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In Work-Love With a Chatbot
Dear Work Friend:
Ever since my 40-year-old boss discovered ChatGPT, he’s running everything through it, even asking it to write drafts and analyze documents. I’m going on 60 and have spent my entire work life relying on my brain and bona fide resources to do my work.
Now, I’ll write up a draft of something, and I’ll hear, “OK, just run that through ChatGPT.” Or “Can you ask ChatGPT if XYZ?” I’ve explained that ChatGPT is NOT always correct, and have literally pointed to specific examples. Also, I’ll give him a draft of something that I wrote, and he’ll revise it, via ChatGPT, and ask me to review an often completely inappropriate, lengthy off-point rendition.
Help!
Anonymous
A tragic fact about bosses is that many of them have never built up a natural immune defense to “stupid ideas.” Because of this, a boss opening LinkedIn can be like a young child attending day care for the first time. An insufficiently immunized supervisor can send an entire business into a tailspin by merely glancing at a post consisting of single-sentence paragraphs.
That is, at least, what I suspect is happening here: He’s been so taken in by breathless columns, podcasts, and posts about the artificial intelligence revolution that he’s unable to distinguish between uses of A.I. that actually make sense for his business and counterproductive ones. Now you’re obligated to play along.
If you’re lucky, this will pass as he begins to understand what A.I. is good for and what it’s not. I’m not saying you should set your boss up for failure, but you might allow him to send out a few badly A.I.-rewritten emails, or attend a meeting with some hallucinated facts prepared, and see what the result is. Embarrassment is a pretty good teacher.
But if that doesn’t work, and A.I. is in your workplace to stay, you may have to become an A.I. enthusiast yourself — after a fashion. From your description, it sounds like your boss is more concerned with making sure you use A.I. at all than he is in the specifics of how you use it — which means you’re free to find the prompts and tools that make sense for the work you do. If he asks you to “run a draft through ChatGPT,” you don’t need to tell him that your prompt was “proofread this and don’t otherwise change it,” or “simply reproduce this exact text so I can tell my doltish boss that I ran the draft through ChatGPT without lying.”
But my real recommendation here is to turn to A.I. as an ally, not an enemy. Your boss clearly won’t listen to you, or to reason, or to experience. But there is one voice that does command his respect. Have you ever tried feeding your boss’ inappropriate, off point, A.I.-authored revisions of your draft back into ChatGPT, or, better yet, a competitor model like Claude, and asking it to review the text based on your specifications for length and topic? Sophisticated models — especially at the better, paid tiers — may not ever have the depth of experience that you do, but they’re good enough to tell when a draft is missing the mark, so long as you explain what the mark is.
It might feel vaguely insulting to have your boss rework your good drafts into unconvincing and meandering ChatGPT prose. But imagine the satisfaction of being able to return to him and say: Boss, the A.I. says this sucks.
Sidelined, but Why?
Dear Work Friend,
I have been working for my current employer for two years. During that time, I and a colleague have been assigned a project that has required little intellectual lift and less creativity. My colleague has presented herself as the manager on this project, even though I’ve been doing the work and taking the creativity as far as the client would allow.
This project has finally come to a successful completion, and even though I had been promised by the director that I’d be put on another, more creative project, instead I was informed that this colleague would be given the creative project. I was assigned another dull, maintenance-type project.
I’m an older employee. I’ve worked as a creative designer and design teacher for 30 years. I have multiple graduate degrees and have been recognized in the past, by other employers, for my work. On my own time, I’ve taught myself how to code using Claude Code and made exciting new projects for family and friends.
I’m left with wondering how I should proceed. If this is age discrimination, I cannot meet it head on, as no one is going to admit to that. If this is dissatisfaction with my work then I should ask at my performance review. Either path would put my manager and the director in an uncomfortable position that will probably backfire.
Is there anything I can do to highlight the work I’ve done without throwing my colleague under the bus? She is the golden girl on the team and I would look like the mean stepmother. How do I find out what the problem is without looking confrontational?
Thank you for any advice you might have for me.
— Old Mean Stepmother
No one wants to be seen as difficult, especially not older women, who face harsher social sanction for being too insistent or direct. It can feel much safer to be accommodating and compliant — you may not always get the credit or opportunities you deserve, but at least you won’t be seen as the “Old Mean Stepmother.”
But, let’s be honest, Lady Tremaine — the wicked stepmother in Cinderella — is not without her virtues. She may be evil and cruel, but she’s also shrewd, ambitious, capable and forthright. In the modern world, freed from the strictures of her patriarchal society and less reliant on her idiot daughters for advancement, one can imagine her ascending the corporate ladder rapidly and skillfully.
I’m not suggesting that you should embrace Lady Tremaine as a model for behavior, to be clear. But there are worse stereotypes to fulfill than “wicked stepmother.” For example “‘cool’ pushover mom,” like Amy Poehler’s character in “Mean Girls”: a cheerful chump, used by her conniving and ambitious daughter.
That’s the stereotype I’m worried you’ve backed yourself into here, given how avoidant you seem. If you want to find out what the problem is without looking confrontational, well, don’t wait until your performance review rolls around. Simply ask what the problem is without being confrontational. You might try something like: “Hey, boss, last time we spoke you promised me a shot at the Fun Creative Type Project, and now you’ve assigned me to the Dull Maintenance Type Project. Why?”
Does that feel confrontational to you? I hope not. If it does, I think you need to start recalibrating your sense of what “confrontation” entails. Your director broke a promise to you, and it’s entirely natural for you to ask for an explanation now, instead of waiting for “the right time.” If anything, I’d think your bosses would expect it.
Indeed, you should be hoping for more than the opportunity to “find out what the problem is,” especially if you suspect the answer will be unsatisfying. If you cannot hold your director to their promise, you can at least make it clear to them that breaking it imposes significant costs to your morale and commitment, not to mention their own sense of social ease.
Depending on how bold you’re feeling, you might say something like: “I was looking forward to working on Fun Creative Type Project, which I was promised and which I think would have been a good fit for my skill set.” Or, “I feel like I’m missing opportunities and it’s not clear to me why, given my credentials and experience.” Or: “I feel that my contributions on my previous projects are going overlooked.”
Would that be seen as confrontational? Perhaps. But being seen as potentially confrontational is not a wholly negative thing. It means that you are able to stand up for yourself even in awkward and uncomfortable situations — and that your colleagues and supervisors should be careful about breaking promises to you.
You worry that demanding an explanation might put your manager and director in uncomfortable positions. But why should you be the only one feeling uncomfortable?
And anyway, confrontation in the workplace is not the end of the world. Had you (mildly, carefully) confronted your colleague earlier over her credit-grubbing, you might not be in this position.
I don’t want to deny that being assertive in the workplace carries risk, especially if you’re worried about ageism. But your experience and knowledge are assets, not weaknesses. If you act from a defensive crouch, it makes age discrimination that much easier. (And, it’s worth saying: It’s never a waste of time to get a free consultation from an employment lawyer. Your bosses may not ever admit to age discrimination to your face, but you’d be surprised what can get turned up in discovery.)
Either way, I think you have overcorrected away from assertiveness so heavily that, so long as you don’t break down the door of your director’s office wielding a weapon, you have a lot of leeway to seek explanation (and perhaps redress) without it tipping over into “confrontational.”
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