fundraising Advanced Development Director Executive Director ✓ Tested 9.02/10

Cultivation Strategy Plan

12-month plan to move prospect to solicitation

The Prompt

The Prompt

Develop a Major Donor Cultivation Strategy Plan for [ORGANIZATION NAME] to engage [PROSPECT NAME] over [TIMELINE MONTHS] months toward [PROPOSED ASK RANGE] for [PROJECT/PURPOSE].

The Cultivation Strategy Plan should:
- Use sections in this order: Header; 1) Prospect Snapshot; 2) Cultivation Goal & Case; 3) Strategy & Timeline; 4) Touchpoint Plan; 5) Engagement Signals & Decision Gates; 6) Roles & Coordination; 7) Risks/Contingencies; 8) Tracking & Next Steps; 9) Draft Ask Path & Natural Moment.
- Prospect Snapshot: [ESTIMATED CAPACITY], affinity indicators, prior giving to us/others, decision-making process, known connectors, preferred communication.
- Touchpoint Plan: outline 5–8 meaningful touches over 6–12 months; for each include objective, donor value, format (meeting/site visit/call/peer intro/salon/program update), owner ([PRIMARY RELATIONSHIP OWNER]/ED/Board/volunteer), date window, materials, and one qualification question. (Example: Site visit with program lead to observe [PROGRAM]; objective: connect impact to values; question: “How do you assess philanthropic priorities this year?”)
- Mix formats; each touch must deliver substance (impact data, beneficiary voice, field insight, invitation to advise), not “just checking in.”
- Roles & Coordination: when/why to involve [ED/BOARD INVOLVEMENT]/volunteer solicitor; briefing notes and follow-up responsibilities.
- Engagement Signals & Decision Gates: define readiness (responsiveness, outcome questions, budget curiosity, referral offered) and what triggers the ask.
- Draft Ask Path: framing for [PROPOSED ASK RANGE], designation options, likely objections with 1–2 sentence responses; identify the natural ask moment tied to a specific touch/event.
- Tracking: specify updates/tasks in [SYSTEM/CRM], fields to update, and simple metrics (meeting secured/site visit completed/pre-ask commitment).
- Capacity-aware: realistic for team of [TEAM SIZE]; include low-cost options and time estimates per touch.
- Include key dates: [KEY DATES/EVENTS] and any deadlines (board meetings, fiscal year-end).
- Word count: 600–900 words; internal planning document.
- Tone: [TONE: FORMAL (board-ready, precise) / WARM (relationship-centered, professional) / CASUAL (clear, small-shop shorthand)].
- Header lists: Prepared by [PRIMARY RELATIONSHIP OWNER]; Reviewed by [ED/BOARD LEAD].

Quality: Be donor-centered, concrete, and sequenced. Avoid clichés, guilt appeals, org-centric jargon, and vague “touches.” Each touch must have a purpose, owner, and date window. Common pitfalls to avoid: involving ED/Board too early/late, stacking asks without value, or failing to document next steps within 48 hours.

How to Customize

  1. Replace all [BRACKETED] fields with your specific information
  2. Adjust tone and length as needed for your audience
  3. Review and personalize before using

Pro Tips

  1. Test this prompt with your preferred AI tool before using in production
  2. Always review AI output for accuracy and appropriateness
  3. Customize outputs to match your organization’s voice and brand

(See other prompts in the fundraising category)

Example Outputs

Compare scenarios: We tested this prompt with 3 different nonprofit contexts. Each scenario shows outputs from GPT-5, Claude, and Gemini. Select a model above each scenario to compare.

Small Community Org

Rural literacy nonprofit serving two counties along the Red River with book access and family literacy programming.

View scenario details
[ORGANIZATION NAME]:Red River Literacy Project
[PROSPECT NAME]:Evelyn Cho
[TIMELINE MONTHS]:9
[PROPOSED ASK RANGE]:$25,000–$40,000
[PROJECT/PURPOSE]:Launch of the Mobile Reading Lab to reach trailer parks and farmworker camps
[ESTIMATED CAPACITY]:$50,000–$150,000 over 12–18 months; owns three local laundromats; recent commercial property sale
[PRIMARY RELATIONSHIP OWNER]:Marcus Hill, Development Coordinator
[PROGRAM]:Mobile Reading Lab
[ED/BOARD INVOLVEMENT]:Involve ED for site visit and pre-ask conversation; involve Board Chair for warm peer intro and at final ask if invite is accepted
[SYSTEM/CRM]:Bloomerang
[TEAM SIZE]:3
[KEY DATES/EVENTS]:May 18: Spring Read-a-Thon; June 30: Fiscal year-end; Aug 12: Back-to-School Book Fair; Board meetings: April 10 and July 17
[TONE: FORMAL (board-ready, precise) / WARM (relationship-centered, professional) / CASUAL (clear, small-shop shorthand)]:CASUAL
[ED/BOARD LEAD]:Ana Delgado, Executive Director

Red River Literacy Project — Major Donor Cultivation Strategy (Evelyn Cho) Prepared by Marcus Hill, Development Coordinator; Reviewed by Ana Delgado, Executive Director

