Short answer: bribe her. Analysis: She has dug in and anything you do will be more of a nuisance to her, which will bite you later (she's just going to keep it up every. single. month. until. you. scream.) Your boss can't help you, and the more you fuss, the more you risk looking bad, just ot make her do something she doesn't want to do. You can't make her want to do it, but you can make her want to do it FOR YOU. Or, at least make her feel guilty for not doing it. Same difference. I would bring her something thoughtful, like if you know she likes a particular muffin, or a type of candle, and just say something like, "I know this is extra work for you. It really must be a pain. It looks like you're incredibly busy. And I just wanted you to know I appreciate it." Then send her an email saying GENTLY something like "Since the last time we spoke it was agreed that these would be paid at this time, can I expect them in this paycheck, will you write a separate check, or do you want me to wait another month?" That way, you're technically presenting her with OPTIONS instead of commenting on something she hasn't done (which will just make her more defensive).
The downsides you are probably already listing in your head are: 1) you don't get to "win" over her, but you can't anyway because she doesn't want to do it and the more you try to make her the more she will make you pay anyway she can. 2) this is supposed to be her job and why the hell can't she just do it? But hey, people suck, And 3) It's not your job to make her want to do hers (subset of part 2, really) so why should you have to go to the extra troubl?. This is true, but again, you want the money, and this is the fastest, easiest, least risky way to get it.
Hmmmmm... I don't think it will work because she knows you want her to do this, and she knows she's not doing it. And now you're asking her to do it as a favor?
The real point of an email is to document that she's not doing it, and she's goign to know that. So really, you're attacking her. Which brings up another point: she may resent the "have a great weekend" "do me a favor" tone in an email that is basically upping the confrontation.
My guess is that this sort of slap will make her either 1) dig in more firmly, comgng up with more and more reasons why she can't just get it done or 2) do it and give you an even harder time next time. Plus, if she's older she's going to be very offended, and probably already is, at you coming at her trying to make her do something she's told you she'll get to when she's good and ready. She does sound like fun, and it sucks that you have to deal with this.
This kind of makes me wonder, are you sure you aren't just tied to the battle of wills? She obviously started it, but someone has to step back for it to be over. Is there any way, short of a gift, you can let her "win" a point? "Ok, you're right that we should streamline the process, make some other secretary do it, whatever you can think of (I'm sure she has a suggestion if you ask)..." Or is there some way to give her options in how to do the job, so she feels like she has more control?
Because a boss's assistant is NOT a good person to mess with, and this is full frontal, no matter how polite you are...
PS - your strongest point is that she already agreed to do this last month. So you're just asking her to do something she's already considered and told you she could do. Anytime you approach her, that has to be sort of front and center when you reframe your request. "Did something happen to make it more difficult than you thought it would be when you agreed to do this?" that sort of thing. Wow, she really is taking up a bunch of your energy just for a little bit of money. I'm so sorry, this kind of person is just no fun...
I understand your promlem very well (see my post in General chat- sigh...I need advice) except my problem has to be addressd directly with my boss which makes me want to barf!!! I think it's just really rude for someone who is older then you to just assume you can get this money whenever and it makes no difference. I think older people assume this because they make more and their paycheck is just their paycheck, when to younger people who make less it is what we live by and base things like fixing our cars and dental work on. I completely know where you are coming from. My advice is that since you are closer to your boss you should say something. If someone is supposed to do something and they aren't I believe the boss has a right to know. It might be risky but maybe ask your boss as if you haven't confronted A yet. Say "Hey, I was wondering when my freelance pay will come into affect on my paycheck" and then she will realize how long it's been and say something to A. Good luck and keep us posted.
Honestly, I can ssee how sometimes it might be ok, but I wouldn't talk to the boss. Really just because I tend to be dealing with people who play by playground rules and PUNISH that sort of thing hard - half the time even the boss is ready to pick on anyone who complains. And, well, it's sort of like telling on her, which she's probably not going to like because she's already freaked out that you caught her not doing something. Besides, the boss doesn't need to know that you can't get along wth someone - it just makes them associate you with a hassle - or that you can't get something done on your own.
I may not be right, but I think what's going on in her head is something like this: "I am sooo busy and I promised to do this, but I'll get to it when I get the chance. Uhoh, I forgot to do that!" and this type HATES to be caught in a mistake, so now she digs in and has to make it your fault "well, I shouldn't have to do this anyway, she can just wait longer. It shouldn't be a big deal." And every time you complain, you hit the sort spot of her not doing it in the first place, and she gets more tied up with it having to be YOUR fault. Going to the boss would probably mean war with her too, because that's bringing other people into the problem she's made by not doing it in the first place and she's already embarrassed.
So she needs a way to back out but still save face. Bribes give her the oppty to be like "oh, well, if it matters to her so much." Asking her if there's a reason why she hasn't done it and then just quietly waiting for her to explain will probably loosen the logjam. And then either offer her options on how to get it done the way you want, or ask her for options. Like I said, she just needs her energy to go somewhere besides blaming you. And she needs to feel NOT attacked so that this doesn't matter to her.
Basically, there is nothing you can do to make her, and ANYTHING you try to do will just make it worse. So you have to give her a way to do what you want, while still saving some face. She'll take it - she wants out of this as much as you do because it hurts her feelings not to be perfect.
Does that make sense?
PS - I don't think you have to back off for a month, either. That just lets her get away with . Obvioulsy it's driving you crazy, and she knows she needs to do it. Personally, I would be at her desk, nicely commenting on how busy she must be, at least once a day until she just does it. That way she can't complain about you being rude to her, but she knows she can't get away with screwing with you either.
I wouldn't bribe her because then she shouldn't expect something to do the job she is already paid to do. If you do that- you will only start a cycle and possibly make yourself a target. Giving gifts only works on nice people who would have already sent in the payroll on the first check anyway. Making her feel guilty might work though....she should already feel guilty since she is holding up someone's money. She has already said she will submit it for the next check so I wouldn't push it before then...it will only irritate her and possibly make her hold on to it longer. At the most I would remind her a day or two before the deadline to submit it. Then if it's not on your check go to your boss and tell him 1-how long it's been 2-that you asked about it and she said she would submit on x date 3-that you reminded her the day before the deadline and if necessary 4 plead your dental bill. The dental bill will help him NOT say "no more freelance". He can't get mad if you are working extra so you can have some dental work done right? and he can understand that it's important for you to be paid sooner than 2 months for your work. I really hope she just puts it in.....I hate having to haggle over money you are owed.
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