Quick Snapshot: Describe Your Program in One Breath

• If you had to describe your planned giving program in one sentence right now, what would you say?
• How many confirmed or documented bequest intentions are actively tracked today? Options: 0, 1–5, 6–20, 21–50, 51+
• Which donor segments generate most of your legacy interest (choose all that apply)? Options: Alumni, Major donors, Board members/Trustees, Monthly givers, Foundations/Organizations, Other
• Who typically leads planned giving conversations at your organization? Options: Planned giving director, Gift officers, Chief Development Officer, External consultants, Volunteer leaders, No one consistently
• Roughly how long have you personally been responsible for planned giving (or closely involved)? Options: Less than 1 year, 1–3 years, 3–7 years, 7–15 years, 15+ years

Are We Leaving Gifts Hidden in Plain Sight?

• What makes you confident—or uneasy—that there are more bequest intentions among your donors than you currently know about?
• How do you discover potential bequest prospects today (select all that apply)? Options: Database flags/segments, Conversations at events, Wealth screening, Volunteer referrals, Legacy society membership lists, Ad hoc/intuition
• When you think of donors who later named you, what early signals did you miss—how long has that pattern repeated?
• How comfortable are your gift officers starting conversations about long-term legacy or wills? Options: Very comfortable, Somewhat comfortable, Uneasy but willing, Avoids these conversations
• Tell us about a recent outreach or campaign to surface legacy interest—what worked, what flopped, and what felt hardest?

Why Forecasting Often Feels Like a Roll of the Dice

• What do you believe is the single biggest reason your planned giving pipeline is hard to forecast?
• Which methods do you currently use to forecast future planned gift revenue (select all that apply)? Options: Historical conversion rates, Weighted pipeline stages, Executive estimates, Actuarial/probabilistic models, No formal method
• How accurate have your forecasts been in the last 3 years? Options: Within 10%, Within 25%, Within 50%, Often inaccurate/unusable, We don't produce forecasts
• When forecasts miss the mark, what are the practical consequences for your budgets, hiring, or program plans?
• What data gaps or trust concerns make forecasting feel risky to you or your leadership?

Who’s Actually Expected to Hold the Baton?

• If planned giving success depends on a handful of people, who would you point to—and what would they tell us is their biggest roadblock?
• Which functions are involved in stewarding a bequest prospect (select all that apply)? Options: Planned giving team, Major gifts officers, Annual giving, Finance/Legal, Marketing/Communications, Volunteers/Committees
• How clear are role boundaries for follow-up responsibilities after a planned giving conversation? Options: Very clear, Somewhat clear, Ambiguous, Nonexistent
• Tell me about a time accountability broke down—what happened to the donor relationship and the intention?
• What training or confidence-building would most change how frontline officers approach legacy conversations? Options: Practical scripts and templates, Hands-on coaching, Technical illustrations training, Peer shadowing, Refresher on legal/compliance basics

Would Donors Say You’re Speaking Their Language—or a Legal Brief?

• How often do you see donors disengage because messaging about legacy giving feels too technical or heavy? Options: Frequently, Sometimes, Rarely, Never sure
• Do you currently use IRS‑compliant gift illustrations in donor conversations, and who prepares them? Options: We generate in-house, We use third-party vendor, We rely on ad hoc manual estimates, We don't use illustrations
• How long does it take, on average, to produce a donor-ready legacy proposal from initial ask to delivery? Options: Same day, 1–3 days, Within a week, More than a week, We don't produce formal proposals
• Share an example of donor language that landed well—or poorly—when you talked legacy. What felt genuine or off?
• Which messaging channels have felt most effective for introducing legacy ideas (select all that apply)? Options: One-on-one conversations, Direct mail, Email campaigns, Events/lectures, Printed legacy society materials, Website content

Reimagining a Pipeline That Actually Predicts the Future

• If you could wake up to one measurable shift in your planned giving program in 12 months, what would it be?
• Which specific metrics would prove success to your leadership (select up to three)? Options: Number of documented intentions, Estimated future gift dollars, Conversion rate from interest to commitment, Time-to-confirmation, Legacy society growth, Forecast accuracy
• What timeline would you consider acceptable to begin seeing meaningful pipeline changes from a new tool or approach? Options: Immediate (weeks), 1–3 months, 3–6 months, 6–12 months, Longer than a year
• How would improved forecasting change conversations you have with finance or executive leadership?
• What would need to feel different about vendor partnerships for you to trust them with donor-facing proposals?

