Of course it’s as rude as fuck and I don’t think it has anything to do with timidity. Someone comes up to you and stares at you and you keep talking to someone else as if the third person isn’t there? That’s fucking mental. Anyone who does that shouldn’t just be interrupted; he or she should be kicked in the shin and then interrupted.
Does she know her job is on the line? I have found that many people will keep doing whatever personality quirks they have as long as people aren’t giving them consequences, but when you tell them “this will change or you will be fired”, they tend to change pretty quickly. Sometimes the right answer is gentle hand-holding, but sometimes it’s tough love. This sounds like the latter case.
I’d arrange a one-on-one meeting, be very explicit that her behavior has been unacceptable, how and why, and if she doesn’t change she will be out of a job. Like you said, she’s a temp, so she will be easy to let go. If she knows that she has a deadline and knows what the consequences will be, she can see that either she needs to assert herself or she will no longer be getting a paycheck from your company.
Unfortunately, not everyone can change their behavior. She may have potential but not the willingness to achieve it. You may not be able to help her and the right thing for both you and her might be to let her go and find someone that fits the role better (and let her find a role that fits her better).
FWIW, I don’t think a $300MM deal is the right place for a “teachable moment” either. When that many zeroes are at stake, that’s a “get your ass over there and do your job now!” moment. You’ve tried the nice method, I think you need to lay it on the line and show some tough love if you want to see a change.
A lot of responders are explaining how to discipline her but I’d like to also suggest offering her carrots. There are many parallels between dog training and people training - mainly you often get the best results from rewarding the desired behavior. If she gets yelled at for interrupting people, even when her interruption was the right thing to do as in this case of delivering this urgent paper, she’s going to become more and more afraid. The trick with this is that there are people - and I suspect Big Scary Lawyer is one of them based on the name - who are inconsistent with such things or yell because of issues irrelevant to the current situation. For example, many years ago I had a boss who would yell at the first person he saw, even if it was someone else who pissed him off. If your office is full of these people, then you’ll need to replace your timid worker with someone who can ignore such nasty attitudes in others.
Yabbut people do this all the freakin time. I was also one of those - and still am to some extent - that waits politely for people to finish. But it is so frustrating when they keep on talking. Now I have learned to politely interrupt when I have something urgent, or go away and come back later if it’s not urgent.
These same people are also the ones that interrupt when YOU are talking to someone.
And there’s a lesson there – they expect you to take the initiative and speak up if you need their attention, just like they speak up if they need yours. And speaking up is more efficient than waiting for someone else to become aware of your presence, evaluate whether or not you need to be addressed, and then make the decision to stop what they’re doing and start talking to you. What’s rude in cocktail party conversation is sometimes the way to get things done in a business setting.
Time to let her go. Your desire to make her your project may reflect poorly on you. She’s a college educated person working as an administrative assistant. A role that clearly doesn’t require the level of education she has, and she’s incapable of even being successful at that.
You’ve told us she has an “invisible disability” and mentioned anxiety - does she have an actual psychological disorder that she has to summon her courage to overcome in order to have social interactions, not mere timidity? If so, you can’t fix that, but maybe you can find a more isolated job for her instead.
Lots to reply to, but I just have to know ASAP:
Why do you say the role doesn’t require a college education? 
She’s a temp. Temp means easy to fire with no chance of unemployment. You cant blame her for being timid.
Even if YOU or some other person does something wrong, they have an easy scrapegoat to blame things on (happened to me) and throw under the bus.
Can you REALLY trust your coworkers?
Example: “I never told you to go into so and so’s office while they are on the phone - you’re fired.”
Now give her a real position, give her something IN WRITING and in front of others saying you WILL back her up if say “big scary lawyer” gets mad, and then she might not be so timid. Maybe a “Get out of jail FREE” card sort of.
PS. Find a bad-ass redneck woman that rides horses, hunts, and shoots guns for fun. You wont have any problems.
I’ve hired administrative assistants that have college degrees, but the majority that I’ve hired do not. The types of skills needed for success in a role like that don’t require an advanced degree. The skills you describe as lacking in your own assistant, aren’t things that would necessitate a college degree.
I wouldn’t go so far as to let her go right now, but it does sound like you’re at the point where you have to tell her to go give the letter to Big Scary Lawyer or that will happen. You say you modeled what to do with several times, so all that’s left now is for her to do it.
I feel kind of sorry for her, I started out pretty shy in life. I had to get over it myself though, nobody led me by the hand. But I can see points in my life where even if I was led by the hand it wouldn’t have helped, and maybe she’s just not there yet.
(my bold)
I think that’s a bit harsh. How to be appropriately assertive is a skill they don’t actually teach at college. Some people pick it out of the atmosphere at five years old, some have to learn
It is true, however, that it will be bloody hard work on her in her 20s trying to learn this skill quickly enough to do a job in which appropriate assertiveness probably comes into nearly everything she does. I consider myself fortunate that my first jobs primarily required technical skills, and it didn’t actually matter that I didn’t learn how to say boo to a goose for ten years.
But on the OTHER other hand it’s a skill that’s basically useful for every job in existence. Perhaps admin assistant to a bunch of statusy hardass lawyers isn’t the best position in the world for her, but it’s still good that Green Bean is trying to teach her this stuff.