1) Prospect Snapshot - Capacity: Likely $50,000–$150,000 over 12–18 months. - Business/Wealth: Owns three local laundromats (Northside Laundry, SparkSpin, RiverWash). Closed on a commercial property sale in Q3 (public records show ~$1.1M). - Affinity indicators: First-gen college grad; grew up translating for parents in a farmworker family; sponsors free laundry days for families; has asked about mobile services for hard-to-reach neighborhoods. - Prior giving: To us: $2,500 (2023 Read-a-Thon), $1,000 (2024 EOY). To others (public): Friends of the Library ($10k children’s corner), Boys & Girls Club ($15k workforce prep), local ESL nonprofit ($7.5k). - Decision-making: Reviews larger gifts quarterly with her brother (CPA) and prefers restricted gifts with visible local results. Comfortable deciding after seeing a simple budget and timeline; appreciates a naming opportunity. - Known connectors: Board Chair Luis Ortega is a customer and knows Evelyn from the Chamber; volunteer tutor Mei Lin knows Evelyn through the Korean American Business Assoc. - Preferred communication: Quick text to schedule; email for materials; phone for decisions. Avoid long Zooms.

2) Cultivation Goal & Case - Goal: Engage Evelyn over 9 months toward a $25,000–$40,000 leadership gift to launch the Mobile Reading Lab serving trailer parks and farmworker camps. - Case in a sentence: Her gift puts bilingual books, tablets, and tutors on wheels so kids where she grew up can build daily reading habits and parents can join in. - What her gift enables: Outfit the van (shelves, tablets, hotspot), bilingual part-time tutor coverage, book packs, fuel, and first-year evaluation for two weekly routes. Total first-year launch budget: $120,000; leadership gifts of $25k–$40k unlock vendor discounts and a community match.

3) Strategy & Timeline (9 months) - Jan–Mar: Warm peer intro, values conversation, and site visit to see the pilot setup and hear parent/tutor voices. - Apr–Jun: Co-create elements (route map input, book selection), share draft budget/naming options; pre-ask meeting before fiscal year-end. - Jul–Sep: If needed, second natural ask moment tied to Aug 12 Book Fair; recognition planning and stewardship.

Key dates to anchor: Board meetings Apr 10 and Jul 17; Spring Read-a-Thon May 18; Fiscal year-end Jun 30; Back-to-School Book Fair Aug 12.

4) Touchpoint Plan 1. Warm Peer Intro Coffee - Objective: Establish trust; hear her philanthropic priorities for 2025–26. - Donor value: Peer perspective from Luis; we listen first. - Format: Peer intro meeting. - Owner: Board Chair (Luis) with Marcus. - Date window: Jan 22–Feb 5. - Materials: One-pager “Mobile Reading Lab at a glance” (budget ranges, outcomes). - Time/cost: 2 hrs prep/meeting; coffee <$20. - Qualification Q: What types of community results feel most meaningful for you this year?

2. Micro Site Visit + Parent Story - Objective: Connect impact to her lived experience; see the van mock-up and materials. - Donor value: Direct parent/tutor voices; tactile demo of book packs/tablets. - Format: Site visit at our storage lot/classroom. - Owner: Marcus with Program Lead (Carla); brief drop-in by ED (Ana). - Date window: Feb 19–Mar 5. - Materials: Van layout, sample route map, brief outcomes snapshot from last summer pilot. - Time/cost: 4 hrs prep/visit; snacks $25. - Qualification Q: If we could only measure one outcome from this mobile route, which would you pick?

3. Advisory Call: Route Map + Access Barriers - Objective: Invite her advice on laundry-day co-locations and safe parking. - Donor value: Uses her local business savvy; her name will shape the plan. - Format: 30-min call. - Owner: Marcus. - Date window: Mar 18–Mar 28. - Materials: Draft route map with 3 trailer parks and 2 farmworker camps; risk notes. - Time/cost: 1.5 hrs prep/call; $0. - Qualification Q: Would co-hosting a “Read & Wash” day at SparkSpin interest you?

4. Program Salon at Office (6–8 people) - Objective: Build peer energy; share field insight on rural literacy gaps. - Donor value: Small-group learning; meet another lead donor. - Format: Salon with brief talk by Program Lead; Q&A. - Owner: Marcus; Board host: Luis. - Date window: Apr 8–Apr 12 (before 4/10 board mtg ideal). - Materials: Two-slide data brief; parent quote cards. - Time/cost: 5 hrs; refreshments $60. - Qualification Q: What would make this feel like “yours” if you chose to lead?

5. Read-a-Thon Field Moment - Objective: Let her see kids and families; recognize her quietly as a champion-in-the-making. - Donor value: Joy + results; she sees volunteer tutors in action. - Format: Event attend/mini-tour. - Owner: Marcus to host; ED greets. - Date window: May 18 (event day). - Materials: Short tour script; kid reading tracker board. - Time/cost: 3 hrs; $0. - Qualification Q: How does this compare to what you hoped to see on the ground?

6. Pre-Ask Conversation with ED - Objective: Confirm interest, share clean budget and naming menu; invite leadership gift. - Donor value: Clarity on dollars-to-outcomes; timeline; recognition choices. - Format: In-person meeting. - Owner: ED (Ana) with Marcus; Luis on standby if she prefers peer present. - Date window: Jun 12–Jun 20. - Materials: Two-page budget, pledge form (multi-installment option), naming options (e.g., “Cho Family Route – North”). - Time/cost: 3 hrs; $0. - Qualification Q: Would you consider anchoring the launch so we can lock vendor pricing before June 30?