What Would It Take for You to Say ‘Yes’?

• When you think about adopting a new planned giving platform, what single objection tends to stop conversations cold?
• Who are the decision-makers that must be convinced to move forward (select all that apply)? Options: Planned giving director, CDO/VP Development, CFO/Finance, Legal/Compliance, Board/Committee, IT/CRM
• How does procurement typically work for technology in your organization—what approval steps slow you down? Options: Budget committee, Legal review, Security/IT review, Executive sign-off, No formal process
• What would a reasonable pilot look like to prove value without asking for full commitment? Options: Small donor segment pilot, Legacy society pilot, Illustration-only pilot, Forecasting model pilot, Admin-only pilot
• If budget were not a barrier, what three capabilities would you prioritize first?

A Few Practical Details Before We Roll Up Our Sleeves

• If your CFO were on this call, what single concern would they raise about integrating a new planned giving system?
• What donor database/CRM do you use, and how mature is your data (completeness/cleanliness)? Options: Raiser’s Edge / Blackbaud, Salesforce / NPSP, Microsoft Dynamics, Other CRM, We use spreadsheets
• Do you have sample records or a test dataset we could use for an integration proof-of-concept? Options: Yes, ready now, Yes, with preparation, No, but can extract, No, not available
• Which integrations are must-haves for you (select all that apply)? Options: CRM donor records, Finance/accounting system, Email/marketing platform, Gift administration ledger, Document management, None
• Who should be our single point of contact for technical and admin coordination (role and contact preference)?

• Pre-Work & Context Confirmation
• Illustration Modeling Workshop (Hands‑On)
• Proposal & Legacy Society Messaging Review (Role‑Play)
• Pipeline Forecasting & Impact Assessment
• Executive Validation & Sign‑Off

• Define integration requirements to automate refresh of illustration and forecast data into the donor database and reporting tools.
• Host to note any gaps where additional data or legal input is required and assign owners to close them.
• Recap Illustration Outputs
• Finalize donor‑ready proposals for each validated illustration scenario with approved compliance language.
• Agree on legacy society messaging variants for prioritized donor segments and identify preferred CTAs.
• Capture common donor objections and equip gift officers with recommended responses tied to the illustrations.
• Host to deliver revised proposal documents and 2–3 legacy society messaging variants per donor segment.
• Customer compliance/legal owner to review and approve required disclaimers and return sign‑off or redlines.
• Gift officer team to prepare a short list of real prospects to pilot the proposals and report back outcomes from initial outreach.
• Recap: From Illustration to Forecast
• Agree on a defensible forecasting methodology that converts validated illustrations into probability‑weighted pipeline values.
• Produce a sample pipeline report showing quantified impact on budgeting horizons.
• Introductions & Objectives
• Host to deliver the forecast model, populated sample report, and a one‑page methodology explanation for finance and leadership.
• Customer to identify technical contacts and provide access details for donor database fields required for integration.
• Both parties to agree a pilot schedule to run the forecast with real prospects and measure actual conversion over the next quarter.
• One‑Sentence Current State & Consequence Recap
• Secure executive sign‑off that the illustrations, proposals, and forecast methodology satisfy acceptance criteria or capture a prioritized change list.
• Ensure executives understand the quantified consequence and how the validated future state mitigates it for budgeting and stewardship.
• Define clear owners and timelines for any remaining work and confirm the next stage of the journey.
• Customer executive to provide formal acceptance or a prioritized list of required changes within 7 business days.
• Host to update artifacts per executive feedback and deliver a final acceptance packet (illustrations, proposals, forecast model, integration spec).
• Both parties to schedule the Solution Scope meeting with agreed owners and timelines if sign‑off is achieved.
• Produce a verified one‑sentence current state describing where illustration/proposal workflows break today.
• Surface and quantify the main consequences (financial, operational, stewardship risk) of the current state.
• Agree a clear, outcome‑focused future state statement to guide the Solution Experience.
• Obtain committed pre-work deliverables (data extract, 3–6 donor scenarios, legal notes, templates) before the modeling workshop.
• Customer to deliver anonymized donor extract and 3–6 prioritized donor scenarios (names redacted) including ages, gift history, and stated intentions.
• Customer to provide current proposal templates, legacy society copy, and any compliance/legal constraints for review.
• Host to draft the single‑sentence current state, consequence, and future state for customer sign‑off and circulate before the modeling session.
• Brief Recap of Current State & Consequence
• Produce finalized, IRS‑compliant illustrations for each supplied donor scenario with documented assumptions.
• Demonstrate how illustration outputs convert to monetary pipeline values under sensitivity assumptions.
• Obtain explicit validation from gift officers that the illustrations reflect realistic donor conversations and compliance needs.
• Host to deliver the completed illustration PDFs and a assumptions workbook for each donor scenario.
• Customer to review illustrations and flag any legal/compliance concerns within 5 business days.
• One‑Sentence Current State
• Proof Artifacts Presentation
• Forecasting Methodology Walkthrough
• Proposal Template Walkthrough
• Modeling Rules & Compliance Check
• Role‑Play: Gift Officer & Donor
• Live Mapping: Sample Pipeline
• Tie Back to Problems
• Live Run: Donor Scenario 1
• Explicit Consequence Statement
• Validation & Feedback
• One‑Sentence Future State
• Legacy Society Messaging Tests
• Live Run: Donor Scenarios 2 & 3
• Reporting & Dashboard Review
• Pre‑work & Data Requirements
• Sensitivity Analysis
• Compliance & Legal Checkpoint
• Decision & Next Steps
• Integration Requirements
• Validation Checkpoint
• Logistics & Success Criteria

