A quick check-in: how planned giving shows up today

• How many recorded bequest intentions does your CRM currently hold? Options: 0, 1-5, 6-20, 21-100, 100+
• Tell me about the donors you currently label as planned giving prospects, how were they identified? Options: Direct disclosure by donor, Legacy society member, We inferred from gifts or age, We analyzed wealth indicators, Other
• When was the last time you generated an IRS-compliant gift illustration for a real donor and what happened next?
• Describe your current legacy society record keeping, who owns it and how often is it updated? Options: Development team owns it, Planned giving director owns it, Shared ownership, No formal owner, Other
• Which roles on your team actively engage in planned giving conversations today? Options: Planned giving director, Gift officers, Major gifts officers, Development VP, Executive leadership, Other
• Which document or artifact do you hand a donor first when discussing a planned gift? Options: Printed proposal, Email proposal, Illustration PDF, High-level brochure, No standard artifact, Other

Where forecast misses are costing you

• Which single forecasting failure would make you stop the project immediately? Options: Pipeline counts are inflated, Timing is wildly wrong, Projected amounts are misleading, We cannot reconcile with finance, Other
• Walk me through the last three planned gifts that moved from intention to confirmed estate notice, what patterns did you notice?
• How do you currently score probability and timing for bequests in your pipeline? Options: Simple probability buckets, Estimated timing window, No formal scoring, External consultant provides estimates, Other
• Which downstream cost or risk matters most to finance if a forecast turns out wrong? Options: Budget shortfall, Audit exposure, Donor expectation mismatch, Staffing misallocation, Other
• If we could provide a visibility improvement, what exact forecast metric would accelerate internal approval? Options: Probability-adjusted pipeline value, Expected receipt timelines, Top 10 donor-level forecasts, Confidence intervals, Other

How donor conversations actually feel and fail

• When you or a gift officer brings up legacy giving, what phrasing or concern most often ends the conversation?
• Tell me about the last time a proposal was rejected by a donor, what reasons did they give? Options: Not interested, Family objections, Legal complexity, Unclear benefits, Other
• Which support material would make your gift officers more confident in a donor meeting? Options: Donor-ready illustration, Short script for officers, Sample proposal letters, Legacy society talking points, Compliance talking points, Other
• How long does it take your team to prepare a tailored proposal for a donor today? Options: Under 1 hour, 1-4 hours, Half a day, Full day or more, We do not produce tailored proposals
• If officers had a tool that produced friction-free donor-ready proposals, what change in behavior would prove it valuable to you? Options: More meetings include legacy ask, Higher acceptance rate, Faster proposal turnaround, Improved donor relationships, Other

Legal, administration, and compliance red flags

• Which legal or state compliance requirement could stop you from rolling out new illustrations? Options: State gift annuity rules, Trust administration requirements, Solicitation registration, Board approval, Other
• Describe the current internal owner for gift administration for trusts and annuities and their relationship with finance or legal. Options: In-house administrator, Shared with finance, Third-party administrator, No dedicated owner, Other
• Who must sign off on compliance reviews for donor-facing illustrations and how long does that typically take? Options: General counsel, Compliance officer, External counsel, Finance leader, No formal review
• How accessible and clean are the donor records needed to generate compliant illustrations, such as birth dates and gift histories? Options: Highly accessible and clean, Mostly ready with gaps, Fragmented across systems, Not available
• If a single compliance gap would halt rollout, which one would that be and why?

Alternatives on the table

• Which options are you actively evaluating right now to improve planned giving outcomes? Options: Stick with current vendor, Build internal tools, Purchase another vendor solution, Engage a consultant, Do nothing for now, Other
• If you kept your current approach, what exact condition would need to be true for you not to change vendors this year?
• Has anyone on your team proposed solving illustrations or administration internally instead of buying a product, and who proposed it? Options: Yes, IT suggested it, Yes, finance suggested it, Yes, planned giving suggested it, No one has proposed internal build, Other
• Which factor—cost, time to value, control, or compliance—matters most in picking between buy and build? Options: Cost, Time to value, Control over workflow, Compliance certainty, Other
• Which competitor capability would force you to choose them over an external partner like us? Options: Better CRM integration, Lower price, Stronger legal compliance, Full-service administration, Better training and adoption support, Other