This. I’m naturally shy too, and it takes time to develop the assertiveness and trust necessary to feel comfortable barging in on a BSL. Knowing that someone higher up has your back makes a huge difference. So does cutting the cord.
If you’re being very direct about what you need from her and you don’t see improvement in the next few weeks, it’s time to move on.
Of course, that’s why being an admin asst. isn’t a degree required occupation. And I would say that walking into someone’s office and handing them a letter hardly requires assertiveness it’s just handing them a letter. It’s recognizing that something needs to be done and you do it.
Note to all who suggested different ways I could have given her the original assignment to bring the paper to BSL - I’m not the one who asked me to do it. Kahuna did. By the time she came back to me, it just needed to get to him ASAP.
Interesting insights, Aspidistra. Thanks. It’s entirely possible that she was raised that way - which would be weird for the greater New York metropolitan area, but it’s certainly possible. She does just tend to stand there looking at you…which is frankly kind of creepy!
That many zeroes are usually at stake. Deals are normally in the 10s or 100s of millions of dollars. Maybe she’s cowed by the size of the transactions? I think it just makes it more fun.
Understood. Except that she’s never been yelled at by anyone for interrupting them! BSL just thanked us nicely and asked a follow-up question. See why I’m confused?
Wow, you have a REALLY nasty view! Our corporate culture just isn’t like that, and our team DEFINITELY is not like that. Of course we’d back her up if BSL had a moment. And I wish it was not a temp position, but that’s all we can do given various constraints.
With regard to your last comment - we’re a little short on rednecks here in Central Jersey. 
Her invisible disability is physical. It’s a condition that is not apparent, but is significant. Doesn’t seem to slow her down any, and she doesn’t need a handicapped plate or anything. But I’m sure growing up with it hurt her confidence. I don’t know if she also has a psychological disorder, but it’s possible that a lot of anxiety stems from that. Maybe being treated for anxiety would help. (If she’s not already)
You clearly have a particular idea of what an administrative job must entail. There is a broad range of positions that fall under that umbrella. Do not assume you understand the position becasue of the title.
…no: all you know is that she hasn’t been yelled at for interrupting them when you accompany her. Have you asked her if she is treated differently when you are not there?
I think she would have told me, but I will inquire.
It’s probably an East Coast thing. Dang, I wish I could afford to move back to the Midwest.
Several things happened today that have made me consider that this may not work in the long term. I will describe them below, and I think you’ll understand why. It’s about more than timidity. It’s also a common sense thing. I was hoping that the task management list would help, and it has, but the failures of common sense are not good.
I was still trying to figure out how to make it work with Jane until a conversation with my brilliant and wonderful sister-in-law, who is in HR for a big gigantic multi-national corporation. One of the complicating factors mentioned above is that the department chief recently got a multi-level promotion to the C-level. His need for administrative support has exploded. This was unexpected, and Jane has been scrambling to get it done along with all the other administrative and transaction-related stuff. The Brilliant and Wonderful Sister-In-Law suggested that perhaps the solution would be to get an experienced executive assistant for the Chief that could also provide full administrative support for the rest of the team. Chief doesn’t really need a full-time exec assistant, so this would work out great.
Jane has taken a lot of work off my desk, but she’s still taking up way way too much of my time with things that an experienced professional admin would be handling on her own by now. We were expecting her to help with a lot of the transaction-related stuff, but that’s just not panning out. If I had an admin who could actually do the job, it would allow me more time to do the transaction stuff. Re-framing the job as an exec assistant thing would make it easy - its not you, our needs have changed. That’s actually true.
The troubling things that happened.
-
She had something for Chief to sign. His door was open. She literally danced from foot to foot just outside his door wondering what to do. He wasn’t even on the phone. You know what he was doing? Chit-chatting with the other guy in the department about Halloween decorations. And she was scared to walk in. What the everloving fuck? I actually came behind her and gave her a little nudge and guided her in to Chief’s office and motioned her to give it to him.
-
She had a budget form to give to Kahuna. I told her it needed to get done today. She flagged him as he was walking by and he said “oh, good. Put it on my chair.” See, Kahuna doesn’t have an inbox. None of us do. His system is simple. If it’s something he actually should look at, hand it to him or if he’s not there, put it on his chair. You know, the one he sits in, so he won’t fail to notice it. (His desk is a mess) Newspapers, junk mail, magazines, and the like go on the chair in front of his desk. He looks at those…well, basically never. I throw it all out every few months. Later today, we had a call. I went to sit on his junk mail, and I noticed that I was about to sit on that budget form. I said “what’s that doing here?” She said “He said to put it on his chair.” :smack: Which chair did she think he meant? The chair where important stuff goes or the chair that is the equivalent to the black hole of Calcutta? She’s only been delivering his mail for 3 months already. If she can’t make these sorts of determinations without being told…
Aw heck, there are more, but I’m going to bed.
What did you say to her after these two events?
“Common sense” is not really common or innate. Indeed, I don’t think it exists. It’s a series of things that have to be taught. And this might be a person who hasn’t been taught them yet. Whether or not you want to be the one to teach her seems to be the question.