As a general rule, do not give advice to people who have not asked for it. However ...
Q: I recently switched jobs and have been training to use a complicated new computer system. The young woman helping me is terrific: kind, innovative and bright. While training, I learned that she was a teen mom and lifted herself from difficult circumstances. She is interviewing very soon for a better position in the company. But I’ve noticed that her grammar is occasionally poor, and I fear it may hold her back. Could I say something to her? She’s never asked for my advice, but we’ve talked about our desire for advancement. — Anonymous
A: Assuming “interviewing very soon” means … well, very soon, I picture an interaction like so: “Denise, you’re terrific, but your grammar stinks. Now, get into that interview room and knock ‘em dead!” You have just enough time to destabilize her, but not enough to teach her subject-verb agreement. Let’s try a different tack.
Write to the human-resources department, or whomever your co-worker is interviewing with, and praise her to the heavens. If she’s the Stephen Sondheim of computer trainers, let the gods of advancement know. Be specific about her ingenuity and underscore her drive to grow. (But leave out the “teen mom” business; she probably told you that in friendly confidence.)
Then, wait and see. She may get the job — bad grammar and all. But if she doesn’t, and you find yourself kibitzing with her again about career advancement, I hereby suspend my rule about not giving advice to people who haven’t asked for it (because usually, it just hurts their feelings without doing much good) and allow you a gentle step in that direction. “Denise, you are so talented. If you spiffed up your grammar, there’d be no stopping you.” If she takes the bait, suggest an adult education class. But if she doesn’t, let it go, OK?
This article originally appeared in The New York Times.