How to Evaluate Enterprise Search: 10-Point Checklist

You have decided your organization needs enterprise search. The next step is evaluating tools — and the market is crowded. Glean, Microsoft Copilot, Notion AI, GoSearch, and a dozen others all claim to solve the same problem. Here are the 10 criteria that actually differentiate them — ordered by what matters most in a real deployment.

The 10-point enterprise search evaluation checklist

1. 1. Does it connect to your actual tools?

   Not the vendor's connector count — your tools. A platform with 100 connectors that does not support Confluence or Jira is useless if those are your core platforms. List the 5-10 tools where your knowledge lives and verify the vendor supports each one. OAuth-based connections that require no file exports are the standard.

2. 2. Is the search semantic or keyword?

   Test this yourself during evaluation. Search for "contract renewal" and see if it finds documents about "agreement extension." Search for "deployment runbook" and see if it finds "production release procedures." If results only match exact keywords, the search is keyword-based regardless of what the marketing page says.

3. 3. How are permissions enforced?

   This is the most important security question. Ask: if someone's access to a document is revoked in Google Drive at 2 PM, when does it disappear from search results? Acceptable answer: immediately. Concerning answer: at the next re-index cycle. Unacceptable answer: it does not.

4. 4. Can you try it on your data before buying?

   A free trial on your actual data with your actual queries is the only reliable way to evaluate search quality. Vendor demos with curated sample data prove nothing about how the tool will perform on your messy, inconsistently-named, scattered-across-systems knowledge. If the vendor requires a paid POC or a sales-led pilot, factor that cost and delay into your evaluation.

5. 5. What does it actually cost?

   Published pricing is a signal of confidence. If the vendor requires a sales call to learn the price, expect negotiation, minimum seat counts, and annual escalation clauses. Calculate the total cost of ownership — not just per-seat price but support fees, infrastructure costs, and renewal increases over 3 years.

6. 6. Is there an audit trail?

   For regulated industries, every search query, every result returned, and every AI-generated answer must be logged with user identity and timestamps. Even for unregulated organizations, audit trails are how you detect anomalous access and debug search quality issues.

7. 7. Does it support workspaces or tenant isolation?

   If your organization manages multiple clients, projects, or regulated data sets, you need workspace-level boundaries that scope search and restrict access beyond document-level permissions. A consulting firm needs client isolation. A healthcare organization needs study-level isolation. Ask how the tool handles this.

8. 8. How fast is time to value?

   Can you connect your first data source and run a useful search in the first hour? Or does deployment require weeks of configuration, custom mapping, and IT involvement? The faster you can evaluate on real data, the faster you can make a decision — and the faster the ROI starts accumulating.

9. 9. Are AI answers cited?

   AI synthesis is only useful if every claim is linked to the source document. Without citations, you cannot verify whether the AI accurately represented the source material. Ask to see a live AI-generated answer with citations — and click through to verify the sources are real and relevant.

10. 10. What happens when you need help?

    Evaluate support responsiveness during the trial, not after you have signed a contract. Send a support question and measure the response time. Check whether documentation exists for common configuration tasks. Ask current customers about their support experience.

How RetrieveIT scores on this checklist