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Choose an enterprise AI assistant by matching a specific product edition, region, feature set, contract and configuration to your company’s required controls. Do not treat a certification, a “business” label or a vendor’s general privacy statement as proof that every workflow is compliant.
Start by documenting your data, jurisdictions, users and intended features. Then verify data handling, retention, identity, permissions, auditability, residency, encryption, subprocessors and contractual coverage. Test the configured service with realistic access and failure scenarios, record unresolved gaps, and approve deployment only when the evidence covers the exact environment you will operate.
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1. Define the decision before comparing products
An assistant can be acceptable for low-risk drafting and unacceptable for regulated records, privileged legal material or production administration. Your first document should therefore describe the deployment you are actually considering, not a list of brand names.
Map laws, contracts and internal policy
List every obligation that could affect the assistant. Include privacy and data-protection laws in the countries where users or data subjects are located, sector rules such as healthcare requirements, contractual confidentiality clauses, records-management rules, export controls, intellectual-property restrictions and your own information-security policies. Identify the accountable owner for each requirement.
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Write each obligation as a testable question. For example: “Can we prevent prompts containing a restricted data class from being sent to an optional search service?” is more useful than “The service must be secure.” A control owner should be able to answer the question with a contract clause, configuration setting, log or test result.
Inventory data and use cases
List the tasks employees want to perform and the information each task requires. Include prompts, uploaded files, generated responses, conversation history, connected repositories, search queries, tool calls, agent actions and administrator telemetry. Record whether information is confidential, personal, regulated, export-controlled, legally privileged, safety-critical or publicly available.
| Use-case tier | Typical examples | Evidence needed before approval |
|---|---|---|
| Low risk | Public-information summaries, style editing and brainstorming without confidential inputs | Acceptable-use rules, account security and basic logging |
| Controlled internal | Internal procedures, project notes and non-public business analysis | Identity integration, permission enforcement, retention settings and administrator audit |
| Restricted | Personal data, customer records, unreleased financial information or source code | Documented data flows, contractual processing terms, residency analysis, deletion controls and a tested access model |
| Regulated or privileged | Healthcare information, legal advice, financial records or safety decisions | Applicable addenda or agreements, qualified configuration, independent assurance and written approval from legal, privacy and security owners |
The tier is a decision aid, not a legal determination. A use case can move to a higher tier when a new connector, agent or external model is enabled.
Turn obligations into a control matrix
Create one row for every requirement and include the evidence you will accept. Require the vendor to identify the exact product edition, region, feature and legal entity covered.
| Requirement | Verification question | Acceptable evidence |
|---|---|---|
| Training use | Are prompts, files, responses or connected content used to improve a general model? | Current terms, product documentation and a written feature-specific statement |
| Retention and deletion | How long are content, safety logs and administrator logs kept, and can an administrator delete them? | Retention controls, deletion procedure, default periods and exceptions |
| Residency | Where are content, metadata, backups and support records stored and processed? | Region list and contractual residency commitment for the selected edition |
| Access | Does the assistant enforce source permissions and least privilege? | Architecture documentation, role settings and a negative-access test |
| Audit | Can investigators identify who used the assistant, what feature was used and when? | Sample audit events, retention period, export method and eDiscovery process |
| Subprocessors | Which organizations process the data, for what purpose and in which countries? | Current subprocessor list, notification process and objection or termination rights |
2. Trace the complete data flow
Review the path of every data object, not only the chat window. Draw a diagram from the user’s device through identity services, the assistant, storage, connected applications, search providers, model providers, support systems and deletion points.
Prompts, uploads and responses
Ask whether prompts and uploaded documents are encrypted in transit and at rest, whether they are isolated from other tenants, and which systems can access them for abuse monitoring, troubleshooting or support. Determine whether generated responses are stored as conversation history, copied into connected systems or retained in backups.
Separate content retention from security and diagnostic logs. A service may allow short conversation retention while keeping access or abuse logs for a different period. Obtain the default and configurable periods for both.
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Connected organizational content
For each connector, identify the source system, synchronization method, index location, permission model and revocation delay. Confirm what happens when a user loses access to a source document. Test a user who should not see a document and verify that the assistant does not reveal it through a summary, citation, autocomplete or generated inference.