Do we have the plumbing: integrations, data, and people

• Which integration failure would halt this project outright? Options: No API access to CRM, No secure data transfer path, Inability to map donor fields, No authentication for endpoints, Other
• Which donor database or CRM endpoints must be available for a realistic pilot, and who owns those endpoints? Options: Constituent record API, Gift history export, Household relationships, No API currently available, Other
• How many engineering or IT hours can your team commit to integrations over a typical 8-week pilot? Options: 0-20 hours, 21-80 hours, 81-160 hours, 160+ hours, Unsure
• Describe the availability of test or anonymized data we could use during configuration and validation. Options: Ready and accessible, Needs preparation, Must be created, Not available
• Are there scheduled compliance or legal reviews that could block timeline, and when are they normally held? Options: Monthly, Quarterly, Ad hoc, No formal reviews
• If API access or data sharing cannot be granted, what alternate path would you use to validate illustrations and proposals? Options: Manual uploads, Limited CSV exports, Sample synthetic data, Project cannot proceed, Other

What success looks like and what will make you say yes

• If a six-month pilot produced a 20 percent increase in identified bequest intentions, what would stop you from signing a contract that week?
• Which adoption metric would make the CFO comfortable including planned gift forecasts in the operating budget? Options: Confidence-weighted pipeline value, Confirmed estate notices, Donor intent documented, Legacy society growth rate, Other
• Who on your leadership team must approve the pilot success criteria and who signs the final contract? Options: Planned giving director, VP of Development, Finance lead, General counsel, Board finance committee, Other
• What acceptance tests must pass during pilot configuration for you to consider the technical implementation complete? Options: Accurate illustrations, CRM sync working, Proposal generation working, Admin workflows validated, Training completed, Other
• How soon do you need validated results to inform next year's budget cycle? Options: Within 1 month, 1-3 months, 3-6 months, Not tied to budget cycle, Unsure

Decision mapping and immediate next steps

• Who are the mandatory approvers for commercial and legal terms if we need a signature this quarter?
• Which contractual term or data permission would you anticipate negotiating most heavily? Options: Data sharing terms, Service-level commitments, Pricing, Intellectual property, Termination terms, Other
• If the pilot meets agreed criteria, how quickly can you allocate budget and resources to proceed to rollout? Options: Immediately, In 30 days, In 60 days, Tied to board cycle, Unsure
• Which single scheduling constraint would force us to delay a pilot start date? Options: End-of-year blackout, Audit window, Staffing vacation window, CRM upgrade, Other
• What would you like the seller to prepare before our next meeting to make approval easiest? Options: Pilot plan and timeline, Data mapping template, Sample donor illustrations, Draft contract terms, Training plan, Other

• Illustrations & Use Cases Solution Experience

• Confirm the current state and its cost
• Customer confirms the demonstrated illustrations meet IRS and state compliance expectations for the tested donor profiles.
• Provide a sample of 10 anonymized donor records with the required fields for the follow-up sample forecast run.
• Proof, live: Illustration calculations on two donor profiles
• Customer confirms the generated donor proposals and legacy society messaging can be used by gift officers without legal rewrite.
• Deliver three tailored illustration templates and a sample forecast run on the provided donor records before the next session.
• Proof, live: Donor proposal and legacy society messaging
• Document specific state compliance constraints and any legal reviewer questions to validate before deployment.
• Customer confirms that running these illustrations against a sample of donor records will produce the forecast metrics needed for budgeting.
• Confirm the acceptance criteria and forecast metric targets required to close the decision gate.
• Proof: Marketing scenario and outreach cadence
• Validate: Is this what you meant when you said you needed scalable, IRS-compliant illustrations and donor-ready proposals that your gift officers can use?
• Agree next evidence and acceptance criteria

• Illustrations & Use Cases Solution Experience
• Solution Experience Deck
• Solution Brief — Illustrations & Use Cases

• meeting
• slides
• document

• Import and Clean Planned Gift Records
• Integrate Planned Giving with Source CRM
• Generate Donor-Ready Bequest Illustrations
• Generate Charitable Remainder Trust Illustrations
• Generate Charitable Gift Annuity Illustrations
• Produce IRS-Compliant Donor Proposals
• Configure State Tax and Compliance Rate Tables
• Deploy Legacy Society Membership Management
• Provide Planned Giving Marketing Content Library
• Train Gift Officers on Solicitation and Platform Use
• Administer Trusts and Annuity Payment Schedules
• Produce Planned Gift Pipeline Forecasts and Reports
• Migrate Historical Gift Documents and Agreements

