Tax, Legal & Admin

I'm organizing my tax documents for [tax year]. I'm going to upload documents one at a time. For each one:\n\n1. Identify what type of document it is (W-2, 1099-NEC, 1099-INT, K-1, etc.)\n2. Extract the key information: payer/source, amount, tax ID\n3. Suggest a standardized filename: [Year]_[DocType]_[Source].pdf\n4. Add it to a running summary table with: document type, source, amount, status\n\nAfter I've uploaded everything, tell me:\n- Which common documents might be missing (based on what you see)\n- A summary I can forward to my accountant\n- Total income by category\n\nContext: I'm [filing status] with [income types].

Review this contract and give me a plain-English assessment:\n\n[upload or paste the contract]\n\n1. **What am I agreeing to?** (summary in 3-5 bullets — no legalese)\n2. **Term and termination** — How long is this for? How do I get out? Are there auto-renewal traps?\n3. **Financial terms** — What do I pay, when, and what triggers additional costs?\n4. **Liability and indemnification** — Am I taking on unusual risk? Is the liability balanced or one-sided?\n5. **IP and data** — Who owns what? Can they use my data? What happens to my data if I terminate?\n6. **Red flags** — Anything I should push back on or get my lawyer to review specifically\n7. **Missing provisions** — Anything a contract like this should have but doesn't?\n\nI'm the [buyer/seller]. Flag anything that's unusual or unfavorable for my side.

I have two versions of a contract — the original they sent me and the revised version after my edits. Compare them:\n\nOriginal: [upload or paste]\nRevised: [upload or paste]\n\n1. List every change, categorized as: favorable to me / unfavorable / neutral\n2. For each unfavorable change, suggest pushback language\n3. Are there any of my requested changes that were NOT incorporated?\n4. Overall: did the revision move in my favor, their favor, or balanced?

Here's a list of business expenses from [time period]. Categorize each one for tax purposes:\n\n[paste expense list — date, vendor, amount, description]\n\nFor each expense:\n1. **Category:** (Office supplies, Software/SaaS, Travel, Meals, Professional services, Marketing, etc.)\n2. **Tax deductible?** (Yes / Likely / Needs CPA review / No)\n3. **Notes:** Any flags (e.g., meals are 50% deductible, personal/business mixed use needs allocation)\n\nAt the end, give me:\n- Total by category\n- Total deductible amount (estimated)\n- Any expenses that look like they might be miscategorized or need receipts

I uploaded my [insurance type] policy. I'm paying [annual premium]. Help me understand what I have:\n\n1. **What's covered** (plain English, not policy language)\n2. **What's NOT covered** (the exclusions and limitations that matter)\n3. **Deductibles and limits** (summarize the key financial exposure)\n4. **Gaps** — Given my situation ([your context]), what risks am I NOT covered for?\n5. **Questions for my broker** — What should I ask about before renewal?\n6. **Is this a reasonable price?** — Based on the coverage level, does this feel in line with typical policies of this type?

Review this NDA and answer these specific questions:\n\n[upload NDA]\n\n1. Is this mutual or one-way? If one-way, who's protected?\n2. What's the confidentiality period? (during the relationship and after termination)\n3. What's excluded from confidential information? (standard carve-outs present?)\n4. Is there a non-solicit or non-compete buried in here? (some 'NDAs' sneak these in)\n5. What jurisdiction/governing law?\n6. Can I sign this as-is, or should I request changes?\n\nKeep the response under 200 words. I've seen a hundred NDAs — just tell me if this one has anything weird.

Draft a [policy type] for my company. Context:\n\n**Company:** [company name], [size], [industry]\n**What prompted this:** [why you need this policy now]\n**Key requirements:** [what the policy needs to cover]\n**Tone:** Professional but not corporate — we're a [size] company, not a Fortune 500\n\nKeep it under [length]. Include an effective date placeholder and a version number. Make it practical — people should be able to read this in 5 minutes and know exactly what's expected.

I have a CSV export from my corporate card. Read the file at [file path] and:\n\n1. Categorize each transaction (use standard IRS categories)\n2. Flag any transactions over $500 that need receipts\n3. Flag potential personal expenses mixed in\n4. Generate a formatted expense report as a PDF\n5. Create a summary by category with totals\n6. Output a CSV that's formatted for upload to [accounting software]

I need to make sure my company is compliant with [regulation/requirement]. Create a checklist:\n\n**Company type:** [your company description]\n**Current state:** [what you think you're already doing]\n**Deadline:** [if applicable]\n\nFor each checklist item:\n1. What's required (plain English)\n2. What evidence/documentation I need\n3. Status: likely compliant / needs review / likely non-compliant (based on what I've told you)\n4. Priority: critical / important / nice-to-have\n\nSort by priority. Flag anything where I should definitely consult a specialist.