A prospect judges fit in the first eleven minutes of the discovery meeting. By the time they decide to sign, they have already formed an opinion on whether the advisor has done the homework — whether the advisor walked in knowing the prospect's career arc, their likely equity-comp picture, the recent liquidity event, the foundation they support, the second marriage and the children from the first. Five minutes of pre-meeting AI-assisted research, done well, is the difference between a prospect who closes and a prospect who ghosts. Done badly — by pasting a name into a public LLM, by repurposing a third-party rating without the Marketing Rule disclosure, by inventing an executive-comp detail the model hallucinated — it is the difference between a closed engagement and the next AI-washing enforcement headline. This lesson installs the 5-minute prospect dossier workflow: career arc from LinkedIn, equity comp from proxy DEF 14A and Form 4, liquidity events from M&A news, charitable footprint from 990-PF, family structure from public records — assembled in Catchlight or an enterprise LLM pipeline, output as a one-page brief with disclosed sources and the Marketing Rule disclaimer.

The Five-Minute Clock and Why It Exists

The five-minute budget is not arbitrary. It is the time an advisor with a 200-household practice and a fully-booked Tuesday can realistically allocate to prospect prep between the 9:30 review and the 10:30 discovery. The Schwab 2026 RIA Benchmarking Study reports advisor adoption of pre-meeting AI more than doubled vs. 2023; the Kitces AdvisorTech map for March 2026 lists Catchlight, SmartAsset, and the broader prospecting AI category as the fastest-growing AdvisorTech segment by ARR. The reason: a prospect dossier produced in five minutes is the leverage point that turns prospecting from a part-time activity into a structural advantage. The advisor who walks into a discovery meeting at 10:30 with a brief naming the prospect's two RSU tranches vesting in November, the foundation grant the prospect's wife runs, and the prior employer's recent acquisition by Salesforce — that advisor closes at a different rate than the one who opens with "tell me about yourself."

The constraint is regulatory. Every piece of third-party content the advisor repurposes is potentially a marketing communication under SEC Rule 206(4)-1 and FINRA Rule 2210. Every prospect-specific fact pasted into a public LLM is potentially a Reg S-P / GLBA exposure. Every uncited claim in a follow-up email referencing the dossier creates a substantiation gap the L4 Ch7 audit cannot close. The discipline is to build the dossier in five minutes within the four constraints — accuracy, source attribution, NPI protection, Marketing Rule compliance — that the L1 Ch4 and L1 Ch5 lessons established.

Catchlight as the Aggregator — and Why It Matters

Catchlight (a Fidelity-Labs-incubated, now standalone, AI prospecting platform with broad RIA adoption) sits at the center of the modern prospect-research workflow in 2026. The product ingests a prospect identifier (email, name + employer, LinkedIn URL), runs against multiple public-data sources (LinkedIn, SEC filings, news, public records, social media), and produces a structured profile: estimated household income, estimated investable assets, career history, equity-comp signals, charitable involvement, marital status, residency, and a propensity-to-engage score. Used inside a Schwab/Fidelity/Pershing-integrated RIA, Catchlight outputs flow into Wealthbox, Salesforce Financial Services Cloud, Practifi, or Redtail Engage as enriched lead records.

The alternative pipeline, for firms that don't use Catchlight, is an enterprise LLM (Microsoft Copilot, OpenAI Enterprise, Google Gemini Enterprise) plus manual orchestration across LinkedIn, SEC EDGAR (DEF 14A, Form 4, 10-K), ProPublica Nonprofit Explorer (990-PF, 990), county property records, and local news. Either pathway works; the discipline is the same.

One regulatory note for Catchlight specifically: Catchlight's outputs include propensity scores that are derived from algorithmic models. If those scores are referenced in client-facing materials (capabilities decks, sales presentations) — they become subject to the Marketing Rule's substantiation requirement. Internal-use only is the default safe posture; client-facing use requires the L4 Ch7 substantiation file framework.

Career Arc — LinkedIn, Press Releases, and the Five-Year Trajectory

The first dossier section is the career arc. The advisor wants to know: current role, current employer, tenure, prior role, prior employer, three-job trajectory, education, professional credentials, board memberships, advisory roles. LinkedIn is the canonical source; Catchlight pulls it automatically, an enterprise LLM with a LinkedIn URL can produce a structured extract.