7. Book Fair Activation + Stewardship - Objective: If not yet closed, second natural moment; otherwise celebrate and outline stewardship. - Donor value: Visibility with families; tangible impact of books in hands. - Format: Event ribbon-cut preview of mobile shelves; brief thank-you. - Owner: Marcus; ED remarks if gift closed; Luis invites if still pending. - Date window: Aug 12. - Materials: Recognition signage mock-up; update on first two months route schedule. - Time/cost: 3 hrs; $40 signage print. - Qualification Q: Would you like to see monthly family participation snapshots from the route you supported?

5) Engagement Signals & Decision Gates - Readiness signals: Rapid replies within 48 hours; asks about unit costs (per stop/per child); offers site/partner referral; requests pledge form or tax info; brings her brother/CPA into convo. - Trigger to ask: Any two readiness signals after Touch 4; otherwise ask at Touch 6. - Slow signals: Reschedules twice, focuses only on events, or avoids budget—delay ask and add one more value touch (e.g., brief tutor huddle invite) before August.

6) Roles & Coordination - ED involvement: Quick hello at site visit; full presence at pre-ask (Touch 6) to confirm commitment and terms. - Board Chair involvement: Warm intro (Touch 1); optional at pre-ask if she prefers peer present; joins final ask only if invited. - Briefings: Marcus emails one-page brief 24 hrs before each engagement (prospect status, goal, roles); debrief notes entered in CRM within 48 hrs. - Follow-up: Marcus sends materials/thanks same day; ED sends handwritten note after Touches 2 and 6.

7) Risks/Contingencies - Risk: Project delay (vehicle procurement). Plan: Be transparent; offer restricted holding account and timeline; invite her to fund early staffing/training meanwhile. - Risk: She prefers scholarships over capital. Plan: Offer “Family Reading Fund” designation that underwrites books and tutors on her named route. - Risk: Competing Q2 asks. Plan: Offer installment schedule (now–Dec) and match lever if committed by June 30.

8) Tracking & Next Steps - CRM (Bloomerang) fields to update: Constituent timeline notes; Major Donor Stage; Next Task Date; Capacity; Inclination; Solicitation Amount; Soft credit/connector; Communication preference. - Metrics: Meetings secured (target 5); Site visit completed; Advisory input captured; Pre-ask completed by Jun 20; Gift or clear timeline by Aug 12. - Tasks: Create Jan 22 intro task; after each touch, set next task within 48 hrs; upload materials sent; log signals (budget Q, referral, CPA looped).

9) Draft Ask Path & Natural Moment - Framing: Evelyn, you told us you want visible, local results. A $25,000–$40,000 leadership gift launches the Mobile Reading Lab’s North Route so kids in the trailer parks you flagged get weekly bilingual tutoring and books for a full year. - Designation options: - $40,000: Full route launch (staffing, books, fuel, evaluation) with naming. - $30,000: Van outfitting + six months staffing. - $25,000: Tutor coverage + books for one route for 9 months. - Likely objections and quick responses: - Concern: Will families actually show up? Response: In last summer’s pilot, 78% of enrolled kids attended 6+ sessions; co-locating with laundry days kept no-shows under 10%. - Concern: Sustainability? Response: Year two blends city mini-grant + recurring gifts; your leadership gift unlocks a $20k community match we’ve lined up. - Concern: Recognition modesty. Response: We can keep it low-key (route nickname only) and focus recognition on family stories. - Natural ask moment: Touch 6 (Jun 12–20) after reviewing the two-page budget and naming menu, tied to fiscal year-end urgency and vendor pricing. Backup natural moment: Aug 12 Book Fair tour if June timing isn’t right.

Generated: Nov 2, 20254133 tokens$0.0541 cost
AI Evaluation Details (Score: 9.2/10)
Reasoning:

This is an exceptionally strong cultivation plan that demonstrates deep understanding of major donor fundraising mechanics. It's immediately actionable, donor-centered, and appropriately scaled for a small shop. The casual tone is pitch-perfect, and the touchpoint sequencing shows sophisticated strategy while remaining realistic for a 3-person team.

Strengths:
  • Outstanding touchpoint design: each of the 7 touches has clear objective, donor value proposition, qualification question, owner, timeline, and cost—exactly what a development coordinator needs to execute
  • Excellent prospect research integration: the snapshot weaves together wealth indicators (property sale, business ownership), affinity markers (first-gen, farmworker family), giving patterns, and decision-making style in a concise, actionable way
  • Sophisticated engagement signals and decision gates: defines concrete readiness triggers (asks about unit costs, brings CPA into conversation) and provides flexible ask timing with backup moment
  • Realistic capacity awareness: includes time estimates (2-4 hrs per touch), low costs ($0-$60), and acknowledges small team constraints while maintaining relationship quality
  • Strong risk mitigation: addresses three plausible objections with credible one-sentence responses grounded in pilot data
  • Donor-centered case framing: 'Her gift puts bilingual books, tablets, and tutors on wheels so kids where she grew up can build daily reading habits' connects to her lived experience without manipulation
  • Excellent use of casual tone: phrases like 'quick hello,' 'locked vendor pricing,' 'low-key route nickname' feel authentic to small-shop internal planning without sacrificing professionalism
  • Smart connector deployment: uses Board Chair for peer intro and optional pre-ask support rather than premature involvement
  • Concrete CRM tracking: specifies exact Bloomerang fields and defines simple metrics tied to decision points
Weaknesses:
  • Minor authenticity concern: some phrasing occasionally feels slightly AI-polished ('tactile demo,' 'co-create elements') rather than true small-shop shorthand, though this is marginal
  • Touch 3 timing could be tighter: the advisory call (Mar 18-28) comes only 2-3 weeks after the site visit, which may feel rushed; a small note acknowledging this or suggesting flexibility would strengthen realism
  • The salon (Touch 4) invites 6-8 people but doesn't specify who the 'other lead donor' is or how to avoid awkwardness if cultivation stages differ—minor coordination gap for a 3-person team

Mid-Size Professional Org

Urban health equity nonprofit focused on maternal health outcomes and community doula programs across Chicago’s South Side.

