Best wishes for ND!
I'm dealing with a woman - not my immediate superior (although she doesn't seem to realize that), but above me in the office hierarchy - who refuses to deal with electronic communications. We do a weekly electronic newsletter, for which I compile information and send it over the vendor who distributes it for us. When the draft comes in (she refuses to review the material before I send it over), she prints out the draft and marks it up. Same thing for PDFs - she prints them out and marks them up. Ditto for the emails we send out.
This means that, when I try to explain something that's being dealt with electronic, I might as well be spouting gibberish. We went through something last week where she'd pulled information from several Word files, cutting and pasting into one document. There were sections that had been numbered and, with Word's auto number function, they were numbered out of sequence. I pulled the info into an InDesign file (for layout) and asked about the numbering - if it was the automatic numbering system going wonky or if she'd meant for them to be numbered out of sequence. We were discussing it and she was huffing, "well, if you CAN'T fix the numbering" ... and I had to try to translate it into something non-electronic.
sigh ....
I think some of this is the ask versus guess thing?
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I am a guesser, and I actually tell the students that I manage that when I say "You might want to do X", I mean "You need to do X".
Although it took me months to realize that when she says "feel free to..." she really means "DO THIS." As in "feel free to remove the comment boxes before you return the file" means "you should remove the comment boxes etc."
It's funny, because I feel like I have the opposite problem: When I ask colleagues (not people who report to me) if they can do a certain thing by a certain time, I am actually asking if that is possible, not giving them an order. I am always surprised when they take it as an order.
Oh man, Sophia -- that is totally what I'm talking about!
Hah. Yep. I'm totally a guesser, though if someone is upfront about being an asker, I can codeswitch.
I am guilty of the "You may want to do X" also but generally it is when I want the person to do X but there isn't a specific process or procedure guideline that requires them to do X that I can point to. I also used to use the "feel free" or "you can" language when I wanted to them to do something but knew it wasn't really critical and was trying really hard not to micromanage. When I'm supervising people in a job that I have a lot of experience with and can do well, providing feedback that is helpful without being obnoxiously directive is tricky. Knowing all of this about myself is why I always tell new hires to ask specific questions if they don't understand something I tell them - I know how frustrating it is to not know what is expected.
I am much better about dealing with askers now that I understand it, and I actually try to assess my student workers to figure out which they are and I try to give really clear directions to them.
I got better at everything once I realized not everyone in the world thought exactly as I did!