• Generate Individual Bequest Illustrations
• Create Charitable Remainder Trust Illustrations
• Create Charitable Gift Annuity Illustrations
• Produce Donor-Ready Proposal Packets
• Integrate With Donor Database
• Set Up Legacy Society Membership Tracking
• Deliver Planned Giving Email Campaign Templates
• Draft Donor Conversation Scripts and One-Pagers
• Administer Gift Annuity Payment Schedules
• Manage Trust Distributions and Recordkeeping
• Provide IRS-Compliant Tax Calculation Reports
• Train Gift Officers in Planned Giving Conversations
• Provide Standard Bequest Language for Wills
• Produce Legacy Society Welcome Kits

Generate Individual Bequest Illustrations

• Should individual bequest illustrations be included in scope? Options: Yes, No
• How many distinct bequest illustration scenarios do you expect to generate initially? Options: 1-5, 6-25, 26-100, 100+
• Which output formats are required for bequest illustrations? Options: PDF (print-ready), HTML/email, Word/Editable, Multilingual
• Do illustrations need to model different bequest types (percent of estate, residuary, specific gift)? Options: Yes, No
• Are state-specific estate/tax rules or disclaimers required for your donor base? Options: Yes, No
• Please list any special calculation rules, accounting assumptions, or organizational policies that must be applied (e.g., assumed estate growth rate, charitable intention likelihood).

Create Charitable Remainder Trust Illustrations

• Do you require CRAT and/or CRUT illustration capabilities? Options: CRAT, CRUT, Both, Neither
• What payout frequency and payment types should be supported? Options: Annual, Semi-annual, Quarterly, Monthly, Lump-sum
• What default actuarial/discount assumptions should illustrations use? Options: IRS Section 664 tables, Custom discount rate, Market-based assumptions, Other
• How many sample donor age/beneficiary scenarios should we preconfigure? Options: 3-5, 6-10, 11-25, Custom
• Do you need illustrations to include projected income to non-charitable beneficiaries and remainder to the charity? Options: Yes, No
• Are trust administration or ongoing reporting tasks (trust setup checklist, trustee forms) required as part of this module? Options: Yes, No

Create Charitable Gift Annuity Illustrations

• Do you want immediate and/or deferred gift annuity illustrations? Options: Immediate, Deferred, Both, Neither
• Which annuity rate schedules should be available (e.g., state-mandated, organization-specific, recommended schedules)? Options: State-mandated, Organization-specific, Recommended industry rates, Custom
• What payment frequencies and escalation rules should be supported? Options: Annual, Semi-annual, Quarterly, Monthly, Escalating payments
• How many donor age/gift-amount examples should be pre-built for gift officer use? Options: 5, 10, 20, Custom
• Do illustrations need to flag state-specific registration or disclosure requirements? Options: Yes, No
• If you administer annuities in-house, what payment and accounting systems must integrate with this module? (list systems or indicate 'None')

