Start with a Story: Your Most Memorable Donor Moment

• Tell us about one recent donor interaction that still shapes how you think about stewardship—what happened and why it matters to you?
• When you think about that story, which emotion stands out most—pride, concern, frustration, relief, or something else? Options: Pride, Concern, Frustration, Relief, Surprise, Other
• How typical is that story of how you wish donors were routinely treated—always, often, sometimes, rarely? Options: Always, Often, Sometimes, Rarely
• What, if anything, about that moment felt like it was driven by a system or process versus an individual relationship? Options: Mostly system/process, Mostly individual relationship, Balanced mix, Not sure
• If you could freeze one element of that interaction and make it repeat across your top portfolios, what would you choose?
• Who on your team remembers this moment and would call it important—roles or names? Options: VP/AVP Advancement, Stewardship Director, Major Gift Officer, Development Operations Manager, Gift Processor, Other

If a Major Donor Walked Out Tomorrow, What Would We Find?

• Imagine your top 10 donors woke up tomorrow and decided to pause their giving—what single stewardship failure would you suspect caused it? Options: Late acknowledgment, No impact reporting, Poor personalization, Mismatch with donor interests, Lack of steward contact, Other
• How many donors at your major gift level have missed an expected acknowledgment or impact update in the last 12 months? Options: None, 1–5, 6–20, 21–50, 51+
• When those misses happen, how soon do you typically discover them—immediately, within weeks, months, or only when a donor complains? Options: Immediately, Within weeks, Within months, Only after complaint, We rarely discover
• Tell me about a time you learned a stewardship task didn’t happen—what did you do and what was the fallout?
• Which consequences worry you most when stewardship slips—revenue loss, reputation damage, internal blame, donor relationships fraying, or something else? Options: Revenue loss, Reputation damage, Internal blame, Donor relationship fraying, Operational burden, Other

Where Stewardship Actually Breaks Down (Behind the Scenes)

• What part of your stewardship process do you suspect is failing most often—and why do you think it keeps failing? Options: Acknowledgments, Impact reporting, Personal outreach, Stewardship plan completion, Data updates, Other
• Walk me through the last time an acknowledgment or report was late—what systems and people were involved at each step?
• How consistent are stewardship plans across gift officers—highly consistent, somewhat consistent, ad hoc, or nonexistent? Options: Highly consistent, Somewhat consistent, Ad hoc, Nonexistent
• When plan steps are missed, what usually explains it—workflow gaps, workload, unclear ownership, CRM limitations, or donor-level complexity? Options: Workflow gaps, Workload, Unclear ownership, CRM limitations, Donor complexity, Other
• How does it feel internally when a major stewardship failure occurs—embarrassing, defensive, motivated to fix, resigned, or something else? Options: Embarrassing, Defensive, Motivated to fix, Resigned, Other

Who Holds the Keys (and Who’s Missing)?

• If we listed every person who must sign off or act to deliver stewardship for a major gift, who would be on that list and who is often absent? Options: Gift Officer, Stewardship Manager/Director, Donor Relations, Development Ops/Database, Finance/Donor Records, Communications/Impact, Executive Leadership, Other
• Who is your final approver for donor-facing impact language or reports—title or role? Options: VP Advancement, Stewardship Director, Communications Lead, Gift Officer, Committee/Board, Other
• How involved are gift officers in operational steps (acknowledgment drafting, sending, tracking) versus relationship-level touches? Options: Mostly operational, Balanced, Mostly relationship-level, Varies by officer
• Which stakeholders would resist a new stewardship system the most—and what is their primary concern? Options: Gift Officers (time), Stewardship Team (control), Development Ops (integration), Communications (content), Leadership (cost/priorities), Other
• Who outside your organization (e.g., board members, volunteer stewards) do we need to consider in communications or governance?

What Does Success Feel Like for Your Donors—and for Your Team?

