Contractor Versus Employee Checklist
Contractor classification isn’t gray area – it’s black and white with expensive consequences. This Contractor Versus Employee Checklist ensures proper classification, protecting against audits, penalties, and reclassification nightmares. Know the difference, document properly, and sleep soundly knowing you’re compliant.
Control Factors
□ Who determines work hours?
□ Who sets the work location?
□ Who provides detailed instructions?
□ Who determines work methods?
□ Who sets deadlines and priorities?
□ Is there direct supervision?
□ Who controls the work sequence?
□ Are there required meetings?
□ Is approval needed for decisions?
□ Who evaluates performance?
□ Can worker decline assignments?
□ Is training provided/required?
Financial Arrangements
□ How is payment structured (hourly/project)?
□ Who provides tools and equipment?
□ Who pays for supplies?
□ Are expenses reimbursed?
□ Is there opportunity for profit/loss?
□ Can worker work for others?
□ Who bears financial risk?
□ Are benefits provided?
□ Is paid time off given?
□ Are taxes withheld?
□ Is there a guaranteed wage?
□ Who sets the pay rate?
Relationship Type
□ Is there a written contract?
□ What is the duration of relationship?
□ Is the work ongoing or project-based?
□ Is the worker integral to business?
□ Can either party terminate at will?
□ Are similar workers employees?
□ Does worker have own business?
□ Does worker advertise services?
□ Is worker available to public?
□ Does worker have multiple clients?
□ Is there exclusive arrangement?
□ What is industry standard?
Behavioral Indicators
□ Who sets work standards?
□ Is uniform or dress code required?
□ Must worker personally perform work?
□ Can worker hire assistants?
□ Who trains any assistants?
□ Who pays assistants?
□ Is worker subject to discipline?
□ Must worker follow procedures?
□ Who owns work product?
□ Are company resources used?
□ Is non-compete required?
□ Is worker listed as employee?
Legal Tests
□ Does worker pass IRS 20-factor test?
□ Does arrangement meet state law?
□ Is worker properly classified for tax?
□ Are labor laws being followed?
□ Is workers’ comp required?
□ Does worker have business license?
□ Is worker incorporated/LLC?
□ Does worker have insurance?
□ Are contracts properly structured?
□ Is documentation maintained?
□ Have audits been considered?
□ Is legal advice needed?
Risk Assessment
□ What is misclassification penalty?
□ Are there previous violations?
□ Is arrangement clearly documented?
□ Would arrangement pass audit?
□ Are similar workers consistent?
□ Is there regulatory scrutiny?
□ What is financial exposure?
□ Are there union considerations?
□ Is insurance coverage adequate?
□ Have complaints been filed?
□ Is reclassification needed?
□ Should legal counsel review?
Documentation Required
□ Written agreement specifying status
□ Business license verification
□ Insurance certificates
□ Tax identification numbers
□ Invoice requirements
□ Statement of work
□ Independent contractor agreement
□ W-9 or W-4 form
□ I-9 verification
□ Confidentiality agreement
□ Intellectual property assignment
□ Compliance certifications
Decision Factors
□ Weight control factors
□ Evaluate financial aspects
□ Consider relationship type
□ Review behavioral indicators
□ Apply legal tests
□ Assess risks
□ Document decision rationale
□ Implement appropriate structure
□ Monitor ongoing compliance
□ Review periodically
□ Adjust if needed
□ Maintain documentation
How the Contractor Versus Employee Checklist works
Input work arrangement details, control factors, and business relationship elements. The AI evaluates against IRS guidelines and state-specific rules. Generate a detailed contractor versus employee checklist with classification criteria, documentation requirements, and red flags. Create audit-ready justification packages.
Misclassification penalties start at $50 per W-2 plus back taxes and interest. Criminal penalties apply for willful violations. This checklist prevents costly mistakes that destroy businesses. It’s the systematic approach employment lawyers recommend.
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