Produce Donor-Ready Proposal Packets

• Do you want templated donor-ready proposal packets included? Options: Yes, No
• Which content blocks must every proposal contain? Options: Gift illustration, Tax language/disclaimers, Next steps and contact info, Organization impact statement, Legacy society invitation
• What branding and personalization elements are required (logo, letterhead, personalized salutation, campaign imagery)?
• What output formats are needed for proposals (single-page one-pager, multi-page PDF, email-friendly HTML, print-ready packet)? Options: One-pager, Multi-page PDF, Email HTML, Print-ready
• Do proposals need an embedded compliance/legal review checklist or sign-off field? Options: Yes, No
• Are localized/state-specific tax or legal notes required inside proposals? Options: Yes, No

Integrate With Donor Database

• Which donor database/CRM(s) should we integrate with? Options: Raiser's Edge (Blackbaud), Salesforce NPSP, iWave/WealthEngine, Other, None
• What direction and cadence of sync is required? Options: One-way (platform → CRM), One-way (CRM → platform), Two-way real-time, Two-way batch (daily)
• Which donor and gift fields must be mapped and kept in sync (e.g., name, contact, pledge status, planned gift intent, legacy society tier)?
• Are there existing API credentials, or will a connector need to be built? Options: Existing connector available, API credentials available, Custom connector required, No API access
• Do you require data transformation rules, deduplication logic, or field normalization during sync? Options: Yes, No
• Are there privacy, consent, or donor opt-in rules we must enforce when syncing data? Options: Yes, No

Set Up Legacy Society Membership Tracking

• Do you want automated legacy society membership tracking and tiering? Options: Yes, No
• What membership tiers or recognition levels does your legacy society use (e.g., Founder, Benefactor, Members)?
• Which membership actions should trigger automated workflows (welcome sequence, anniversary outreach, donation confirmation)? Options: Welcome sequence, Anniversary outreach, Event invitations, Renewal reminders, Other
• What member data and privacy choices must be recorded (public recognition opt-in, preferred contact method, spouse/partner info)?
• Do you need printable rosters, nametags, or membership certificates generated automatically? Options: Yes, No
• Should legacy society membership be visible on donor profiles in your CRM via integration? Options: Yes, No

Deliver Planned Giving Email Campaign Templates

• Do you want a library of planned giving email templates for different donor segments? Options: Yes, No
• Which donor segments should templates target? Options: Major donors, Recurring donors, Lapsed donors, Older adult cohorts, Prospects identified by wealth indicators
• How many campaign templates and drip lengths should be included (e.g., 3-email drip, 6-email nurture)? Options: 3-email drip, 6-email drip, Single outreach templates, Custom
• Do templates need to be preloaded for specific channels (email HTML, print mail merge, social posts)? Options: Email HTML, Print mail merge, Social copy, SMS
• Should templates include A/B test variations for subject lines or calls-to-action? Options: Yes, No
• Are there legal or compliance review requirements (CAN-SPAM, state solicitation) for template wording? Options: Yes, No

Draft Donor Conversation Scripts and One-Pagers

• Do you want scripted conversation guides for gift officers included? Options: Yes, No
• Which audiences should scripts and one-pagers address (e.g., long-time annual donors, major donors, alumni, volunteers)? Options: Annual donors, Major donors, Alumni, Volunteers, Board members
• What tone and language restrictions should be applied (e.g., non-legal, non-mortality-focused, donor-first language)?
• How many one-pager templates and topics do you need (e.g., bequest steps, FAQ, sample bequest wording)? Options: 3-5, 6-10, 11-20, Custom
• Do you want role-specific variants (gift officer, development VP, legacy society liaison)? Options: Yes, No
• Should scripts include suggested discovery questions and acceptance criteria for moving a prospect to a planned-gift pipeline stage? Options: Yes, No

Administer Gift Annuity Payment Schedules

• Will your organization administer annuity payments in-house or rely on a third party? Options: In-house, Third-party administrator, Hybrid
• What payment methods and frequencies must be supported (ACH, check, wire; monthly/quarterly/annual)? Options: ACH, Check, Wire, Card, Monthly, Quarterly, Annual
• Do you require automated payment scheduling, retry logic, and payment history reporting? Options: Yes, No
• Are beneficiary changes, stops, or transfers a process we must support via the system? Options: Yes, No
• What accounting codes or GL integration is required for annuity payment reconciliation?
• Do you need donor portal access for annuitants to view payment history and tax documents? Options: Yes, No