• If you could guarantee one measurable outcome from improving stewardship, which would you pick—retention, upgrade rate, time-to-acknowledgment, donor satisfaction, or something else? Options: Retention rate, Upgrade rate (increased gift size), Faster acknowledgments, Higher donor satisfaction, Stronger relationship metrics, Other
• What specific metric or signal would make you say 'this worked' after a pilot—percent retention lift, reduction in missed acknowledgments, NPS change, or a qualitative board story? Options: Retention lift (%), Missed acknowledgments reduction (%), NPS/Donor satisfaction, Increase in re-solicitation readiness, Board/donor anecdote, Other
• Describe one donor reaction that would prove the system is delivering impact—what did they say or do?
• How quickly would you expect to see early signs of improvement—weeks, one quarter, two quarters, or longer? Options: Within weeks, One quarter, Two quarters, Longer than two quarters
• Which internal stakeholders would you need to celebrate success with to keep momentum—roles or teams? Options: Gift Officers, Executive Leadership, Board/Volunteers, Development Ops, Communications, Finance

Data, Systems, and the Pieces We Patch Together

• What blind spots in your data would surprise your leaders if they looked today—stewardship history, acknowledgment timestamps, donor interests, or other gaps? Options: Stewardship history, Acknowledgment timestamps, Donor interests/attributes, Gift purpose/linkages, Volunteer/liaison notes, Other
• Which systems hold the truth about a gift—CRM, finance system, spreadsheets, shared drives—and which one do you consider the system of record? Options: CRM, Finance system, Shared spreadsheets, Custom stewardship tool, Combination (no single source)
• How reliable are your CRM data fields for stewardship workflows—accurate, patchy, unreliable, or unknown? Options: Accurate, Patchy, Unreliable, Unknown
• What migrations or integrations have caused pain in the past—failed mappings, lost notes, duplicate records, or timing issues? Options: Failed mappings, Lost notes, Duplicate records, Timing/latency issues, Other
• Which donor data sources would you want stitched together for a coherent stewardship view—gift history, engagement events, portfolio notes, volunteer reports, or third-party research? Options: Gift history, Engagement/events, Portfolio notes, Volunteer reports, Third-party research, Other
• Describe any security, privacy, or compliance constraints we must honor when accessing or moving donor data.

What Would Make a Pilot Impossible to Say No To?

• If I told you we could run a one-off pilot that proved we stopped donor lapses in one portfolio, what would your immediate skepticism be? Options: Data quality will fail, Gift officers won't adopt, It won't scale, Costs hidden later, Timeline unrealistic, Other
• What must be in the pilot scope for you to sign off—specific metrics, number of donors, integration depth, or handoff plan? Options: Specific metrics, Number of donors, Integration depth, Training included, Clear governance/ownership, Other
• How would you measure pilot success internally—who approves and what thresholds matter?
• What would make you pull the plug on a pilot early—low adoption, data loss, donor complaints, cost overruns, or leadership pushback? Options: Low adoption, Data loss, Donor complaints, Cost overruns, Leadership pushback, Other
• Who needs to be in the room for a pilot kickoff and who must approve pilot acceptance at the end? Options: Gift Officer(s), Stewardship Director, Development Ops, VP Advancement, Communications, Finance, Other

Next Steps, Signals, and the Small Commitments That Matter

• What small, low-risk next step would feel acceptable to try in the next 30 days—data export, one-off acknowledgment automation, or a workflow checklist? Options: Data export/assessment, One-off acknowledgment automation, Workflow checklist, Training session for one officer, Integration feasibility call, Other
• Which internal approval or timeline constraint would block starting within the next month—budget cycle, leadership availability, IT security review, or nothing? Options: Data readiness, Budget cycle, Leadership availability, IT/security review, Nothing blocks
• What would be the one hard no—an absolute dealbreaker—that would stop you from moving to a pilot or implementation? Options: Inability to integrate CRM, Risk to donor data, No gift officer buy-in, Unclear ROI, Cost exceeds budget, Other
• Who else should we speak to next (role and ideal topic) to keep momentum and get a realistic green light?

