Enabling semantic search on SharePoint using Microsoft 365 Copilot, starting with Jim Mullan's Construction & Development folders.
Employees across Southwest Properties struggle to find information stored in SharePoint ("Simon"). The search function returns irrelevant results or misses relevant content entirely. Staff waste time daily searching for documents, asking colleagues, browsing folders manually, or recreating files they can't locate.
"I should be able to say 'show me any correspondence or agreement with Shannix that relates to long term care or assisted living' and then it's going to go through, flag the multiple documents, and give me a summary." Jim Mullan, VP Construction & Development
Today, that search requires downloading files from SharePoint, opening them in Bluebeam, and manually searching within documents across hundreds of pages.
Construction & Development (Jim Mullan's team)
Jim identified three folder areas for the initial pilot:
Five discovery calls across four departments revealed varying levels of search satisfaction:
| Department | Satisfaction | Notes |
|---|---|---|
| Construction (Jim) | Low | Searches historical agreements, project files, design documents across 15+ years of content. Can't search within documents. |
| HR (Jacqueline) | Moderate | Running a parallel SharePoint cleanup initiative. First department to complete reorganization. |
| IT (Derrick) | N/A (admin) | 16 Copilot licenses exist but semantic search features are not configured. Needs support understanding modern SharePoint capabilities. |
| Finance (Emily) | High (~7-8/10) | Good naming conventions, well-organized. Search frustrations exist but are manageable. |
| Accounting (Leslie) | High (~7-8/10) | Similar to Finance. Strong record-keeping practices minimize the search challenge. |
Southwest already has 16 Microsoft 365 Copilot licenses. Semantic indexing and Copilot search are capabilities built into these licenses. Rather than introducing new tools or building a separate search portal, this pilot enables features that are already paid for but not yet configured.
| # | Action | Who |
|---|---|---|
| 1 | Enable SharePoint indexing for the three designated folder areas | Derrick |
| 2 | Configure Copilot search access for Jim's account | Derrick |
| 3 | Enable Copilot search in Outlook for Jim | Derrick |
| 4 | Verify Jim can search across indexed content using natural language | Matt + Jim |
| 5 | Confirm permissions are scoped correctly (Jim sees only what he should) | Derrick |
Matt is available to support Derrick on any configuration questions or roadblocks.
Jim blocks out 30 minutes, 2-3 times per week to test search with real work tasks. During each block:
These notes become the raw input for evaluating the approach before broader rollout.
15-minute check-in to review:
| Criteria | How We Measure It |
|---|---|
| Jim can find historical documents faster | Self-reported comparison: time to find a specific document before vs. after. Target: noticeable improvement in most searches. |
| Copilot returns relevant results | During testing blocks, >70% of searches return useful results in the first attempt. |
| No wrong content surfaced | Copilot does not expose documents outside Jim's authorized access. No PII surfaced from unsanitized areas. |
| Process is repeatable | Configuration steps documented well enough that Derrick can replicate for the next department without Matt's involvement. |
| Jim recommends continuing | At the Phase 3 check-in, Jim sees enough value to advocate for broader rollout. |
| Risk | Impact | Mitigation |
|---|---|---|
| Unclean data returns wrong results | Copilot surfaces outdated or duplicate files | Scope limited to three folders Jim knows well. He can distinguish correct vs. incorrect results and flag issues for cleanup. |
| SharePoint cleanup conflict | Pilot conflicts with 10-month cleanup initiative | Pilot scoped to Jim's areas only, avoiding departments in active cleanup. Jacqueline and Derrick briefed on Feb 18 to ensure alignment. |
| PII exposure | Indexed content may contain sensitive information | Indexing respects existing SharePoint permissions. Jim only sees content he already has access to. PII remediation handled by cleanup initiative. |
| Low adoption | Jim doesn't have time to test consistently | Testing is lightweight (30 min, 2-3x/week) and tied to real work, not artificial test scenarios. |
| Copilot limitations | Semantic search doesn't work on images, charts, or files over 512MB | Set expectations upfront. Construction documents are primarily text-based agreements and correspondence, which are well-supported. |
"Really what I'm looking for is something that can search all the different departments. I don't want that to be siloed." Jim Mullan, VP Construction & Development
This pilot is designed as the template for exactly that. Once we prove it works for Construction, the playbook becomes: