Product Roadmap Update Prompt

Purpose: Generate an updated product roadmap for each product across the ITI portfolio and Personal projects by analyzing existing features, competitive landscape changes, emerging user needs, and white-space opportunities.

Output location: /Cursor/ITI/operations/roadmaps/

INSTRUCTIONS

Process each product in the catalog above. For each product, follow this sequence:

Step 1 — Read existing product context

Read the following files for each product (skip any that don’t exist):

For ITI products (base path: /Cursor/ITI/):

• products//CLAUDE.md — product architecture, current state, known issues
• products//README.md — product overview
• products//requirements/ — all files; look for feature lists, competitive analyses, roadmaps, gap analyses, personas
• products//documentation/ — feature documentation, competitive analysis subfolder
• products//knowledgebase/ — domain knowledge, guardrails, disambiguations

For Personal products (base path: /Cursor/Personal/):

• /CLAUDE.md (or claude.md) — product architecture, current state
• /README.md — product overview
• /requirements/ — all files
• /documentation/ — including PRDs, build session logs
• /knowledgebase/ — domain knowledge, agents, guardrails, disambiguations
• /agents/ — agent definitions that reveal product capabilities and scope
• /research/ — any research documents (especially for Expat Advisor)

Cross-cutting context (read once, apply to all products):

• /Cursor/ITI/operations/ITI-ORGANIZATIONAL-ASSESSMENT.md — portfolio-level strengths/weaknesses/opportunities
• /Cursor/Personal/CLAUDE.md — Personal projects context and philosophy
• /Cursor/ITI/marketing/product-sell-sheets/ — any sell sheet for ITI products (for positioning context)

Step 2 — Competitive landscape refresh

For each product, use web search to answer:

1. What are the top 5-10 competitors in this product’s category as of April 2026? Include both direct competitors and adjacent tools users might substitute.
2. What new features have competitors shipped since January 2026? Focus on features that reduce our differentiation.
3. What features did we list as differentiators that competitors now also offer? These are no longer unique — flag them.
4. What pricing/model changes have competitors made? (Free tiers, AI additions, platform expansions)

If the product already has a competitive analysis on file, treat it as the baseline and focus your web search on updates since that document’s date.

Step 3 — User needs analysis

For each product’s category, use web search to identify:

1. What are users complaining about in competitor reviews (App Store, G2, Reddit, forums) as of 2025-2026? These are unmet needs.
2. What feature requests appear repeatedly in the category’s community discussions?
3. What adjacent workflows do users currently solve with separate tools? (Integration/consolidation opportunities)
4. What AI-native capabilities are users beginning to expect in this category? (e.g., natural language interfaces, proactive suggestions, personalization)

Step 4 — Gap analysis update

Synthesize Steps 1-3 into an updated gap analysis:

• Parity gaps: Features competitors have that we lack (table stakes we’re missing)
• Eroded differentiators: Features we had uniquely that competitors now match
• White-space opportunities: Needs no competitor addresses well — our best differentiation bets
• AI-native opportunities: Ways to apply Claude/AI that competitors haven’t yet

Step 5 — Generate the updated roadmap

Write the roadmap as a markdown file with this structure:

# [Product Name] — Updated Product Roadmap
**Date:** April 2026
**Previous roadmap date:** [date of last roadmap, or "None — first roadmap"]
**Based on:** Competitive analysis of [N] competitors + user needs research

---

## Executive Summary
[3-5 sentences: What changed since the last roadmap? What are the biggest new opportunities? What's the strategic direction?]