Import and Clean Planned Gift Records

• Do you have an export of existing planned gift records from your current CRM or donor database? Options: Yes, No
• How many planned gift records require import (including bequests, trusts, annuities, and pledged intentions)? Options: Less than 50, 50-250, 251-1,000, More than 1,000
• Which specific fields appear on your planned gift records that must map into the platform (choose all that apply)? Options: Donor name, Donor mailing address, Planned gift type, Estimated gift amount, Designation/Restriction, Date of intent, Scanned agreement/document, Executor contact, Custom legacy society tag
• Describe the quality issues present in your exported records (for example: duplicate donor IDs, missing beneficiary names, inconsistent state residency flags).
• Specify the matching threshold you require to accept imported donor matches to existing CRM contacts (for example percentage match on name+dob+address). Options: Exact match required, 90% name+address match, 75% fuzzy match with manual review, Custom threshold
• Which acceptance criteria will validate successful import and cleaning (for example: percentage of records matched, number of duplicates resolved, percentage of records with scanned agreement attached)? Options: % records matched to CRM, Duplicates resolved count, % records with document scans, Manual review backlog threshold

Integrate Planned Giving with Source CRM

• Which entity in your source CRM will house planned gift records (Contact, Opportunity, Custom Object, Other)? Options: Contact, Opportunity/Deal, Custom Object, Other
• Identify the CRM integration endpoints available for us to use (REST API, bulk export CSV, scheduled FTP, webhook feed). Options: REST API, Bulk CSV export, Scheduled FTP/SFTP, Webhook feed
• Provide the expected sync cadence for planned gift data with the CRM (for example: real-time on change, nightly batch, weekly export). Options: Real-time/webhook, Hourly, Nightly, Weekly
• List the CRM field names (or sample CSV headers) that must map to platform fields for gift illustrations and proposal generation.
• Indicate whether your CRM enforces state residency or domicile flags used to select state tax/compliance rules for illustrations. Options: Yes - state field present, No - needs enrichment, Partial coverage
• Who in your organization will own API credentials and change control for the CRM endpoint (role or title)?

Generate Donor-Ready Bequest Illustrations

• Which bequest illustration templates do you require (residual bequest, fixed legacy amount, percentage of estate)? Options: Residual bequest, Fixed dollar bequest, Percentage of estate, Contingent language examples
• Describe the donor profile samples we should use to build illustrations (example: 75-year-old, single, $1.2M estate, charitable designation to operations).
• Specify the actuarial or IRS assumptions you want applied to bequest illustrations (mortality table, discount rate, estate tax assumption). Options: IRS Table (latest), Custom mortality table, Assume estate tax at X%, No estate tax assumption
• Which delivery formats do you need for bequest illustrations (PDF proposal insert, web-viewable donor page, CSV for finance)? Options: PDF, Web view, CSV export, Printable one-pager
• Which evidence will confirm illustration accuracy for bequests (for example: sign-off by your finance director, comparison to sample IRS calculation)? Options: Finance sign-off, Actuary audit, Sample calculation review, Automated unit tests

Generate Charitable Remainder Trust Illustrations

• Which CRT payout structures do you offer and want modeled (unitrust percentage, annuity trust fixed payout, net income with makeup)? Options: Unitrust (percentage), Annuity trust (fixed $), Net income with makeup, Hybrid
• Provide the range of payout rates or percentages your organization prefers for CRT illustrations. Options: 1%–3%, 4%–6%, 7%–9%, Custom range
• State which IRS forms and compliance checks must be referenced in CRT outputs (Form 5227 reporting fields, charitable remainder calculation steps). Options: Form 5227 reference, Present value calculation steps, Charitable deduction worksheet, All required IRS citations
• Describe the trustee administration workflows we should assume for CRTs (in-house trust officer, external trustee, hybrid), including who records distributions. Options: In-house trustee, External bank trustee, Hybrid arrangement
• Which donor documents should be linked to each CRT record in the platform (signed trust instrument, trustee acceptance, funding instructions)? Options: Signed trust instrument, Trustee acceptance, Funding wiring instructions, Tax ID documentation
• Estimate the number of active CRTs to model during implementation to validate calculators and reporting. Options: None (pilot only), 1-10, 11-50, 50+

Generate Charitable Gift Annuity Illustrations

• Which annuity rate tables (state-specific or organizational schedule) should be used for CGA calculations? Options: State-mandated rates, Organization's published rates, Actuarial custom table, Combination
• Identify any state residency rules that change annuity eligibility or payout levels for your donors. Options: State residency enforced, State residency varies by donor, No state residency impact
• Which payout frequency do you support for annuity payments (monthly, quarterly, semiannual, annual)? Options: Monthly, Quarterly, Semiannual, Annual
• List the documents we must generate or store for CGA transactions (annuity contract, disclosure statement, wiring instructions, beneficiary designation). Options: Annuity contract, Disclosure statement, Wiring instructions, Beneficiary designation
• Describe administrative constraints for CGA payments (payment by check only, ACH allowed, trustee escrow required). Options: Check only, ACH allowed, Trustee escrow required, Other
• Indicate the test scenarios you want executed to validate the annuity calculator (example: 70-year-old single life vs. 70-year-old joint life with spouse age 68).