The discovery insight from the career arc: the prospect who has been Chief Revenue Officer at three SaaS companies over twelve years has a very different equity comp picture (multiple ISO / NQSO / RSU tranches across employers, possibly 83(b) elections from early-stage years, possibly QSBS Section 1202 eligibility on early shares) than the prospect who has been at one employer for twenty years (single 401(k) plan, likely NUA opportunity, likely deep deferred-comp). The career arc tells the advisor which planning lever to lead with in discovery.

The prompt for the career-arc extract (assuming an enterprise LLM with LinkedIn URL provided): "You are a senior CFP-certificant advisor preparing for a discovery meeting. Given the LinkedIn profile at [URL], extract: current role, current employer, employment start date, prior three roles and employers with tenure, education with year and institution, professional credentials, board memberships, public-company affiliations. Format as a one-page structured table. Do not infer or invent. If a field is not present in the profile, write 'not on profile.' Do not paste any of this content into client-facing materials without source attribution and Marketing Rule disclosure review."

Equity Comp Clues — DEF 14A Proxies, Form 4 Insider Filings, and What They Tell You

For a prospect who is an executive officer or director at a US public company, the SEC's EDGAR system contains a goldmine of equity-comp information that vastly outperforms what the prospect will volunteer in the first meeting.

DEF 14A Proxy Statements — RSUs, Performance Stock, Cash Bonus Structure

The annual proxy statement (DEF 14A) for public companies contains the Compensation Discussion and Analysis (CD&A), the Summary Compensation Table, the Grants of Plan-Based Awards Table, the Outstanding Equity Awards Table, the Option Exercises and Stock Vested Table, and the Pension Benefits / Nonqualified Deferred Compensation tables for "named executive officers" — the CEO, CFO, and typically the next three highest-paid. If the prospect is one of the NEOs, the proxy contains the prior year's equity grants (number of RSUs, performance-stock units, options), the vesting schedule, the cliff-vs-graded structure, the prior-year vesting events, the open-but-unvested balance, and the deferred-comp balance.

Form 4 — Real-Time Insider Trading and Vesting Disclosures

Form 4 is the SEC filing an insider (officer, director, 10%+ holder) files within two business days of any change in their beneficial ownership. For the executive prospect, Form 4 filings reveal: every RSU vesting and the share-withholding for taxes (the model can compute approximate gross share value and approximate net-of-tax retained shares), every option exercise (with the strike price and same-day-sale election), every open-market sale (often under a 10b5-1 plan), and any gift or charitable transfer. Pulled together, the prior twelve months of Form 4 filings produce a real picture of the executive's recent realized comp and concentrated stock position.

10-K — Pension Plan, Frozen DB Plans, and Deferred-Comp Detail

The 10-K's footnotes on Retirement Benefits, Stock-Based Compensation, and (for executive officers) Director and Executive Officer Compensation supplement the proxy with plan-level detail. For a prospect at a Fortune 500 company with a frozen defined-benefit pension, the 10-K confirms the plan freeze date, the actuarial methodology, the lump-sum-vs-annuity election timing, and the discount-rate sensitivity — all of which become discovery-meeting questions.

The prompt for the equity-comp extract: "You are a senior CFP-certificant advisor preparing for a discovery meeting with [Prospect Name], who is [Title] at [Employer, public ticker]. Pull the most recent DEF 14A proxy statement and the prior 12 months of Form 4 insider filings from SEC EDGAR. Extract: (1) the outstanding equity awards as of the proxy date — RSUs, PSUs, options with strike — and the vesting schedule, (2) the realized equity from the prior year per the Option Exercises and Stock Vested Table, (3) the deferred-comp balance per the Nonqualified Deferred Compensation Table, (4) the prior 12 months of Form 4-reported vestings, option exercises, and open-market sales. Cite the filing URL and filing date for each fact. Do not infer current values that are not in the filings; for any current-value estimate, note that the share price is as of the filing date. Do not state any FRA, RMD age, SS maximum, or other annual figure unless I have provided it."

Liquidity Events — M&A News, IPO Lockup Expirations, Tender Offers

A liquidity event is the most predictable advisor opportunity in the prospect pipeline. The prospect whose private-company employer just announced an acquisition (8-K filing, press release, news coverage) is six to twelve weeks from a cash, stock, or mixed payout — and is a high-conversion prospect because the planning need is concrete and time-bound. The IPO-lockup expiration similarly: a prospect at a company that IPO'd six months ago is one quarter from a 180-day lockup expiration and a likely 10b5-1 plan setup.