Do not assume that a connector inherits permissions merely because the source application does. Verify whether group membership, sensitivity labels, document-level controls and administrative exclusions are honored at query time.
Web search, agents and external models
Optional capabilities can create a separate processing path. A web-search feature may send a rewritten query outside the assistant’s primary tenant boundary. An agent may call a third-party service, write to a business system or retain tool output. An external model option may have different training, retention or residency terms.
For every optional feature, document the data sent, destination, purpose, retention, contractual coverage, administrator control and disablement method. Treat the feature as unapproved until those answers are complete.
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Read the governing terms
Obtain the data processing addendum, product terms, privacy terms, acceptable-use policy, service description, subprocessor list and support terms that apply to the proposed purchase. If regulated health information is involved, determine whether a business associate agreement is available for the exact service and workflow.
Check definitions carefully. “Customer data” may exclude search queries, telemetry, de-identified information or data sent to an optional service. Confirm the vendor’s rights to retain, disclose, transfer, delete or use each category.
Scope certifications and reports
A certification or attestation applies only to the service, edition, legal entity, period and controls named in the report. Ask for the report or bridge letter rather than relying on a logo. Record whether the report covers the region and connectors you will use, and whether your configuration responsibilities are listed as complementary controls.
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Request an evidence pack
- Current terms and data-processing documents for the selected edition.
- Feature-level data-flow diagrams for chat, file upload, connectors, search and agents.
- Subprocessor names, locations, processing purposes and change-notification procedure.
- Encryption design, key-management options and customer responsibilities.
- Identity, role, permission-inheritance and administrator-control documentation.
- Audit-event catalog, export format, retention options and investigation workflow.
- Independent assurance reports and the exact scope and period of each report.
- Incident-notification commitments, support access controls and deletion procedures.
Mark each item as verified, contractually committed, configuration-dependent, unavailable or unresolved. “Vendor says it is secure” is not an evidence status.
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4. Compare the operational controls that affect daily risk
Use the same questions for every shortlisted assistant. A feature that exists in one plan may be absent, limited or separately priced in another, so record the edition and plan beside every answer.
| Control area | Questions to ask | What to test or document |
|---|---|---|
| Identity | Does it support SAML single sign-on, multifactor enforcement, automated provisioning and rapid deprovisioning? | Login flow, group-to-role mapping and termination test |
| Roles and administration | Can separate administrators manage users, data, connectors, audit and billing? | Role catalog, least-privilege settings and privileged-action logs |
| Source permissions | Are source ACLs, groups and document-level restrictions enforced at retrieval time? | Allow-and-deny tests using accounts with different access |
| Labels and policy | Are sensitivity labels and retention policies inherited or applied to generated content? | Label propagation behavior and policy conflict handling |
| Audit and investigation | What events are recorded, how detailed are they, and can they be exported to your monitoring system? | Sample events, timestamps, actor identifiers, query scope and retention |
| eDiscovery and records | Can legal holds, search, export and deletion exceptions be handled? | Documented workflow and responsibility split |
| Location | Where are primary data, backups, metadata and support access located? | Region-specific commitment and exception list |
| Encryption and keys | Is customer-managed encryption available, and which services are excluded? | Key lifecycle, rotation, revocation and recovery procedure |
| Network boundaries | Can traffic be restricted with private networking or service perimeters? | Architecture diagram and blocked-egress test |
5. What current product documentation indicates
Microsoft Copilot
Microsoft states that organizational Copilot use is governed by its Data Protection Addendum and Product Terms. Its documentation describes encryption at rest and in transit, tenant isolation and privacy commitments. It also describes permissions, sensitivity labels, retention policies, interaction audits and administrator settings.
“Copilot respects your identity model and permissions, inherits your sensitivity labels, applies your retention policies, supports audit of interactions, and follows your administrative settings.”
Microsoft qualifies that specific controls vary with the subscription plan. A buyer must therefore verify the exact plan rather than treating the statement as universal. Microsoft also says properly configured Copilot implementations support HIPAA, while web-search queries are outside the stated Data Protection Addendum and business associate agreement scope. If your workflow uses web search, assess that path separately or disable it.