• Pre‑Workshop: Current State, Consequence & Future State Alignment
• Solution Experience: Live Scenario Walkthrough
• Acknowledgment & Impact Reporting Simulation
• Integration & Data Mapping Triage
• Validation & Pilot Commitment

• Agree on integration test cases, owners, and rollback/mitigation procedures for identified risks.
• Capture any uncovered gaps or exceptions to triage in the integration/technical session.
• Seller to record validation statements for each scenario and compile into a one‑page validation summary.
• Customer to confirm which gift officers and portfolios will be included in the pilot and provide access lists.
• Seller to prepare pilot configuration (workflows, templates, dashboards) for the chosen pilot candidates.
• Seller to list any functional gaps or additional requirements discovered for the Integration & Data Mapping Triage meeting.
• Recap Validation Points
• Demonstrate consistent acknowledgment timeliness that meets the customer’s SLA targets.
• Validate donor-facing impact reports meet content and personalization expectations.
• Confirm exception handling process reduces manual rework and is acceptable to gift officers.
• Customer to provide final acknowledgment language, impact report content, and acceptable SLA thresholds.
• Seller to tune templates, SLA timers, and re-run simulations if thresholds are not met.
• Seller to produce a KPI report from the simulation for inclusion in the pilot acceptance criteria.
• Integration Architecture Overview
• Produce a finalized mapping file and transformation spec that ensures accurate acknowledgments and reporting.
• Introductions & Objective
• Remove data-related blockers that could invalidate the Solution Experience when run on production data.
• Customer IT to provide full CRM schema, API credentials (or secure export), and sample problematic records.
• Seller engineering to deliver a mapping template, ETL/transformation rules, and a test harness for integration tests.
• Both teams to schedule an integration test window and define sign‑off criteria for migration readiness.
• Recap: Current State, Consequence, Future State
• Mutual sign‑off on pilot scope, explicit acceptance criteria, and success metrics.
• Agree timeline, pilot owners, and governance for go/no‑go decisions at pilot completion.
• Commit to the pilot kickoff date and immediate pre‑pilot deliverables.
• Customer to sign pilot scope and acceptance criteria and nominate pilot gift officer(s).
• Seller to provision pilot environment, import agreed pilot data, and confirm readiness checklist completion.
• Both teams to schedule recurring pilot checkpoints and define reporting cadence for KPI tracking.
• Seller to deliver a one‑page pilot playbook capturing steps, contacts, and escalation paths.
• Achieve a single, crystal‑clear current‑state sentence agreed by all stakeholders.
• Document an explicit, quantified consequence that creates urgency to act.
• Agree a single future‑state outcome in operational terms that the experience must prove.
• Secure required data and artifacts so the Live Scenario Walkthrough can use real customer context.
• Customer to deliver 8–12 representative donor scenarios, recent lapse examples, and a CRM export sample (fields and 30–100 records).
• Customer to share acknowledgment templates, donor preferences, and any SLA targets for acknowledgments/impact reporting.
• Seller to prepare a mapped test dataset and confirm environment/setup for the live walkthrough.
• Seller to circulate meeting recording and the agreed one‑sentence current state/consequence/future state.
• Re‑state One‑Sentence Artifacts
• Prove, using customer data, that the platform produces the defined future‑state outcomes for each critical scenario.
• Obtain explicit validation from the customer that each demonstrated workflow addresses their stated problem.
• Identify 1–3 pilot candidate gift officer portfolios and their representative scenarios for the pilot phase.
• Review CRM Export & Mapping Gaps
• Summary of Demonstrated Proof Points
• Confirm Current State (one sentence)
• Scenario 1 — Lapsed Donor Recovery (Diagnosis)
• Configure Acknowledgment Workflow
• Review Pilot Scope & Acceptance Criteria
• Surface Consequence (one sentence + metric)
• Run Acknowledgment Simulation
• Scenario 1 — Proof & Validation
• Define Transformation Rules & Business Logic
• Roles, Timeline & Governance
• Define Future State (one sentence)
• Run Impact Report Simulation
• Scenario 2 — Acknowledgment SLA Enforcement (Diagnosis)
• Error Scenarios & Mitigation
• Integration Test Plan & Ownership
• Decision & Next Steps
• Exception Handling & Overrides
• Scenario 2 — Proof & Validation
• Pre‑work & Data Checklist

