os-new-item

name	os-new-item
description	Add a new item to any portfolio project. Reads the portfolio's CLAUDE.md for item name and template path. Creates the item folder from templates/item/, updates TRACKER.md. Works for any portfolio type (opportunities, ideas, articles, etc.).
user_invocable	true

/os-new-item — Add a New Item to a Portfolio

Generic skill for adding a new item to any portfolio project. Works for job opportunities, ideas, reading lists, or any other portfolio type.

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Step 1 — Identify the portfolio

If called from within an active portfolio session (i.e. os-start has already loaded a portfolio): use that portfolio's project path automatically.

If called standalone (no active portfolio context): read projects.md, filter to entries where **Type:** portfolio, and ask:

Which portfolio are you adding to?

1. [Portfolio Name]
2. [Portfolio Name]

Wait for selection.

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Step 2 — Read portfolio configuration

Read the selected portfolio's CLAUDE.md. Extract from the ## Portfolio section:

• **Item name:** — what a single item is called (e.g., opportunity, idea, article)
• **Items folder:** — where items live (e.g., opportunities/, ideas/)
• **Tracker:** — tracker file name (default: TRACKER.md)

Read the templates/[item-name]/[item-name].md file to understand what fields the item template expects.

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Step 3 — Gather inputs

Ask for the minimum needed to create a useful item record. Base questions on the item template fields. At minimum, always ask:

1. "What's the [item name] called?" (name or title)
2. "One sentence — what is it or why does it matter?"
3. "What's the first action you'll take on this?"

If the template has additional frontmatter fields (e.g., stage, fit, source), ask for those too — but only what's useful now. Don't ask for fields the user can fill in later.

If the user has already provided some of this in their message, don't re-ask.

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Step 4 — Generate the slug

Create a kebab-case slug from the item name: [key-words-from-name]

Examples:

• "Acme Corp — Senior PM" → acme-corp-senior-pm
• "A feature for async notifications" → async-notifications
• "The Art of Strategy by Dixit & Nalebuff" → art-of-strategy

Confirm the slug with the user before creating files.

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Step 5 — Create the item folder

Copy projects/[portfolio-name]/templates/[item-name]/ to projects/[portfolio-name]/[items-folder]/[slug]/.

Populate the main [item-name].md file with:

• Frontmatter filled from Step 3 inputs
• Body sections from the template, with what's known filled in and blanks left rather than guessed

Ensure these subfolders exist (create with .gitkeep if the template didn't include them):

• intelligence/meetings/
• intelligence/docs/raw/
• intelligence/chats/
• intelligence/notes/
• memory/
• people/
• context/

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Step 6 — Update TRACKER.md

Add a row to the active items table in the portfolio's TRACKER.md.

Use the stage from the item frontmatter (default to first stage if not set). Match the column format of the existing table.

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Step 7 — Update .current-session

Write to [workspace-root]/.current-session:

[Portfolio Name] / [Item Display Name]

Example: Ideas / Interview Follow-Up Engine

This makes the new item the active session context so subsequent skills (os-save, ctx-doc, etc.) target it automatically.

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Step 8 — Post-create actions (portfolio-declared)

Some portfolios declare an action to run automatically right after an item is created. Read the portfolio's CLAUDE.md ## Portfolio section for an **On create:** field. If it's absent, skip this step.

tailor-cv (job-opportunities)

When **On create:** includes tailor-cv, immediately tailor Simon's CV to the new opportunity so it's ready the moment the job is created — no separate skill run per application:

1. Capture the full JD. The opportunity needs the complete job description, not the 500-char screener excerpt.
   • Ask: Paste the full JD for [company] — [role] (or type "fetch" to try the source URL).
   • On paste: save it to [items-folder]/[slug]/intelligence/docs/raw/jd.md with frontmatter (type: job-description, company, role, location, source URL, captured date). Preserve the body as received; note any OCR/transcription artefacts in frontmatter rather than silently rewriting.
   • On "fetch": try WebFetch on the JD/source URL from the candidate file or frontmatter. If it returns the full JD, save as above. If it's blocked (LinkedIn and Greenhouse commonly block automated fetches), say so and fall back to asking for a paste. Never tailor from the screener excerpt — the swaps need the full JD to find truthful verbatim terms.
2. Run the tailoring. Apply /cv-tailored-to-job with projects/job-opportunities/context/cv.md as the base and the saved jd.md as the target. Write [items-folder]/[slug]/cv-[company].md per that skill's structure (Tailoring Summary table + per-change Before/After blocks, character-neutral-or-shorter swaps, surplus routed to the cover-letter section).
3. This is a draft for review, not a silent final. Auto-running skips the per-swap approval gate, so surface the Tailoring Summary table in the Step 9 confirmation and tell the user to review it before submitting.
4. Never block item creation on the CV step. If the base CV or the JD can't be obtained, skip tailoring, create the opportunity anyway, and flag exactly what's missing so the user can finish it manually.

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Step 9 — Confirm and suggest next step

Show the user:

[Item name] added: [Display name]
Folder: [items-folder]/[slug]/
Active session: updated → [Portfolio Name] / [Item Display Name]
[if tailor-cv ran: JD saved → intelligence/docs/raw/jd.md · CV tailored → cv-[company].md (N swaps — review the Tailoring Summary before submitting)]

Next: [most logical first action based on next_action field or Step 3 answer]

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Notes

• This skill replaces the need for portfolio-specific add skills (jobs-new-opportunity, ideas-new) over time. Those skills remain valid for portfolios that already use them.
• If the template folder doesn't exist, tell the user: "No template found at templates/[item-name]/. Create one first or run /os-project-design to set up the portfolio structure."