The craft · AI-for-X · exit plannersFor boutique M&A advisorsPairs with /comparison/advisor-vs-exit-planning

AI-for-X · exit planners

AI on the deal: throughput on the work, the file stays sealed.

Deal mechanics are repetitive. Deal data is the most sensitive material a small advisor handles. AI cuts the mechanical cost without ever seeing the live deal under loose terms. This manual draws the line, names the workflows, and gives you the second-brain stack a boutique M&A firm can actually run.

AudienceBoutique M&A and exit advisors
First deploy~2 weeks
Hard floorDeal confidentiality & MNPI
See the scope diagram Owner-side pre-work
Exit planner running an AI-supported comparable transactions scan.

What this work actually is

AI for exit planners is throughput on the mechanical layer with a sealed file at the centre.

AI for exit planners is the deliberate use of LLMs and structured automation on comparable transactions research, deal-document drafting from templates, financial model sanity checks, communications drafts, and diligence prep. It runs inside the firm's tenant. The live deal file does not enter shared models.

The hard floor is deal confidentiality, MNPI handling, and the disclosure rules of the regulator. Workflows that respect all three compound. Workflows that do not lose the deal and the next mandate.

One leak ends a boutique. The model never sees the live file. The market reads everything else.

The scope diagram

Three columns. The third one is the deal's life.

Human owns

Where the advisor sits and AI does not.

  • Buyer outreach and price guidance.
  • The negotiation table.
  • The recommendation to the seller.
  • Engagement-letter terms with the client.
  • Buyer qualification and conflict checks.
  • Closing-table judgment.
Non-delegable · the work the fee is for
AI assists

Where AI cuts the mechanical cost.

  • Comparable-transactions research from public filings.
  • Sector and buyer-universe scans.
  • CIM and IM drafting from sanitized templates.
  • Financial model formula audits.
  • Diligence checklist generation per sector.
  • Client communication drafts in firm voice.
Drafted by AI · verified and signed by the advisor
Never AI

What does not enter a model.

  • The live target's name in any non-tenanted prompt.
  • Live deal terms during a mandate.
  • Indicative bid letters and term sheets in shared models.
  • Buyer identity during exclusivity.
  • Personal data of management teams.
  • Anything that breaches the engagement letter or NDA.
Hard floor · deal confidentiality & MNPI
Figure 01 · scope diagram Drawn version sits here in v2: HUMAN (the table) · AI ASSISTS (mechanical layer) · NEVER (the live file). Used as the cover page of the boutique's AI policy.

What changes when this is done well

~3x
Comp transactions surveyed
Wider initial scan, sharper short-list. Multiples logic gets richer source material.
~50%
CIM drafting time
From sanitized templates and prior-deal patterns. Voice of the firm preserved.
0
Live target names in shared models
Code-name only inside the brain; the real name lives in the data room.
1
Engagement-letter clause
Disclosure of which workflows touch AI; opt-out mechanics for the seller.

What you need before you start

Five prerequisites. The first one is non-negotiable for every mandate.

01 · A code-name protocol

Every mandate gets a code name from day one.

Project Aurora, Project Birch. The real name does not appear in prompts, file titles, search queries, or chat names. The protocol is mechanical and survives staff turnover.

02 · A tenanted model with no-train terms

The vendor terms decide whether the mandate stays sealed.

Consumer chats are out for any mandate-related material. Default to vendors with a data-processing addendum and a tenant the firm controls.

03 · A redaction macro

Names, financials, and identifiers stripped before paste.

Even on the tenant. The discipline survives a vendor change and a regulator question.

04 · A firm voice file

How the firm writes CIMs, teasers, and buyer letters.

Loaded into every drafting brief. Stops the deliverable from collapsing into a generic banker voice.

05 · An engagement-letter clause

Sellers informed in writing, in plain English.

Which workflows touch AI, how the firm verifies output, the right to opt out. Drafted with risk counsel, versioned with the firm policy.

The split workflow

Six deal workflows. Each shows what stays human and what AI handles.

01

Human owns

Mandate intake and seller diagnosis.

What the seller actually wants. What the business is. The structural read. Owned by the advisor.

AI assists

Sector scan and recent-transactions sweep.

Public M&A activity, multiples, recent buyers, sector themes. Treated as raw material, not citations. Built on code-name only.

02

Human owns

Buyer-universe shortlist.

Who fits, who pays the highest, who closes. Owned by the advisor with knowledge the model does not have.

AI assists

Long-list candidate research.

Strategic acquirers, financial buyers, family offices, sponsor portfolios. Public information only. The advisor narrows.

03

Human owns

The CIM's positioning and headline.

What story the document tells. Owned by the advisor with the seller in the room.

AI assists

CIM mechanics from a sanitized template.

Section drafts, financial summary tables, market-context paragraphs. Real numbers added later by the advisor in the secure environment.

04

Human owns

Build the financial model.

Structure, drivers, scenarios. The model carries the deal's argument. Owned by the advisor.