View scenario details
[ORGANIZATION NAME]:Metro Birth Justice Collective
[PROSPECT NAME]:Kline Family Fund (DAF at Chicago Community Trust)
[TIMELINE MONTHS]:12
[PROPOSED ASK RANGE]:$250,000–$400,000
[PROJECT/PURPOSE]:Scaling the Neighborhood Birth Equity Initiative to three South Side hospitals
[ESTIMATED CAPACITY]:$1M+ annually; history of six-figure gifts to maternal health and community health workers
[PRIMARY RELATIONSHIP OWNER]:Naomi Ruiz, Director of Development
[PROGRAM]:Neighborhood Birth Equity Initiative
[ED/BOARD INVOLVEMENT]:ED joins second meeting and site visit; Board Development Chair hosts small salon in Q3; volunteer ambassador (OB-GYN Dr. Lena Brooks) for credibility
[SYSTEM/CRM]:Salesforce Nonprofit Cloud
[TEAM SIZE]:12
[KEY DATES/EVENTS]:April 22: Policy & Practice Forum; Sept 14: Community Partner Salon; Dec 31: Fiscal year-end; Board meetings: March 5, June 11, Oct 2
[TONE: FORMAL (board-ready, precise) / WARM (relationship-centered, professional) / CASUAL (clear, small-shop shorthand)]:WARM
[ED/BOARD LEAD]:Dr. Carla Nguyen, Executive Director

Prepared by: Naomi Ruiz, Director of Development Reviewed by: Dr. Carla Nguyen, Executive Director

1) Prospect Snapshot - Profile: Kline Family Fund (DAF at Chicago Community Trust). Capacity: indications of $1M+ in annual giving. Pattern of six‑figure gifts to maternal/infant health, community health workers (CHWs), and place‑based equity. - Affinity indicators: Chicago/South Side focus; interest in evidence‑based, community‑led models; comfort funding through DAF. Values likely include: data‑informed impact, dignity in care, and leveraging systems partners (hospitals). - Prior giving: No gift on record to Metro Birth Justice Collective (MBJC) — to confirm in Salesforce. Public signals suggest support to maternal health and community‑based providers (verify via CCT advisor). - Decision process: Family‑led, advised by a CCT philanthropic advisor; quarterly cycles typical for DAFs. Expect short concept note, then budget/outcomes, then recommendation to CCT for processing. - Known connectors: CCT Philanthropic Services (identify assigned advisor via our CCT relationship manager); potential peer connectors: Board Development Chair’s network; OB‑GYN volunteer Dr. Lena Brooks’ South Side hospital colleagues. To confirm appropriateness before outreach. - Preferred communication: Brief, data‑rich emails followed by scheduled calls; concise 2–3 page briefs; well‑run site visits. Avoid high‑gloss events; emphasize substance.

2) Cultivation Goal & Case - Goal: Secure a lead gift of $250,000–$400,000 toward scaling the Neighborhood Birth Equity Initiative (NBEI) to three South Side hospitals in 2025, positioning Kline as a catalytic partner. - Why them: Their focus mirrors NBEI’s CHW/doula integration, hospital partnership, and closing racial gaps in birth outcomes. - What their gift makes possible (illustrative): launch at 3 hospitals; train and deploy 18 CHWs/doulas; serve 900 birthing people/year with prenatal–12‑month postpartum supports; shared data/evaluation; hospital learning collaborative.

3) Strategy & Timeline (12 months; capacity‑aware) - Phase 1: Qualify and align (Mar–May). Objective: Secure warm introduction, confirm fit, and schedule site visit. - Phase 2: Co‑design and deepen (Jun–Sep). Objective: Engage in outcomes/budget conversation; show hospital partner readiness; invite advisory input. - Phase 3: Ask and close (Sep–Dec). Objective: Present tailored proposal and secure DAF recommendation before Dec 31 fiscal year‑end; steward decision.

4) Touchpoint Plan (7 touches; each 1.5–6 hours staff time incl. prep/follow‑up) 1. Peer‑intro email and 20‑min discovery call - Objective: Establish fit and secure permission for deeper materials. - Donor value: Efficient overview; option to opt in. - Format: Peer intro via CCT advisor, then Zoom. - Owner: Naomi (lead). - Date window: Mar 11–Apr 5 (prep before Board 3/5; debrief after). - Materials: 2‑page NBEI brief; 1‑page outcomes snapshot. - Qualification question: What outcomes or communities are top‑of‑mind for your family this year?

