how can I help my mentee set more realistic expectations about work?

A reader writes:

I’m writing for some advice on how to help my mentee set expectations at work. I work at a small educational site. Alice came to us through an independent living program for young adults with disabilities, and she was absolutely fantastic as a volunteer. She was extremely passionate about the work and already had independently picked up a bunch of extremely niche skills (for anonymity let’s say it’s reconstructing historical rice sculptures) that would normally take years of training, so most of the guidance I was giving her was more in relation to her soft skills and building confidence in her own abilities.

She also has A Lot going on in her personal life. It isn’t my place to go into any of the details but, long story short, she really needs to find an independent living situation away from her family.

I pushed hard for us to hire her. As a small nonprofit, we didn’t have full-time or permanent positions available, but we did have a part-time seasonal position at our sister site, which she took.

It hasn’t gone well.

Now, some of this is due to the fact that the site she joined is perpetually understaffed, so everyone there has to wear a bunch of hats. Part of it is due to the fact that the supervisor at that site has no expertise in her niche specialization and doesn’t realize how long projects like, say, rice sculptures should actually take. Part of it is because it’s her first job, and she doesn’t know how to say, “Six rice sculptures in a month is impractical, you’re getting four at most.” But some of it is more along the lines of, “She was asked to cover the front desk during someone else’s lunch, and this was Bad” or “She was asked to help with a school tour, and it was Bad.”

I can understand looking at the circumstances and saying, “This is more stressful than what I signed on for,” but she’s describing it to me as “an abusive hellhole” and … it’s just not that. It’s a little hectic, but if she pushed back on the unreasonable expectations, I know that the supervisor would agree. I’ve worked with the guy intermittently for three years. He’s perpetually overwhelmed, but he isn’t malicious.

And I feel bad about this on both ends, because Alice hates the job I pushed for her to get, and she isn’t doing that job well. I would still gladly write a reference for whatever she chooses to do after the seasonal position ends, but … I also wouldn’t push for her to be rehired, having seen how she’s handled it this time.

Since I supervised her as a volunteer, she looks up to me as a mentor. I’m trying to help her adjust her expectations and parse the difference between “hectic but unavoidable,” “bad management,” “actually abusive,” and “actually completely normal.” Do you have any advice?

There are two paths you could take here, and you could do either or both.

The first one is to just give Alice very calm, reality-based responses as things come up in the moment. For example:

Alice: “It’s ridiculous that Jim expects me to do six rice sculptures a month. There’s no way that’s possible.”
You: “Six a month is unrealistic, but he’s almost certainly relying on you to speak up and tell him if that’s the case. He hired you in part because you have expertise on this that he doesn’t have, and so he figures you’ll tell him what is and isn’t doable. Do you feel comfortable doing that? We can talk through how to have that conversation if you want.”
Alice: “It just seems bananas to me!”
You: “It’s pretty normal for your boss to need your input on what is and isn’t realistic. It would be a mistake to assume there’s no room for you to reset those expectations. In fact, part of doing your job well is sharing that perspective!”

Alice: “I can’t believe they asked me to cover the front desk during someone’s lunch.”
You: “I’m not that surprised by that. That kind of thing can be unavoidable at really small organizations.”

Alice: “It’s ridiculously chaotic here, I’m being pulled into X and Y and Z and they just expect me to do all of it.”
You: “It’s pretty normal at small organizations to be expected to wear a lot of hats — so that part isn’t surprising; it’s just the nature of the work. But they’re probably relying on you to speak up about how much you can and can’t get done; they won’t know unless you tell them, and there’s usually an assumption that you will speak up if you need help or have been assigned too much.”

Alice: “It’s an abusive hellhole!”
You: “Hmmm, from everything you’ve said it sounds like a pretty typical small organization. If it’s not for you, that’s of course completely legitimate. But I think it’s helpful to recognize that a lot of this is pretty normal, even if it’s not your cup of tea, so that you can calibrate your reactions and also so that you know what is and isn’t realistic to expect as you’re looking at other jobs.”

The other approach is to address it as a more big-picture conversation — framing it, for example, as: “I wanted to talk to you about how things are going at SisterOrg. I’ve noticed you seem pretty unhappy about things like X and Y, and I wanted to be straight with you that that stuff is really normal in this field. You can definitely decide you don’t like it and want to work in a field with different norms, but I worry when I hear you characterizing it as a hellhole, because I think you might be bringing some unrealistic expectations to the field.”

I’d probably go with the first path — calm, reality-based corrections in the moment — and see if they seem to affect her thinking or not. If they don’t, at that point you could move to the bigger-picture conversation.

It’s also worth remembering that you don’t have to solve this for Alice. It’s a kindness to give her candid, realistic feedback, but what she does with it from there is up to her. If she’s just not be in a place to hear it or accept it right now, that’s not a failing on your part.

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