Produce IRS-Compliant Donor Proposals

• Which proposal templates should include IRS-required language or disclaimers (bequest, CRT, CGA templates)? Options: Bequest template, CRT template, CGA template, All templates
• Specify required fields that must always appear on a donor proposal for tax substantiation (tax ID, charity legal name, charitable deduction calculation). Options: Tax ID, Charity legal name, Charitable deduction worksheet, Statement of no goods/services
• Provide the approval workflow for finalizing donor proposals (gift officer draft, legal review, finance sign-off). Options: Gift officer draft only, Gift officer + legal review, Gift officer + finance + legal, Custom approval flow
• Which output formats do you require for donor proposals delivered to donors and for internal records (PDF with signature fields, secure web link, archival PDF)? Options: PDF for donor, Secure web link, Archival PDF for records, Editable Word/PDF
• Describe any donor-facing language constraints we must respect (example: avoid legalese, include legacy society invitation text, limit tax terminology to plain language).
• How will you verify proposal compliance and readiness for donor delivery (examples: legal checklist, sample sign-off email, completed disclosure fields)? Options: Legal checklist, Sample sign-off, Automated template validation, Manual QA

Configure State Tax and Compliance Rate Tables

• Which states must be covered by the compliance and tax rate tables at go-live? Options: All states, Selected states only, Home state + top 5 donor states, Custom list
• Provide the authoritative sources you want used for state gift/annuity compliance (state insurance departments, state attorney general publications). Options: State insurance depts, Attorney general guidance, Organization counsel guidance, Third-party actuarial source
• List any state-specific rules that alter illustration outputs (minimum annuity reserve requirements, registration requirements for charitable solicitation).
• Indicate how frequently you require rate table updates (monthly, quarterly, annual, as-regulation-changes). Options: Monthly, Quarterly, Annually, On regulatory change
• Which owner in your organization will approve changes to state compliance tables (title/role)?
• Specify any fallback rule when a donor's state is unknown for illustration (use donor mailing address, use filing state, apply most conservative state rule). Options: Use mailing address, Use filing state, Apply conservative state rule, Require enrichment

Deploy Legacy Society Membership Management

• How do you currently identify legacy society members in your CRM today (tag, custom field, separate list)? Options: Tag, Custom field, Separate list, No formal identifier
• Which membership attributes must be tracked for each legacy society member (join date, recognition level, communication preferences, gift type)? Options: Join date, Recognition level, Communication preferences, Gift type, Recognition naming
• Describe the recognition tiers and eligibility rules that should be configurable in the platform (example: donors with documented bequest of $100k+ are Silver).
• Do you require public-facing export formats for legacy society lists (web roster with opt-outs, PDF brochure extract)? Options: Web roster, PDF extract, CSV export, No public export
• Which acceptance criteria will confirm a successful legacy society deployment (for example: roster synced with CRM, automated welcome letter sent, recognition level populated for X% members)? Options: Roster sync complete, Welcome letter automation, Recognition populated %
• Who will own membership updates and opt-out management for ongoing legacy society maintenance (role/title)?

Provide Planned Giving Marketing Content Library

• Which content types do you want preloaded in the library (email drips, brochure copy, donor-facing one-pagers, legacy society invites)? Options: Email drips, Brochure copy, Donor one-pagers, Legacy society invites, Social media posts
• Describe your tone and compliance constraints for donor outreach content (for example: non-coercive language, no specific tax advice, plain-language estate examples).
• Specify whether content should be personalized by donor attributes (name, planned gift type, estimated gift amount) and which attributes to use. Options: Personalize by name, Personalize by gift type, Personalize by estimated amount, No personalization
• Do you need translated materials or accessibility-compliant versions of marketing content (Spanish, large-print, screen-reader friendly)? Options: Spanish, Large-print, Screen-reader friendly, None
• List any brand or legal copy requirements content must include (logo usage, legal footer, solicitation disclosure language).
• How will you measure marketing content success for planned giving outreach (click-through rate, donor engagement, number of proposal requests)? Options: Click-through rate, Donor engagement, Proposal requests, Conversions to intentions