2. Policy & Practice Forum invitation (April 22) - Objective: Demonstrate field leadership and hear beneficiary voices. - Donor value: Curated learning; seat with clinical partners. - Format: Event invite with hosted meet‑and‑greet. - Owner: Naomi; Dr. Brooks greets; brief ED hello. - Date window: Apr 22. - Materials: Agenda; speaker bios; 90‑sec video story. - Qualification question: Which parts of today’s discussion felt most actionable to you?

3. Site visit with program lead at South Side hospital - Objective: Connect NBEI model to hospital workflow and outcomes. - Donor value: See CHW/doula integration; hear partner commitment. - Format: Site visit + debrief. - Owner: Program Lead + Naomi; ED joins this second meeting. - Date window: May 13–Jun 7. - Materials: Logic model; draft expansion timeline; letters of intent from hospitals. - Qualification question: What would you need to see to feel confident anchoring the expansion?

4. Outcomes and budget working session - Objective: Invite input on milestone design and reporting cadence. - Donor value: Influence measurement that matters to them. - Format: 45‑min Zoom. - Owner: Naomi + Evaluation Manager. - Date window: Jun 24–Jul 12. - Materials: 12‑month budget (range), milestone options, sample dashboard. - Qualification question: Which 3 indicators should we commit to report to you quarterly?

5. Field insight memo + CHW roundtable - Objective: Share what we’re learning across sites; elevate CHW voice. - Donor value: Real‑time insight; operational credibility. - Format: 4‑page memo emailed; optional 30‑min roundtable Zoom. - Owner: Naomi; Dr. Brooks moderates. - Date window: Aug 5–16. - Materials: Memo PDF; brief audio clip from CHW. - Qualification question: Where do you see the biggest leverage for your philanthropy in the next 12 months?

6. Community Partner Salon (Sept 14) hosted by Board Development Chair - Objective: Normalize peer support; preview funding consortium. - Donor value: Peer learning; social proof; potential match opportunity. - Format: Small salon (10–12 guests). - Owner: Board Dev Chair hosts; Naomi produces; ED brief remarks (5 min). - Date window: Sept 14. - Materials: One‑page “Expansion at a Glance”; draft recognition options. - Qualification question: Would a leadership match be of interest to you?

7. Post‑salon debrief and ask - Objective: Present tailored $250k–$400k request and close on timeline. - Donor value: Clear plan; designation options; reporting commitment. - Format: 45‑min Zoom or in‑person. - Owner: Naomi leads; ED present; Dr. Brooks available as credibility voice. - Date window: Sept 16–27. - Materials: 4‑page proposal, detailed budget, outcomes schedule, DAF recommendation instructions. - Qualification question: Which designation resonates most for you and your family?

5) Engagement Signals & Decision Gates - Readiness signals: Rapid responses (<5 business days); brings family member/advisor; asks outcome/budget or hospital MOU questions; requests draft language for DAF; offers referral. - Decision gates: 1) After site visit + outcomes session and receipt of budget interest → schedule ask. 2) If they attend Salon and request follow‑up → make the ask in Touch 7. 3) If they decline Salon but ask for proposal → move to ask via Zoom within 2 weeks.

6) Roles & Coordination - Naomi: Quarterback; preps briefs; logs in Salesforce; sends follow‑ups within 48 hours. - ED (Dr. Nguyen): Joins second meeting and site visit; present for ask; escalates institutional questions. - Board Development Chair: Hosts Sept 14 salon; opens/close with 2‑minute framing; provides prospect notes to Naomi same day. - Dr. Lena Brooks (volunteer ambassador): Clinical credibility; co‑hosts Forum table; attends site visit; optional co‑solicitor if rapport strong. - Briefing: 2‑page prep memo sent 48 hours before each touch; roles/timeboxed remarks; single ask lead identified. - Follow‑up: Thank‑you within 24 hours; recap and next steps within 48 hours; attach materials.

7) Risks/Contingencies - Gatekeeper timing at CCT → build 2–3 week buffer; provide concise concept note. - Hospital scheduling slips → offer virtual walkthrough video. - Preference for program‑only funding → present budget with clear non‑lobbying, direct program lines. - Decision delay past Dec 31 → propose pledge with Jan recommendation; secure written intent.

8) Tracking & Next Steps (Salesforce Nonprofit Cloud) - Create Account: Kline Family Fund (DAF) and Contact(s); link Soft Credit to individual(s). - Opportunity: “Kline—NBEI Expansion—FY2025,” Amount Range field ($250k–$400k), Stage (Qualification → Cultivation → Solicited → Committed), Close Date: Dec 15. - Tasks/Activities: Log each touch within 48 hours; attach materials; Next Step with due date. - Campaign attribution: “NBEI Expansion 2025.” - Metrics: Discovery call secured; Site visit completed; Outcomes session completed; Salon attended; Pre‑ask signal recorded; Ask made; Verbal yes; DAF recommendation received; Funds deposited.