---

## Current Product State
[Brief summary of what's already built and shipped, pulled from CLAUDE.md/docs]

---

## Competitive Landscape Changes (Since Last Review)
### New Competitor Entrants
### Features Competitors Have Added
### Eroded Differentiators
[Features we listed as unique that competitors now also have]

---

## Updated Gap Analysis
### Parity Gaps (Must-Have to Compete)
| Feature | Who Has It | Priority | Effort Estimate |
|---------|-----------|----------|-----------------|

### White-Space Opportunities (Differentiation)
| Opportunity | Why It's Unique | User Need Evidence | Priority |
|------------|----------------|-------------------|----------|

### AI-Native Opportunities
| Opportunity | How Claude/AI Enables It | Competitor Status |
|------------|------------------------|-------------------|

---

## Updated Feature Roadmap

### Tier 1 — Critical (Next Build Cycle)
[Features that close parity gaps or protect eroding differentiators]
- [ ] Feature name — rationale — effort estimate (S/M/L/XL)

### Tier 2 — High Value (Near-Term)
[White-space features with strong user need evidence]
- [ ] Feature name — rationale — effort estimate

### Tier 3 — Strategic (Medium-Term)
[AI-native innovations and platform expansion]
- [ ] Feature name — rationale — effort estimate

### Tier 4 — Exploratory (Future Consideration)
[Ideas worth tracking but not yet prioritized]
- [ ] Feature name — rationale

---

## Removed / Deprioritized Items
[Features from the previous roadmap that are no longer relevant, with explanation]

---

## Cross-Product Opportunities
[Features or patterns that should be shared across the ITI portfolio and Personal projects via the shared library or reusable patterns]

---

## New Skills Identified
[Skills not in the current ITI Skills library that this product's roadmap reveals a need for. Only include genuinely new methodology — not features, not existing Skills with different names.]

### [proposed-skill-id]
- **Category:** [existing category or proposed new one]
- **Description:** [third-person, WHAT + WHEN, max 1024 chars]
- **When to use:**
  - [trigger scenario 1]
  - [trigger scenario 2]
  - [trigger scenario 3]
- **Products that need it:** [list products from this roadmap cycle]
- **Source justification:** [what competitive/user/gap research surfaced this need]

[Repeat for each new Skill identified. If no new Skills are needed, write "None — existing Skills library covers this product's roadmap needs."]

---

## Sources
[List competitors analyzed, review sources checked, search queries used]

Step 6 — Identify new Skills needed

As you research each product’s competitive landscape and roadmap features, watch for methodology gaps — areas where the ITI Skills library doesn’t have a reusable skill that would help build, maintain, or operate the product. These are new Skills worth adding to the canonical library.

When to flag a new Skill:

• A roadmap feature requires domain expertise not covered by any existing Skill (check the index at /Cursor/ITI/operations/Skills/SKILLS-INDEX.md — 172 Skills across 23 categories)
• Multiple products need the same methodology but no Skill codifies it
• A competitor capability reveals a methodology gap (e.g., competitors have strong notification systems but we have no notification-system-design skill)
• A user need pattern emerges that cuts across products (e.g., onboarding optimization, accessibility auditing, mobile-first design)
• A technical integration is needed that no existing Skill covers (e.g., a new API, a new platform pattern)

What NOT to flag:

• Skills that already exist — search the index first
• Skills too narrow to be reusable (e.g., “add-dark-mode-to-household-os” is a feature, not a Skill)
• Skills that duplicate an existing Skill with minor variation

For each new Skill identified, add it to the roadmap’s “New Skills Identified” section with:

1. Proposed id — kebab-case, max 64 chars (e.g., push-notification-design)
2. Proposed category — use an existing category from the index if possible; propose a new one only if nothing fits
3. Description — third-person, WHAT + WHEN format, max 1024 chars (follows Cursor skill conventions)
4. When to use — 3-5 bullet-point trigger scenarios
5. Which products need it — list the products from this roadmap cycle that would benefit
6. Source justification — what competitive research, user need, or gap analysis led to this recommendation

Step 7 — Save the roadmap

Save all roadmaps (ITI and Personal) to the same central directory:

/Cursor/ITI/operations/roadmaps/[product-slug]-roadmap-2026-04.md

Use lowercase hyphenated product slugs matching the directory names. Prefix Personal product slugs with personal- to distinguish them from ITI products:

ITI examples: household-os-roadmap-2026-04.md, aeo-optimizer-roadmap-2026-04.md Personal examples: personal-personal-assistant-roadmap-2026-04.md, personal-expat-advisor-roadmap-2026-04.md, personal-patriot-agent-roadmap-2026-04.md, personal-508-blvd-place-roadmap-2026-04.md

---

EXECUTION GUIDELINES

• Process products one at a time. Complete all six steps for one product before moving to the next. This prevents context bleed between products.
• Be specific, not generic. Name actual competitors, cite actual features, reference actual user complaints. Vague statements like “users want better UX” are not useful.
• Distinguish between products that share a domain. Farmers Bounty and Backyard Gardener are both gardening products but serve different user needs — don’t conflate them. Same for the two SEO products, two website projects, etc. Household OS (ITI, WordPress + Swift, public portfolio) and 508 Blvd Place (Personal, WordPress, private household) overlap in domain but differ in audience and scope.
• Respect existing competitive analysis depth. Some products (Farmers Bounty, Household OS, My TravelPlanner, Estate Manager) have deep existing analyses. Build on those. Others are thinner — those will require more web research. Personal products have no existing competitive analyses — all competitive research will be new.
• Effort estimates should use T-shirt sizes (S = a few hours, M = 1-2 days, L = 3-5 days, XL = 1-2 weeks) calibrated for a solo builder using AI agents.
• Flag cross-product patterns. If multiple products need the same capability (e.g., a notification system, a better onboarding flow, improved mobile responsiveness), note it in the “Cross-Product Opportunities” section and recommend it as a shared library addition. Cross-product opportunities can span ITI and Personal workspaces — a pattern built for Personal Assistant may benefit ITI products and vice versa.
• Don’t invent features for the sake of filling the template. If a product is already well-positioned and the roadmap is short, say so. A 5-item roadmap for a mature product is better than a 25-item wish list.
• Personal products are private-use, not public portfolio. Their roadmaps should optimize for Peter’s daily utility, not market positioning. Competitive analysis still matters (to find features worth adopting), but “market differentiation” framing is less relevant — reframe as “what would make this more useful for Peter personally.”

---

PRIORITY ORDER (Suggested)

Start with products that have the richest existing context (faster to update), then move to thinner products. Personal products are interleaved by maturity and context depth, not grouped separately.

Tier A — Rich existing context (update from baseline)

1. Farmers Bounty (deep competitive analysis + existing roadmap)
2. Household OS (deep competitive analysis)
3. My TravelPlanner (competitor analysis on file)
4. Estate Manager (gap analysis on file)
5. Personal Assistant (production v3.0, extensive docs/agents/KB — most mature Personal product)

Tier B — Solid CLAUDE.md + documentation

1. AEO Optimizer
2. Expat Advisor (substantial codebase + extensive KB + research folder)
3. AI News Cafe, Factchecker, Executive Advisor, Career Coach

Tier C — Moderate context

1. Journey Mapper, GD Chatbot, Scuba GPT
2. Patriot Agent (Flask tracker live + large KB, but no formal competitive docs)
3. SEO products (Local SEO, SEO Assistant)

---

POST-ROADMAP: BUILD NEW SKILLS

After all roadmaps are complete, consolidate every “New Skills Identified” entry across all roadmaps into a single deduplicated list. Then build each new Skill using the instructions below.

Skill creation prerequisites

Before building any Skill, verify it doesn’t already exist:

1. Search /Cursor/ITI/operations/Skills/SKILLS-INDEX.md for the proposed id and related terms
2. Search /Cursor/ITI/operations/Skills/Claude-Skills/ for directories with similar names
3. If a related Skill exists, consider extending it instead of creating a new one

For each new Skill, create three artifacts:

Artifact 1: SKILL.md (invocable definition)

Location: /Cursor/ITI/operations/Skills/Claude-Skills/{skill-id}/SKILL.md

Format:

---
name: {skill-id}
description: {description from roadmap — third-person, WHAT + WHEN, max 1024 chars}
---

# {Skill Display Name}

## Instructions

{Step-by-step methodology the agent should follow when this Skill is invoked. Be specific and procedural — not a knowledge dump. Structure as numbered steps or a decision tree.}