Manage Trust Distributions and Recordkeeping

• Which trust types require distribution management (charitable remainder trusts, charitable lead trusts, other)? Options: CRTs, CLTs, Other, None
• How often are distributions processed and recorded (monthly, quarterly, annual) and do you need workflow automation for approval steps? Options: Monthly, Quarterly, Annual, On-demand
• What level of document retention and audit trail is required for trust administration? Options: Standard (7 years), Extended (10+ years), Per legal counsel guidance, Other
• Do you need integration with accounting software for trust entries and tax reporting? Options: Yes, No
• What trustee roles and permissions must be modeled in the system (internal trustee, external advisor, co-trustee)?
• Are beneficiary communications and scheduled notices part of the distribution workflow requirements? Options: Yes, No

• Statement of Work (SOW)
• Master Services Agreement (MSA)
• Pricing & Payment Schedule
• Data Processing & Security Addendum (DPA)
• Integration & Data Access Authorization
• Third-Party Connector Authorization
• Compliance Responsibilities & Regulatory Acknowledgment
• Service Level Agreement (SLA) & Support Terms
• Acceptance & Go‑Live Criteria
• Implementation Timeline & Change Order Process
• Executive Approval Sign-off
• Renewal, Maintenance & Termination Terms

• Quarterly Pipeline Review & Forecast Reconciliation
• Legacy Society Operations & Stewardship Confirmation
• Issue Triage & Enhancement Backlog Sync
• Executive Success Review & Renewal Readiness

• Schedule the next pipeline review and identify pre-work owners for data refresh.
• Identify and schedule required automation/integration work to reduce manual handoffs.
• Agree on stewardship messaging and a rollout plan for staff adoption.
• Publish updated legacy society SOP and stewarding playbook.
• Create or update communication templates and add to the platform library.
• Open integration tickets for identified automation gaps and assign technical owners.
• Schedule training sessions for gift officers and admin staff on the new workflows.
• Shared channel health & metrics
• Ensure critical issues are triaged with clear owners and timelines for resolution.
• Agree a prioritized enhancement list for the next delivery window aligned to business impact.
• Maintain a clear support SLA and escalation path to reduce time-to-resolution.
• Keep the shared channel healthy and ensure stakeholders know how to surface and track issues.
• Log prioritized enhancements in the roadmap tool with acceptance criteria and owners.
• Escalate and resource P1/P2 incidents to get commitments from engineering/support teams.
• Publish updated SLA and escalation contact list to the shared channel.
• Schedule the next backlog sync and define pre-meeting data needed (ticket exports, dev estimates).
• One-sentence current state & consequence
• Gain executive alignment on program outcomes and the value delivered relative to forecast.
• Secure a clear decision or defined path toward renewal/expansion with necessary approvals and timelines.
• Identify material risks that require executive attention and agree mitigations and owners.
• Prepare and send a concise executive summary pack (1–2 pages) with KPI callouts and renewal recommendation.
• If approved, issue renewal/expansion proposal and draft contract addendum for legal review.
• Assign executive sponsor(s) and set quarterly executive check-ins to monitor agreed KPIs.
• Produce a reconciled forecast with clearly documented assumptions and scenarios.
• Identify and document the root causes driving variance and their dollar impact.
• Assign owners, deadlines, and a review cadence to close gaps and track progress.
• Ensure all stakeholders validate that the new forecast reflects operational reality.
• Deliver reconciled pipeline report (data export + narrative) within 3 business days.
• Update forecast in the platform and label assumptions used for each scenario.
• Initiate targeted outreach to top 10 at-risk intentions with assigned gift officer owners.
• Pre-meeting data snapshot
• Current membership & management state
• Confirm an end-to-end legacy society operating model with owned roles and documented workflows.
• Validate the model against live donor records to ensure it works in practice.
• Open critical issues review
• Performance vs KPIs and ROI
• Current state summary (one sentence)
• Stewardship cadence and messaging
• Enhancement backlog review
• Variance & consequence analysis
• Risk assessment & mitigation plan
• Operational workflows & integrations
• Compliance, documentation & acceptance criteria
• Root-cause diagnosis
• Value realization & expansion opportunities
• Prioritization & next-quarter roadmap
• SLA & escalation refinement
• Decision, approvals, and procurement readiness
• Forecast adjustment & scenario modeling
• Sample donor journey validation
• Executive owners and go-forward timeline
• Action owners & cadence
• Escalation & fulfillment handoff
• Validation & stakeholder sign-off
• Owners, actions, and cadence
• Action assignment and training plan