9) Draft Ask Path & Natural Moment - Framing: We’re inviting you to anchor the South Side expansion of NBEI across three hospitals. A leadership gift of $250,000–$400,000 will train and deploy CHW/doula teams, stand up data and evaluation, and ensure hospital readiness—touching 900 families in year one. - Designation options: 1) CHW/Doula Cohort and Supervision ($150k–$220k) 2) Hospital Launch and Integration ($60k–$100k) 3) Data/Evaluation and Learning Collaborative ($40k–$80k) 4) 10% flexible within program for rapid response (non‑lobbying) - Likely objections and responses: • Concern: We avoid funding ongoing operations. Response: This gift catalyzes time‑bound launch costs with hospital co‑funding ramping by year two; we’ll share signed MOUs and a sustainability plan. • Concern: DAF can’t fund advocacy. Response: Funds are restricted to program and evaluation; no lobbying included. • Concern: Prefer matching structure. Response: We can structure your gift as a 1:1 challenge to peer funders and hospitals with defined milestones. - Natural ask moment: Post‑Salon debrief (Touch 7), when interest and peer context are fresh and before Oct 2 Board meeting update. - Internal checkpoints: Board updates Mar 5 (green‑light plan), Jun 11 (approve proposal elements), Oct 2 (close status). Aim for DAF recommendation by Dec 1; fiscal year‑end Dec 31. Low‑cost execution throughout (Zoom, concise PDFs, short video).

Generated: Nov 2, 20255189 tokens$0.0698 cost
AI Evaluation Details (Score: 9.2/10)
Reasoning:

This is an exceptionally strong cultivation plan that demonstrates deep understanding of major donor fundraising mechanics. It balances strategic rigor with relationship-centered warmth, provides actionable detail at every touchpoint, and anticipates real-world contingencies. The plan is immediately usable by a development professional.

Strengths:
  • Outstanding touchpoint design: each of the 7 touches has clear objective, donor value proposition, qualification question, owner, and realistic time windows—avoiding the common pitfall of vague 'check-ins'
  • Excellent DAF-specific knowledge: acknowledges CCT advisor gatekeeping, quarterly cycles, concept note requirements, and DAF recommendation mechanics that many AI outputs miss
  • Sophisticated engagement signals and decision gates: defines concrete readiness indicators (response time, questions asked, referral offered) with clear if-then logic for moving to ask
  • Realistic capacity awareness: includes time estimates per touch (1.5-6 hours), low-cost execution options (Zoom, PDFs), and appropriate delegation across 12-person team
  • Strong risk mitigation: identifies specific contingencies (hospital scheduling, gatekeeper delays, program-only preference) with practical workarounds rather than generic concerns
  • Actionable Salesforce tracking: specifies exact fields, stages, campaign attribution, and metrics—not just 'use your CRM'
  • Natural ask sequencing: the post-salon ask moment (Touch 7) is strategically timed after peer context and before board deadline, with clear framing and objection responses
  • Warm, professional tone throughout: avoids jargon while maintaining precision; relationship-centered without being saccharine
  • Excellent role clarity: defines when/why ED and board engage, with briefing protocols and 48-hour follow-up discipline
Weaknesses:
  • Minor: The prospect snapshot could more explicitly flag the need to verify 'no prior giving' assumption before first outreach—it mentions 'to confirm in Salesforce' but doesn't make this a gate-zero task
  • The 'field insight memo' (Touch 5) is slightly less concrete than other touches—what specifically will the memo contain beyond 'what we're learning'? A sentence on content themes would strengthen it
  • Touch 2 (Forum invitation) could benefit from a brief note on how to gracefully handle a 'no' without losing momentum, since event attendance is less controllable than scheduled meetings

Large Established Org

Statewide coastal conservation organization with research labs and marine restoration projects along the Pacific Coast.

View scenario details
[ORGANIZATION NAME]:Pacific Coast Conservancy
[PROSPECT NAME]:Ravi Narayanan
[TIMELINE MONTHS]:10
[PROPOSED ASK RANGE]:$2,500,000–$5,000,000
[PROJECT/PURPOSE]:Blue Carbon Coastal Resilience Program—kelp forest restoration and community science
[ESTIMATED CAPACITY]:$10M–$20M+ near-term; tech founder with 2022 IPO, significant appreciated stock
[PRIMARY RELATIONSHIP OWNER]:Sophia Liang, Senior Major Gifts Officer
[PROGRAM]:Blue Carbon Coastal Resilience Program
[ED/BOARD INVOLVEMENT]:CEO provides scientific briefing at lab tour and closes the ask; Board Ocean Council member introduces peer network and hosts dinner
[SYSTEM/CRM]:Blackbaud CRM
[TEAM SIZE]:18
[KEY DATES/EVENTS]:June 20: Board retreat; Sept 30: Fiscal year-end; Oct 12: Oceans Gala; November: Kelp restoration dive season window; December: Year-end portfolio review
[TONE: FORMAL (board-ready, precise) / WARM (relationship-centered, professional) / CASUAL (clear, small-shop shorthand)]:FORMAL
[ED/BOARD LEAD]:James Holloway, CEO

Prepared by: Sophia Liang, Senior Major Gifts Officer Reviewed by: James Holloway, CEO

1) Prospect Snapshot - Capacity: $10M–$20M+ near-term liquidity; founder of a cloud security company that IPO’d in 2022; holds significant appreciated stock and options; active family office. - Affinity indicators: Public statements on ocean health and climate adaptation; invests in climate-tech; recreational diver; follows blue-carbon market developments; attended regional ocean policy forums. - Prior giving (to verify/partially confirmed): Six-figure gifts to climate and STEM nonprofits; mid-five-figure sponsorship at a local marine institute; PCC: event attendance in 2023; subscribed to our research briefings. - Decision-making process: Primary decider with input from family office CIO and a philanthropic advisor; prefers data-driven cases with clear unit economics and credible third-party validation; comfortable with program-restricted, milestone-based grants. - Known connectors: Ocean Council member Maya Chen (mutual with Ravi via Stanford Engineering alumni circle); corporate counsel knows PCC Board Treasurer. - Preferred communication: Efficient email followed by scheduled calls; values concise memos with links to technical appendices; appreciates site-based experiences that include scientists and community partners.

