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Choose an enterprise AI assistant by mapping your company’s obligations to verifiable controls, then testing the exact product edition, region, features, and configuration you intend to deploy. A certification or vendor privacy statement is not proof that every workflow is covered. Your decision record should show how prompts, responses, uploads, connected data, search queries, identities, logs, retention, encryption, and contractual terms are handled—and identify every unresolved gap before rollout.
Start with requirements, not product labels
“Enterprise” is a sales category, not a compliance conclusion. The same assistant can have different controls by subscription, geographic region, connected service, or optional feature. Begin by documenting what your organization must protect and why.
Build a requirement register
Translate laws, contracts, internal policy, and customer commitments into testable requirements. Avoid entries such as “must be secure.” Write requirements that a procurement or security reviewer can verify in documentation, configuration, a demonstration, or a contract.
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- Processing purpose: define approved uses, prohibited uses, and whether the assistant may summarize, classify, draft, search, retrieve, or take actions.
- People and jurisdictions: list employees, contractors, customers, and other data subjects, plus the countries or states whose rules apply.
- Systems: inventory identity providers, document stores, ticketing systems, email, code repositories, data warehouses, and other systems the assistant might connect to.
- Retention and records: specify how long prompts, responses, uploaded files, logs, and investigation exports may be retained, and when they must be deleted.
- Assurance: define the certifications, reports, contractual commitments, and independent evidence your risk process requires.
Assign an owner and acceptance test to each requirement. For example, “Users in the European tenant cannot retrieve documents outside their authorized workspace” can be tested with a permission matrix and a controlled retrieval exercise. “Prompts are not used to train a shared model” requires an applicable contractual or product statement, not a salesperson’s verbal assurance.
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Separate mandatory controls from preferences
Mark every requirement as mandatory, conditionally mandatory, or desirable. A company handling protected health information may require a business associate agreement and a properly configured implementation. A team using only public marketing copy may treat customer-managed keys as desirable. This separation prevents a polished feature list from obscuring a disqualifying gap.
Map the complete data flow
Review more than the chat window. Draw the path of every input and output, including information sent to optional services.
Data elements to trace
- Prompts and responses: determine where they are processed, whether they are logged, who can administer or investigate them, and whether they are used for model training or service improvement.
- Uploads: establish file size and type limits, malware scanning, indexing, storage location, retention, deletion, and whether a file remains available after a conversation ends.
- Connected organizational content: verify which permissions are evaluated at retrieval time, whether source labels flow through, and what happens when a source permission changes.
- Generated outputs: decide whether responses become business records, whether they are stored in your systems, and how users must review them before external use.
- Search and grounding requests: identify the provider receiving the query, the terms that govern it, the region used, and whether the request is inside or outside your data-processing agreement.
- Agents and actions: document every tool an agent can call, the credentials it uses, approval gates, write permissions, and the audit trail for each action.
- External models and subprocessors: list model providers, hosting entities, subprocessors, and the roles each plays in processing.
Require a feature-level data-flow diagram from each finalist. If a vendor cannot explain where a web-search query, connector request, or agent action goes, treat that feature as unapproved until clarified.
Check contractual scope before relying on a compliance claim
Read the governing terms for the exact service and edition. The relevant documents may include product terms, a data processing addendum, a business associate agreement, service-specific terms, subprocessor disclosures, and regional transfer provisions.
Questions for the contract review
- Which legal entity provides the service and signs the agreement?
- Which product name, edition, region, and features are covered?
- Are prompts, responses, uploads, connector content, and search queries treated differently?
- Is customer content used to train or improve a shared model? If an exception exists, can an administrator disable it?
- What retention and deletion commitments apply, and do backups or security logs follow different periods?
- What subprocessors may access content, where are they located, and how are changes notified?
- What assistance is provided for data-subject requests, breach response, investigations, and regulatory inquiries?
- What transfer mechanism and supplementary safeguards apply when data crosses jurisdictions?
- What service suspension, termination, export, and deletion rights exist?
- Does the agreement cover the intended regulated workflow, or only the underlying platform?
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, privacy commitments, and controls that vary by subscription. Microsoft also says properly configured Copilot implementations support HIPAA, while web-search queries are outside the stated DPA and BAA scope. That distinction means a healthcare buyer must assess ordinary organizational retrieval and web search as separate workflows.
Evaluate identity, permissions, and least privilege
An assistant is safe only when its retrieval and action permissions are safe. A broad connector can turn an existing access mistake into a fast, natural-language disclosure.
Identity controls
- Require SAML single sign-on or the identity method approved by your security team.
- Support automated provisioning and deprovisioning so a departed user loses access promptly.
- Use multifactor authentication through your identity provider where required.
- Define administrator roles separately from content access and model-management roles.
- Apply groups, regions, departments, and data classifications through centrally managed policy.
- Set session, device, network, and conditional-access requirements appropriate to the data.
Permission inheritance and labels
Test whether the assistant enforces source permissions at query time, not merely when a connector is configured. Include users with different roles, recently changed permissions, shared links, inherited folders, and denied documents. Check whether sensitivity labels, information barriers, and retention labels remain effective when content is summarized or quoted.
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Microsoft’s stated behavior is concise: “Copilot respects your identity model and permissions, inherits your sensitivity labels, applies your retention policies, supports audit of interactions, and follows your administrative settings.” The same documentation qualifies that specific controls vary with the subscription plan. Treat the sentence as a control description to validate against your purchased plan, not as blanket coverage for every feature.
Assess retention, deletion, and records handling
Ask separately about conversational history, uploaded files, indexed copies, audit events, safety telemetry, backups, and exports. A “delete conversation” button may not mean immediate deletion from every system.
Retention questions to test
- Can administrators set different periods for users, departments, or regulated workloads?
- Can legal holds, eDiscovery, or records schedules preserve required interactions?
- Are deleted conversations removed from search indexes and connector caches?
- How long do security, abuse-prevention, and access logs remain?
- Can users export their data, and can administrators restrict exports?
- What happens to content after account closure or contract termination?
Decide whether generated answers are drafts, official records, or merely transient assistance. If users copy responses into a case system, the retention and audit obligations may move to that system. Document the handoff and the required human review.
Review auditability and investigations
Procurement should demand a realistic investigation demonstration rather than a screenshot of an audit-log menu. Ask the vendor to show how an administrator can determine who asked a question, what sources were retrieved, what answer was returned, which policy applied, and whether an external service was called.
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Minimum audit capabilities
- Timestamped user, tenant, session, and request identifiers.
- Visibility into prompts, responses, files, connector calls, searches, and agent actions at a level consistent with your privacy policy.
- Administrator access controls and separation of duties for investigators.
- Configurable log retention, export, and integration with your security information and event management platform.
- Evidence of permission decisions and policy changes.
- Search, filtering, preservation, and export for incident response or eDiscovery.
Confirm whether audit events are available for every edition and region. Google’s Gemini Enterprise documentation describes audit logging and document-level access controls, but some statements are limited to particular editions. Do not assume that a control listed for one edition is present in another.
Verify residency, encryption, and network boundaries
“Data residency” can refer to storage, processing, backups, support access, or only a selected service tier. Ask the vendor to define each term and identify exceptions.
Encryption and key management
- Confirm encryption in transit and at rest, including connector traffic and backups.
- Determine whether customer-managed encryption keys are available for the exact edition and region.
- Ask who can use the keys, how rotation and revocation work, and what happens if a key is unavailable.
- Check whether key management covers indexes, caches, logs, and temporary processing.
Regional and network controls
Google Cloud lists data residency, customer-managed encryption keys (CMEK), VPC Service Controls, and Access Transparency for specified Gemini Enterprise editions. Its documentation states that CMEK and Access Transparency are not supported in the global region and identifies a caveat for the listed controls when Grounding with Google Search is used. A deployment that requires regional processing therefore needs a feature-by-feature regional test, not just a regional product selection.
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Also assess private connectivity, firewall boundaries, egress controls, domain allowlists, proxy support, and whether administrators can block unapproved external models or web search.
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Investigate optional features as separate services
Connectors, web search, agents, code execution, voice, image handling, and external models can introduce different processors, terms, regions, and retention behavior. Put each optional capability through its own approval gate.
Web search and grounding
Determine whether the assistant sends the full prompt, a rewritten query, document excerpts, or metadata to a search provider. Test whether users can include confidential text in a query and whether administrators can disable the feature. Microsoft specifically states that web-search queries are outside its stated DPA and BAA scope. Google’s listed Gemini Enterprise controls include a Grounding with Google Search caveat. These are reasons to create a policy that blocks regulated or confidential content from web-search workflows unless your legal and security reviews approve them.
Agents and connectors
Give agents the least privilege needed for the task. Prefer read-only connectors initially, require confirmation before writes, restrict destinations, and log every action. Test prompt injection from a connected document, malicious instructions in a ticket, and attempts to make the agent reveal secrets or bypass approval.
Compare the major enterprise control areas
| Area | Evidence to request | Acceptance test |
|---|---|---|
| Data use | Training policy, service terms, retention and deletion description | Submit a controlled prompt and verify the documented treatment and administrator setting |
| Contractual scope | Data processing terms, subprocessor list, business associate agreement where needed | Match each workflow and feature to an executed document |
| Identity | SSO, provisioning, role and conditional-access documentation | Disable a test account and verify access termination |
| Permissions | Source permission, label, and inheritance behavior | Run cross-role retrieval tests after changing source permissions |
| Audit | Event schema, retention, export, eDiscovery, and SIEM integration | Reconstruct a test interaction end to end |
| Location | Storage, processing, backup, support, and transfer commitments | Confirm the selected region and test every optional feature |
| Encryption | Encryption architecture and CMEK availability | Rotate or revoke a test key and observe the documented behavior |
| Feature limits | Connector, web-search, agent, and external-model data flows | Attempt prohibited actions and verify they are blocked and logged |
| Assurance | Certification or report scope, period, service, entity, and region | Check that the cited evidence covers the purchased deployment |
Use a weighted evaluation and evidence register
Score only evidence-backed controls. A practical register has these fields: requirement, risk owner, product edition, region, feature, evidence link or document name, configuration dependency, test result, exception, compensating control, decision, and review date.
