ManiWe chase polish in business writing. We edit. We proofread. We run emails through tools that fix commas, tone, and style. We do this because neat writing signals care. It signals competence. Yet a new twist has arrived: an AI that does the opposite and is being dubbed ‘Anti‑Grammarly AI’. It adds small errors on purpose. You read that right.
A tool called Sinceerly, built by Ben Horwitz and others, spoofs perfection. It deliberately drops in tiny slips, a missing letter, a casual phrasing, or a quick “bet” instead of “best.” For many, those slips trigger a human reaction. They make the message feel real. They make the writer feel reachable.
I’ve led teams and run companies. I’ve also lived with the paranoia of a typo. Dyslexia made me hyper-aware of errors. I taught myself to triple-check every message. Still, when I experimented with “perfectly imperfect” outreach, something shifted. Response rates rose. People replied faster. They wrote back in plain language. They didn’t assume an algorithm wrote the first line for them.
Why this matters
First, people build trust with people. Second, our inboxes now hold automated content — AI-generated outreach, templated responses, and sterile newsletters. Those messages look polished. They also feel mass-produced. A small human slip can break that illusion. It signals a real person sits behind the send button.
Real-world example: a sales manager I know switched half of his outreach templates to include a natural typo or an informal closing. He then A/B tested the messages. The “imperfect” versions won. More recipients replied. More calls booked. He didn’t run the test forever. He controlled where and when to use those messages.
Practical business uses
– Sales outreach: Use sparing typos to reduce the “blitz” feel of mass email. Test results, then scale what works.
– Recruiting: Candidates often ignore polished recruiter messages. A casual note can start a two-way conversation.
– Customer care: Add small, human touches to follow-ups to show the reply didn’t come from a bot.
– Internal comms: When you want candid feedback, less polish invites more honesty.
How to use this responsibly
You won’t randomly add errors to every line. That ruins clarity and weakens brand. Instead, adopt rules. Test. Measure. Then refine.
First, pilot in low-risk channels. For example, split test outbound prospecting emails. Track reply rates, quality of replies, and conversion. Then expand to parts of the business where authenticity matters more than legal formality.
Second, keep your brand voice consistent. Your voice should still reflect your company values. Typos should read like human shorthand. They shouldn’t introduce confusion. Avoid mistakes that change meaning. Always preserve clarity where it counts: contracts, legal notices, financial reports, and formal customer refunds.
Third, train your teams. Marketing should understand when to use the tool. Sales must know not to rely on typos as the only lever. Your customer support team should never use purposeful errors for compliance-sensitive replies.
Security and risk: what your security team will say
Bring your security leaders into the conversation early. An experienced CISO will flag two things immediately. First, the risk of social engineering increases if you normalize errors. Attackers already mimic human mistakes to phish. Second, any extension that touches emails can introduce data risk. Treat the tool like any other vendor. Conduct a security review. Limit access by role. Log and audit usage.
An information technology executive should weigh integration and governance. Ask whether the extension stores message drafts or processes data in the cloud. A CIO leadership perspective will consider scale and support. Who maintains the extension? How does it update? What happens if it breaks? Here, CIO expertise pays off. Design controls and incident playbooks before broad rollout.
Ethics, accessibility, and perception
Do not ignore accessibility. Many readers rely on screen readers. Intentional errors can confuse assistive tech. Also, some audiences may interpret mistakes as disrespect or incompetence. Tailor usage to audience segments. For high-touch clients or regulated industries, skip the gimmick.
Measure, don’t guess
Put metrics in place before you start. Track open rate, reply rate, conversion, and sentiment. Use short test windows. Then iterate. If the numbers favor authenticity, scale the approach. If not, stop and learn.
Checklist for CEOs and senior leaders
– Pilot in a controlled setting.
– Include your experienced CISO and information technology executive in vendor review.
– Use your CIO leadership to set governance, data access, and rollback plans.
– Design A/B tests and measure outcomes.
– Train teams on when to use the tool and when to avoid it.
– Preserve clarity in formal, legal, and compliance contexts.
– Consider accessibility and audience sensitivity.
We live in an era when AI can make prose flawless. Yet our audience craves real connections. Small, deliberate imperfections can restore that link. They can humanize outreach and boost engagement. But they also introduce risk. As a CEO, balance curiosity with discipline. Test boldly. Govern tightly. And remember: authenticity wins when it feels honest, not engineered.
In short: treat “perfectly imperfect” tools like any strategic lever. Use them with intent. Measure their impact. Protect people and data. Do this right, and you’ll create messages that sound like a human — because they actually are.
Crafting a Business Strategy That Fits You
Business owners often compromise on personal time for their business. This sacrifice makes having a focused strategy even more crucial to maximize returns while minimizing wasted effort.
This “anti-Grammarly” idea teaches a startup to trade flawless polish for believable human voice. For example, small, intentional typos or casual phrasing can make cold emails feel like they came from a person, not a bot. Therefore teams should experiment in controlled A/B tests to find the right level of imperfection that increases opens and replies. However, the trick must match your brand and context so it never looks sloppy or unprofessional.
On the other hand, ignoring this lesson keeps your messaging sterile and forgettable. As a result, you may get lower engagement, weaker trust, and fewer organic referrals. Consequently, growth channels that depend on personal connection—like outreach, partnerships, and customer retention—can underperform. In short, deliberately humanized communication can be a small change with outsized impact, while omitting it risks slower, more costly growth.
From the Author
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Mani Masood
