It happens to professionals across industries: you write, “Alex submitted their report ahead of the deadline,” and your grammar checker underlines their with a red squiggle—labeling it “pronoun-antecedent disagreement” or “inconsistent number.” You pause. You double-check. Alex is one person. You used they/them intentionally—not out of carelessness, but respect. Yet the tool insists it’s “wrong.” This isn’t a typo. It’s a collision between linguistic evolution and algorithmic inertia.
That red underline doesn’t reflect grammatical error—it reveals a gap between modern usage standards and the static training data baked into many AI writing assistants. Understanding that gap empowers you to use inclusive language confidently, correct misflagged suggestions, and even retrain your tools over time. This article unpacks the technical, historical, and practical reasons behind these false positives—and gives you concrete strategies to navigate them without compromising professionalism or integrity.
The Historical Roots of Singular ‘They’
Singular they is not new. It appears in the works of Chaucer, Shakespeare, Austen, and Orwell. In 1385, The Canterbury Tales includes: “And whoso fyndeth hym out of swich blame, / They wolde have thankes.” By the 18th century, prescriptive grammarians began discouraging it—not because it violated logic or clarity, but because they sought to impose Latin-based rules onto English, where Latin has no singular gender-neutral pronoun. Their preference for he as generic was never widely adopted in speech and collapsed under scrutiny by the mid-20th century.
What changed decisively was identity recognition. As nonbinary and gender-expansive people asserted their right to self-identification, they/them became the most widely accepted, linguistically natural, and socially respectful option for referring to individuals whose gender isn’t binary—or isn’t disclosed. Major institutions now endorse it: the Associated Press (2017), the Chicago Manual of Style (17th ed., 2017), the American Psychological Association (2020), and Merriam-Webster (2019 Word of the Year).
“Singular ‘they’ is one of the most common constructions in spoken English—and increasingly in formal writing. Its rejection reflects outdated norms, not linguistic deficiency.” — Dr. Anne Curzan, Professor of English Linguistics, University of Michigan
How Grammar Checkers Get It Wrong: The Data Problem
Most AI-powered grammar checkers—including those embedded in Microsoft Editor, Grammarly Free, and older versions of ProWritingAid—rely on statistical models trained on large corpora of published text. That training data skews heavily toward pre-2015 sources: academic journals, legal documents, corporate memos, and news archives where singular they was either rare or actively suppressed.
These models learn patterns like:
- Each student must submit his assignment → high-confidence “correct” pattern
- Every employee should update their profile → lower-confidence, flagged as “inconsistent”
The model sees “every employee” (singular) paired with “their” (plural form) and triggers its agreement rule—ignoring centuries of usage and current style guides. Worse, many tools lack fine-grained context awareness. They don’t distinguish between:
- Students left their books in the classroom (plural antecedent → correct plural their)
- Jamal prefers their workspace quiet (singular antecedent + intentional singular they)
Without access to real-time style guide updates or user-defined preferences, the tool defaults to conservative, legacy assumptions. It mistakes sociolinguistic progress for syntactic error.
Real-World Impact: A Case Study from Tech Communications
In early 2023, Maya R., a senior product manager at a SaaS company headquartered in Austin, drafted an internal announcement introducing her team’s new accessibility initiative. She wrote: “Taylor joined us last month and brings deep expertise in inclusive design. We’re thrilled to support their leadership in this work.”
Grammarly flagged their with “Pronoun-antecedent disagreement” and suggested “his or her” instead. Maya declined the suggestion—but when she shared the draft with her manager, he asked, “Is this technically correct? I don’t want HR to question it.” She spent 20 minutes compiling APA, Chicago, and AP citations before sending a follow-up email explaining why their was both accurate and ethically necessary.
The incident delayed the announcement by two days—and revealed a deeper issue: tools weren’t just flagging language; they were shifting the burden of justification onto marginalized employees. After Maya presented data to her company’s writing standards committee, they updated their internal style guide and disabled Grammarly’s pronoun agreement rule for all company-managed accounts. Within six weeks, team-wide adoption of correct singular they increased by 64%, per internal comms audits.
Actionable Strategies: What to Do When Your Tool Misfires
You shouldn’t have to defend basic linguistic competence every time you write an email. These evidence-based actions help you respond efficiently, educate colleagues, and reclaim control over your writing workflow.
Tip: In Microsoft Word or Outlook, right-click the flagged pronoun and select “Ignore Rule” — then choose “Ignore all instances of this rule in this document.” For permanent relief, go to File > Options > Proofing > Writing Style > Settings, and uncheck “Pronoun agreement.”Step-by-step: Customizing Your Grammar Checker
- Identify your tool: Is it Grammarly, Microsoft Editor, LanguageTool, or a custom enterprise plugin?
