Help Me Help My Timid Assistant

In My Humble Opinion
1

I acquired an assistant, Jane, about 3.5 months ago. She started off strong, but has been having some performance issues lately. Many of them seem to be related to her timidity, unwillingness to assert herself, and apparent fear of interacting with anybody but me. This includes asking crucial follow-up questions and for clarifications.

I guess you could call me the department coordinator. Jane was hired to get administrative and/or time consuming tasks off my desk, but she also provides administrative support to the other 3 members of the team. (We coordinate and execute the purchase and sale of assets for the company.) We are entering a period of unprecedented activity, and I desperately need the help. *

Jane is turning out to be a bit of a fixer-upper, but she’s smart and has a good work ethic, and I think she has potential. I’m willing to put in extra effort in order to help her succeed, but I’m at a loss as to what to do to help her with the timidity thing. I was hoping someone had some useful advice.

Perhaps the most obvious manifestation of Jane’s timidity is being afraid to approach or “disturb” people, especially when they are in their offices. We have discussed this many times, and I have modeled what to do many times as well. Some progress has been made, but not enough.

The below incident happened late last week:

I noticed her standing timidly near my desk. I asked her what was up. She told me that one of the guys in our department, Kahuna, had asked her to bring a paper over to Big Scary Lawyer right away. (Big Scary Lawyer sits way across the floor.) BSL was on the phone when she got to his office, so she came back to ask me what to do. I said “go in and give it to him!!” (Remember that we had had similar conversations before)

I looked at the paper, and saw why Kahuna had specified “right away:” it was a time-sensitive letter crucial to the negotiation of a particularly important $300,000,000 deal.

Realizing that if I sent her back over by herself, she would probably quietly rap on the door jamb and wait outside the door until Big Scary Lawyer told her it was okay to approach instead of just handing him the damn thing – assuming the door was open and he even heard her timid little knock. I don’t know what she would have done had the door been closed.

I quickly walked her back over BSL’s office. He was indeed on the phone with the door open– on a call about the letter in question with Kahuna and someone outside the company. I walked in and handed to him. He had clearly been waiting for it.

A 10-minute delay in getting the letter to him wasn’t the end of the world, but it wasn’t good, and the delay was caused entirely by Jane’s dithering and having to making an additional round trip and all that. And this was to hand a letter to someone she already knew.

Unfortunately, the guys are starting to wonder whether Jane is a good fit for the job, and as she’s still a temp, so it would be very easy to let her go. I’m not sure she’s an ideal fit either, but like I said above, I think she has potential. This last incident has shaken my faith a bit.

So, advice?

  • Like with any other situation, there are all sorts of additional factors that I haven’t mentioned, but I’m trying to avoid TLDR, and I’m not sure they’re even relevant to the underlying problem.
2

You’ve described what she was doing quite clearly, but do you understand why she is behaving in that way? Did she have some bad experiences in a previous role? Is she from a very hierarchical culture?

I feel like, if you’re going to help her, you’re first going to need to understand her.

3

Good questions, and I realize that I probably should have included the following in the OP:

I knew Jane before she was hired, and brought her in because I knew she had the basic competencies needed. I knew she was a bit insecure and figured she might have to come out of her shell a bit, but I had no idea that it would be anywhere near this bad. I regularly see her interact normally with people!

I know her first job out of college was in a corporate environment, and that it “wasn’t a good fit,” but I don’t know the particulars. I suspect she hasn’t had the easiest time in life, especially since she has an “invisible disability” and some other health issues, but those issues don’t seem to hinder her in her work or anything. In other words, those could be having an indirect effect, but they’re not the direct cause.

In terms of culture, she’s a standard-issue college-educated upper-middle-class white chick from central New Jersey working at a corporation in central New Jersey full of college-educated upper-middle-class people from the greater NY area. Culturally, she should be a perfect fit.

4

Are you providing a formal introduction for her? For many shy people breaking the ice is important, once they’ve been able to interact with someone else things will work better. I know you may feel you shouldn’t have to do that, but these days competent assistants are hard to find, I’d go the extra mile to help her work better with others.

5

Yeah, the ice has been broken.

She has interacted before with Big Scary Lawyer, usually indirectly, but I know they’ve had a friendly little chat or two.

