---
name: nonprofit-major-gifts
description: "Sets major and principal gift strategy: rating prospect capacity and readiness, setting a specific ask amount, structuring a gift proposal or one-page case document, and drafting/negotiating gift agreements including multi-year pledges and named-gift terms. Use when a user asks how much to ask a specific donor for, wants help structuring a major-gift proposal or gift agreement, needs a capacity/readiness rating for one prospect, or is preparing a solicitation visit. Does not cover moving a prospect through general pipeline stages (use nonprofit-donor-pipeline), bequests/estate and legacy gifts (use nonprofit-planned-giving), or campaign-wide gift tables and campaign leadership (use nonprofit-capital-campaigns)."
license: MIT
metadata:
  supervision: "expert-required"
  supervision_note: "Gift agreements, multi-year pledges and naming rights are enforceable commitments."
  date_added: "2026-09-07"
  date_added_source: "git:1860ed47a83901ff5e6d45abc4a2ef05be8fd4cd"
---

# Major & Principal Gift Strategy

## When to Use This Skill

Use this skill for the strategy and mechanics of a specific major or principal gift ask — not for
tracking where a prospect sits in the general pipeline (`nonprofit-donor-pipeline`), not for
bequests or legacy society gifts (`nonprofit-planned-giving`), and not for a capital campaign's
overall gift table or leadership structure (`nonprofit-capital-campaigns`, which then calls this
skill for the mechanics of each individual ask within the campaign). Typical triggers:

- "How much should we ask this donor for?"
- "Help me structure a proposal for a $500K gift"
- "Draft a gift agreement for a named endowment fund"
- "Rate this prospect's giving capacity and readiness"
- "Prep me for a solicitation meeting next week"
- "What should our multi-year pledge structure look like?"

Most organizations define "major gift" as a threshold relative to their own median gift (commonly
the top 1-10% of donors or a fixed floor like $10K-$25K+); "principal gift" typically denotes the
top tier within major gifts (often $1M+ or the organization's own defined ceiling tier). Confirm
the org's own threshold before applying generic figures.

## Capacity & Readiness Rating

Score each prospect on three independent axes before setting an ask:

1. **Capacity** — estimated financial ability to give, from wealth indicators (real estate,
   business ownership, stock holdings/SEC filings, past gift sizes to peer organizations, art/
   foundation affiliations). Express as a *range*, not a point estimate (e.g., "$50K-$150K
   capacity over 3-5 years").
2. **Affinity/Linkage** — strength of connection to the mission and to an inside champion (board
   member, staff, peer donor) who can open or accompany the ask.
3. **Readiness** — timing signals: recent liquidity event, life stage, past response to
   cultivation moves, explicitly stated interest. A high-capacity, high-affinity prospect with low
   readiness should not be solicited yet — return to cultivation.

A common failure mode is setting the ask from capacity alone; always multiply the capacity/affinity/
readiness signals together, not add them — a weak score on any one axis should sharply reduce
confidence in a near-term ask.

## Setting the Ask Amount

1. Anchor to actual data: largest prior gift to your org, largest known gift to any peer
   organization, and stated or inferred capacity range.
2. Apply a stretch multiplier appropriate to relationship depth — typically 1.5x-3x the donor's
   largest previous gift for a well-cultivated relationship; higher stretch requires higher
   confidence in capacity and cultivation depth.
3. Set a specific number, not a range, in the internal strategy — asking "for a gift between $25K
   and $50K" externally is acceptable, but the internal team must agree on a real target and a
   walk-away minimum before the meeting.
4. Decide the ask structure: outright cash, multi-year pledge (typically 3-5 years), or a
   blended cash + appreciated stock/DAF gift. Multi-year pledges let you propose a materially
   larger total commitment at a comfortable annual cash-flow level for the donor.
5. Identify the right asker (peer-to-peer solicitation by a board member or major donor
   consistently outperforms staff-only asks) and confirm they are briefed and rehearsed.

## Standard Deliverables

- **One-page case/proposal summary** — problem, solution, specific funding need tied to a concrete
  budget line or project, requested amount, naming/recognition offered, timeline.
- **Formal proposal document** (for $100K+ or campaign gifts) — narrative case, budget detail,
  organizational credibility section, gift structure options, next steps. If this proposal targets
  a foundation/institutional funder rather than an individual, the drafting mechanics live in
  `nonprofit-grant-writing`; this skill covers the individual/family major-donor version.
- **Gift agreement** — legally reviewable document specifying: gift amount and payment schedule,
  restriction/designation of funds, naming rights and duration, reporting commitments back to the
  donor, and a variance/redirection clause if the named purpose becomes impossible to fulfill
  (essential — its absence is a recurring legal and PR risk for named endowments and building
  gifts).
- **Solicitation briefing memo** — for the asker: relationship history, ask amount and rationale,
  anticipated objections, and a fallback ask if the primary number is declined.

## Concrete Steps

1. Confirm the prospect has cleared Cultivation and is marked ready in the pipeline system
   (`nonprofit-donor-pipeline` handoff point).
2. Complete the capacity/affinity/readiness rating; do not proceed to ask-setting on capacity
   alone.
3. Set the specific ask number and structure (outright vs. multi-year vs. blended) using the
   anchoring method above.
4. Draft the proposal or one-pager matched to the ask size and the donor's stated interest area.
5. Identify and brief the asker; rehearse the ask, including handling a "no," a "not now," and a
   counter-offer.
6. Conduct the solicitation; record the outcome, amount, and any conditions immediately.
7. On a "yes," draft the gift agreement within 5-10 business days while intent is fresh; route
   through legal/finance review before signature for any gift with naming rights or restrictions.
8. On a multi-year pledge, set up pledge reminder and payment tracking (a stewardship handoff to
   `nonprofit-donor-retention`).

## Common Failure Modes

- **Underasking**: staff self-censor and ask well below true capacity out of discomfort — counter
  with the anchoring formula and peer-comparison data, not intuition.
- **No walk-away number**: going into a solicitation without an agreed minimum acceptable gift
  leads to accepting a token amount that undervalues the relationship.
- **Undefined restrictions**: accepting a highly restricted gift without confirming the org can
  actually deliver the restricted purpose long-term — always negotiate a variance clause.
- **Wrong asker**: sending a junior staffer to ask a peer-level relationship a board member should
  be asking.
- **Proposal-agreement mismatch**: gift agreement terms that drift from what was actually proposed
  and verbally agreed — reconcile documents before signature.

## For Advisors

Bring an outside, dispassionate capacity read — clients routinely underestimate their own top
donors' capacity because staff proximity breeds caution. Use documented peer-gift comparisons to
justify a stretch ask to a skittish ED or board. When a client's proposal-to-close ratio is low,
diagnose whether the failure is at ask-amount-setting (asking wrong) versus asker selection (wrong
messenger) versus readiness (asking too soon) before recommending training — these have different
fixes. Always insist on a written gift agreement template with a variance clause as a standard
deliverable; its absence is a governance red flag worth raising with the board directly.