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I’m a millennial and work at a job where I manage several remote contract writers. It’s my first time managing this many people and I really enjoy it. However, I have one person who I get periodically frustrated with, and she happens to be the oldest person I manage. She’s probably at least in her 60s, if I had to guess. I’m frustrated with her, and worried I’m perpetuating age discrimination in our office.
She does pretty good work when I push her, but it doesn’t come easily. I have to ask her repeatedly to follow instructions that seem to come a lot easier to my other employees. The job involves writing, and she complains that she can’t come up with ideas to write about, but when I send out content ideas to all my writers she never takes any of them.
With any other writer I wouldn’t let this slide, but there are two factors keeping me from parting ways with this one: One, every time I’ve expressed disappointment in her work, she’s told me pretty dire things like “I’m desperate for this job” and “This is my only source of income.” One time, her payment was a little late and she said if she wasn’t paid soon, she wouldn’t have any money in her account (I used to be a freelancer so I know the struggle, but I also had more than one gig). And, making all of this worse, she recently experienced the sudden death of a close family member. I can’t hear these things and not be affected by it.
Second, I worry that some of my frustrations have to do with ageism. The fact is that my other younger writers are more responsive via email, better at using digital tools, and just better at writing for the internet. Some are millennials, like me, while others are in their 40s. They’re more nimble and versatile, and they take direction well. With this other writer I wonder if I just need to be more patient, because the rest of us are the same age and work at the same pace.
This employee is really sweet, and like I said, she can do good work sometimes. But I get really frustrated and I feel like if her performance gets worse, I’ll never be able to sever ties with her because I’ll feel too bad.
How should I manage this employee without letting my emotions or ageism get in the way? Help!
Ageism would be things like “I just can’t shake the sense that Jane doesn’t fit in here” (because she’s in a different stage of life than the rest of you) or “I don’t think Jane will ever grasp social media like the rest of us do, since she didn’t grow up with it.”
Legitimate complaints about her work, like how she doesn’t follow instructions, come up with ideas on her own, or grab any of the ideas you circulate — that’s not ageism. These are real performance issues.
It is true that different people will need different types of management, and so you don’t want to assume that what works for the rest of your staff will work for her. It’s possible that she needs you to more clearly and explicitly articulate what you need from her. And if you haven’t already directly told her what you want her to do differently, you absolutely need talk to her before you draw any conclusions. Make sure you’re very clear and explicit. Don’t hint or sugarcoat it, or she may miss the message.
You might feel awkward having a conversation like this with someone who’s older than you. That’s actually a common way ageism does play out in the workplace, and you should make sure it’s not happening here. Sometimes managers give less feedback to people who feel different from them — because they’re intimidated or they worry about how it’ll go over, or they just don’t feel the same rapport as they would with an employee of the same age (or race or sex or so forth). It can feel weird to tell someone older and more experienced than you, “Nope, your work isn’t good enough.” But as a manager, it’s part of the job — and it’s really unfair to her if you don’t give her the same feedback you’d give someone you were more at ease with. (I’m not assuming you’re guilty of that, I’m just flagging it as something that happens a lot.)
While this “you’re not hitting the bar I need” conversation can be hard to have, it’s truly the kindest thing you can do. She deserves to know that her work is falling short of what you want, and she deserves to have an opportunity to hear how she can change that, and then get a bit of room to try. Otherwise you’re going to go on being frustrated by her, and might end up firing her at some point — and it’s not fair to do that without first having been straightforward with her about what needs to change. But even if it doesn’t get to that point and you keep her on, it’s still in her best interests to understand what she needs to do differently in order to build the kind of professional reputation that she probably hopes to build — to get the assignments and recognition she’d probably like, and come out of this job with a glowing reference rather than a lukewarm one.
If she can’t or won’t make the changes you want, you’ll still be doing her a favor by letting her know where she stands, so that she’s not confused or blindsided by it later.
(One caveat here: You’ve referred to her both as an employee and as a contract worker. If she’s a freelancer in the usual sense of the term, you don’t have the same obligations to give feedback and try to develop her skills and work habits as you’d have if she were a regular employee. But if you consider her a team member — in other words, if this is a role where you normally give feedback and coach people, rather than just not sending freelancers more assignments if they’re not working out — all of the above applies.)
Now, let’s talk about your reluctance to cut ties if that starts to look like the right move. It’s hard to let anyone go under the best of circumstances, and it’s even harder if you know they’ve had personal struggles. One thing you might remind yourself of: She’s told you she’s “desperate” for the job, but she also hasn’t taken you up on pretty easy ways to improve her performance (like volunteering for ideas you send around, after she complained she can’t come up with her own). You can’t care more about her job than she does.
But most importantly, if you follow the advice above and talk with her openly about the problems you see and what she needs to do differently, you’re giving her a chance to meet the job’s requirements. She’ll have the benefit of hearing clearly that she’s not where you need her to be, and a clear, explicit explanation of what you need from her instead. She may rise to the occasion as a result — sometimes people do! But if she doesn’t, she’ll have a clear warning that her work with you could be in jeopardy, so it won’t come out of nowhere if you do need to let her go.
That still won’t make it easy — but it does make it open, fair, and transparent, and that’s the best way to navigate this as a manager.
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