Discovery questions to identify prospect needs, pain points, and alignment with OpenRails capabilities. Use these during initial conversations to qualify opportunities.
If so, which tools, and what tasks do they handle? What is working well, and what is not?
Why ask: Establishes baseline and identifies gaps OpenRails can fill.
Think about report generation, data entry, document processing, ticket routing, or information lookup.
Why ask: Identifies automation opportunities for agent orchestration.
Do they search a wiki, ask colleagues, dig through file shares, or rely on tribal knowledge?
Why ask: Reveals the value proposition for RAG and knowledge management.
How do you currently validate AI-generated outputs?
Why ask: Positions OpenRails' sourced answers, evaluation framework, and HITL capabilities.
Have you experienced pricing changes, feature deprecations, or API instability?
Why ask: Highlights the multi-LLM advantage and provider flexibility.
PII, PHI, financial records, legal documents, intellectual property, classified information?
Why ask: Determines the need for security levels, PII pipelines, and encryption.
HIPAA, SOX, GDPR, FedRAMP, ITAR, or industry-specific regulations?
Why ask: Identifies compliance requirements that drive on-premise and governance features.
Must data remain in a specific country, on specific infrastructure, or within a specific network boundary?
Why ask: Positions on-premise deployment and air-gap capability.
How do you currently classify and label documents by sensitivity? How many classification levels do you use?
Why ask: Maps to OpenRails' tiered security controls and governance framework.
Project management, CRM, ERP, file storage, communication, databases?
Why ask: Identifies connector requirements and integration scope.
REST APIs, internal microservices, legacy SOAP services, database direct access?
Why ask: Assesses custom integration needs via MCP and the REST API connector.
Intranets, customer portals, helpdesk interfaces, operational dashboards?
Why ask: Positions the widget embedding capability.
Active Directory, Azure AD, Okta, custom SSO, LDAP?
Why ask: Determines authentication integration requirements for the OpenRails platform.
Consider both active power users and occasional users. Are there external users (customers, partners) who would use embedded widgets?
Why ask: Sizes the deployment and licensing requirements.
Thousands of documents? Terabytes of data? Growing at what rate?
Why ask: Determines infrastructure sizing and data lake architecture needs.
On-premise data centers, cloud (AWS/Azure/GCP), hybrid? Do you have GPU-equipped servers available?
Why ask: Determines deployment model and local LLM feasibility.
Has the organization already approved spending, or is this an exploratory conversation?
Why ask: Gauges buying stage and urgency.
Are you looking to pilot within weeks, deploy within a quarter, or planning for next fiscal year?
Why ask: Aligns engagement approach (quick POC vs. extended evaluation).
IT leadership, business unit heads, procurement, compliance/legal, executive sponsor?
Why ask: Maps the buying committee and identifies which benefit pages to share.