2) Cultivation Goal & Case - Goal: Secure a $2,500,000–$5,000,000 commitment within 10 months for the Blue Carbon Coastal Resilience Program, focused on kelp forest restoration and community science. - Case themes for Ravi: Scalable coastal climate impact with measurable carbon and biodiversity outcomes; opportunity to accelerate state-leading kelp restoration and a community science model that improves monitoring density at low cost; option to contribute appreciated stock across tranches with milestone gates.

3) Strategy & Timeline - Months 1–3 (Qualification & Alignment): Establish values fit; share credible impact baselines; involve peer validator; secure site experience. - Months 4–6 (Co-Design & Budget Preview): Present unit costs, 3-year roadmap, and validation plan; invite technical input; align on designation and milestones; leverage Oct 12 Oceans Gala for peer reinforcement. - Months 7–10 (Close & Structure): Use November dive window to cement conviction; present final proposal in December aligned with year-end portfolio review; close and schedule funding tranches by January; public recognition (optional) by March.

4) Touchpoint Plan 1. Introductory strategic call - Objective: Confirm fit and priorities; secure agreement for site visit. - Donor value: Concise overview + tailored options; time-respectful. - Format/Owner: 30-min Zoom; Owner: Sophia Liang. - Date window: Early June (before June 20 Board retreat). - Materials: 2-page Blue Carbon Brief + link to technical appendix. - Qualification question: “How do you assess philanthropic priorities this year?” - Time/Cost: 2 hrs prep + 0.5 hr call; no cost.

2. Targeted science briefing at lab - Objective: Demonstrate scientific rigor and monitoring methods. - Donor value: Direct access to lead scientist; methods transparency. - Format/Owner: Lab tour + briefing; CEO/ED leads; Sophia facilitates. - Date window: Week of June 20 (adjacent to Board retreat; 60–75 mins). - Materials: Monitoring dashboard demo; third-party validation letter. - Qualification question: “Which outcome metrics would give you confidence to scale?” - Time/Cost: 6 hrs prep; light refreshments <$150.

3. Peer dinner hosted by Ocean Council - Objective: Social proof; expose to practitioner and funder peers. - Donor value: Curated conversation on blue-carbon innovation. - Format/Owner: Small dinner (8–10); Host: Board member Maya Chen; Sophia attends. - Date window: Late July. - Materials: 1-page outcomes map; guest list bios. - Qualification question: “Where do you see private capital and philanthropy intersecting in blue carbon?” - Time/Cost: 8 hrs coordination; dinner underwritten by host.

4. Field site visit: kelp restoration operations - Objective: Connect impact to place; showcase community science. - Donor value: Meet dive team and community monitors; observe protocols. - Format/Owner: Site visit; CEO joins for Q&A; Program Lead present; Sophia owns logistics. - Date window: Late August or early November (primary: November dive window). - Materials: Site packet with safety plan and real-time transect data. - Qualification question: “What would you need to see to commit multi-year support?” - Time/Cost: 10 hrs planning; transport <$300; safety insurance covered.

5. Pre–fiscal year-end budget preview - Objective: Share 3-year scale plan with unit costs and milestones. - Donor value: Transparency on costs, risks, and gating. - Format/Owner: 45-min Zoom + annotated budget; Owner: Sophia with CFO on standby. - Date window: Mid-September (before Sept 30 FY-end). - Materials: Budget, Gantt milestones, risk register. - Qualification question: “Would milestone-based tranches fit your giving structure?” - Time/Cost: 5 hrs prep; no cost.

6. Oceans Gala + backstage briefing - Objective: Reinforce momentum; showcase beneficiary voices. - Donor value: Recognition environment; meet community science leaders. - Format/Owner: Event attendance + 15-min backstage briefing; CEO greets; Sophia manages. - Date window: Oct 12. - Materials: Impact sizzle reel; beneficiary remarks. - Qualification question: “Which aspect of the program resonated most tonight?” - Time/Cost: 6 hrs event shepherding; tickets comped.

7. Year-end investment conversation (ASK) - Objective: Present formal proposal; discuss structure and timing. - Donor value: Tax-efficient pathways; stock transfer facilitation; naming options. - Format/Owner: 60-min meeting (in person or Zoom); CEO and Sophia. - Date window: Early–mid December (aligned with portfolio review). - Materials: Proposal with options, draft grant agreement, DTC stock instructions. - Qualification question: “Would you prefer a single stock transfer or a two-tranche approach across calendar years?” - Time/Cost: 6 hrs prep; no cost.

8. Post-commitment technical advisory invite - Objective: Deepen engagement; invite to 2 advisory sessions/year. - Donor value: Influence roadmap; periodic data reviews. - Format/Owner: Written invitation + calendar hold; Owner: Sophia; Program Lead to follow. - Date window: January. - Materials: Advisory charter; annual learning agenda. - Qualification question: “Which quarterly metrics would you like on your dashboard?” - Time/Cost: 3 hrs prep; no cost.

