When having a detail-oriented supervisor is good, it's very, very good. When it's bad, it's horrible.
This guy tends to be meticulous, detail-oriented, voluble and jovial. All that stuff combined makes him a treasure in some cases and an insufferable loon in others. I can switch from loving him to hating him several times per day.
He has a personal system for organizing projects that never changes, is logical and intuitive, and lines up perfectly with the "official" system when it matters. He also takes care of all that himself rather than leaving it up to me to fumble through. That might sound anal, but considering how closely it relates to what I do and how much of a mess some projects become and how much effort he puts into preventing that, it's awesome. Sometimes I have got lumps in my throat and choked up with gratitude by contrasting his style with other RDMs.
He's equally detail-oriented in conversation. This is how he starts to get annoying. I wish he wouldn't go over when and where and how and what if that doesn't work and what exactly to do if that doesn't work either for totally routine tasks.
For example, this is the guy who asked me to work on the PowerPoint presentation. My buildup and letdown could have been avoided had he made it clear how minor the work would be before asking me about my schedule for the next two weeks.
And more recently, last week, we worked on comments from DHS on a document. He happened to warn me about it a couple days before there was actually any work to do. He spent 20 minutes just explaining that in exhaustive detail. When I say that it takes him 20 minutes to say "heads up," that's not hyperbole.
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