- Locate settings: Look for “Preferences,” “Style Guide,” or “Custom Rules” (often under account or editor settings).
- Disable or override: Turn off “Pronoun-antecedent agreement” or add an exception for singular they.
- Add a custom dictionary entry: Some tools (e.g., LanguageTool) allow you to define “they” as acceptable with singular antecedents via rule exceptions.
- Test & verify: Paste sample sentences (“Riley updated their calendar”; “Someone left their badge”) to confirm flags disappear.
Do’s and Don’ts for Professional Email Clarity
| Action | Do | Avoid |
|---|---|---|
| Introducing pronouns | Include them in email signatures: “Taylor Kim (they/them)” | Assuming pronouns based on names or appearance |
| Referring to unknown individuals | “If a client has questions, they can reply directly.” | “If a client has questions, he or she can reply…” (clunky, exclusionary) |
| Editing others’ drafts | Change “he/she” to “they” unless the author specifies otherwise | Inserting “(s)he” or “s/he”—these are not standard orthographic forms |
| Responding to flags | Cite your organization’s style guide or link to APA/Chicago guidance | Accepting “his or her” as default without questioning its impact |
| Training teams | Share a 90-second internal video explaining singular ‘they’ in your org’s voice | Requiring employees to “prove” their pronoun usage is valid |
Building Institutional Resilience: Beyond the Individual Fix
Fixing your own settings helps—but systemic change requires organizational literacy. Forward-thinking companies treat inclusive language not as a “preference” but as a component of communication compliance—like accessibility (WCAG) or data privacy (GDPR). That means integrating it into onboarding, editing workflows, and vendor evaluations.
When evaluating grammar tools, ask vendors three questions:
- “Does your model distinguish between generic singular they (e.g., ‘Everyone should bring their ID’) and specific singular they (e.g., ‘Sam uses their pronouns’)?”
- “When was your core training corpus last updated—and does it include post-2020 inclusive language corpora like the Gender-Inclusive Language Corpus (GILC) or APA’s Inclusive Language Guidelines?”
- “Can administrators disable pronoun agreement rules globally—or whitelist terms like ‘they,’ ‘them,’ and ‘their’ for singular contexts?”
If the answer to any is “no,” consider alternatives. LanguageTool (open-source, customizable), Hemingway Editor (lightweight, no aggressive pronoun policing), or the built-in accessibility checker in Google Workspace (which aligns with APA standards) offer more flexible, up-to-date frameworks.
FAQ: Addressing Common Concerns
Isn’t singular ‘they’ grammatically ambiguous? Could readers confuse whether I mean one person or multiple?
No—context eliminates ambiguity in nearly all cases. Compare: “The developer said they’d fix the bug” (one person, clear from “the developer”) vs. “The developers said they’d fix the bug” (multiple people). Human readers parse this instantly. In fact, studies show readers process singular they faster than clunky alternatives like “he or she.” Ambiguity arises only in poorly constructed sentences—never from the pronoun itself.
My boss says ‘they’ sounds unprofessional. How do I respond without sounding confrontational?
Cite precedent: “Major law firms like Latham & Watkins and global banks like HSBC use singular ‘they’ in client-facing materials. The U.S. Supreme Court used it in Obergefell v. Hodges. It’s not informal—it’s precise, inclusive, and legally sound.” Then pivot to impact: “Using the correct pronouns reduces turnover risk, strengthens trust with diverse clients, and aligns with our DEIB commitments.”
What if I accidentally misgender someone—even with good intentions?
Correct yourself briefly and move on: “Thanks, Jordan—I meant they,” then continue the conversation. Over-apologizing draws attention and creates discomfort. Under-apologizing dismisses impact. A single-sentence correction signals accountability without centering your feelings. If it happens repeatedly, review your note-taking habits: record pronouns in contact fields (e.g., Slack bios, CRM notes) and use autocomplete tools like Pronouny or NameDrop.
Conclusion: Language Is Infrastructure—Treat It With Intention
Grammar checkers are tools—not arbiters. When they mislabel singular they, they expose not your error, but their limitations: outdated data, insufficient nuance, and failure to evolve alongside human expression. You don’t need permission to use language that affirms dignity, reflects reality, and communicates clearly. What you do need is the knowledge to act decisively—to customize your tools, cite authoritative standards, educate thoughtfully, and lead by example.
Every time you decline a false “correction,” you reinforce that professionalism includes precision *and* respect. Every time you update a team style guide, you make inclusion operational—not aspirational. And every time you normalize “they” in a board memo or client proposal, you expand what “formal English” can be.
💬 Your voice matters in shaping workplace language. Share this article with your comms lead, IT admin, or DEIB council—and tag one colleague who’s navigated this exact red-squiggle moment. Let’s build tools—and cultures—that get it right.