• Import and Clean Donor and Gift Data
• Migrate Historical Stewardship Notes and Attachments
• Integrate Bi-directional Sync with Donor CRM
• Configure Stewardship Plan Templates by Donor Tier
• Automate Gift Acknowledgment Workflows (Email/Print)
• Set Up Impact Report Templates and Automated Delivery
• Deploy Personalized Communication Sequences by Interest
• Enable Re-solicitation Readiness Flags and Alerts
• Launch Gift Officer Dashboards and Portfolio Views
• Provision Donor Portal for Impact and Giving History
• Enable Endowment Performance and Distribution Reports
• Train Gift Officers on Live Stewardship Workflows

Import and Clean Donor and Gift Data

• Do you have existing donor and gift data to import? Options: Yes, No
• Which formats contain your donor and gift data? Options: Spreadsheet (CSV/Excel), Export from CRM, Database dump (SQL), Proprietary system export, Other
• Approximately how many donor and gift records will be ingested? Options: Less than 5,000, 5,000–25,000, 25,000–100,000, More than 100,000
• Do you require deduplication and identity resolution (e.g., merging multiple records for one donor)? Options: Yes, No
• Are there common data quality issues we should expect (e.g., missing contact info, inconsistent gift codes)? Please list.
• Do you need assistance mapping legacy fields to platform fields during import? Options: Yes, No
• Will offline gifts (checks, pledges, in-kind) be included in the import? Options: Yes - include all types, Yes - only select types, No
• What acceptance criteria will determine a successful data import (e.g., X% match rate, no orphaned gifts)? Options: Standard validation (no critical errors), Custom acceptance criteria (define below), TBD
• Who will own import validation and sign-off on your side (role/title)?

Migrate Historical Stewardship Notes and Attachments

• Do you have historical stewardship notes and attachments to migrate? Options: Yes, Partial set only, No
• What types of attachments exist (e.g., PDFs, images, scanned letters, Word docs)? Options: PDF, Image, Word/Office docs, Scanned documents, Other
• How are notes currently structured (free-text, templates, tagged by gift)? Options: Free-text, Tagged/structured, Mixed
• Do notes require redaction or privacy review before migration? Options: Yes, No, Unsure
• Are there retention or compliance rules for older attachments we must enforce? Options: Yes, No, Not sure
• Do you require linking migrated notes to specific gift records or donor profiles? Options: Yes - link to gifts, Yes - link to donors, Both, No
• What volume of notes/attachments will be migrated (approx. total files / GB)?
• Which role will be responsible for validating migrated notes and attachments?

Integrate Bi-directional Sync with Donor CRM

• Which donor CRM(s) must we integrate with? Options: Raiser's Edge / Blackbaud, Salesforce Nonprofit Cloud, Microsoft Dynamics, Other, Custom/Proprietary
• Do you require bi-directional sync (platform changes reflect in CRM and vice versa)? Options: Yes - full bi-directional, Yes - limited fields up sync only, No - one-way import only
• Which CRM objects need to sync (donor profile, gift, pledge, soft-credit, notes)? Options: Donor profile, Gift, Pledge, Soft-credit, Notes/Activities, Other
• What is your desired sync frequency? Options: Real-time/webhook, Every 15 minutes, Hourly, Daily, Manual sync
• Are there custom fields or record types in the CRM that require mapping? Options: Yes, No, Unsure - need discovery
• Who is responsible for configuration and API credentials on the CRM side?
• What are your acceptance tests for the integration (e.g., create gift in CRM -> appears in platform within X minutes)?
• Do any governance or security rules (IP allowlists, scopes) restrict integration methods? Options: Yes, No, Unsure

Configure Stewardship Plan Templates by Donor Tier

• Do you segment donors into tiers for stewardship (e.g., Major, Principal, Leadership)? Options: Yes - predefined tiers, Yes - need to define tiers, No
• How many stewardship templates do you anticipate creating? Options: 1-3, 4-7, 8+
• Which elements should each template include (ack timeline, reporting cadence, steward assignment)? Options: Acknowledgment timeline, Impact reporting schedule, Steward assignment, Touchpoint types (call, visit, event), Other
• Do templates require conditional logic (e.g., different flows for restricted vs unrestricted gifts)? Options: Yes, No
• Will templates be applied automatically by rules (tier + gift amount) or manually by users? Options: Automatic rules, Manual selection, Hybrid
• Who will own template creation and ongoing updates on your team?
• What acceptance criteria define a correctly configured template (e.g., assigned steward, tasks generated)?

