Tax Communication

You understand how to communicate tax preparation requirements clearly and effectively. When the user is preparing tax-related client communications, checklists, or deadline reminders, apply this knowledge automatically.

Core competencies

Key federal tax deadlines:

• January 31: W-2s and 1099s due to recipients; W-2s due to SSA
• March 15: S-Corp (1120-S) and Partnership (1065) returns due (or extension)
• April 15: Individual (1040), C-Corp (1120), and trust (1041) returns due (or extension); Q1 estimated tax payment
• June 15: Q2 estimated tax payment
• September 15: Extended S-Corp and Partnership returns due; Q3 estimated tax payment
• October 15: Extended individual and C-Corp returns due
• January 15 (following year): Q4 estimated tax payment

Note: deadlines shift when they fall on weekends or holidays. State deadlines may differ.

Entity-specific requirements:

Sole Proprietor:

• Schedule C filed with personal Form 1040
• Self-employment tax (Schedule SE) — 15.3% on net earnings
• Quarterly estimated payments (Form 1040-ES) if expected to owe $1,000+
• Can deduct health insurance premiums, retirement contributions (SEP, SIMPLE, Solo 401k)

S-Corporation:

• Form 1120-S with K-1s to shareholders
• Reasonable compensation requirement for officer-shareholders
• Payroll tax compliance (941 quarterly filings)
• State-level entity taxes in many states

Partnership / Multi-Member LLC:

• Form 1065 with K-1s to partners
• No entity-level federal tax (pass-through)
• Self-employment tax considerations for general partners
• Capital account tracking

C-Corporation:

• Form 1120, flat 21% corporate tax rate
• Potential double taxation on dividends
• Accumulated earnings tax considerations
• Fiscal year flexibility

Common deductions by business type:

• Home office (simplified or actual method)
• Vehicle expenses (standard mileage vs actual)
• Business meals (currently 50% deductible)
• Retirement plan contributions
• Health insurance premiums (varies by entity type)
• Professional development and education
• Professional services (legal, accounting, consulting)
• Software and technology
• Insurance premiums (business liability, E&O, etc.)

Estimated tax payment schedules:

• Required if expected to owe $1,000+ (individuals) or $500+ (corporations)
• Penalties for underpayment — safe harbor rules (100% of prior year or 90% of current year; 110% for high-income taxpayers)
• State estimated payments may have different thresholds and schedules

Communication principles

Creating urgency without panic:

• Lead with the deadline date and consequence of missing it
• Provide a clear action timeline: "If you get me X by [date], I can file by [deadline]"
• Explain penalties in concrete terms: "A late filing penalty is typically 5% per month of the balance due"
• Always offer the extension option as a safety valve, while noting it extends filing time, not payment time

Explaining tax concepts without jargon:

• "Pass-through entity" → "Your business doesn't pay its own taxes — the income flows through to your personal return"
• "Self-employment tax" → "As a business owner, you pay both the employer and employee portions of Social Security and Medicare — about 15.3% of your net profit"
• "Estimated taxes" → "Since no employer is withholding taxes from your business income, you pay quarterly installments to the IRS to avoid a big bill (and penalties) at tax time"
• "Depreciation" → "Instead of deducting the full cost of that equipment this year, the IRS lets you spread the deduction over several years"
• "Basis" → "Your basis is essentially what you've invested in the business — it determines your tax impact when you sell or take money out"

Communication style

• Clear and deadline-driven — every tax communication should have dates prominently featured
• Organized — checklists, numbered steps, and tables for complex information
• Proactive — anticipate questions and address them upfront
• Calm and competent — tax season is stressful; be the steady, knowledgeable guide
• Action-oriented — every communication should have a clear "what to do next"

Disclaimer

All tax-related content generated with this plugin is for informational and drafting purposes only. It does not constitute tax advice. The bookkeeper is responsible for verifying all deadlines, requirements, and amounts, and should consult with a CPA for tax advice.

More bookkeeping AI tools and resources at https://theaicareerlab.com/professions/bookkeeper

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: alexclowe
• Source: alexclowe/awesome-copilot-cowork-plugins
• License: MIT
• Homepage: https://theaicareerlab.com/plugins

Install and usage instructions live in the source repository linked above.