AI assists

Formula audit and assumption pressure-test.

Read the spreadsheet structure (without live numbers if needed), flag inconsistencies, propose alternative assumptions. Sanity check, not source of truth.

05

Human owns

Buyer outreach and price guidance.

The conversations. The price signals. The negotiation. Always the advisor.

AI assists

Diligence checklist per sector.

Standard requests, sector-specific items, recent-deal patterns. The advisor edits and sends from the data room.

06

Human owns

The closing table.

The judgment that closes the deal. The signature on the engagement deliverable. The advisor's relationship.

AI assists

Post-close summary and lessons-learned.

Anonymized after close. Patterns extracted into the firm's prior-deals library, code-name only.

Figure 02 · deal swim lanes Six-step swim-lane diagram lives here in v2. Top lane: advisor. Bottom lane: AI. Sealed-file block runs across all six steps as the constant constraint.

How to know AI is hurting the firm

Six tells the seal has cracked.

Tell 01

A target's real name appeared in a prompt.

The code-name protocol failed. Audit the chat history, repair the leak, retrain the team, tighten the prompt template so the friction is mechanical.

Tell 02

Live deal terms reached a non-tenanted model.

A regulatory exposure and a confidentiality breach. Disclose to the client per the engagement letter; review with risk counsel; tighten the workflow.

Tell 03

A CIM section read like a generic banker's voice.

The voice file slipped. Pull the firm's recent CIMs, rebuild the voice file from the older ones, refresh the brief blocks.

Tell 04

A long-list candidate appeared that turned out not to exist.

A hallucination got through. Pull the long list, repair the entry, add the failure to the prompt library so it does not repeat.

Tell 05

A diligence checklist missed a sector-specific item that bit at signing.

The checklist was generated and not edited by sector experience. Restore the senior-on-every-checklist rule.

Tell 06

The post-close summary identified a live target by accident.

The anonymization pass failed. Read the summary, repair, tighten the post-close rule before the next close.

Tools and tactics

A second brain shaped for a boutique advisory.

The brain holds prior deals, prompt blocks, and voice file. The live file lives in the data room, not in the brain.

The Second Brain · boutique M&A stack

Stan's adapted stack for exit advisors

One folder per mandate, code-name only. Voice file pinned to every drafting brief. Five named brief blocks: sector scan, long-list research, CIM mechanics, model audit, diligence checklist. Prior-deals library code-name only, refreshed at close. AI usage log per mandate.

  • One folder per mandate, code-name only.
  • Voice file pinned to every drafting brief.
  • Five named brief blocks.
  • Prior-deals library: anonymized at close.
  • AI usage log: prompt, output, verifier, signer.
  • Quarterly review of three random outputs read blind.

Documented in full inside the engagement · teaser here

Tactic 02

The code-name protocol

Every mandate, every chat, every file. Code names are issued at mandate intake and used until the close-and-anonymize pass. The protocol survives staff turnover because it is mechanical, not memory-based.

  • Issued at intake.
  • Used in every prompt, file title, and chat.
  • Reviewed at close.

Tactic 03

The redaction macro

Find-and-replace template tied to the active mandates. Strips live names and financials before any paste. Built once, used forever. Removes the friction that breaks the protocol.

  • Per-mandate redaction list.
  • Runs in your text editor.
  • Updated at intake and at close.

Tactic 04

The post-close anonymization pass

One structured pass after every close. Strip the target name, the buyer name, and any unique identifier from the working files before they enter the prior-deals library. Without the pass, the library leaks across mandates over time.

  • Run within thirty days of close.
  • Reviewed by a second person.
  • Files moved to prior-deals only after the pass.

Coming soon

Three rooms held open inside this manual.

Built for boutiques that want the policy and the stack pre-assembled.

In build

The Boutique M&A AI Policy Pack

Firm AI policy, code-name protocol, intake disclosure clause, AI usage log, voice file, redaction macro. Drafted with risk counsel.

Scoped

The Sector Brief Library

Named brief blocks per sector: software, services, manufacturing, healthcare. Released when the boutique pack has been stable for one quarter.

Scoped

The Pre-Marketing Audit

A small structured engagement: read of mandate folder, gap report against confidentiality and MNPI rules, fix list before going to market.

What this work is not

A planner sequences the deal. AI does the mechanical work around it.

This page makes the mechanical layer faster. The closing table stays human.

The throughput is on volume and precision. The judgment that closes the deal is the advisor's. The comparison page sets the structural difference between sequencing the deal and examining whether it is the right one.

Read advisor vs. exit planner →
Pull AI back out of the workflow when
  • A code-name protocol failure occurred.
  • Live deal terms reached a non-tenanted model.
  • A long-list entry was hallucinated.
  • A CIM read in a generic voice.

When the deal question is the wrong question

Run the policy and the stack for one mandate.
If the firm is still stuck, the question is structural.

Application-gated. Personal reply within 48 hours.

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