You fired an employee last Tuesday. You had your reasons. She was late constantly, rude to customers, and last week she told a coworker to go to hell in front of a dining room full of guests.

Open and shut, right?

Then the demand letter arrives. She’s claiming discrimination. Her attorney wants every document you’ve ever created about her employment. Performance reviews. Coaching notes. Write-ups. Witness statements.

You pull the file. It’s thin. One offer letter. A signed handbook acknowledgment. And a termination notice dated last Tuesday.

That’s it. That’s your whole defense.

Welcome to the paper trail. Or in your case, the lack of one.

This is what I see every single week. Not bad employers. Not people who wanted to break the law. Just business owners who were too busy running the business to document what was happening inside it. And now they’re sitting across from me, trying to reconstruct months of conversations, coaching, and warnings from memory.

Memory doesn’t win lawsuits. Paper does.

I’ve been practicing employment law for years. I’ve represented employers in investigations, audits, mediations, and trials. I’ve helped businesses build HR systems from scratch and I’ve helped them dig out of the wreckage when those systems didn’t exist.

Here’s what I’ve learned: the difference between an employer who wins and one who writes a check almost never comes down to whether they did something wrong. It comes down to whether they can prove they did something right.

That’s the paper trail. That’s what this newsletter is about.

Welcome back to Done Right. Every week, this newsletter breaks down one employment law topic in plain English. No legalese walls. No “it depends” without telling you what it depends on. Just the rules, the risks, and the real-world steps you need to take to protect your business.

This first series is called Paper Trail to Hell, because that’s exactly where you end up when the documentation doesn’t exist. We’re starting with the single most important topic in employment law: your paper trail.

We cover wage and hour compliance, harassment prevention, documentation, discipline, termination, hiring, leave management, and everything in between. We focus heavily on New York and New Jersey law, and we pay special attention to hospitality employers because that’s where the stakes are highest and the margins for error are thinnest. 

Here’s the truth that every employment attorney knows and most employers learn too late: in a courtroom, in a mediation, in a Department of Labor audit, the only things that exist are the things you can prove.

You told her she was late too many times? Prove it. You coached him on his attitude? Show me the note. You warned the whole team about the new policy? Where’s the signed acknowledgment?

It doesn’t matter what you said. It matters what you wrote down.

This isn’t about being paranoid or bureaucratic. It’s about being professional. The same way a doctor charts every patient interaction and a contractor documents every change order, an employer needs to document every meaningful employment event.

And “meaningful” is broader than you think. It’s not just write-ups and terminations. It’s:

All of it. All documented. All in the file.

Not all documentation is created equal. After years of litigation, I can tell you there are five categories of records that come up in virtually every employment dispute. These are the files that judges ask for, auditors demand, and plaintiff attorneys pray you don’t have.

Everything related to the employment relationship: offer letter, handbook acknowledgment, job description, performance reviews, coaching memos, written warnings, commendations, and any changes to role, pay, or schedule.

Hours worked, wages paid, overtime calculations, tip credits, meal break records, and pay stub copies. New York requires employers to maintain these for six years. The federal requirement is three years, but if you’re in New York, the state wins.

Proof that employees received required training: sexual harassment prevention (annual in New York), safety training, policy acknowledgments, and any role-specific compliance training. Dates, attendees, and content covered.

Every complaint received, the investigation conducted, the findings, and the corrective action taken. This file should be separate from the personnel file and access-restricted.

ADA accommodation requests, FMLA paperwork, doctor’s notes, interactive process documentation, and any medical information an employee has shared. This file MUST be separate from the personnel file under federal law.

_{[Note: This is a hypothetical scenario based on common employer mistakes, not an actual case.]}

A popular brunch spot in Williamsburg employed about 30 servers, bartenders, and kitchen staff. One of their senior servers, employed for two years, had been a growing problem. Showing up late, taking extended breaks, snapping at newer staff during busy shifts. Three different managers had spoken to her about it at various points. “Come on, you know better than this.” “We need you to step it up.” “This can’t keep happening.”

No one wrote any of it down. Not once.

In November, the server filed an internal complaint alleging that the kitchen manager had made sexually suggestive comments to her. The owner asked the accused manager about it. The manager denied it. The owner decided it was a “he said, she said” situation and took no further action. No investigation. No documentation of the complaint or the response.

Two weeks later, the owner terminated the server for “ongoing performance issues.”

The server filed a retaliation claim with the EEOC, alleging she was fired for making a harassment complaint. Her attorney requested the personnel file. It contained an offer letter, a W-4, and the termination notice.

