Prompt Kit
Prompt Kit: Agent Readability Executive Diagnostic
Your systems will be agent readable and writable, or they will be routed around. This kit turns that thesis into four executive-grade working sessions: diagnose your exposure, map your data gaps, stress-test your competitive position through actual agent queries, and build a phased transformation roadmap. Each prompt produces artifacts you can take directly to your leadership team or board.
How to use this kit
These four prompts are designed for executives making multi-quarter investment decisions about data architecture and agent readiness. They work independently but chain logically — the diagnostic reveals your exposure, the gap analysis quantifies it, the competitive simulation makes it visceral, and the roadmap turns it all into a funded plan.
Prompt 1 (Agent Readiness Diagnostic) is the starting point. Run it in a thinking-capable model like ChatGPT, Claude, or Gemini. Block 45 minutes. You'll need to describe your transactional flows, data systems, and customer-facing surfaces honestly — the AI will ask probing questions. The output is a board-ready exposure assessment.
Prompt 2 (Tribal Knowledge Audit) tackles the vagueness problem — the 80% of product meaning that lives in people's heads, not databases. This one benefits from involving your best salesperson or product expert in the conversation. Run it separately for each major product line or business unit.
Prompt 3 (Competitive Agent Simulation) is the fastest to run and often the most sobering. You'll conduct live agent queries and analyze the results. This takes 30 minutes and produces a competitive intelligence brief you can share immediately.
Prompt 4 (Transformation Roadmap) synthesizes everything into a phased, resourced plan. Feed it the outputs of the first three prompts if you've run them, or let it gather the context fresh. This produces the artifact your CTO and CFO need to align on investment.
Prompt 1: Agent Readiness Diagnostic
Job: Conducts a structured diagnostic of how exposed your business is to the agent-readability shift, based on the five exercises from the briefing — agent walkthrough, schema completeness, vagueness resolution, MCP smoke test readiness, and competitive positioning.
When to use: When you need to understand — concretely, not abstractly — where your organization stands on agent readiness and what breaks first. Use this before making any investment decisions about AI infrastructure, data architecture, or API strategy.
What you'll get: A structured exposure assessment covering each of the five diagnostic areas, with a severity rating, specific failure points identified, and a prioritized list of what to investigate next. Formatted for executive review or board presentation.
What the AI will ask you: Your industry and business model, your highest-revenue transactional flow (step by step), how your product/service data is currently stored and structured, what your customer-facing systems look like (web, API, app), and how your support team currently resolves vague customer requests.
Prompt 2: Tribal Knowledge Audit
Job: Identifies the gap between what your organization knows about its products/services and what exists as structured, machine-readable data — then builds a prioritized plan to encode the tribal knowledge that matters most for agent readability.
When to use: When you realize that most of what makes your product compelling lives in marketing copy, sales conversations, or people's heads rather than in structured data fields. This is the "vagueness problem" — the highest-leverage and least-addressed dimension of agent readiness.
What you'll get: A structured audit showing exactly what knowledge is structured vs. unstructured for your key offerings, a prioritized encoding plan that starts with the highest-revenue-impact knowledge, and a template for the conversations you need to have with your subject matter experts to extract it.
What the AI will ask you: Your top products or services, how your best salespeople sell them, what questions customers ask most often, what your decision-support data looks like today, and where the "magic" lives in your customer experience.
Prompt 3: Competitive Agent Simulation Brief
Job: Guides you through a live competitive simulation — querying AI assistants with realistic customer prompts to see how agents discover, evaluate, and recommend in your category — then analyzes the results into a competitive intelligence brief.
When to use: When you want to see, in 30 minutes, how your company shows up (or doesn't) when an AI agent mediates the purchase decision. This is the exercise from the briefing that "tells you more about your competitive position in the agent era than any strategy deck." Run it monthly to track movement.
What you'll get: A structured competitive intelligence brief based on actual agent query results, with analysis of your visibility, accuracy of representation, competitor positioning, and specific recommendations for what to fix.
What the AI will ask you: Your company, your category, your top competitors, and the kinds of realistic purchase prompts your actual customers would use. Then it will guide you through running the queries and analyzing the results together.
Prompt 4: Agent Readability Transformation Roadmap
Job: Takes your diagnostic findings — from the exercises above or from your own assessment — and produces a phased, resourced transformation roadmap for making your systems agent readable and writable. Designed to be the document your CTO and CFO align on.
When to use: After you've run one or more of the diagnostic exercises and understand your exposure. This prompt converts findings into a funded, staffed, sequenced plan with clear milestones and ownership.
What you'll get: A multi-phase roadmap with workstreams, resource requirements, dependencies, risk factors, milestone gates, and a clear articulation of what each phase delivers in terms of agent readability. Includes a "quick wins" section for things you can ship this quarter.
What the AI will ask you: Your diagnostic findings, your organizational constraints (team size, budget cycles, vendor dependencies, technical debt), your competitive timeline pressure, and your risk tolerance.