And amongst the people that she is afraid to approach is our department head. :frowning:

6

I think you might point out BSL has his speciality, but she has hers, too. She has to view her contribution as equally important as his. As an integral part of the team, she isn’t “bothering” him, she’s performing her cog in the wheel, just as you are performing yours and he’s performing his. Levelling the playing field is what she needs, I think.

She needs to value her role in the process.

7

You knew that the letter was extremely urgent, but did she know that. Maybe if you impress upon her that when she’s delivering something to someone, she’s not just doing them a favor, it’s her JOB.

If you can get across to her how important she is, and her job is, to the operation of the team, she will feel a little less like an underling, and more of a partner in the office. If she feels more equal (even though she isn’t really) to BSL and the other guys, she shouldn’t be as timid.

Edited: I hate getting ninja’d. Second time today.

8

Maybe take the person out of it. Tell her to put deliverables in his inbox. She doesn’t have to interact with the scary human at all. Just put the object in his box and leave.

That said, I would not have been kind about having to walk her over there like she’s a little kid.

9

Until you can talk directly with this woman as an adult you’re not going to get anywhere. And so far I see no evidence that you’ve done that. Every time there’s a timidity event you need to interrogate her on why she did what she did. And explain what she should have done instead and why. After about the 3rd event of same problem with no learning or improvement, it’s time to show her the door.

In the alternative, cut your losses now and start training the replacement you already know you’re going to need.

It also sounds like maybe she’s in one of those “team” environments where she doesn’t have one supervisor; instead she has several people she’s supposed to somehow collectively support. Which means each one has their own ideas of what should be done and how. That is a recipe for total paralysis for a non-confident support person. In that sense her failing might be partly or even mostly the company’s fault. But that doesn’t alter the fact that her failure is harming your department and you. She’s either quickly trainable, or she’s demonstrated she should work elsewhere.

10

…yep, thats what it sounds like to me. Why exactly do you call “Big Scary Lawyer” Big Scary Lawyer? Does he deserve the title?

Jane started off strong but has gotten more timid. Do you think that she is just getting more timid, or is there a possibility she is getting “snapped at” and yelled at by the other lawyers for behaving the way that you are asking her to behave? Maybe if she doesn’t quietly rap on the door jamb and wait outside the door until Big Scary Lawyer told her it was okay to approach she gets a bollocking. Maybe she can’t “follow your model” because the lawyers behave differently when she is on her own than when you are there. Just throwing out a few ideas.

11

It’s nice you want to help someone, but not everyone is right for every job.

The workplace is full of bullies, indifferent people and those who just don’t have time, even if they do.

And people have to learn to cope. You can only help people 50% of the way and they have to help themselves the rest.

It’s up to you to decide to keep helping her or not. But if you’re giving her the tools and she’s not using it, and more importantly isn’t showing signs of progress, than you may have to cut your losses.

She may have to seek an entire different line of work for the moment. Assertiveness training classes may also be in order for her.

12

I think maybe you didn’t do her any favours by walking the letter over to BSL. In her eyes, there was a thing she didn’t want to do, she dithered for a while, and you did it for her. Success!

Next time, be more direct. “Jane, BSL needs this right away. Please deliver it to him - and you have my permission to interrupt him if he’s on the phone or in a meeting, this is urgent.”

13

I don’t have answers, but I’m pretty sympathetic. I’ve gotten snapped at twice in the last month for walking into someone’s office at the wrong time (hint: If you really don’t want to be disrupted eating your lunch, close your damn door) and it’s not a pleasant feeling. I can’t imagine dealing with stuff like that in an environment where pretty much everyone is higher up than you.

I agree that she needs to feel like an integral part of the team, and to understand not just that a task is urgent, but why-- and even more importantly, to understand how critical her roles is in it. She knows she is the lowest worker on the totem pole, and that’s just reality. But she needs to see that her tasks aren’t the least important tasks on the totem pole. Right now, she probably thinks basically anything anyone else is doing is more important than what she’s got.

It would probably also help to loop her in to more meetings so that she can come to understand the office dynamics. It can be intimidating when you know there are all kinds of tensions and alliances above you, but you have no idea what they are or where the sensitivities lie.

I don’t think she’s a lost cause. She may very well bloom in a situation where she has a bit of authority.

