Should I hire W-2 or contractor? (small business)

Top picks

Protocol

1. 1

   Paste facts (5–8 min).

   Assemble only what you actually know. Mark gaps [MISSING] / [NEED FACT]. Do not invent rates, BATNA, legal outcomes, or benchmarks. Distinct from job-posting-from-role-notes: that assumes you already decided to hire. This small-business tree is the classify-then-hire gate. Paths are leans from your paste, not determinations.

   Paths at a glance

   Path	Lean this way when (from your paste)
   A — W-2 lean	You need to control how/when/where work is done; ongoing role; tools/benefits/integration look employee-like per your facts.
   B — Contractor lean	You control mainly the result; worker sets methods; provides own tools; time-bounded deliverable—per facts you paste.
   C — Restructure as project	Need is real but role shape is ambiguous—buy a scoped deliverable first instead of an open-ended hire.
   D — Don't hire yet	Overtime, deferral, or process fix covers the gap; classification facts incomplete → [NEED COUNSEL] / [MISSING].

2. 2

   Lock decision-tree rules (step 2).

   Paste the rules first so the model cannot mint a legal determination, tax savings, or a safe classification.

   Copy-paste prompt

   Copy

   Help me run a W-2 vs CONTRACTOR decision tree for one role/need.
   Hard rules:
   - Use ONLY control/independence facts I paste. Do not invent legal outcomes, tax savings, penalties, or safe classifications.
   - Frame IRS-style categories (behavioral, financial, relationship) as a READING AID for my facts—not a determination.
   - Mark state-law issues [NEED COUNSEL]. Not legal, tax, or HR advice.
   - Paths: Path A W-2 lean / Path B Contractor lean / Path C Restructure as project / Path D Don't hire yet.
   - Do not pick for me. No invented rates or headcount ROI.
   Confirm in one sentence, then wait for my pack.

3. 3

   Fill pack (step 3a) and generate (step 3b).

   Paste the pack, then send the generate command. The model must not pick a path for you.

   Paste pack

   Copy

   ROLE / NEED IN PLAIN LANGUAGE: [ ]
   DURATION (ongoing role vs time-bounded project): [ ]
   BEHAVIORAL CONTROL FACTS (who sets hours, methods, training, where work happens): [ ]
   FINANCIAL CONTROL FACTS (who provides tools, expenses, how paid, opportunity for profit/loss): [ ]
   RELATIONSHIP FACTS (benefits, exclusivity, key-to-business, written agreement notes): [ ]
   STATE(S) WHERE WORK IS PERFORMED: [ ] → flag [NEED COUNSEL] for state tests
   TEMP / AGENCY OPTION I ACTUALLY HAVE: [or NONE]
   CAN I RESTRUCTURE AS A FIXED-SCOPE PROJECT?: [yes/no + notes]
   ALTERNATIVES TO HIRING (overtime, defer, automate)—real only: [or NONE]

   After you send the filled pack, copy the Generate command in the next box and paste it into the SAME chat so the AI runs the decision tree / produces the output.

   Generate command — copy and send this next (same chat)

   Copy

   Build the decision tree now:
   1) Facts vs [MISSING]
   2) Scorecard table: Criterion | My fact | Lean (+/0/− or NEED FACT) | Note
   3) Path A W-2 lean / Path B Contractor lean / Path C Restructure as project / Path D Don't hire yet — for each: when it fits, what must be true from my pack, 3 owner-verify bullets
   4) Do NOT pick for me. Do not invent facts.

4. 4

   Choose a path (step 4); optional wording.

   Only after you pick a labeled path. Owner-verify: facts still match your pack; [MISSING] gaps filled or accepted; any sendable wording uses only terms you authorize.

   Path wording

   Copy

   I chose Path [A/B/C/D]. Draft a short internal decision note (not a legal opinion) summarizing my pasted facts and next owner steps.
   If Path A/B, list what I still need from counsel/payroll. No invented compliance claims.

5. 5

   Second-model check (step 5).

   In the other tool, paste the tree plus your fact pack:

   Second-model check

   Copy

   Here is a W-2 vs contractor tree from another assistant plus my fact pack.
   Find: (1) invented legal determinations or tax savings, (2) missing [NEED COUNSEL] where state rules matter, (3) control facts twisted to force contractor status, (4) any prescription presented as law.
   Return only corrections. Not legal advice.

6. 6

   Human decide and act (step 6).

   Pick one path. Fill [NEED FACT] gaps from real sources. Send or implement yourself—AI drafts are not approvals, contracts, classifications, or tax elections. After a W-2 lean, use the job-posting how-to for the public posting.

When not to

• Not legal, tax, or HR advice. Misclassification risk is real—use counsel/payroll for determinations.
• Do not paste SSNs or full employee files into consumer AI tools.
• Union, government contractor, or counsel-owned classification reviews—use their process.
• Skip if you have no control/independence facts yet—write those down first.