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url: /docs/diligence-02-how-tos-and-workflows.md
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# Diligence — How-Tos & Workflows

## Start a workspace

1. Go to **Diligence**.
2. Click **New Workspace**.
3. Enter the company name and, if it exists in your Deal Pipeline,
   optionally link it to that deal.
4. Save.

## Upload a document

1. Open the workspace and go to the **Documents** tab.
2. Choose a category (Financial Statements, Legal, Cap Table, Management,
   Market Analysis, Technical, or Other) and upload your file.
3. The document appears in the Document Vault under its category, with a
   status of pending, uploaded, reviewed, or flagged.

Uploads are limited to 25 MB per file.

## Preview a document

In the **Documents** tab, select a document in the Document Vault. PDFs
and images (PNG, JPG, GIF, WEBP, SVG) preview directly in the workspace.
Word, Excel, and PowerPoint files preview through Google Docs Viewer — see
[Advanced & Customization](diligence-03-advanced-and-customization.md) for
what that means for the document's privacy. Use **Open in new tab** to
download any document directly.

## Extract financial metrics

1. Open a workspace that has at least one uploaded document.
2. Go to **AI Analysis → Financial Extraction**.
3. Click **Extract Metrics**. Cairn Intelligence reads your uploaded
   documents and returns what it can find: ARR, revenue, revenue growth,
   gross margin, NRR, burn rate, runway, headcount, and a short summary.
4. Run it again any time — click **Re-extract** to refresh the metrics
   after uploading new documents. Each run replaces the previous result.

> **Example: checking a deck's numbers.** The Lumen Health deck claims
> "$8M ARR". After uploading the deck and the latest management accounts,
> **Extract Metrics** returns ARR of $6.1M, because that's what the
> management accounts say. The difference is visible before anyone repeats
> the deck's number in a memo, and **Generate Thesis** then quotes the
> exact line it comes from.

## Generate an Investment Brief

Needs **Run Cairn Intelligence** (Admin, Partner, or Analyst). Viewers can
read a brief but not generate one or edit its notes.

1. Open a workspace that has at least one uploaded document.
2. Go to **AI Analysis** and choose **Investment Brief**.
3. Click **Generate brief**. Cairn Intelligence reads your documents and
   returns:
   * a summary of **strengths**, **risks surfaced**, and **open questions**;
   * **key findings**, each with **View supporting evidence** showing the
     exact quotes, and a link that opens the source document;
   * **questions to resolve** with management;
   * **document coverage**, showing which documents were read in full and
     which only in part.
4. Add your interpretation in **Analyst notes** and click **Save notes**.
   Save before regenerating; your saved notes carry over.
5. If documents change, the brief shows a warning. Click **Regenerate
   brief** to use the current documents.
6. Click **Download PDF** to share it.

> **Example: preparing for a first partner call.** Lumen Health's data
> room has 40 documents and the partner has 20 minutes. The analyst
> generates a brief: two strengths (a 130% net revenue retention figure and
> a three-year hospital contract), one risk (40% of revenue from one
> customer), and three questions, including "Can management share the
> renewal terms for the largest customer?". Each finding opens to the
> quote it came from, so the partner can trust it without reading the
> deck. The analyst adds a note on what they want to test, and the
> partner takes the questions into the call.

## Generate a Cairn Thesis

1. Open a workspace that has at least one uploaded document.
2. Go to **AI Analysis → Cairn Thesis**.
3. Click **Generate Thesis**. Cairn Intelligence reads your documents and
   returns cited findings (strengths, risks, observations) and material
   assumptions, each with an evidence status of supported, contradicted,
   or not established.
4. Set your own bear/base/bull ARR growth scenarios on the **Scenarios**
   tab, and edit any assumption's interpretation in the **Assumptions**
   tab — your edits are kept separately from what Cairn Intelligence
   originally found.
5. Click **Regenerate Thesis** any time to produce a new version. Every
   version is kept — use the version dropdown to browse prior theses. Your
   analyst notes carry forward into the new version automatically.
6. Click **Download PDF** to export the current version.

If a citation Cairn Intelligence returns can't be matched back to your
actual document text, the generation is rejected and your previously
saved thesis is left unchanged — try generating again.

> **Example: an assumption that doesn't hold.** The thesis lists the
> assumption "Net revenue retention above 120%" as **contradicted**,
> quoting the customer cohort file: "2025 NRR: 104%". The analyst adds a
> note explaining what they'll ask management, and sets the **Scenarios**
> to 40% / 70% / 110% ARR growth for bear, base, and bull. When new
> documents arrive, **Regenerate Thesis** creates a new version; the old one
> stays in the version list, so the team can see how the view changed.

## Generate an IC Memo

1. Make sure the workspace already has a Cairn Thesis and a Financial
   Extraction — IC Memo synthesizes both. If either is missing, generating
   a memo fails with a message telling you which one to create first.
2. Go to **AI Analysis → IC Memo**.
3. Click **Generate Memo**. Cairn Intelligence produces an executive
   summary, a thesis narrative, market/management/risk findings, a
   comparable-companies section (only populated if your documents actually
   mention comparable companies), a valuation section built from your
   Thesis's bear/base/bull scenarios, and a recommendation.
4. Add your own analyst notes in the notes field — these carry forward
   across regenerations.
5. Click **Regenerate Memo** to produce a new version once your
   underlying documents, Thesis, or Financial Extraction have changed. The
   memo flags itself as stale if any of those three have changed since it
   was generated.
6. Click **Download DOCX** to export the current version as a Word
   document.

> **Example: the night before IC.** With the Thesis and Financial
> Extraction done, the analyst clicks **Generate Memo**. The draft has an
> executive summary, financials, risks, a valuation section built from the
> bear/base/bull scenarios, and a recommendation, each finding quoting the
> documents. The analyst edits the notes, downloads the Word file, and
> spends the evening on judgement rather than formatting. If someone
> uploads a new document afterwards, the memo shows as stale until it's
> regenerated.

## Manage the checklist

In **Checklist & Flags**, add checklist items and update each item's
status as you work through diligence: not started, in progress, complete,
or not applicable.

## Track red flags

In **Checklist & Flags**, add a red flag with a title, detail, severity
(high, medium, or low), and optionally a source. Red flags are entered by
you — Cairn Intelligence doesn't detect them automatically today.

## Manage advisors

In the **Advisors** tab, add an advisor with their firm name, type of
advisory work, scope, status, and expected completion date. Update their
status or remove them as the engagement progresses.