Buyer Guide Updated April 2026

How to Evaluate an AI Assistant for Microsoft Teams or Google Chat

Most enterprise AI vendors show you a polished demo. This guide gives IT leads and procurement teams a practical checklist to evaluate what matters in a production deployment - security, native platform support, permissions, analytics, and total cost.

See how ChatGridAI scores All guides
"Native bot" vs "integration"Ask if it works as an actual Teams or Google Chat bot - not just a linked web app
Ask about per-department isolationShared workspace vs separate bots per department is a core security question
Understand true total costPlatform fee plus token markup plus minimum seats can vary 5x between vendors
Run a single-department pilot firstThe fastest path to org-wide rollout is a successful HR or IT pilot, not a big bang deployment
Platform Integration

Platform integration checklist

The most important platform questions come before everything else. If the tool does not work natively in your chat platform, all other features are irrelevant.

  • Does it run as a native Microsoft Teams bot that employees can @mention in any channel?
  • Does it run as a native Google Chat bot with the same capability?
  • Can it be used in both Teams and Google Chat if your org uses both?
  • Does it require employees to visit a separate web portal, or is it fully chat-native?
  • Can it be invited to specific Teams channels or Google Chat spaces (not just DMs)?
  • Does bot setup require IT admin rights in Teams/Google Workspace, or can it be done without them?
  • Is the bot visible in the Teams app store or does it require custom sideloading?
  • Is there a mobile experience in the Teams or Google Chat mobile apps?
Security

Security evaluation checklist

Security evaluation should happen before the demo ends - not after you have signed.

  • Does the vendor support BYOK - bring your own OpenAI or Azure OpenAI API key?
  • Where exactly is a BYOK key stored? Ask for confirmation it is in an encrypted secret manager.
  • Are document stores isolated per department, or shared with row-level filtering?
  • Is there an audit log of all user queries that you can export?
  • Are conversation logs stored separately per customer (not commingled with other tenants)?
  • What per-user rate limits exist to prevent cost abuse?
  • Is SOC 2 Type II certified? Can you provide the report?
  • When was the last penetration test? Was cross-tenant data access in scope?
  • Does the vendor use your data (queries, documents, feedback) for any model training?
  • Is there a data processing agreement (DPA) available for signing?
Permissions and Access Control

Permissions and access control checklist

  • Can different departments (HR, IT, Finance) have separate bots with separate knowledge bases?
  • Can you restrict which employees can interact with which bot?
  • Is RBAC enforced at the document retrieval level, not just the login level?
  • Can you restrict the bot to specific Teams channels or Google Chat spaces?
  • Can individual documents be marked as restricted to a subset of users?
  • What happens when an employee asks a question and the relevant document is in another department's knowledge base?
  • Can an admin revoke a specific employee's access without affecting others?
Connectors and Actions

Connectors and action execution checklist

  • Can the bot create tickets in Jira from a chat conversation?
  • Can it submit ServiceNow incidents or change requests?
  • Does it support custom webhooks for proprietary internal systems?
  • Is there a confirmation step before any action is taken on behalf of the user?
  • Can you connect Google Drive or SharePoint as a live knowledge source?
  • Does document ingestion support PDF, Word, and plain text at minimum?
  • Is there a size limit on uploaded documents and how is it handled?
Analytics and Rollout

Analytics, pricing, and rollout checklist

Analytics questions

Is there a per-department usage dashboard? Can you see query volume per user? Can you monitor token consumption in real time? Can you export usage data for internal reporting? Are there alerts when usage exceeds a threshold?

Pricing transparency

What is the per-seat platform fee? Is there a token markup on top? What is the minimum seat count? Are there annual commit requirements? Are there separate fees for connectors or action execution? What does total cost look like for your expected seat count and usage level?

Rollout planning

Can you pilot with one department before org-wide rollout? What does the onboarding process look like? How long does initial setup take for a new department bot? Is there a customer success contact or is onboarding self-serve? What SLA applies to support requests?

Evaluation Framework

How to score vendors across these dimensions

After running through these checklists with each vendor, score them on five dimensions that matter most for enterprise deployment:

  1. Native platform fit: Does it genuinely work as a bot inside Teams or Google Chat, or is it a web app with a chat widget? Native is non-negotiable for adoption.
  2. Security architecture: BYOK, isolated stores, audit logs, and SOC 2. Vendors who cannot answer these questions specifically should be disqualified.
  3. Permission granularity: Can you give HR, IT, and Finance separate bots with no document crossover? Flat shared workspaces create risk.
  4. True total cost: Platform fee plus token costs plus connector fees at your expected seat count. Some vendors look cheap at the platform fee level but add markup that triples the actual cost.
  5. Rollout realism: Can you be live with one department in a week? Vendors requiring three-month implementation cycles have a different risk profile than those with self-serve admin setup.

Weight these dimensions based on your organization's priorities. Security-first organizations should weight items 2 and 3 heavily. Cost-sensitive teams should normalize for true total cost before comparing features.

FAQ

Evaluating enterprise AI - common questions

A Teams bot runs natively inside Teams - employees can @mention it in any channel or DM it directly, and the interaction happens entirely within Teams. A Teams integration typically means the product opens in a Teams tab (a web frame showing the vendor's web app) or uses a connector to post notifications. For employee Q&A workflows, only a native bot delivers the friction-free experience that drives adoption.
With a well-designed product, a single-department pilot should be achievable in one week: day one for bot registration and admin setup, days two and three for document upload and system prompt configuration, days four and five for internal testing with a small group. Vendors requiring more than two weeks for initial setup have an implementation model, not a product-led deployment model.
Always start with a single department pilot. HR is the most common choice because the use case is clear (policy Q&A), the documents are well-defined (handbook, benefits guide, PTO policy), and the department head can be a strong internal champion. A successful HR pilot generates organizational confidence for IT, Finance, and Onboarding rollouts. A rushed org-wide launch without a proven pilot risks adoption failure across all departments simultaneously.
Reasonable benchmarks in 2026: $5 to $10/seat/month for a focused enterprise chat bot with BYOK; $20 to $30/seat for broader knowledge discovery platforms; $30+/seat for deeply integrated productivity suites like Microsoft Copilot. At $5/seat with BYOK, total cost including API tokens is typically $6 to $8/user/month at normal usage. At $25/seat without BYOK, you are paying $25+ regardless of usage levels.

ChatGridAI checks every box on the evaluation checklist.

Native Teams and Google Chat bot. BYOK. Per-department isolation. Audit logs. $5/seat. Live in one day.

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