knows I'm on a learning curve.