14

Does Jane report to many people or just to you? If it’s “many people”, this may not be fixable.

I do like the idea of focusing on the importance of her role, rather than reaming her out for not being more forward. Tell her the “why”, and impress upon her that the business doesn’t run smoothly without you (and her).

15

Wow, so much good feedback! Thanks.

I’ve tried to help her understand that her role is crucial and that all work is valued. (It really is!) It hasn’t worked. Anxiety seems to be overcoming common sense.

I actually do bring her to virtually every meeting I attend, tell her about various projects and relationships and so forth.

The more I can get her to function on her own, the better off I am, but she seems more comfortable in a really subordinate role. Maybe I’d be better off keeping her more narrowly focused. There are a number of ways I can manage the scope of her work.

That said, I still need her to be able to give a damn letter to Big Scary Lawyer if she has to.

16

Timid person chiming in here. You have to push her out of her comfort zone. I would give her more tasks that require assertive behavior.

What would happen if instead of going to the BSL yourself and giving him the letter, you asked her to do it? I would have waited until she completed the task herself and not offered any help.

If you are worried about her standing outside his door until he acknowledged her, then
I would specifically direct her to walk in and hand him the letter.

As an aside, I also find it difficult to disturb an attorney on the telephone. And I happen to be an attorney myself.

17

“Jane, Team Guy said ‘right away,’ right? When we say ‘right away,’ it means now. You don’t have to run, but walk briskly.”

18

Jane seems pretty normal to me. I mean, unassertive end of normal, but still pretty normal. As an ex-Jane, let me give you my thoughts :slight_smile:

First off, I used to have the “don’t interrupt” thing so SO bad. I can’t tell you how much time I wasted in corridors and offices going up to pairs of people talking, where I needed to say something to one of them, and waiting for them to Give Me Eye Contact so that I could say what I needed to say. Because in my world, that was how it was done. I grew up in a small intellectual middle-class family, and that was just how social interaction worked - you signalled to someone that you wanted to talk by standing in front of them looking straight at them, and they signalled back by - bare minimum - looking at you, and much more often by stopping talking to the other person, and asking what’s up. Then you knew that it was ok to talk.

So after twenty-five or so years of Adulting I’ve pretty much come to terms with the fact that most people don’t actually do that, they’re not going to give me the signal I want and expect no matter how long I stand there obviously wanting to talk. But it took me a long time. So the two things I’d say to Jane are:

a) Non Verbal Communication for the win! I mean, in the case you describe, you didn’t actually have to say anything to BSL. He certainly didn’t have to say anything back. Pointing out how much she can do just by smiling vaguely and waving pieces of paper in front of people’s faces would probably help. Want something signed? Clipboard, pen, smile, offer the pen to the hand, display the piece of paper. They can read it first if they want to - but in any case, you’re not interrupting their conversation which is probably the big thing for her.

b) People won’t signal. They just won’t, 90% of the time. If she’s expecting that, she has to stop expecting it. People will, in fact, keep on yammering away at each other, while you’re bobbing and smiling, LOOKING at them with a hundred-watt stare. Personally I find this rude as fuck, and try not to do it to other people ever, but lots and lots of people just won’t stop talking for you, or won’t invite you in when you knock, and pointing out to her that this is normal, and something she’s just got to accept, is probably also helpful.

19

Do you think she may have Asperger , people confuse if as being timid . I have a niece that has Asperger and doctors told her mom she was just ‘shy’ .
She is very intelligence and she would had done the same as your assistant .
Just a thought , some people really never get over being timid . It’s really hard to try and ‘fix’ a person . I feel you’ll waste time trying to help her , it’s very nice that you want to but on the job is really not the place try and help a person to get over being timid. I feel this could made her feel uncomfortable
seeing you trying to fix her in front of other people.

20

I am her direct supervisor. I’ve delegated certain functions to her, which require she work directly with other members of the team. So if they need a meeting set up, they go directly to her. She is also doing a lot of work for me directly.

She’s getting better about asking about prioritization.

I wasn’t going to hold up a $300 million deal while I engaged in a training exercise! :stuck_out_tongue:

I’ve done what you’ve suggested in other cases already. You can see why this incident was so frustrating.
ETA - oh dang, more responses snuck in while I was writing that!