Why is so much administrative writing so bad?
For the same reason that many syllabi are so horribly written.
In a word, contexts. When writing, you can never be sure of the context in which what you wrote will be read.
You'll be read by many with goodwill, which is lovely. You'll also be read by some with axes to grind. You'll be read by amateur lawyers, trying to twist every ambiguous phrase or quirk of syntax into a new entitlement. (A professor once responded to an email by accusing me of using "menacing ellipsis." I decided that "menacing ellipsis" would be a great name for a band.) You may be read by actual lawyers in the context of some sort of legal action; if so, you can't anticipate the agenda, other than to say it won't be positive.
In the context of personal writing -- writing to a friend, say -- it's easy to assume a shared context. Even there, it's possible to get into trouble -- we're all warned about conveying tone in emails -- but it's usually broadly possible. If all else fails, you can just pick up the phone and say "what was that?" In the context of disciplinary writing, it's often safe to assume that the only readers will be people in that discipline, so you can rely on certain interpretive conventions.
But when you're under scrutiny from people who are looking to score political points against you, you can't assume that your words will be read in good faith. If anything, it's usually prudent to assume the opposite.
That's probably why, after all these years, I still have this writerly space largely to myself. My colleagues don't blog, or if they do, they don't blog about higher ed policy. Hell, I used a pseudonym for years until I felt like I had found a voice with which I was comfortable. Putting ideas out there can draw fire. I think of that as a form of leadership, though I've also heard it called risky. Probably both.
In this sense, administration is closer to politics than to teaching. Politicians' relationship to language is notoriously sketchy, going at least back to the Sophists. The Sophists actually make an instructive case. The term "sophist" forms the root of "sophistry," which we use to mean lying. But it also forms the root of "sophisticated." An acute awareness of the consequences of the misuse of language will lead, in the early stages, to forced or overly-safe constructions. It takes a while to get comfortable enough with the externally-invisible conventions to be reliably able to hit the narrow overlap in the Venn diagram between "professional" and "human." It's especially difficult when exhausted. Some insist on being human, and eventually get nailed for something impolitic; most take refuge in cliche. Moving from sophistry to sophistication takes time and practice, and the safe spaces in which to develop the skill to do that barely exist.
To be fair, there are more mundane reasons for painful administrative prose, as well. Sometimes it comes from acronym overload. Sometimes it comes from the overuse of internal shorthand, a temptation to which many academic researchers are also prone. Sometimes it comes from extremely scrupulous adherence to various legal terms of art. Sometimes it comes from time pressures. And yes, some people are just lousy writers.
But in thinking about what would improve the caliber of administrative writing overall, we might want to be careful what we wish for. (See "take refuge in cliche," above.)
It would be easy to adopt a more freewheeling and natural communication style if we just got all the skeptics to back off.
But what, exactly, would that entail?
Richard Sennett noted forty years ago that the great irony of "transparency" is that it forces a much more powerful self-censorship. That's not necessarily a bad thing; our first impulses aren't always in our best interest. The old "hydraulic" model of catharsis -- blowing off steam, say -- assumes that once you've "gotten something out of your system," it's gone. But that's not how the world works. If I respond to the umpteenth silly request with "oh, bite me," I haven't resolved anything; in fact, I've created a whole new level of problem. "Oh, bite me" might more accurately reflect my "authentic" state of mind in the moment, but it won't lead anywhere good. And I certainly prefer a world in which most people don’t respond that way to me. Catharsis is likelier to generate tension than to resolve it.
Put differently, some forms of self-censorship are what make organized life possible. Self-censorship sometimes comes from considering the needs of others. The act of thinking before speaking -- or writing -- may be tiring and frustrating, and in the hands of the less-skilled, may result in stilted prose. But it pushes us in directions we need to be pushed. If other people matter, then their opinions matter. If they’re free to express those opinions, then folks in the public eye may be expected to craft their words carefully to avoid unhelpful conflict. To flip Hannah Arendt on her head, banality isn’t necessarily evil; it may be a symptom of freedom.
Acronyms, on the other hand… (See “menacing ellipsis,” above.)