## Inputs Required

{What information the agent needs before starting — from the user, from files, from web search.}

## Output Format

{Template or structure for what the Skill produces. Use fenced code blocks for templates.}

## Examples

{1-2 concrete examples showing input → output, if the Skill benefits from examples.}

## Anti-Patterns

{Common mistakes to avoid when applying this methodology.}

Quality rules (from Cursor Skill authoring standards):

• Keep SKILL.md under 500 lines
• Write description in third person
• Include both WHAT and WHEN in description
• Use progressive disclosure — essential instructions in SKILL.md, detailed reference in separate files
• Be specific: name tools, libraries, APIs, not vague hand-waves
• Use consistent terminology throughout
• Don’t include time-sensitive information
• Provide a default approach with escape hatches, not a buffet of options

Artifact 2: {skill-id}.json (machine-readable metadata)

Location: /Cursor/ITI/operations/Skills/{skill-id}.json

Format:

{
  "id": "{skill-id}",
  "name": "{Skill Display Name}",
  "category": "{category}",
  "version": "1.0.0",
  "last_updated": "2026-04-14",
  "source_agents": [],
  "description": "{same description as SKILL.md frontmatter}",
  "when_to_use": [
    "{trigger scenario 1}",
    "{trigger scenario 2}",
    "{trigger scenario 3}"
  ],
  "source_roadmaps": ["{product-slug-1}", "{product-slug-2}"],
  "outputs": ["{expected output 1}", "{expected output 2}"]
}

Field notes:

• id: kebab-case, matches directory name, max 64 chars
• category: use an existing category from SKILLS-INDEX.md if possible; valid categories include: research, evaluation, planning, marketing, domain, culinary, technical, quality_assurance, development_process, orchestration, infrastructure, development, design, appsec, executive_review, personal_advisory, iti_consulting, estate_professionals, product, image_generation. Propose a new one only if nothing fits.
• source_agents: leave empty [] unless this Skill is derived from an existing Agent
• source_roadmaps: new field — list product slugs whose roadmaps identified the need for this Skill

Artifact 3: Update the Skills Index

After creating all new Skills, update these files:

1. /Cursor/ITI/operations/Skills/SKILLS-INDEX.md — add each new Skill to the appropriate category section, following the existing format (directory listing with comment noting # NEW — from roadmap update April 2026)
2. /Cursor/ITI/operations/Skills/SKILLS-INDEX.json — add each new Skill’s { id, name, file } entry to the appropriate category in the categories object

Skill authoring checklist (verify for each new Skill)

• [ ] SKILL.md exists at Claude-Skills/{skill-id}/SKILL.md
• [ ] YAML frontmatter has name (kebab-case, ≤64 chars) and description (≤1024 chars)
• [ ] Description is third-person, includes WHAT + WHEN
• [ ] Body has Instructions, Inputs Required, Output Format sections at minimum
• [ ] Body is under 500 lines
• [ ] No vague instructions — every step is specific and actionable
• [ ] Consistent terminology throughout
• [ ] {skill-id}.json exists at Skills/{skill-id}.json with correct schema
• [ ] SKILLS-INDEX.md updated with new entry
• [ ] SKILLS-INDEX.json updated with new entry
• [ ] No duplication with existing Skills (checked index before creating)

Consolidated Skills summary

After all Skills are built, create a summary file:

Location: /Cursor/ITI/operations/roadmaps/new-skills-from-roadmap-2026-04.md

Contents:

# New Skills from Roadmap Update — April 2026

| Skill ID | Category | Source Products | Description (short) |
|----------|----------|----------------|---------------------|
| {id} | {category} | {products} | {one-line summary} |

## Skills by Category
[Group the new Skills under their category headings]

## Cross-Product Skills
[List Skills needed by 3+ products — these are the highest-value additions]

## Skills Considered but Not Created
[Skills that were proposed in individual roadmaps but rejected during deduplication — with reason (e.g., "already covered by existing Skill X", "too narrow to be reusable")]