Gemini Enterprise
Google Cloud’s compliance and controls documentation identifies supported compliance programs for specified Gemini Enterprise editions and lists data residency, customer-managed encryption keys, VPC Service Controls and Access Transparency. The same documentation states that customer-managed encryption keys and Access Transparency are not supported in the global region.
The listed controls also carry a Grounding with Google Search caveat. Confirm whether enabling that capability changes the covered service, location or contractual terms. Google’s FAQ describes audit logging, data residency, customer-managed keys and document-level access controls, with some statements limited to particular editions. Record the exact product name, edition and region in your evaluation; do not generalize an edition-specific control to the whole product family.
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OpenAI’s business-data documentation describes business data protection, alignment with privacy and security frameworks, data-residency options, SAML single sign-on and audit logs. It also describes a business associate agreement for ChatGPT for Healthcare and API healthcare customers to support HIPAA requirements.
These are vendor statements, not a determination that your deployment complies with a law. Verify the current service scope, available regions, selected features, agreement language and configuration responsibilities for your organization. A healthcare workflow should not be approved solely because a BAA exists; confirm that the BAA covers the product and data path you intend to use.
6. Resolve region, encryption and feature exceptions
Residency is more than a data-center selector
Ask where prompts, responses, indexes, backups, logs, support sessions and subprocessors operate. Determine whether residency applies to storage only or also to processing and support access. Document transfers that occur when a selected region lacks a feature.
Customer-managed keys have boundaries
If your policy requires customer-managed encryption keys, verify which stores and services actually use your key. Check whether search indexes, logs, backups, abuse-monitoring systems and connected applications are included. Confirm what happens when a key is disabled, rotated or unavailable.
Network controls can change functionality
Private networking or service-perimeter controls may block connectors, search or administrative endpoints. Obtain a supported architecture, list required egress destinations and test both permitted and denied paths. A control that cannot be enforced without breaking the approved workflow should be recorded as a risk, not assumed away.
Regulated data needs a qualified configuration
Where a vendor says a properly configured implementation supports a requirement, obtain the configuration guide and identify every customer responsibility. Use a change-control record so later connector, search, model or retention changes trigger a reassessment.
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- Freeze the initial scope. Name the user groups, data classes, countries, integrations and features for the first release. Exclude optional search, agents and external models unless they are explicitly being evaluated.
- Build the control matrix. Assign an owner and evidence requirement to each obligation. Add a “must not” condition for unacceptable processing, residency or access outcomes.
- Issue the same questionnaire. Ask each vendor for edition, region, feature, legal entity, subprocessor and contract details. Require written answers where a marketing page is ambiguous.
- Review legal terms in parallel. Compare data definitions, training rights, retention, deletion, transfers, incident notice, audit rights, liability, termination assistance and regulated-data agreements.
- Design the reference configuration. Specify SSO, groups, administrator roles, connector allowlists, labels, retention, logging, network boundaries and disabled features.
- Run a controlled pilot. Use synthetic or de-identified data first. Test normal use, denied access, account removal, connector revocation, retention expiry, export and incident investigation.
- Close evidence gaps. Convert every unresolved answer into a named risk, owner, deadline and interim control. Do not count an unverified vendor promise as a pass.
- Approve or reject the exact deployment. The decision record should identify the edition, region, configuration, permitted features, prohibited features and conditions for expansion.
8. Design a pilot that tests failure, not just usefulness
A successful demonstration shows that the assistant can produce a helpful answer. A security pilot must also show that it refuses, limits or records actions correctly.
| Test | Method | Pass condition |
|---|---|---|
| Permission boundary | Ask a user without access to summarize a restricted document. | No restricted content, metadata or revealing inference is returned. |
| Revocation | Remove source access, then repeat the request after the documented synchronization interval. | The assistant stops retrieving the content within the stated interval. |
| Label handling | Submit documents with different sensitivity labels and generate output. | Label and sharing behavior follow the documented policy. |
| Retention | Create conversations, delete them and check administrator and user views. | Deletion and retention outcomes match the contract and settings. |
| Audit | Perform user, administrator, connector and export actions. | Events identify actor, time, action and target with usable detail. |
| Search exception | Enable web grounding with a harmless test query. | Destination, query handling and contractual scope are understood and approved. |
| Agent boundary | Attempt an action outside the agent’s allowlist. | The action is blocked, requests approved authorization or creates the required audit event. |
| Account removal | Disable a pilot user and attempt sign-in and token use. | Access is revoked within the organization’s required time. |
Keep test prompts free of real personal, privileged or regulated information until the service and configuration have passed the initial controls. Preserve test evidence, timestamps and configuration versions in the decision record.