The prompt for liquidity-event detection: "You are a senior CFP-certificant advisor. Given [Prospect Name] is at [Employer], search public news and SEC filings for: (1) any 8-K, S-4, or press-release announcement of an acquisition, merger, or sale of [Employer] in the prior 18 months, (2) any IPO filing (S-1) with a public offering date and 180-day lockup expiration date, (3) any tender offer (Schedule TO) or secondary offering, (4) any material announcement of restructuring, divestiture, or executive transition. For each, cite the filing or news source URL and date. Do not speculate on personal compensation impact; flag the event and the planning conversation it invites."

Charitable Footprint — 990-PF, Donor-Advised Funds, and Foundation Boards

For a prospect with charitable intent, the public-record paper trail is rich. The IRS Form 990 (private operating and non-operating foundations file 990-PF; public charities file 990) is publicly available via ProPublica Nonprofit Explorer, Candid, and IRS Tax Exempt Organization Search. The 990-PF for a private foundation discloses the foundation's annual giving, the directors and trustees (often family members), the principal investments, the related-party transactions, and the qualifying distributions for the 5% minimum payout under IRC §4942.

The prospect who is a director of a $40M family foundation is a candidate for sophisticated charitable strategies — CRT pre-sale, CLAT for estate-tax purposes (the L3 Ch5 advanced-vehicle decision tree develops these), DAF coordination, QCD coordination at 70.5+. The prospect whose family runs a smaller (sub-$1M) foundation may be a candidate for collapsing the foundation into a DAF for administrative simplicity.

The prompt for charitable-footprint extract: "You are a senior CFP-certificant advisor. Search for any IRS Form 990 or 990-PF filings naming [Prospect Name] or [Prospect Spouse] as a director, trustee, officer, or substantial contributor in the prior five years. For each: name the organization, the EIN, the most recent fiscal year filed, the role of the prospect, the foundation/charity's total assets, and the prior year's qualifying distributions. Cite the filing source (ProPublica Nonprofit Explorer URL, Candid URL, or IRS TEOS URL). Do not infer charitable intent from foundation directorship alone — flag it as a discovery question."

Family Structure — Public Records, Property, Marriage, and the Second-Family Pattern

The L3 Ch7 lesson on non-standard family structures (divorce, special-needs, blended families) treats family structure as a primary planning vector. Pre-meeting, the prospect's family structure is detectable from county property records (real estate ownership including spouse), county marriage-license records, public obituary databases for prior-spouse cases, social media for children's names and ages, and LinkedIn for adult children. The prospect with a $4.5M primary residence in Greenwich, CT, owned jointly with a spouse with a different last name; a second residence in Stowe, VT, owned solely; and an adult son from a prior marriage who is a beneficiary of a 2003 SLAT — that is a blended-family planning picture before the discovery meeting begins.

Two regulatory cautions for family-structure research. First, Reg S-P / GLBA NPI rules apply to information the firm collects in the course of providing financial services — but for a prospect, the firm has not yet entered the advisory relationship, and the information is public-record. The exposure is downstream: once the prospect signs, the firm's NPI obligations attach to everything it holds, including the pre-engagement dossier. The discipline is to store the dossier in an approved system (Wealthbox, Salesforce FSC, Practifi) under the firm's data-classification policy from the moment of meeting, never in a personal Notion or Google Doc. Second, any client-facing reference to the prospect's family structure — in a follow-up email, an IPS draft, an Owl-of-Athena-style profile shared with the prospect — should be sourced and consent-verified during the meeting. Inferred family detail repeated back to the prospect without verification is a trust-breaker.

Assembling the One-Page Brief — Format, Sources, and the Marketing Rule Disclaimer

The five extracts (career arc, equity comp, liquidity events, charitable footprint, family structure) assemble into a one-page brief the advisor reads in ninety seconds before walking into the meeting. The brief format that works at the L2 Ch1.1 anatomy standard:

Header. Prospect name, meeting date/time, meeting type (initial discovery / second meeting / referral source).

Section 1: Headline (one sentence). The single most important planning fact about the prospect. "Sarah is a CRO at [Public SaaS Co], with three RSU tranches vesting Nov 15 totaling ~$340K pre-tax at the current share price, plus a frozen DB pension from a prior employer (Goldman, frozen 2018) with a $610K lump-sum estimate."

Section 2: Career arc (three bullets). Current role + start, prior two roles + tenure, key credentials. Sourced to LinkedIn URL.

