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Chief
Lol. Nope, but if you figure it out let me know.
Another ten years and much more bourbon may be required.
First off go at her with respect. You don’t have to grovel. But if she is older than you (especially old enough to be your mother) lack of respect will get under her skin. Second. I always approached my assistants like we are a team. And as a team we need to get a good work product to the client. So how can we do that and how can we do it better. I need to do X but assistant, I need you to do Y. Also, as an associate, it is possible that you are not clear about the instructions you give. Before you go at your assistant think about your role in the work output. I say that as a 30 year attorney. But associates sometimes don’t know what they don’t know. Or your assistant might just suck and you have to figure out how to work with what you have unless you have the ability to change assistants.
Pro
Ah but see that SOUNDS like a team approach... It's not. That's a Me approach (I can't bill for this), which is where I struggled for a while. And it's not an unreasonable way to address in many ways, but it's not going to be successful.
Start by asking her if she feels supported and part of your team. Does she feel like she can come to you if she makes a mistake and work through solutions with your together? Or would she be afraid to tell you? If the answers aren't what you want, it's a trust issue.
Ask her what skills she wishes she could learn to make her more indispensable. Then tell her you're going to suggest to management that she be provided training for those.
It won't make her magically able to combine a PDF, but it's the beginning step. Once the relationship of trust is established, she'll feel more invested in YOUR work and seeing YOU succeed. That includes learning new skills and retaining them.
Dont forget, assistants probably don't get positive feedback from anyone. So when they hear you want to give them feedback, they know it is going to be constructive/negative. Maybe there's some admin staff politics and she's already on the defensive. So let her feel like she has an advocate.
Again, my assistant isn't great (mostly because the partners never used her for the things I need so it's a brand new skill set). But we have a great relationship, which overcomes a lot of that.
Give the negative and give some positive with it. The previous replies are spot on. I struggle with having much older assistant get up to speed in technology and being forgetful. But she’s really knowledgeable on other things. So encourage the tech and praise the good stuff
The print scan email then save in a electronic file location seems to be what is most logical for a certain subset of staff. Sounds so crazy to those of us who’ve grown up with email and PDFs etc. 😕
I totally gave up on using my assistant. I do everything myself and it's much a much more efficient way of doing things, plus I can still bill the time
I joined a company as in house three weeks ago and have now been overseeing one of the assistants who’s basically had free reign of all filing and her tasks for over a year. She was tasked with organizing pretty much everything. I come in and realize she hasn’t really been doing shit. She doesn’t really have anyone overseeing her or her job. We have a big transaction coming up that requires everything to be organized that I’m a part of... guess who’s now responsible for making sure she is actually doing her job. It was so painful for two weeks figuring out what she’s actually doing and then having to be like ... sending 6 emails and moving one minute book over should not take you all afternoon