Weight mandatory controls heavily or treat them as pass/fail. Do not allow a high score for user experience to offset a missing business associate agreement, unsupported residency requirement, or untestable permission model. Record verbal answers only as leads; require written terms or reproducible demonstrations before approval.
Evidence hierarchy
- Executed contract and feature-specific terms.
- Current service documentation and configuration references.
- Independent assurance reports whose scope matches the deployment.
- Recorded product demonstrations and test results.
- Vendor statements that are not incorporated into the agreement.
- Sales presentations and general marketing claims.
Validate the shortlisted configuration in a pilot
A pilot should use synthetic or de-identified data until the controls pass. Recreate the highest-risk workflows, not just a successful question-and-answer session.
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- Define the boundary: name the tenant, edition, region, users, connectors, search settings, agents, and administrators under test.
- Load test identities: create users with intentionally different source permissions, labels, regions, and employment states.
- Run data-flow tests: submit ordinary, confidential, regulated, and prohibited prompts; test uploads, retrieval, web search, and external-model options separately.
- Test leakage resistance: ask users to retrieve denied documents, expose hidden instructions, and combine information across restricted sources.
- Test lifecycle events: change a permission, disable an account, delete a conversation, rotate a key, and apply a retention or legal hold.
- Test investigations: export logs and reconstruct who did what, when, with which source and policy.
- Document exceptions: record failed tests, compensating controls, owners, deadlines, and whether the feature will be disabled.
Use the pilot results as procurement evidence. A control that works only after a manual step should have that step converted into a managed policy or operating procedure.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Product-specific points to verify
Microsoft Copilot
Microsoft describes encryption at rest and in transit, tenant isolation, privacy commitments, permissions, sensitivity labels, retention policies, interaction audits, and administrator settings. It says the controls vary by subscription. For healthcare use, Microsoft says properly configured implementations support HIPAA, but web-search queries are not covered by the stated DPA and BAA. Verify the purchased subscription, configuration, and every enabled search or connector feature.
Gemini Enterprise
Google Cloud identifies compliance programs for specified Gemini Enterprise editions and documents data residency, CMEK, VPC Service Controls, Access Transparency, audit logging, and document-level access controls. Some capabilities are edition-specific. CMEK and Access Transparency are unavailable in the global region, and Grounding with Google Search has a documented caveat for the listed controls. Confirm the current product name, edition, region, and feature scope directly in the applicable documentation and contract.
ChatGPT Enterprise
OpenAI describes business-data protections, alignment with privacy and security frameworks, data residency, SAML single sign-on, and audit logs. It describes a business associate agreement for ChatGPT for Healthcare and API healthcare customers to support HIPAA requirements. These are vendor statements; verify the current service scope, executed terms, region, enabled features, and intended workflow before relying on them.
Common procurement failures and fixes
Failure: treating certification as universal coverage
Fix: record the exact service, edition, legal entity, region, period, and feature covered by each report or certification.
Failure: approving the chat feature but ignoring search and connectors
Fix: maintain a separate approval record and data-flow diagram for every optional service.
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Fix: review training, logging, support access, backups, deletion, and legal-hold behavior as separate controls.
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Failure: assuming source permissions automatically prevent disclosure
Fix: run cross-role retrieval tests, including recently changed permissions and shared resources.
Failure: collecting evidence only during a sales cycle
Fix: make evidence part of the approval record, assign an owner, and set a recurring review for terms, subprocessors, regions, and configuration changes.
Approve, restrict, or reject with a clear decision
At the end of the review, choose one of three outcomes for each workflow: approve as configured, approve with documented restrictions and compensating controls, or reject until a gap is closed. State which users may use the assistant, what data they may enter, which features are disabled, where outputs may be stored, how incidents are reported, and when the decision will be revisited.
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Frequently Asked Questions
Does an enterprise label prove that an AI assistant is compliant?
No. Compliance claims are scoped to a service, edition, region, feature, configuration, and legal entity. Verify those boundaries and match them to your workflow.
Should web search be treated differently from normal assistant prompts?
Yes. Web search may send queries to a separate provider and may fall outside the main data-processing or healthcare agreement. Review and approve it as a separate data flow.
What should a healthcare organization verify first?
Confirm the applicable business associate agreement, the exact product and configuration, retention and access controls, and whether search, connectors, or other optional features are covered.
What evidence should procurement retain?
Keep the executed terms, product and regional scope, subprocessor information, assurance reports, configuration settings, pilot results, exceptions, compensating controls, and review date.
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