Section 3: Equity comp (three bullets). Outstanding RSUs/options, prior-year realized, deferred-comp balance. Sourced to DEF 14A URL and Form 4 filing list.

Section 4: Liquidity events (one bullet or none). Pending M&A, IPO lockup, secondary. Sourced to 8-K / S-1 / press release URL.

Section 5: Charitable / family / other (two bullets). Foundation board, blended family flag, property concentration. Sourced to 990-PF URL and county records (with privacy disclaimer).

Section 6: Three discovery questions to lead with. Specific, evidence-driven, non-leading. Example: "Tell me about your November vesting — what's the plan?" Not: "Are you worried about your November vesting?"

Footer: Sources and disclaimer. A short list of every source cited (URLs); plus the Marketing Rule disclaimer for any third-party content the firm might later repurpose in client-facing materials: "Brief prepared from public sources for internal advisor use only. Any external repurposing requires Marketing Rule 206(4)-1 compliance review under firm policy."

The Marketing Rule Disclosure Discipline for Third-Party Content

The dossier is internal-use. The moment any of its content moves into a follow-up email, a capabilities deck, an LinkedIn DM, or a client-facing brief — the SEC Marketing Rule fires. The 2024-2025 AI-washing enforcement cluster and the January 2026 staff FAQs together establish the operating discipline: the firm cannot repurpose a third-party rating, a Google review, a press-release quote, or any other third-party content in client-facing materials without (a) substantiation, (b) "clear and prominent" disclosure of the source and any compensation, and (c) the L4 Ch7 substantiation file logging the use. The L1 Ch4.1 lesson on the SEC Marketing Rule developed the disclosure templates; the L2 Ch5 same-day follow-up lesson will apply them to the discovery follow-up specifically.

The simple rule: any sentence in a client-facing artifact that originates from the prospect dossier must either (a) come from the prospect's own statement in the meeting, (b) come from a public source the firm cites and discloses, or (c) be removed. The dossier is the advisor's prep; it is not the advisor's client communication.

Monday Morning Deployment

The first deployment: pick the next three discovery meetings on the calendar. For each, run the five-extract pipeline (career arc, equity comp, liquidity events, charitable, family) in either Catchlight or an enterprise LLM. Assemble the one-page brief. Spend ninety seconds reading it before the meeting. Note which three discovery questions the brief surfaced. Capture in the post-meeting (L2 Ch4 covers live note capture in Jump or Zocks) which of the brief's hypotheses were confirmed and which were wrong. After ten meetings, the prompt library has a refined "Discovery-Brief-v1.2" prompt that produces clean briefs in under five minutes. The L3 Ch2 50-household Roth conversion screen, the L3 Ch5 estate gap audit, and the L3 Ch6 equity-comp exercise modeling all build on this same source-and-extract foundation.

Key Takeaways

• Five-minute prospect dossier in five extracts — career arc (LinkedIn), equity comp (DEF 14A + Form 4 + 10-K), liquidity events (8-K + S-1 + press), charitable footprint (990-PF + ProPublica), family structure (county records + social) — assembled into a one-page brief.
• Catchlight is the aggregator pathway; enterprise LLM + manual orchestration is the alternative for non-Catchlight firms. Both feed into Wealthbox, Salesforce FSC, Practifi, or Redtail Engage as enriched lead records.
• Equity comp extraction from DEF 14A and Form 4 outperforms what the prospect will volunteer — outstanding RSU / PSU / option balances, vesting schedules, prior-year realized comp, deferred-comp balance, Form 4 vesting and sale events.
• The dossier is internal-use only by default. Any content moved into client-facing materials triggers SEC Marketing Rule 206(4)-1 substantiation and "clear and prominent" disclosure requirements under the January 2026 staff FAQs and the 2024-2025 AI-washing settlement framework.
• The Reg S-P trap is downstream of engagement. Pre-engagement public-record research has limited NPI exposure; the moment the prospect signs, all collected information becomes regulated NPI under the May 2024 Reg S-P amendments — store accordingly from the start.
• Three discovery questions to lead with is the deliverable section that turns research into meeting performance — specific, evidence-driven, non-leading questions that confirm or refine the dossier's hypotheses.
• The L4 Ch7 substantiation file is the cross-cutting artifact for any client-facing repurposing of dossier content; the L2 Ch5 same-day follow-up lesson applies the disclosure templates to the discovery follow-up email.