Automate Gift Acknowledgment Workflows (Email/Print)

• Do you currently send acknowledgments by email, printed letter, or both? Options: Email, Printed letter, Both, Other
• What acknowledgment timelines do you need enforced (e.g., within 48 hours, 7 days)? Options: 24–48 hours, 3–7 days, Within 30 days, Other
• Do acknowledgments require customization per donor (name, gift purpose, steward message)? Options: Yes - personalized content, Yes - tokenized fields only, No - generic
• Will any acknowledgments require legal/regulatory wording (e.g., tax receipts) or special templates? Options: Yes, No, Some - for specific gift types
• Do you need print workflow (PDF generation, batching, export to vendor)? Options: Yes - generate print-ready PDFs, Yes - export to mail vendor, No
• What failure modes should be reported (e.g., email bounce, missed acknowledgment SLA)? Options: Email delivery failure, Missed SLA alert, Missing template data, Other
• Who will approve acknowledgment templates and final sign-off on automated sends?

Set Up Impact Report Templates and Automated Delivery

• Do you produce impact reports currently and in what format? Options: PDF reports, Web pages/links, Email summaries, Other
• Which donors should receive impact reports (all major donors, only restricted gifts, by campaign)? Options: All major donors, Restricted gift donors only, By campaign, By steward/portfolio
• What content blocks are required in impact reports (narrative, financials, photos, program metrics)? Options: Narrative impact story, Financial summary, Performance metrics, Photos/video, Donor-specific attribution
• How frequently should impact reports be delivered (quarterly, annual, milestone-based)? Options: Milestone-based, Quarterly, Annual, Custom schedule
• Do impact reports require data pulls from other systems (program databases, endowment reports)? Options: Yes - multiple sources, Yes - CRM only, No
• Should impact report delivery be automated (email with PDF/link) or manual review before send? Options: Fully automated, Automated with steward review, Manual send only
• What acceptance criteria will validate impact report delivery (open rates, delivered within X days of milestone)?

Deploy Personalized Communication Sequences by Interest

• Do you tag donors by interest areas (e.g., research, scholarships, healthcare)? Options: Yes - existing tags, No - want to create
• What channels should sequences cover (email, phone task, printed mail, events)? Options: Email, Phone/task, Printed mail, Event invitations, Other
• Should sequences be triggered by events (gift received, anniversary) or by schedule? Options: Event-triggered, Scheduled cadence, Both
• Do you require A/B testing or variant messaging for sequences? Options: Yes, No
• How granular should personalization be (salutation only, tailored paragraphs, full custom content)? Options: Salutation/tokenized, Tailored paragraphs, Fully custom per donor
• Who will maintain and approve content for interest-based sequences?
• What metrics will determine sequence effectiveness (open rate, steward follow-up completion, re-gift rate)? Options: Open/CTR, Task completion, Re-gift/retention, Other

Enable Re-solicitation Readiness Flags and Alerts

• Do you maintain re-solicitation rules (e.g., wait X months after gift, restrict asks after certain touchpoints)? Options: Yes - defined rules, No - want to define rules
• Which conditions should block or flag a donor as not-ready for solicitation? Options: Recent major gift, Outstanding stewardship tasks, Recent complaint/negative feedback, Other
• Do you want automated alerts for upcoming solicitation windows or blocked donors? Options: Yes - alerts to steward, Yes - central team only, No
• Should re-solicitation readiness be visible on donor and gift records and in dashboards? Options: Yes - all views, Only donor record, Only dashboard
• Do you require workflow actions when a donor is flagged (create task, notify manager)? Options: Create task, Send email notification, Prevent ask-related actions, Other
• What acceptance checks will you use to confirm flags are correct (audit sample, steward confirmation)?