No performance documentation. No coaching memos. No investigation file. No record that anyone had ever spoken to her about performance concerns before the complaint.

The EEOC found reasonable cause. The restaurant settled for $85,000 plus two years of compliance monitoring.

The performance problems were real. Every manager in the building knew it. But knowing it and proving it are two different things.

^{[Note: This is a hypothetical scenario illustrating best practices, not an actual case.]}

A boutique hotel group in Jersey City employed about 80 staff across two properties. Their HR coordinator had implemented a simple documentation system: every significant employee interaction got a brief written summary, emailed to the employee’s file within 24 hours.

One of their front desk associates had been struggling. Arriving late two to three times a week. Failing to complete the nightly audit checklist. Getting guest complaints about abruptness.

The HR coordinator documented each incident. Quick emails, two to three sentences each. “Met with David today regarding his 9:15 arrival for his 9:00 shift. This is the third late arrival this month. David acknowledged the issue and committed to improvement. Next review: two weeks.”

At the 30-day mark, a formal coaching memo. At 60 days, a written warning with a performance improvement plan. David signed both. His file showed a clear, consistent, escalating pattern of documented concerns and documented opportunities to improve.

On Day 85, David filed a complaint alleging his supervisor had made a racially insensitive comment. HR immediately opened an investigation, documented every interview, and substantiated the complaint. The supervisor was disciplined.

On Day 95, David missed three consecutive shifts without calling in. The hotel terminated him for job abandonment per their documented attendance policy.

David’s attorney filed a retaliation claim. The hotel’s attorney responded with a 40-page personnel file: three months of consistent documentation, coaching memos, a signed performance improvement plan, the investigation file showing the complaint was taken seriously and acted upon, and the attendance records showing three consecutive no-call no-shows after the investigation was already completed.

The claim was withdrawn. Total legal cost: one attorney letter.

This is the mental model I want you to take from this article and carry into every employment decision you make.

Before you coach someone, ask: what will the file say?

Before you terminate someone, ask: what story does this file tell?

Before you respond to a complaint, ask: will the file show we took this seriously?

The file is your witness. It’s the one witness who never forgets, never changes their story, and never gets nervous on the stand.

Here’s what your file should show for every employee, at minimum:

Offer letter, signed handbook acknowledgment, WTPA wage notice (signed), job description, and proof of all required first-week training. (Remember: I-9s go in a centralized I-9 folder by year, not in the individual personnel file.)

Performance reviews (at least annual), coaching memos for any issues, written recognition for good work, any changes to role or compensation with signed acknowledgment, and records of all required ongoing training.

Every documented conversation about performance or conduct concerns, progressive discipline records, signed acknowledgment of warnings, improvement plans with specific goals and timelines, and the employee’s response or rebuttal.

The termination decision memo (why, when, who was involved), final paycheck records, benefits information provided, return of property documentation, and any separation agreement.

If you’re in hospitality, documentation isn’t just important. It’s survival.

Restaurants, bars, and hotels face the highest concentration of wage and hour claims, harassment complaints, and DOL audits of any industry. Your workforce is large, your turnover is high, your schedules are chaotic, and half your managers were promoted because they’re great with food or guests, not because they’re great with paperwork.

That’s exactly why the paper trail matters more for you than anyone else.

Hospitality-specific documentation priorities:

This article is a starting point. Over the next 40 weeks, Done Right is going to walk you through every major employment law topic that affects your business. The Paper Trail to Hell series continues next week, and then we’re branching into:

We’re also partnering with the Queens Chamber of Commerce for a monthly webinar series covering these topics live, with downloadable resources and Q&A. More details coming soon.

I called this series Paper Trail to Hell for a reason. Because that’s where you end up when the paper trail doesn’t exist.

Every lawsuit I’ve ever defended, every audit I’ve ever navigated, every mediation I’ve ever sat through comes down to the same question: what does the file say? Not what do you remember. Not what you meant to do. Not what your policy manual says you’re supposed to do. What does the actual, physical, documented record show?

The employers who win are the ones who build the file before they need it. Five minutes a day. A quick email after a coaching conversation. A signed acknowledgment after a policy change. A dated note when something goes sideways.

It’s not glamorous work. It’s not the reason you got into business. But it’s the thing that keeps you in business when someone decides to make your life difficult.

The paper trail starts here. And it starts with you.

Keep fighting the good fight.

_{Legal Disclaimer: This article provides general information about employment law documentation best practices and is not legal advice. Every situation is unique. For specific guidance on your circumstances, consult with an employment attorney licensed in your jurisdiction. Attorney Advertising}