9. Use a transparent scoring and veto model
A score helps compare services, but it must not allow a high usability score to offset a disqualifying compliance gap. Set veto conditions before seeing the results.
| Category | Suggested evaluation question | Example treatment |
|---|---|---|
| Data use and retention | Are training use, storage, deletion and logging acceptable for each data tier? | Score evidence quality and configuration control; veto unapproved use of restricted data. |
| Contractual coverage | Do the DPA, BAA where needed and product terms cover every enabled feature? | Require signed terms before production. |
| Identity and access | Can the organization enforce SSO, least privilege and source permissions? | Require passing negative-access and deprovisioning tests. |
| Audit and response | Can security teams investigate, export and retain relevant events? | Require sample events and an operational owner. |
| Location and encryption | Do residency, key and network controls meet policy? | Veto an unapproved region or an unavoidable transfer. |
| Feature exceptions | Can search, agents, connectors and external models be governed independently? | Disable features that lack evidence rather than granting a blanket approval. |
| Assurance | Does independent evidence cover the exact edition, region and legal entity? | Record scope and period; do not award credit for an out-of-scope report. |
Keep usability, accuracy and cost as separate decision factors. They matter to adoption, but they do not compensate for missing contractual coverage or a failed access-control test.
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10. Operate the assistant as a controlled service
Control onboarding and changes
Publish approved use cases, prohibited data classes, user guidance and an escalation route. Require review before enabling a new connector, region, model, search capability, agent action or retention setting. Track configuration changes with an owner and effective date.
Monitor access and data handling
Send available interaction and administrator events to the organization’s monitoring process. Review unusual bulk retrieval, repeated denied requests, new connectors, privilege changes and unexpected geographic activity. Establish how investigators obtain conversation, connector and administrator evidence while respecting privacy and legal holds.
Reassess periodically
Set reviews based on contract renewal, major product changes, subprocessor changes, new jurisdictions, regulatory developments and changes to the data classification scheme. Recheck vendor documentation because plan features and regional limitations can change.
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11. Common selection mistakes and how to correct them
- Choosing by a certification logo. Correct it by recording the covered service, edition, region, period and customer configuration duties.
- Approving the chat feature while ignoring search and connectors. Correct it by creating a separate data-flow and contract review for every optional capability.
- Assuming source permissions are inherited. Correct it with allow-and-deny tests, revocation tests and documented synchronization timing.
- Confusing encryption with residency. Correct it by checking processing, storage, backups, logs and support access independently.
- Treating a BAA as automatic compliance. Correct it by verifying the exact product, enabled features and required configuration.
- Using production secrets in a proof of concept. Correct it with synthetic or de-identified data until controls pass.
- Accepting “not applicable” without a data-flow explanation. Correct it by asking which component receives the data and which terms govern it.
- Failing to document unresolved gaps. Correct it with a risk owner, compensating control, deadline and explicit approval authority.
12. Production decision checklist
- The approved use cases, users, data classes, countries and product edition are named.
- Every enabled feature has a documented data flow and contractual scope.
- Training use, retention, deletion, backups and logs are understood and configured.
- SSO, administrator roles, source permissions, labels and deprovisioning have been tested.
- Audit events can support investigation, export, retention and legal requirements.
- Residency, subprocessors, encryption keys and network boundaries match policy.
- Regulated workflows have the required agreement and qualified configuration.
- Search, agents, connectors and external models are either approved separately or disabled.
- Independent assurance evidence covers the exact service and deployment scope.
- Open gaps have owners, deadlines and an approving risk authority.
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