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Question

How do I choose an AI assistant for a small team?

Verified Oct 17, 2026 Review by Jan 15, 2027 6 sources
Short answer

Start from where your work lives. If it's in Google Workspace, test Gemini inside Workspace first; otherwise compare ChatGPT, Claude and Gemini business plans on your three most common tasks. Check data terms, admin controls and connectors before price.

What it is

An AI assistant is the chat app most staff use daily. See AI assistants for the category.

How it works

  1. List the three tasks people most want help with.
  2. Shortlist assistants that connect to your core tools.
  3. Run the same tasks in each for a week with two or three staff.
  4. Compare quality, admin and data controls, then cost.

Team plans (checked 2026-10-17). Claude Team costs $20 per standard seat a month billed annually ($25 monthly) for 2 to 150 people. ChatGPT Business starts at 2 users and includes SSO, roles and admin controls; check its pricing page for the current rate. Google Workspace’s Business plans cover up to 300 users, and Google says Gemini in Workspace doesn’t use your content for training outside your domain without permission.

Benefits

  • Choice grounded in your real work.
  • Fewer duplicate subscriptions.
  • Easier policy and training with one standard tool.

Limits and risks

  • Vendors leapfrog each other; revisit yearly. IonBin doesn’t rank assistants.
  • Connectors and features vary by plan.
  • Staff may still prefer other tools; set a policy (see AI use policy).

Checked specs

Snapshot from official sources on Oct 17, 2026.

Claude plans (checked 2026-10-17)Pro $17 a month billed annually or $20 monthly; Team standard seat $20 annually or $25 monthly, for 2 to 150 people [2]
ChatGPT plansFree, Go, Plus and Pro for individuals; Business from 2 users and Enterprise for organizations; Business prices not shown in page text [1]
Admin controlsChatGPT Business includes MFA, roles, GPT controls, SAML SSO and basic analytics [4]
Google WorkspaceBusiness Starter, Standard and Plus available for up to 300 users; Gemini content not used for training outside your domain without permission [5]

Best-fit stacks

Stack 06

Ops & admin automation

Hand repeat admin (receipts, logs, notices, handoffs) to workflows your agent can trigger.

Agent compatibility

Tool in this entryHow agents connect
ChatGPT Agent platform API/CLIBulk import
Claude Agent platform API/CLIBulk import
Gemini (Google) Agent platform API/CLIBulk import
Google Workspace (Gmail, Drive, Sheets) MCPAPI/CLIBulk import

Levels come from each tool's recorded, sourced compatibility. How the levels work.

Sources

  1. ChatGPT plans and pricing · OpenAIofficial accessed Oct 17, 2026
  2. Claude pricing · Anthropicofficial accessed Oct 17, 2026
  3. Gemini (Google) website · Googleofficial accessed Oct 17, 2026
  4. Business data privacy, security, and compliance · OpenAIofficial accessed Oct 17, 2026
  5. Generative AI in Google Workspace Privacy Hub · Googleofficial accessed Oct 17, 2026
  6. Google Workspace pricing · Googleofficial accessed Oct 17, 2026

Practitioner views are restated in our words and labeled as views, not measured results. Product facts come from official sources dated above.

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