Train Gift Officers on Solicitation and Platform Use

• How many gift officers will require instructor-led training on donor conversation scripts and platform workflows? Options: 1-3, 4-10, 11-25, More than 25
• Which training formats do you prefer for solicitor readiness (live webinar role-play, on-demand videos, step-by-step job aids)? Options: Live webinar, On-demand videos, Job aids/cheat sheets, Role-play workshops
• Specify the solicitation scenarios to be covered in training (initial estate conversation, legacy society enrollment, delivering a donor proposal). Options: Initial estate conversation, Legacy society enrollment, Delivering a donor proposal, Handling objections
• Describe success criteria for training (for example: X% of trainees able to generate an illustration and send a proposal without assistance).
• Indicate whether you require certification or a knowledge check for gift officers after training. Options: Yes - certification, Yes - quiz only, No
• Who will coordinate scheduling and attendance tracking for training sessions (role/title)?

Administer Trusts and Annuity Payment Schedules

• Which payment schedules do you administer in-house and expect the platform to support (monthly annuity, quarterly trust distribution, ad hoc distributions)? Options: Monthly annuity, Quarterly distribution, Semiannual, Ad hoc

• Subscription Agreement
• Order Form (Commercial Schedule)
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Data Processing Agreement (DPA)
• Data Sharing and Use Addendum
• Service Level Agreement (SLA)
• Acceptance Criteria & Rollout Sign-off
• Operational Roles and Gift Administration Matrix
• Change Order Agreement
• Confidentiality Agreement (Mutual NDA)
• Industry Compliance Addendum

• Go-live health check
• First measurement review
• Acceptance gate review (day 90)
• Quarterly success review

• Schedule targeted refresher training for segments with falling proposal generation rates.
• Produce a documented acceptance decision that records pass/fail status for each criterion listed in the Mutual Commit stage.
• For any failed criteria, agree remediation tasks and clear re-verification dates prior to final rollout.
• Ensure the acceptance decision and remediation plan are published to the shared workspace for traceability.
• Publish the acceptance decision record, including pass/fail per Mutual Commit criterion and any conditional acceptance notes.
• Open remediation tickets for failed criteria with defined completion dates and verification steps.
• Schedule a short re-verification checkpoint after remediation completion to confirm the fixes closed the gaps.
• Review realized pipeline versus forecast
• Confirm whether forecast accuracy % and planned-gift pipeline dollar value are meeting the agreed quarterly targets.
• Prioritize the enhancement backlog and confirm which items will be worked in the next cycle.
• Agree next quarter measurable targets and the cadence for progress updates.
• Publish a prioritized enhancement backlog from the shared channel with target delivery windows for top-priority items.
• Record next quarter numeric targets for forecast accuracy % and pipeline dollar growth and share them in the workspace.
• Re-confirm acceptance criteria and owners
• Validate that integrations are functionally live with documented evidence of CRM syncs and illustration outputs.
• Record early adoption metrics: number of gift illustrations generated and count of trained gift officers, and confirm they meet minimal expected thresholds.
• Create a short remediation plan with owners and dates for all critical open issues.
• Provide detailed logs for any failed CRM syncs and a diagnostic summary within 48 hours.
• Deliver the training completion roster and a list of users who require follow-up training within 72 hours.
• Open remediation tickets for all high-priority blockers with target resolution dates and post updates in the shared channel.
• Present first-window outcome data vs Mutual Commit targets
• Determine whether planned-gift pipeline dollar value and number of donor proposals generated are trending toward the Mutual Commit targets.
• Identify root causes for any metric gaps and agree corrective actions with timelines that conclude before the acceptance gate.
• Confirm a clear path and dates for resolving outstanding items that would block acceptance at day 90.
• Publish the measurement dashboard with source data and calculation method used for pipeline and proposal metrics.
• Create remediation tickets for the top 3 root causes with target resolution dates that align to the acceptance gate.
• Schedule focused training or process coaching for segments with low proposal generation rates.
• Restate acceptance criteria from the Mutual Commit stage
• Deployment and integration validation
• Present outcome data against each criterion
• Adoption and usage trends
• Root-cause analysis for gaps
• Open issues and enhancement backlog
• Agree corrective actions and timeline
• Early adoption signals
• Document pass/fail per criterion and acceptance decision
• Confirm readiness criteria for the acceptance gate
• Agree remediation plan for any failed criteria
• Agree next quarter metrics and checkpoints
• Blockers and open issues
• Agree immediate remediation actions