Should I teach my boss the simple things I do?
July 8, 2020 2:44 PM   Subscribe

My boss is a lovely and extremely busy person. She's an expert in her field, but doesn't learn new computer stuff comfortably, which has led her to rely on me to do a lot of little tech things for her.

This includes really simple things like adding signatures to PDFs, which can be done with Acrobat Reader and is very easy (I click the "sign" option and plop her saved signature where it should be). I'm happy to do this, especially as she is often very busy.

But it does still require her to email the document to me, wait for me to see and deal with it, and send it back, and then she sends it on where it needs to go. And I worry that she thinks I'm doing something complicated or which requires Acrobat Pro (which I do have and use for other tasks) - and she's always so grateful I feel like a bit of a fraud.

So my question is more one of interpersonal relations: should I tell her how very easy it is, or just keep mum and do it for her? It's just that I don't want her to be dependent on me, especially if it's less convenient to her. (I know that sounds funny when talking about your boss, but she's a friend as well, and I would want my friend to teach me how to do something like this.)
posted by jb to Human Relations (15 answers total) 1 user marked this as a favorite
Just say something when she's not busy like -- "[Boss], I'm happy to do these kinds of things for you, but if you ever want me to teach you, I'm sure you could pick it up -- just let me know, I'd be happy to help."
posted by Rock 'em Sock 'em at 2:46 PM on July 8, 2020 [12 favorites]

Also as someone who is extremely busy (sometimes) and who delegates work to other people, it's often not that it's difficult or that it takes more time than emailing my paralegal(s). Instead, I delegate because it's much easier for me to have a single workflow -- (1) email paralegal -- rather than ten different work flows : (1) sign PDF (2) run versioning software (3) rename file etc....

Doing ten different things takes up more brain space than doing one thing over and over ten times.

Plus if I'm busy I want someone who is not busy to do little detail things so that I can't fuck them up and can use my concentration on things that only I can do.
posted by Rock 'em Sock 'em at 2:48 PM on July 8, 2020 [34 favorites]

I often have to remind myself that me finding these things easy while my boss thinks they’re complicated is the reason I have a job.
posted by penguin pie at 4:24 PM on July 8, 2020 [39 favorites]

I think this is really dependent on what your role is. Are you an admin, and meant to be handling these tasks? Then definitely assume your boss is like Rock 'em Sock 'em's second answer above, and keep on keepin' on.

But if your role is meant to be a subject matter expert, and not an admin? I would push back at least a bit - such as the offer to teach your boss how to do it for herself, or doing it a bit slowly (say, after the more specialist tasks on your to do list).
posted by amelioration at 4:49 PM on July 8, 2020 [5 favorites]

I have to do this for my boss, for exactly the same reasons. Things like set up an out of office message for her gmail, share her calendar, look up a reference in the library she uses every day... Except I hate it, because it's not my job, and I took this job specifically because I didn't want to be a personal assistant anymore. I tried, for a long time, to teach her how to do these things herself. Gently and cheerfully, presenting them as 'look how easy this is to do! It will help you so much to do it youself!'

But she resisted it completely.

She can do email, so her way of dealing with anything administrative is to email me telling me to do it instead. Then it's done and she doesn't have to think about it at all. I understand from her perspective, as someone who is super busy, learning something new (even if it is tiny) is more effort than she thinks she can spare. As far as she's concerned, I am there to do these things so the problem is solved.

So, just to warn you, even if you think this would make her life easier, she might still prefer not to do any of these things.
posted by EllaEm at 5:23 PM on July 8, 2020 [2 favorites]

Keep in mind that If she’s on the older side, she might not be able to master this stuff without a ton of effort.
Please do not keep that in mind. It is not accurate, and is more likely to be Confirmation Bias and maybe older people buying the myth and thinking they can't learn. There are and have always been old people who learn new stuff. We are discriminated against in IT, ask me how I know. In case you were wondering, women can use technology competently, as well.

Mention that she could save some time by learning certain tasks, offer to teach her.
posted by theora55 at 5:34 PM on July 8, 2020 [34 favorites]

She’s not doing these things because she doesn’t want to, not because she doesn’t know how to.

If she wanted to learn, she would ask.

I get where you’re coming from, but I think it would be a potentially damaging faux pas to offer to teach her how to do these tasks.
posted by rue72 at 6:12 PM on July 8, 2020 [2 favorites]

Keep in mind that If she’s on the older side, she might not be able to master this stuff without a ton of effort

Seconding this as not being accurate. The main reason older people resist learning "new" things, specially as they relate to technology is that they have had a life time of new things they've learned, that they had to unlearn & learn the next new shiny thing 2 years later. It's not that they can't learn it as they can't see the benefits of learning yet another new thing that won't be using in a few years.