Launch Gift Officer Dashboards and Portfolio Views

• How many gift officer roles and portfolio sizes exist (avg. donors per officer)? Options: 1-5 officers, 6-20 officers, 21-50 officers, 50+

• Statement of Work (SOW)
• Commercial Terms & Pricing
• Pilot Plan & Success Metrics
• Data Migration & Ownership Agreement
• Integration & API Access Agreement
• Governance & Decision Rights
• Acceptance Criteria & Final Sign-off
• Service Level Agreement (SLA) & Support
• Data Processing Agreement (DPA) & Security Addendum
• Software License & Subscription Terms
• Change Order & Scope Management
• Termination, Renewal & Exit Plan

• Quarterly Success Review — Retention & Engagement
• Lessons Learned & Process Improvement Workshop
• Enhancement Prioritization & Roadmap Planning
• Donor Communications & Impact Story Review
• Ongoing Support, Escalation & Shared Channel Setup

• Finalize and publish approved acknowledgment and impact-report templates.
• Draft updated stewardship SOPs reflecting agreed process changes.
• Schedule and deliver targeted training for affected gift officers within 4 weeks.
• Implement a 30‑day pilot of redesigned handoffs and report back with metrics.
• Usage & Feedback Summary
• Produce a prioritized list of enhancements tied to retention or operational risk reduction.
• Set realistic release windows and pilot scopes for high-priority items.
• Establish governance for ongoing backlog triage and change approvals.
• Create feature spec for top-priority enhancement and assign product owner.
• Add selected items to development pipeline with agreed sprint targets.
• Identify pilot gift officers and schedule pilot start dates for new features.
• Sample Review: Acknowledgments & Impact Reports
• Ensure all donor-facing templates meet institutional standards and acceptance criteria.
• Confirm timing rules prevent donor-facing delays and miscommunications.
• Validate personalization produces appropriate, non-robotic donor experiences.
• Welcome & Objectives
• Configure and test timing rules for acknowledgment and impact-delivery SLAs.
• Train gift officers on template usage and escalation triggers.
• Support Model & SLA Review
• Create a single persistent channel for triage, status, and enhancement requests.
• Agree clear SLAs and escalation steps to reduce time-to-resolution.
• Set recurring operational cadence and owner responsibilities.
• Create the shared CustomerNode channel, invite stakeholders, and publish channel norms.
• Document triage/escalation workflow and distribute to support and gift-officer teams.
• Configure alerting thresholds on dashboards and assign monitoring owners.
• Confirm whether retention and engagement metrics are meeting the agreed targets.
• Identify the top three causes behind any negative trends and agree immediate interventions.
• Assign owners and timelines for corrective actions and monitoring.
• Surface successful stewardship examples to replicate across portfolios.
• Owner to investigate top 10 lapsed donors and report root causes within 10 business days.
• Update KPI dashboard to include acknowledgment SLA and impact-report delivery rate by donor tier.
• Communicate agreed interventions and owner list to gift officers and leadership.
• Pre-work Review & Incidents Summary
• Surface and document the root causes of missed stewardship actions.
• Agree on 3–5 process changes or controls to eliminate recurring failures.
• Define a pilot plan and training schedule to validate process changes.
• Ensure accountability by assigning owners and deadlines for each change.
• Enhancement Requests Review
• Timing & Sequence Validation
• KPI Dashboard Review
• Shared Channel Standards
• Incident Timeline Walkthrough
• Triage & Escalation Workflow
• Cohort & Trend Analysis
• Personalization & Segmentation Rules
• Prioritization Exercise
• Root Cause Breakouts
• Root-Cause Spotlight
• Process Redesign Proposals
• Roadmap Alignment & Release Windows
• Donor Scenario Simulations
• Operational Cadence
• Wins & Donor Stories
• Backlog & Governance Rules
• Training & Adoption Actions
• Approval & Handoff
• Monitoring & Alerting
• Decisions & Interventions
• Decision & Implementation Plan
• Confirm Owners & Launch