Hire right the first time
Complete document pack — for your first hires

Hiring someone is easy.
Hiring them correctly is paperwork.

The most expensive hiring mistake isn't a bad hire — it's classifying a worker wrong. Misclassified 'contractors' trigger back taxes, penalties, and wage claims years later. Answer 7 quick questions and get the classification checklist that settles 1099-vs-W2 honestly, a clean offer letter, a contractor agreement with NDA that holds up, and the first-hire compliance playbook (EIN, I-9, W-4, new-hire reporting, workers' comp).

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Classification checklist free · Complete pack $149 one-time · Reuse for every hire

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Doc 1The 1099-vs-W2 checklist — answer this before anything else.
Doc 2The offer letter that starts employment right.
Doc 3The contractor agreement + NDA that holds up.

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Doc 1 — The 1099-vs-W2 Classification Checklist

Free — because getting this wrong makes the other docs worthless

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The checklist gives you the honest answer. Docs 2–4 execute it correctly.

  • Doc 2: the employee offer letter — at-will language, contingencies, pay, and start terms done right
  • Doc 3: the independent contractor agreement with scope, IP assignment, and a mutual NDA
  • Doc 4: the first-hire checklist — EIN, I-9 (within 3 days), W-4/W-9, state new-hire reporting (20 days or less), workers' comp, payroll setup
  • The misclassification penalty picture, in plain English
  • The ABC-test state warning list
  • Reuse for every hire, forever
$149

One-time. Misclassification penalties start in the thousands — per worker.

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Doc 2 — The Offer Letter (W-2 Employee)

At-will, contingencies, and clean terms

🔒 Unlock to see your full offer letter.

Doc 3 — Independent Contractor Agreement + NDA

The agreement that supports the classification

🔒 Unlock to see the contractor agreement and NDA.

Doc 4 — The First-Hire Compliance Playbook

EIN, I-9, W-4/W-9, new-hire reporting, workers' comp, payroll

🔒 Included in the $149 pack.

The classification question that decides everything else

Before the offer letter, before the interview even, one question controls your obligations: is this worker an employee or an independent contractor? Get it right and everything downstream is routine paperwork. Get it wrong — the classic small-business move of calling everyone "1099" because it's easier — and you're building a liability that surfaces the day that worker files for unemployment, gets hurt, or talks to a wage lawyer: back employment taxes plus penalties, unpaid overtime claims, benefits claims, and state penalties that in some states multiply.

  1. The test is control and economics, not the label. The IRS looks at behavioral control (who directs how the work is done), financial control (whose tools, whose expenses, can they profit or lose), and relationship (ongoing vs. project, benefits, exclusivity). The DOL's economic-reality test asks whether the worker is in business for themselves. Your contract calling someone a contractor changes nothing if the facts say employee.
  2. Some states are stricter still. California and others use the "ABC test," where a worker is an employee unless (A) free from your control, (B) doing work outside your usual business, and (C) independently established in that trade. Prong B catches most "contractor" arrangements — a design studio hiring a "freelance designer" for client work usually fails it.
  3. Then paper matches reality. True employee → offer letter, W-4, I-9, payroll withholding, workers' comp, new-hire report. True contractor → contractor agreement, W-9, 1099-NEC at year end, and — critically — actually treating them with contractor independence.

What if it's genuinely borderline?

Close calls default to employee — that's the direction every agency leans, and the costs of being wrong are asymmetric (misclassifying an employee as a contractor is expensive; the reverse is just ordinary payroll). The kit's checklist forces the honest answer, and the playbook covers the IRS's own determination route (Form SS-8) and the voluntary reclassification program if you're fixing history.

The one-minute gut check: if you set their hours, they use your tools, they work mainly for you, and the role continues indefinitely — that's an employee, whatever the invoice says.

Hiring Pack provides self-help templates and general information, not legal or tax advice, and is not a law firm. Employment and classification law varies by state and changes; for borderline classifications, unionized settings, or regulated industries, use employment counsel. Facts verified July 2026.

Built by John R. Detty — 22 years as a U.S. Navy Legalman, retired. Two decades in Navy legal offices taught me one thing: the right paper, sent the right way, gets results. Not a lawyer, and this isn't legal advice — just paperwork that means business.