If you want to get your boss on board with learning how to do these things, you are going to have to demonstrate that her doing it herself benefits her or her goals in her department in some way. Be it helps her get the thing off her to do list faster or improves her workflow or saves the company money whatever it is or how it is wasting the company money with you doing it if that is not your job area, & that it would be better handled by an admin person if you don't want to do it.
posted by wwax at 6:19 PM on July 8, 2020 [2 favorites]

I am in a grey zone re admin work. I'm not technically an admin, but her actual admin retired in May and has not been replaced, and I like doing admin work. I'm more worried someone else will be annoyed that I'm doing admin work rather than my actual job (research project management and recruitment).

Like I said, I really don't mind doing this - and it doesn't even take much time. Maybe it's because I really respect her that I think she'd want the control, but if it suits her, I'm happy to keep doing it.

The tech thing is definitely not her age (she's only a few years older than I am, and substantially younger than my early adopter FIL), but I think she's never been that interested / comfortable with computers.
posted by jb at 10:10 PM on July 8, 2020 [1 favorite]

Like I said, I really don't mind doing this - and it doesn't even take much time. Maybe it's because I really respect her that I think she'd want the control, but if it suits her, I'm happy to keep doing it.

Think of it like a kindness to her and a sign that she (appropriately!) trusts you -- you obviously are trustworthy, care about her, and will do your best, so it sounds like she is right. I would relax and enjoy one of the best "work" feelings there is -- being genuinely helpful to someone you care about.
posted by Rock 'em Sock 'em at 11:03 PM on July 8, 2020 [1 favorite]

You might make a "how to" document with instruction for all the little tasks. Try to include things that aren't totally trivial. Let the boss know it exists "in case she has to call on someone else in your absence".
posted by SemiSalt at 4:33 AM on July 9, 2020 [3 favorites]

It's always good to document your job -- not so they can replace you more easily, but to show that you understand it thoroughly and so that you are free to take a vacation day without the wheels falling off. :7)

If your boss chooses to try following the directions someday, great! (But don't count on it...) On the other hand, if the boss feels more confident to hire a new admin because she can use those docs to train in New Hire, then that's really great!
posted by wenestvedt at 6:55 AM on July 9, 2020

Hi, I used to write training materials to help very non-tech-savvy people use a complicated system. I think you're getting good advice here, but one tiny adjustment I'd make: don't tell her it's 'easy.' Often, when people are avoiding doing something because they think it will be hard or complicated, telling them it's easy doesn't reassure them the way you're trying to reassure them - it makes them feel stupid. Instead, I'd suggest phrases like "pretty straightforward" or "doesn't take very long."
posted by Ragged Richard at 7:08 AM on July 9, 2020 [11 favorites]

Just echoing the above, earlier in my career I didn't really fully understand why people higher up couldn't just book a meeting or make a copy, take notes, etc. Now I manage a team of about 25 and run a business function and J. F. C. do I need someone to just book the meeting for me, mostly because 3 seconds later someone is asking me something else or I'm in a new meeting and now I forgot.

You are concerned that she has to wait on you to do it but she isn't like sitting there the whole time worrying about it. If she is anything like me, she handed it off to you and then it was COMPLETELY gone from her brain until you returned it to her. Which is an amazing feeling, having someone you trust that much that you can hand it off and not have to worry about it.

Definitely document, especially if this isn't your main job, there's a chance you might get asked to move to something else. She will love you to death if you leave her with instructions. It also allows you to take PTO without feeling guilty.
posted by magnetsphere at 7:52 AM on July 9, 2020 [6 favorites]

I am a line manager for a research group and I see the sorts of things you are talking about are routinely done by people in project manager roles. Yes it would be more efficient for an administrative assistant to do them but it is often a lot easier to justify hiring a more expensive project manager than a less expensive administrative assistant.

In your place, I would just keep doing this stuff unless it is actually getting in the way of you accomplishing your other duties. If it is you should chat with your manager about that and the solution might be (a) the manager learning how to do it, (b) accelerating the hire of extra admin help, or (c) you continuing to do it because the backlog your manager has is so much greater than the backlog that you have.

I am fortunate enough to have admin help and when I am on the phone I will often forward emails to my admin to deal with. If I were at my computer I could deal with them in seconds so I don't bother, but on my phone it's stupid for me to leave it in a queue of emails to be dealt with later when my admin has time to handle it today. This can mean the difference between someone else's request being handled immediately or not at all.
posted by grouse at 9:02 AM on July 9, 2020 [1 favorite]

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