5) Engagement Signals & Decision Gates - Readiness signals: Rapid replies (<48 hrs); asks outcome/ROI questions; requests budget detail; introduces family office/advisor; offers referral or in-kind support; asks about timing, tranche sizes, or stock transfer. - Ask trigger: Any two of the above observed by or before October 12, or explicit interest during November site visit; otherwise proceed to December ask aligned to portfolio review.

6) Roles & Coordination - CEO: Lead scientific briefing at lab; attend site visit Q&A; co-lead December ask; confirm terms. - Board/Ocean Council (Maya Chen): Warm intro; host July peer dinner; serve as volunteer solicitor at Gala table; provide peer validation. - Sophia: Overall quarterback; briefing notes (24 hrs prior) and contact reports (within 48 hrs after); manages materials and CRM updates; coordinates with Program Lead, CFO, and Family Office Liaison for stock gifts.

7) Risks/Contingencies - Scheduling conflicts: Offer virtual ROV live-stream if dive is weathered out. - Market volatility: Provide tranche and pledge flexibility; offer collar timing for stock. - Gatekeeper delays: Proactively brief family office; provide short memos for forwarding. - Reputational/recognition preferences: Default to private recognition unless invited. - Bandwidth: Limit attendees at each touch; reuse core materials; leverage board host underwriting.

8) Tracking & Next Steps - Blackbaud CRM: Create Opportunity “R. Narayanan – Blue Carbon” with range $2.5–$5M; Stage: Qualification to Solicitation; Target Close: December 20. - Fields to update: Capacity rating; inclination score; next-step date; solicitor team; strategy notes; contact reports for each touch; documents attached (briefs, budgets, proposal). - Metrics: Meetings secured (target 6+); site visit completed; pre-ask commitment indicator (verbal/email); response time trend; number of qualification questions logged. - Immediate tasks: Schedule June call; hold lab briefing slot near June 20; confirm Maya’s July dinner date; pencil Nov dive window; draft December proposal template.

9) Draft Ask Path & Natural Moment - Framing: “Ravi, with your leadership, we can restore 1,200 acres of kelp and train 500 community scientists, creating a validated blue-carbon model for the Pacific Coast. We’re seeking $2.5–$5M to execute a three-year scale-up with milestone gates.” - Designation options: 1) $4M over 3 years: $3M program expansion + $1M Innovation & Validation Fund. 2) $2.5M naming of the Community Science Hub + monitoring endowment seed. 3) $5M challenge: $3.5M program + $1.5M 1:1 match to crowd in co-funders. - Likely objections and responses: - Market uncertainty: “We can structure two calendar-year tranches and accept appreciated stock to optimize timing.” - Proof of impact: “We’ll report against pre-defined ecological and social KPIs with third-party validation twice yearly.” - Overhead concerns: “Direct and indirect costs are disclosed; monitoring and data integrity require modest, critical shared services.” - Preference to pilot first: “A $1M first-year tranche with go/no-go gates de-risks while reserving the full commitment.” - Natural ask moment: Immediately following the November site visit if readiness signals present; otherwise at the December year-end investment meeting aligned to his portfolio review and before Dec 31 deadlines.

Generated: Nov 2, 20254416 tokens$0.0583 cost
AI Evaluation Details (Score: 9.2/10)
Reasoning:

This is an exceptionally strong cultivation plan that demonstrates sophisticated major gifts practice. It's board-ready, strategically sequenced, and includes the concrete details (owners, dates, qualification questions) that make it immediately actionable. The formal tone is pitch-perfect for a $5M prospect at an established organization.

Strengths:
  • Outstanding touchpoint design: each of the 8 touches has clear objective, donor value proposition, specific owner, date window, materials list, and a substantive qualification question—not generic 'check-ins'
  • Excellent donor-centricity: acknowledges Ravi's decision-making process (family office, advisor input), preferred communication style (efficient, data-driven), and offers tax-smart stock transfer options with tranche flexibility
  • Sophisticated engagement signals and decision gates: defines concrete readiness indicators (response time, budget questions, referrals) and clear triggers for moving to the ask, avoiding premature solicitation
  • Realistic capacity planning: includes time estimates (2-10 hrs per touch) and low-cost execution (<$500 total out-of-pocket), appropriate for even well-resourced teams
  • Strong role choreography: CEO and Board member Maya Chen are deployed strategically (not too early/late), with clear briefing and follow-up protocols
  • Practical risk mitigation: addresses weather contingencies, market volatility, gatekeeper delays, and recognition preferences with specific solutions
  • Excellent ask path: three distinct designation options at different levels, four likely objections with crisp 1-2 sentence responses, and two clearly identified natural ask moments tied to specific touches
  • CRM tracking is concrete: specifies Blackbaud fields, opportunity stages, and simple metrics that teams actually track
Weaknesses:
  • Minor authenticity concern: the language is almost *too* polished in places ('crowd in co-funders,' 'time-respectful')—real internal plans often have more shorthand, though this matches the formal tone requested
  • Touch #8 (post-commitment advisory invite) is slightly premature to include in a cultivation plan before the gift is secured; it could be moved to a footnote or 'stewardship preview' section
  • The prospect snapshot could benefit from one more sentence on *how* capacity was estimated (public filings, wealth screening, peer intel) to model due diligence documentation

Test Summary: Generated Nov 2, 20253 scenarios • 9 total outputs • Average quality score: 9.02/10 • Total validation cost: $0.3711