Reader: I recently joined a small team at a nonprofit. My supervisor is knowledgeable, hard-working, well connected, full of ideas and kind. Unfortunately, her documents are peppered with typos, and reading her emails is like solving a puzzle. As her program’s support person, I spend a lot of time deciphering and correcting her grammar mistakes. I don’t mind it, but I’m trying to come up with solutions to help her communicate more effectively. Our team is constantly buried in work, and fixing this one issue would make everyone’s life a little easier, especially hers.

I consider this an accessibility and equity issue. I believe in solutions and tools. She has a Grammarly account and regularly checks her work, which means that she is also aware of the issue and wants to correct it. I suggested getting a large monitor, as I suspect eyesight may be a factor, but it didn’t happen.

As her subordinate, I’m unsure how to go about this. The fastest solutions would add considerable work to my plate and could also come off as insulting and hand-holding. When I brought my concerns to another staffer, I was scolded for being inconsiderate. I know I can be a bit of an overbearing busybody. Whether it’s a solution or a reality check, I’m open to any suggestions.

Karla: There is a time for helping people improve, and a time for meeting them where they are.

If your boss were explicitly asking for your guidance and coaching on better communication, you could send back marked-up versions of her messages for her to approve, so she can see what she’s doing wrong. But that may be the burdensome, insulting approach you’re trying to avoid. And it’s possible your boss has reached the point where struggling to refine her writing skills produces so little improvement that it’s not the best use of her paid time and energy.

You might be right about this being an accessibility issue — but you might be trying to accommodate the wrong disability. If your boss has a processing condition such as dyslexia or dysgraphia, a larger monitor probably won’t help. Speech-to-text applications, as suggested by the Job Accommodation Network ( and, might help your boss dictate her thoughts more clearly, but even those results need proofreading.

But — hear me out — what if the most efficient accommodation for your boss is a human interpreter with a talent for distilling ideas into clear, concise messages?

You say you “don’t mind” correcting grammar and typos. Perhaps it comes easily to you, so you underestimate its importance and how challenging it is for others. But doing it makes your boss look good and helps her get her messages out — so maybe, instead of a nuisance task, you should start viewing it as an essential part of your support role.

Of course, even if your boss realizes writing isn’t her strong suit, offering to compensate for that weakness takes some diplomacy. One approach: Get in the habit of taking notes during all discussions and meetings. When she mentions needing to contact someone on a topic, offer to save her time by typing up your notes and sending them along for her review.

I understand if you’re not interested in becoming the office Babel fish, especially if you have your own ideas to promote. And your boss may insist on continuing to craft her own messages as a point of pride. But then again, she might be relieved at being able to hand off a chore, and if she comes to rely on your messaging skills, she might be willing to find ways to relieve you of some of your other tasks.

Allow me to riff on the client service credo: “Fast, cheap, good. Pick two.” In this case, the three options are smart, kind and well written. With your boss, you’re getting the first two. As someone whose day job revolves around helping people communicate clearly and correctly, I can tell you there are much worse bosses to have than smart, kind people whose grammar needs polishing.