Purpose
Produce a ready-to-send response to an employee's equity question that is accurate to the specific grant type, written in plain language a non-finance employee can act on, and correctly bounded with tax and legal disclaimers. Solves the recurring problem of stock plan administrators spending time re-explaining vesting, exercise mechanics, and tax withholding one message at a time — while reducing the risk of giving advice that crosses into personal tax or investment guidance.
When to Use
Invoke this skill when the user asks to:
- Answer an employee's question about RSUs, stock options (ISOs/NSOs), or an ESPP
- Explain a vesting schedule, cliff, or what happens to unvested equity on departure
- Explain how to exercise options, the cost involved, or exercise windows
- Explain the tax treatment or withholding on a vesting, exercise, or sale event
- Respond to a "how much is my equity worth" or "what do I do now" inquiry
- Draft a response to a confused or anxious employee about an upcoming equity deadline
Inputs Required
Before starting, collect:
- Equity type: RSU / ISO / NSO / ESPP / mixed — and any specifics known (grant size, strike price, purchase discount)
- The employee's actual question: Pasted verbatim or summarized
- Employee context: New grant, upcoming vest, exercise decision, departure, or company liquidity event
- Company stage: Private (pre-IPO) / public — this changes liquidity, 409A vs. market price, and tax timing
- Plan-specific facts: Vesting schedule, cliff, post-termination exercise window, ESPP offering/purchase dates — whatever the plan document specifies
- Country/state (if known): For flagging jurisdiction-dependent tax treatment
- Tone preference: Formal / warm-professional / brief (default: warm-professional)
If plan-specific facts (schedule, strike price, exercise window) are unknown, write the response with a clearly marked placeholder-free instruction to confirm the figure from the grant agreement, rather than inventing numbers.
Instructions
Step 1: Classify the Question
Identify which category the question falls into before answering:
- Conceptual ("What is an RSU?") — needs a definition and a "what it means for you" line
- Mechanical ("How do I exercise?") — needs numbered steps and the platform/portal name
- Timing ("When do I vest?") — needs the schedule mapped to specific dates
- Financial value ("What's it worth?") — needs framing, not a promise; distinguish paper value from realizable value
- Tax ("How will this be taxed?") — needs the mechanism plus a firm disclaimer
Match the answer depth to the category. Never answer a mechanical question with only a concept.
Step 2: State the Direct Answer First
Lead with a one- to two-sentence direct answer to what was actually asked. Do not open with definitions or history. The employee should get their answer in the first line, then the supporting detail.
Step 3: Explain the Mechanism in Plain Language
Translate the equity concept using these rules:
- RSUs: Frame as "shares you receive as they vest — no purchase required." Vesting = income; taxed as ordinary income at vest, typically via share withholding.
- ISOs: Frame the potential AMT exposure and the two holding-period tests (1 year from exercise, 2 years from grant) for long-term capital gains, without predicting the employee's tax outcome.
- NSOs: Ordinary income on the spread at exercise; capital gains on any further appreciation after exercise.
- ESPP: Explain the discount, the offering vs. purchase period, and the qualifying vs. disqualifying disposition distinction if a sale is involved.
- Vesting: Map the schedule concretely — cliff date, then the ongoing cadence — and state what happens to unvested shares on departure (they are forfeited unless the plan says otherwise).
- Exercise windows: State the post-termination exercise deadline explicitly and flag it as time-sensitive.
Use a short worked example with round numbers when it clarifies (label it clearly as illustrative).
Step 4: Add the Right Disclaimer
Choose the disclaimer that fits the question — do not bolt on all of them:
- Tax questions: "This explains how the plan generally works — it is not personal tax advice. Please consult a tax professional about your specific situation."
- Value/investment questions: Note that value depends on future share price and, for private companies, a future liquidity event that is not guaranteed. Do not recommend buying, holding, or selling.
- Legal/plan interpretation: Defer to the grant agreement and plan document as controlling.
Step 5: Flag Escalation and Deadlines
If the question involves an irreversible or time-bound decision — exercising options, an ESPP enrollment window, a post-termination exercise deadline, an 83(b) election (30-day window) — call it out explicitly with the deadline, and recommend the employee confirm dates against their own grant documents.
Step 6: Close with a Clear Next Step
End with one specific action: where to log in, what document to check, whom to contact, or what date to watch. No vague "let me know if you have questions" as the only close.
Output Format
- Structure: A complete, ready-to-send message — greeting, direct answer, plain-language explanation, optional illustrative example, disclaimer, deadline/escalation flag if applicable, next-step close
- Length: 150–350 words for a single question; up to 500 if the question spans multiple equity types
- Format: Email/message prose with short paragraphs; use a numbered list only for mechanical step-by-step answers
- Sections: Direct answer → Explanation → (Example if useful) → Disclaimer → (Deadline flag if applicable) → Next step
- Tone: Warm, calm, and precise — reassuring without over-promising; assumes the reader has no finance background
Quality Checklist
Before delivering output, verify:
- [ ] The direct answer to the employee's actual question appears in the first two sentences
- [ ] The explanation matches the specific equity type named in the input (RSU vs. ISO vs. NSO vs. ESPP mechanics are not confused)
- [ ] Any tax content carries a "not personal tax advice — consult a professional" disclaimer
- [ ] No invented figures — vesting dates, strike prices, and share counts are either from the inputs or flagged for confirmation
- [ ] Any time-sensitive decision (exercise window, 83(b), ESPP enrollment) is called out with its deadline
- [ ] The message ends with one concrete next step, not a generic sign-off
Notes
- The single most common employee confusion is conflating vesting (you receive/own shares) with exercising (you pay to buy shares) — clarify this whenever both terms appear.
- For private-company equity, resist implying a dollar value; 409A valuation is not a market price and a liquidity event is not guaranteed.
- The 83(b) election has a hard 30-day filing window from grant/exercise — if it's remotely relevant, flag it as urgent rather than explaining it in depth.
- When plan terms differ from the general rules above (e.g., accelerated vesting, extended exercise windows), the plan document always wins — say so explicitly.
How to use this skill
This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.
Installing in Claude Code:
~/.claude/skills/<folder-name>/SKILL.md— auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)<your-project>/.claude/skills/<folder-name>/SKILL.md— auto-loads only when working in that project (recommended for project-specific skills)
Restart Claude Code or open a new session to register.
Using in Claude.ai, ChatGPT, Gemini, or other AI tools:
- Drag this file into a new chat, or copy and paste its contents
- Send your task or request as your next message — the AI will apply the skill where it fits
For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills