Health, Education & Government Nonprofit & Philanthropy Major Gift Fundraising

Major Gifts

Mission-driven engagements where donor relationships, program delivery, and governance determine impact.

Bloomerang Blackbaud Salesforce NPSP Raiser's Edge
Inside this journey
  1. Customer Discovery

    Align on fundraising goals, portfolio health, key stakeholders, and measurable success signals for major gift programs.

    Discovery Questions

    A Friendly Introduction: Your Major Gifts Snapshot

    • Give us a one-sentence snapshot of your role and one thing about your major gifts program you're most proud of.
    • Which title best describes your primary role? Options: Chief Development Officer, VP of Development, Major Gifts Director, Director of Advancement, Other
    • How many gift officers do you directly manage (or coordinate)? Options: 1-3, 4-7, 8-12, 13-20, 20+
    • On average, how many prospects does each gift officer manage? Options: <50, 50-99, 100-199, 200-299, 300+
    • What is your organization's annual major gifts target (approx.), and what percentage of total revenue do major gifts represent?
    • Which CRMs or donor databases are you actively using today? Options: Raiser's Edge NXT, Salesforce/NPSP, Blackbaud CRM, Personify, Other, We don't use a formal CRM

    What If Your Best Prospects Keep Slipping Away?

    • How often do you realize a high-capacity prospect was under-engaged only after they've given elsewhere or gone quiet? Options: Frequently, Occasionally, Rarely, Never
    • Can you share a recent example where a strong prospect moved backward or disappeared — what happened and why do you think it slipped?
    • What signals do you currently use to know a prospect is ready for solicitation (e.g., engagement, wealth indicators, volunteer activity)? Options: Engagement/events, Wealth screening, Recent giving history, Peer/prospect referrals, Volunteer involvement, Other
    • How often are prospect readiness signals standardized across gift officers versus being based on individual judgment? Options: Mostly standardized, Partly standardized, Mostly individual judgment, No standard process
    • Who on your team typically moves a prospect to 'ask-ready' status, and how is that decision documented? Options: Gift officer, Gift officer + manager, Major gifts committee, Prospect scored automatically, Not documented/varies
    • How does it feel when a top prospect falls out of view — frustrated, resigned, urgent — and who most feels that pain?

    Where Does the Team Spend Its Time — and Does It Matter?

    • If you had a stopwatch for your gift officers, would it show them spending most of their day on high-value cultivation or on admin tasks that could be automated? Options: Mostly cultivation, Mostly admin/manual work, Split evenly, Unsure
    • Roughly what percentage of a gift officer's time is spent on: prospect research, outreach/calls, proposal writing, stewardship, and data entry? Options: Prospect research, Outreach/calls, Proposal writing, Stewardship, Data entry/CRM maintenance, Other
    • Which of these activities currently lacks reliable tracking or visibility for managers? Options: Research activity, Meeting outcomes, Proposal status, Stewardship tasks, Time spent per prospect
    • How do you onboard new gift officers — do you have documented playbooks, shadowing, or is it mostly on-the-job learning? Options: Structured playbook + training, Shadowing + mentoring, Mostly on-the-job, Formal certification program, Other
    • When a departing gift officer takes institutional knowledge with them, which gaps hurt you most: relationships, cultivation strategy, donor intel, or CRM records? Options: Relationships, Cultivation strategy, Donor intel/research, CRM records, All of the above
    • If you could free up one hour per day per officer by reducing busywork, what would you want them to do with that time instead?

    Are Your Portfolios Built or Just 'Believed In'?

    • Is your portfolio segmentation driven by clear data and criteria—or by gut calls about who 'feels' important? Options: Data-driven criteria, Mostly gut-based, A mix, Unsure
    • What criteria do you currently use to segment portfolios (capacity, affinity, engagement, strategic priorities)? Options: Capacity/wealth score, Affinity/relationship strength, Recent engagement, Institutional ties, Volunteer/board status, Other
    • How often do you refresh wealth screenings or research on high-priority prospects? Options: Monthly, Quarterly, Annually, Only on special requests, Never
    • What data sources do you rely on for research and how confident are you in their accuracy? Options: Internal giving history, Commercial wealth screening, Public records/press, Network referrals, We're unsure of accuracy
    • Describe a current portfolio where you feel the match between officer capacity and prospect potential is poor—what's causing the mismatch?
    • How comfortable are you with automated scoring or suggested moves for prospects versus manager discretion? Options: Very comfortable, Somewhat comfortable, Prefer human-only decisions, Unsure

    Who Really Decides 'Priority' Around Here?

    • When priorities clash—program needs vs. donor interest—who usually wins and why? Options: Development leadership, Program leadership/exec, Board/major donors, Fundraising committee, Varies by case
    • Which stakeholders are essential to major gift asks, and how aligned are they on strategy? Options: Gift officers, Development leadership, Program directors, President/CEO, Board members, Other
    • How are decisions about solicitation timing, ask amounts, and engagement strategy documented and approved? Options: Formal approval workflow, Email/meeting notes, Ad hoc conversations, Not documented
    • Have there been situations where misalignment caused lost momentum or missed asks? Tell the story briefly.
    • Do you have a governance rhythm (e.g., weekly portfolio review, pipeline committee) that holds teams accountable? Options: Yes, regular cadence, Occasional reviews, No formal rhythm, We're setting one up
    • If we needed to involve a 30-minute executive sponsor briefing as part of implementation, who would that be and what would likely concern them most?

    What Would Success Really Look Like — Beyond the Big Number?

    • If you hit your numeric goal next year but your managers still couldn't say why any single gift closed, would you call that real success? Options: No—need causal clarity, Partly—goal matters most, Unsure, Yes—dollar win is enough
    • Which non-monetary signals matter to you (e.g., conversion rate from cultivation to ask, time-to-ask, officer adoption, proposal accuracy)? Options: Conversion rate, Time-to-ask, Officer adoption, Proposal accuracy, Donor satisfaction, Other
    • What magnitude of improvement in those signals would feel meaningful in 12 months (percent or absolute example)?
    • Are there stories or qualitative outcomes you want the platform to help capture (e.g., donor stewardship narratives, impact conversations)? Options: Yes—stewardship narratives, Yes—impact storytelling, No, mostly quantitative, Other
    • How will you measure adoption and coaching effectiveness among managers and gift officers? Options: Dashboard metrics, Regular 1:1 reviews, Training completion, Observed behavior changes, Other
    • Who needs to sign off on the success criteria, and how do we know they’ll consider the project successful?

    If We Could Solve One Operational Bottleneck, Which Would You Choose?

    • If a single change could reliably increase solicitation-ready prospects each quarter, which bottleneck would you fix first? Options: Prospect identification, Research quality, Portfolio assignment, Proposal tracking, CRM integration, Officer adoption
    • Why does that bottleneck exist today—process, people, data, or tooling? Options: Process, People/skills, Data quality, Technology/tools, Multiple of the above
    • What would be the immediate downstream impact if that bottleneck disappeared?
    • What internal constraints might slow fixing it (e.g., IT bandwidth, budget cycles, competing priorities)? Options: IT/tech constraints, Budget timing, Staff bandwidth, Cultural resistance, Other
    • Have you tried to solve this before? What worked, what didn’t, and how long ago?
    • If we delivered a pilot solving this in 90 days, what success checkpoint would convince you to expand?

    Ready to Take a First Step Together?

    • What's been the real reason similar initiatives haven't stuck here—was it lack of people, unclear ROI, or simply too many competing priorities? Options: People/skills, Unclear ROI, Competing priorities, Change fatigue, Other
    • What’s an acceptable timeline for a phased implementation from kickoff to first usable insights? Options: 30-60 days, 60-90 days, 3-6 months, 6+ months, Unsure
    • Which pieces of data and access would we need to start integration—CRM, giving history, contact records, wealth screens? Options: CRM access, Giving history export, Contact records, Existing wealth screens, Org charts/relationships
    • Who on your side would be the implementation lead, the data owner, and the executive sponsor (names/titles)?
    • How would you prefer a pilot to be structured—coaching-heavy, tool-first, research-led, or a blended approach? Options: Coaching-heavy, Tool-first, Research-led, Blended approach, Other
    • Realistically, how likely are you to pursue a pilot in the next quarter? Options: Very likely, Somewhat likely, Unlikely, Unsure
    • What would reassure you most about working with us on a pilot (e.g., clear ROI model, reference from a peer institution, hands-on training)? Options: Clear ROI model, Peer references, Hands-on training, Data security assurances, Flexible scope
  2. Solution Experience

    Translate the customer’s context into a tested path showing how research, portfolio workflows, and analytics move priority prospects toward solicitation.

    Experience Meetings

    • Solution Experience Kickoff — Current State & Consequence
    • Prospect Path Mapping Workshop
    • Live Solution Experience — Research, Prioritization & Workflow Proof
    • Analytics Calibration & Coaching Loop Proof
    • Validation & Mutual Confirmation — Move to Scope
    • Identify any data quality or integration gaps that must be resolved for accurate analytics.
    • Customer to mark and annotate the sample prospect records that represent the chosen use-cases.
    • Seller to prepare scenario scripts for each selected use-case, mapping each step back to the documented friction and success metrics.
    • Seller and customer data lead to confirm access method and sanitized sample data transfer schedule.
    • One-line Recap & Success Criteria
    • Prove, with customer data, that research + workflows produce prioritized prospects ready for solicitation.
    • Validate that analytics provide the manager signals needed to coach gift officers and move prospects faster.
    • Obtain explicit validation (accept/reject/adjust) for each mapped acceptance criterion.
    • Customer to mark each use-case as 'validated', 'needs adjustment', or 'rejected' and specify required changes if any.
    • Seller to document demo outcomes, adjustments, and produce a short 'Proof Summary' mapping each acceptance criterion to demo evidence.
    • Seller to schedule any follow-up micro-demos to address 'needs adjustment' items within agreed timeline.
    • Recap Validated Use-Cases & Demo Evidence
    • Confirm analytics inputs, scoring thresholds, and the coaching triggers managers will use.
    • Agree on an expected range of impact (qualitative and quantitative) from the analytics-driven coaching loop.
    • Introductions & Meeting Goals
    • Seller to run a backtest report on a larger sample of historical portfolios and share projected impact numbers.
    • Customer data lead to confirm availability of the historical fields required for analytics calibration.
    • Seller and customer to draft a short manager playbook that ties dashboard alerts to concrete coaching actions.
    • Executive Recap of Current State, Consequence, and Future State
    • Receive explicit customer confirmation to move validated outcomes into the Solution Scope stage.
    • Convert validated use-cases into a draft scope with clear in-scope modules and outstanding dependencies.
    • Assign owners and timelines for remaining data or validation gaps before contracting.
    • Customer to provide formal sign-off status for each acceptance criterion (validated/needs work/rejected).
    • Seller to produce the Solution Scope input document that lists modules, responsibilities, acceptance criteria, and open dependencies.
    • Both parties to confirm timelines and owners for resolving any 'needs work' items prior to contract finalization.
    • Produce and lock a single-sentence current state describing what is breaking today.
    • Quantify the business consequence of the current state with at least one metric or example.
    • Co-author a single-sentence future state (operational outcome) the experience must prove.
    • Agree on 3–5 measurable success signals and acceptance criteria for the Solution Experience.
    • Customer to provide 3 sample portfolios and CRM extract (due date) for use in the Live Solution Experience.
    • Seller to draft and circulate the locked one-sentence current state, consequence summary, and future state for customer sign-off.
    • Seller to list required data fields and mapping template needed for the Live Experience and send to customer.
    • Recap Current/Future State & Success Metrics
    • Document explicit workflow maps for the top prospect paths the customer wants to improve.
    • Agree on 1–3 high-impact use-cases that the Live Solution Experience will prove.
    • Identify specific friction points and decision triggers to be addressed in the demo.
    • Customer Current State Statement
    • Analytics Model Walkthrough
    • Diagnosis: Show Evidence of Current State in the Data
    • Walkthrough of Typical Portfolio Workflows
    • Review of Validation Results
    • Decision: Proceed to Solution Scope
    • Proof 1 — Research to Identification
    • Thresholds & Alerts for Manager Coaching
    • Journey Mapping for 2–3 Priority Prospect Types
    • Consequence Quantification
    • Define Scope Inputs & Open Items
    • Define Future State Outcome
    • Proof 2 — Portfolio Assignment & Workflow
    • Identify Friction Points & Decision Triggers
    • Backtest & Expected Impact
    • Validation Check: Manager Playbook
    • Prioritize Use-Cases for Live Experience
    • Proof 3 — Analytics & Move-Metrics
    • Agree Next Steps, Owners, and Timeline
    • Agree Success Metrics & Acceptance Criteria
    • Validation Checkpoint & Pre-work for Demo
    • Interactive Validation Exercises
    • Confirm Sample Data & Logistics
    • Wrap-up: Gaps, Confirmations, and Next Test Steps
  3. Solution Scope

    Define included modules (research, portfolio management, CRM integration, proposals, stewardship, analytics), responsibilities, and acceptance criteria.

    Scope Configuration

    • Import and Clean Donor/Prospect Data
    • Integrate CRM and Donor Database
    • Run Wealth Screening and Enrichment
    • Generate Prospect Research Profiles
    • Create Relationship Maps and Network Diagrams
    • Configure Gift Officer Portfolio Views
    • Deploy Cultivation Activity Tracking
    • Set Up Proposal Tracking Workflows
    • Deploy Stewardship Workflow Automation
    • Migrate Historical Engagement Records
    • Configure Manager Dashboards and Goal Tracking
    • Enable Analytics Linking Activities to Outcomes
    • Launch Mobile Access for Field Officers
    • Deliver Gift Officer Platform Training

    Scope Questions

    Import and Clean Donor/Prospect Data

    • Do you have a single export/file for donor/prospect data or multiple sources to consolidate? Options: Single file/export, Multiple files/exports, Multiple systems/databases, Unsure
    • What file formats or systems contain your data? Options: CSV/Excel, Legacy CRM export, SQL/database dump, Third-party research provider, Other
    • Approximately how many total contact and prospect records need import? Options: Less than 1,000, 1,000-5,000, 5,001-20,000, More than 20,000, Don't know yet
    • Do records include attachments (e.g., PDFs of proposals, correspondence) that must be migrated? Options: Yes, many, Yes, some, No, Unsure
    • Are there required canonical fields that must be present for every record (e.g., preferred name, primary contact email, constituent ID)? List them.
    • Do you require deduplication and merging rules to be applied during import? Options: Yes, strict merge rules, Yes, manual review for merges, No, not at this time, Unsure

    Integrate CRM and Donor Database

    • Which CRM/donor database(s) do you use or plan to integrate with? Options: Raiser's Edge NXT, Salesforce (Education/Nonprofit Cloud), Microsoft Dynamics, Blackbaud CRM, Other/Custom, Unsure
    • Do you require real-time sync, scheduled batch sync, or one-time import? Options: Real-time (API), Scheduled batch (e.g., nightly), One-time import only, Hybrid/Other
    • Can you provide a technical contact and sample data extracts for mapping and testing? Options: Yes - contact and samples ready, Yes - will provide on request, No - needs coordination, Unsure
    • Which key CRM objects must be mapped (e.g., constituent, household, gift, pledge, opportunity)? List any custom objects.
    • Are there existing unique identifiers (constituent IDs) we should use to match records? Options: Yes - consistent IDs across systems, Yes - but inconsistent, No unique IDs, Unsure
    • Are there security, compliance, or vendor approval requirements for connecting to your CRM (IP allowlist, vendor contract, SOC reports)? Options: Yes - specify in details, No, Unsure

    Run Wealth Screening and Enrichment

    • Do you want wealth screening/enrichment applied to all records or a subset (e.g., top prospects only)? Options: All records, Top N prospects only, Custom segment, Unsure
    • Which enrichment data points are highest priority (e.g., capacity estimate, real estate, philanthropic history, stock ownership)? Options: Capacity estimate, Real estate holdings, Philanthropic history, Political contributions, Board affiliations, Other
    • Do you have an existing vendor/license for screening (e.g., LexisNexis, WealthEngine) or need us to recommend/procure? Options: We have a vendor, We need recommendation/procurement, We will use Customer-supplied data, Unsure
    • How frequently should enrichment refreshes run (one-time, quarterly, monthly)? Options: One-time, Monthly, Quarterly, Annually, Custom schedule
    • Are there opt-out/privacy constraints that should exclude certain records from enrichment? Options: Yes - exclude donors with opt-outs, No restrictions, Unsure - need guidance
    • Do you want enriched attributes written back into CRM fields or stored in the platform profile only? Options: Write back to CRM fields, Store in platform only, Both, Unsure

    Generate Prospect Research Profiles

    • What profile depth do you need per prospect (e.g., summary one-pager, comprehensive dossier, executive brief)? Options: One-page summary, Comprehensive dossier (5+ pages), Executive brief (1-3 paragraphs), Custom template
    • How many profiles should be produced initially and on an ongoing cadence? Options: Less than 50 initially, 50-200, 200-1,000, More than 1,000, Unsure
    • Which content elements must each profile include (e.g., giving history, wealth signals, biography, relationship map, solicitation strategy)? Options: Giving history, Wealth signals, Biography & employment, Relationship map, Suggested solicitation ask, Other
    • Do you require standardized research templates or customized templates per campaign/unit? Options: Standardized template, Customized per campaign/unit, Mix of both, Unsure
    • Who will review and approve profiles (gift officer, manager, central research team)? Options: Gift officer, Manager, Central research team, External consultant, Other
    • What is the acceptable turnaround time for a new profile request? Options: 48 hours, 3-5 business days, 1-2 weeks, Depends on complexity

    Create Relationship Maps and Network Diagrams

    • Do you want automated relationship maps generated from CRM + enrichment data or manual curation options? Options: Automated generation, Manual curation only, Automated + manual editing, Unsure
    • Which relationship types are important to display (e.g., family, board, philanthropic colleagues, financial advisors)? Options: Family, Board/Trustees, Philanthropic colleagues, Professional advisors, Peers/Alumni, Other
    • How many network layers do you want visible by default (e.g., direct connections only, two degrees, three degrees)? Options: Direct only (1 degree), Up to 2 degrees, Up to 3 degrees, Custom
    • Do you require exportable diagrams for inclusion in proposals or briefings (PDF/PNG/SVG)? Options: Yes - PDF/PNG, Yes - SVG, No export needed, Unsure
    • Should relationship maps include time-based interaction overlays (e.g., last contact date, recent meetings)? Options: Yes, No, Optional

    Configure Gift Officer Portfolio Views

    • How many gift officers need portfolio views configured initially? Options: 1-5, 6-15, 16-50, More than 50, Unsure
    • What is the typical portfolio size per officer? Options: Less than 50, 50-100, 100-200, 200+
    • Which default filters and segments should be available in officer views (e.g., gift stage, capacity band, last contact)?
    • Do you want automated portfolio balancing or reassignment rules (by capacity, geography, caseload)? Options: Yes - automated rules, No - manual assignment only, Hybrid (suggested rebalancing)
    • What permission levels should gift officers vs. managers have for editing portfolios? Options: Officers: view/edit, Managers: admin, Officers: view only, Managers: edit, Custom role definitions required, Unsure
    • Do you require portfolio snapshots and historical views for performance reviews? Options: Yes, No, Optional

    Deploy Cultivation Activity Tracking

    • Which activity types must be tracked (e.g., calls, visits, proposals, events, stewardship touches)? Options: Calls, In-person visits, Emails, Events/attendances, Proposals/asks, Stewardship touches
    • Should activities be entered via mobile, desktop, or both? Options: Mobile only, Desktop only, Both mobile and desktop, Depends on activity type
    • Do you need activity templates and required fields (outcome, next step, follow-up date)? Options: Yes - templates required, No - freeform entries, Mix of templates and freeform
    • Do you want automated reminders and nudges for overdue or high-priority activities? Options: Yes - email/push reminders, Yes - in-app only, No reminders, Unsure
    • Should activities feed into manager coaching dashboards and scorecards? Options: Yes - link to dashboards, No - separate reporting, Optional
    • Are calendar/email integrations required to capture activities automatically? Options: Yes - calendar + email integration, Calendar only, Email only, No automatic capture

    Set Up Proposal Tracking Workflows

    • What proposal stages do you require (e.g., concept, draft, approval, submitted, follow-up, closed-won/closed-lost)?
    • Do proposals require multi-step approvals and who are the approvers (titles/roles)? Options: Single approver, Multi-step approval, No formal approval, Unsure
    • Should proposal documents be stored/versioned in the platform or linked from external storage (e.g., SharePoint)? Options: Stored & versioned in platform, Linked from external storage, Mix of both
    • Do you need proposal templates and autogenerated ask language/ask amounts based on research? Options: Yes - templates + auto suggestions, Yes - templates only, No templates needed
    • What volume of proposals do you expect per month to size workflow capacity? Options: Less than 10, 10-50, 50-200, 200+
    • Do you want reporting on proposal conversion rates and time-in-stage metrics? Options: Yes - standard reports, Yes - custom reports, No

    Deploy Stewardship Workflow Automation

    • Which stewardship touchpoints should be automated (acknowledgements, anniversary notes, impact reports)? Options: Acknowledgements, Anniversary/renewal notes, Impact reports, Event invitations, Other
    • Do stewardship workflows vary by donor segment or gift size? Options: Yes - by segment/gift size, No - same for all donors, Some variation required
    • Should stewardship tasks be assigned to gift officers, central stewardship team, or both? Options: Gift officers, Central stewardship team, Both
    • Are templated messages and reporting packages required as part of stewardship automation? Options: Yes - messages and reports, Messages only, Reports only, No templates
    • Do you require escalation rules if stewardship actions are overdue? Options: Yes - escalate to manager, Yes - escalate to central team, No escalation

    Migrate Historical Engagement Records

    • What historical date range of engagement records do you want migrated (e.g., last 2 years, last 10 years, lifetime)? Options: Last 2 years, Last 5 years, Last 10 years, Lifetime/All history, Custom range
    • What types of historical records are in scope (meeting notes, emails, event RSVPs, phone logs, proposals)? Options: Meeting notes, Emails, Event records, Phone logs, Proposals/documents, Other
    • Are historical records standardized or do they need normalization and enrichment before import? Options: Standardized and clean, Require normalization/enrichment, Mixed - some clean, some messy, Unsure
    • Do attachments and file formats need conversion or special handling (e.g., scanned PDFs, email threads)? Options: Yes - conversion needed, No special handling, Some files require manual review
    • Is there a required archiving policy or retention rule for older records post-migration? Options: Yes - archive older than X years, No - keep all records active, Unsure
    • Do you require a reconciliation report mapping legacy record IDs to new platform IDs after migration? Options: Yes - reconciliation required, No, Optional

    Configure Manager Dashboards and Goal Tracking

    • Which KPIs should managers see by default (e.g., pipeline value, ask amounts, contact frequency, conversion rates)? Options: Pipeline value, Ask amounts, Contact frequency, Conversion rates, Gift officer activity metrics, Other
    • Do you need goal-setting and tracking per officer, team, and organizational levels? Options: Officer-level, Team-level, Org-level, All levels, No goals required
  4. Mutual Commit

    Finalize commercial terms, contract modules, timelines, governance, and mutual obligations for implementation and success.

    Agreement Modules

    • Non-Disclosure Agreement (NDA)
    • Master Services Agreement (MSA)
    • Statement of Work (SOW)
    • Pricing & Payment Terms
    • Implementation & Project Plan
    • Acceptance Criteria & Go-Live Checklist
    • Data Processing & Security Addendum (DPA)
    • Integration & Third-Party Services Consent
    • Training & Support Agreement
    • Change Order & Scope Management
    • Roles, Governance & Escalation Plan
    • Renewal, Termination & Exit Plan
  5. Deployment

    Operationalize rollout with readiness checks, enablement, and outcome validation.

    1. Pre-Deployment Readiness

      Confirm CRM data access, mapping, sample data, user roles, and timelines required to start integration and training.

      Readiness Questions

      Let’s Start with the Big Picture — Your Program in One Breath

      • What is your title and the primary scope of the major gifts program you oversee (unit, campus, national, etc.)? Options: Chief Development Officer, VP/Director of Advancement, Major Gifts Director, Gift Officer / Portfolio Manager, Other
      • Size of the team focused on major gifts and the typical portfolio size per gift officer? Options: 1–3 staff (portfolios 100–200), 4–7 staff (portfolios 75–150), 8–15 staff (portfolios 50–120), 16+ staff (varied portfolios)
      • What is your annual major gifts target (range)? Options: <$1M, $1M–$5M, $5M–$20M, $20M–$100M, >$100M
      • Describe one recent win that felt like your program was working well—what specifically made it successful?
      • Who else on your leadership team needs to feel confident about major gifts performance (roles/titles)?

      Are You Settling for ‘Good Enough’ in Major Gifts?

      • What part of your major gifts process do you suspect is hiding the biggest opportunity (but you don’t yet have evidence)? Options: Prospect identification, Portfolio assignment, Cultivation tracking, Proposal tracking, Manager coaching, Data & CRM quality, Other
      • How often do you feel your team relies on intuition rather than repeatable data when deciding who to prioritize? Options: Almost always, Often, Sometimes, Rarely
      • Tell us about a time when relying on an instinct led to missed opportunity—what happened and how did it feel?
      • Which common assumption about your program might be wrong (for example: ‘we already know our top prospects,’ or ‘our CRM tells the whole story’)?
      • If you could uncover one hidden cause that would immediately improve major gift outcomes, what would you want it to be?

      Who Actually Holds the Institutional Memory?

      • What would happen to your pipeline if your top three gift officers left next month—who would retain knowledge, and what would be lost? Options: We could backfill easily, We’d lose donor context, We’d lose proposals/asks in flight, We’re not sure
      • How do you currently capture relationship context, cultivation plans, and proposal history so others can act on it? Options: CRM notes, Shared docs/spreadsheets, Dedicated portfolio tool, Mostly in officers’ heads, Other
      • How long does onboarding for a new gift officer typically take before they manage a full portfolio effectively? Options: <1 month, 1–3 months, 3–6 months, 6–12 months, 12+ months
      • Which types of donor knowledge feel most fragile right now (wealth info, relationship map, proposal drafts, stewardship promises)? Options: Wealth and capacity, Relationship map/introductions, Proposal language/terms, Event/personal history, Stewardship commitments, All of the above
      • How would it change your team’s confidence if two critical pieces of context were always accessible and structured in the system?

      Where Your Portfolio Spends Its Time — and Why That’s Not Working

      • Who decides which prospects get prioritized, and what’s the current decision rule (gut call, giving history, capacity score, manager assignment)? Options: Gift officer discretion, Manager assigns by intuition, CRMs/scorecards, Fundraising office algorithm, Other
      • Approximately what share of an officer’s time goes to their top 10% of prospects versus the bottom 50%? Options: Top 10%: >70%, Top 10%: 40–70%, Top 10%: 20–40%, Top 10%: <20%
      • How are prospects graded or tiered today (labels, scores, RFM, custom), and how consistent is that across the team? Options: Standardized scorecard, Local grading by officer, CRM tags only, No consistent system, Other
      • Share an example of a prospect that seemed low priority but later produced—what was missed in your early view?
      • If you could change one workflow so gift officers spent more time on genuinely moveable prospects, what would that be?

      What Counts as Success — Dollars and the Signals That Predict Them

      • Beyond total dollars raised, which signals do you use today to show a prospect is moving toward a major gift (e.g., in-person visits, proposal stage, giving capacity updates)? Options: In-person/virtual meetings, Proposal sent, Wealth update, Introductions made, Volunteer engagement, Giving frequency, Other
      • Which KPIs would make your board and executive team feel confident about progress (select up to three)? Options: Pipeline value, Number of solicitations, Conversion rate to ask, Average gift size, Time-in-stage, Portfolio coverage by top prospects, Officer activity score
      • How predictable are your asks turning into gifts today (conversion rate estimate)? Options: >60%, 40–60%, 20–40%, <20%, Unsure
      • How long from active cultivation to solicitation and then to gift on average for your major gifts? Options: <6 months, 6–12 months, 1–2 years, 2+ years, Highly variable/unsure
      • Which non-monetary outcomes would you want our platform to make visible to demonstrate progress early? Options: High-quality contacts, Proposal drafts complete, Shared stewardship plans, Manager coaching moments, Predictive capacity signals, Other

      Data and Systems: Are Your Tools Helping or Hiding the Truth?

      • When was the last time your CRM or data tools gave you a false sense of progress on a prospect—and what created that gap?
      • Which CRM or donor database do you use, and how would you describe your current integration maturity? Options: Salesforce (NPSP/EDA), Raiser's Edge NXT, Blackbaud CRM, Microsoft Dynamics, Other/Custom, Multiple systems
      • Do you have a current single source of truth for donor contact history, wealth data, and proposal status? Options: Yes, fully integrated, Partially—some synced, some manual, No, largely disconnected, We’re unsure
      • Which of these data items are available and reliably maintained today (select all that apply)? Options: Contact history/touches, Wealth screening/enrichment, Proposal status, Relationship maps, Meeting notes, Pledge/pledge fulfillment status
      • How comfortable are your IT and data teams sharing sample data, mappings, and access roles to start an integration project? Options: Ready now, Need planning/approval, Concerns about privacy/security, Not possible at this time
      • If we were to map a sample prospect record together, what would be the one missing field that matters most?

      If We Built Your Ideal Process — What Would Change Tomorrow?

      • Imagine a world where every gift officer knows their top 20 moveable prospects—what would that mean for your results and daily rhythm?
      • Which workflows are non-negotiable for you to automate right away (portfolio assignment, meeting capture, proposal state, stewardship reminders)? Options: Portfolio assignment, Meeting/activity capture, Proposal tracking, Stewardship reminders, Analytics/reporting
      • How would you like manager dashboards to change your weekly coaching conversations? Options: Focus on closed opportunities, Focus on activity quality, Predictive next steps, Portfolio risk indicators, All of the above
      • What type and cadence of training would make new workflows stick (one-off, phased training, monthly coaching, train-the-trainer)? Options: One-off onboarding, Phased implementation + sessions, Monthly coaching & refreshers, Train-the-trainer model, Combination
      • If we could pilot a change with one team for 90 days, which team would you choose and what would success look like?

      Deciding Together — Red Flags, Must-Haves, and the Path Forward

      • What is a non-negotiable requirement that would make you decline a vendor even if everything else looked great (security, custom fields, data ownership, cost, single sign-on)? Options: Data ownership, Security/compliance, CRM fidelity/custom fields, Budget/cost limits, No long-term lock-in, Other
      • Who are the decision-makers and influencers we need to involve for purchase and implementation sign-off?
      • What timeline feels realistic for an initial integration, training, and first measurable adoption milestone? Options: 30–60 days, 60–90 days, 90–180 days, 180+ days
      • Which measurable acceptance criteria would make you consider the deployment a success at go-live (data sync accuracy, active users, proposal tracking working, dashboard visibility)? Options: >95% data sync accuracy, Active users >60%, Proposal tracking live, Manager dashboards showing top 20, Adoption checkpoints met
      • What concerns or change-management risks keep you awake at night when you think about adopting a new major gifts platform?
      • If we agree on a small set of pilot success metrics now, would you be willing to commit to a short cross-functional kickoff to validate them? Options: Yes — ready to schedule, Maybe — need to align stakeholders, Not yet — need more info
    2. Deployment Enablement

      Execute integrations, configure workflows, deliver gift officer and manager training, and calibrate analytics and reports.

    3. Validation Checklist

      Verify data sync, workflow automation, proposal tracking accuracy, dashboard visibility, and adoption checkpoints against acceptance criteria.

      Validation Questions

      Putting Your Major Gifts Program into One Clear Sentence

      • In one sentence, how would you describe your major gifts program's primary focus right now?
      • Which title best describes the person we're speaking with today? Options: Chief Development Officer / VP of Advancement, Major Gifts Director, Gift Officer / Frontline Fundraiser, Advancement Services / CRM Lead, Executive Director / CEO, Other
      • How many gift officers currently manage major gift portfolios at your organization? Options: 1–3, 4–7, 8–15, 16–30, 31+
      • Roughly how many active prospects does each gift officer carry? Options: Under 50, 50–100, 101–150, 151–200, 201–300, 300+
      • What percentage of your annual revenue typically comes from major gifts? Options: Less than 25%, 25–50%, 51–75%, 76–90%, Over 90%
      • Who are the primary internal decision-makers for fundraising technology purchases? Options: VP/Director of Development, Chief Development Officer, Advancement Services / CRM Lead, Finance/CFO, IT/Procurement, Board or Governance Committee, Other

      Are You Settling for Informal Plans?

      • How often do you find that the most important donor strategies exist only in someone's head rather than in shared plans? Options: Almost always, Often, Sometimes, Rarely, Never
      • When you say plans live in someone's head, where does that tend to show up most often? Options: Gift officer notes, Email threads, Unofficial spreadsheets, CRM free-text fields, Not recorded anywhere, Other
      • How long does it typically take for a new gift officer to feel fully prepared to manage a transferred portfolio? Options: Less than 1 month, 1–3 months, 4–6 months, 6–12 months, More than 12 months
      • Which elements of portfolio knowledge are hardest to transfer when staff change roles or leave? Options: Solicitation strategy/timing, Relationship nuances and preferences, Outstanding proposals and commitments, Research/wealth context, Stewardship history, Other
      • Tell us about a recent occasion when lack of documented plans or institutional memory impacted a solicitation or relationship.
      • How does it tend to feel inside the team when a key officer departs and knowledge walks out the door? Options: Demoralized and overwhelmed, Operationally disrupted but recoverable, Frustrated but confident we can rebuild, Minimal emotional impact, Unsure

      What If Your Best Prospects Stay Hidden?

      • How confident are you that your highest-capacity prospects are being consistently prioritized and actively moved toward solicitation? Options: Very confident, Somewhat confident, Neutral/uncertain, Not confident, We don't have a way to know
      • How do you currently surface or identify priority prospects? Options: Periodic wealth screenings, Internal giving history & propensity, Board/referral nominations, Dedicated research team, Predictive scoring models, Ad-hoc/frontline intuition, Other
      • How frequently is prospect research refreshed and communicated to frontline staff? Options: Weekly, Monthly, Quarterly, Annually, Rarely/Never
      • What specifically would increase your confidence that top-capacity prospects are never overlooked?
      • Which outcomes do you use (or wish you used) to evaluate whether prospect prioritization is working? Options: Number of solicitations, Average gift size, Conversion rate to solicitation, Time-to-close, Increase in identified capacity, Officer move activity

      Are Your Workflows Helping or Hiding Progress?

      • Are your existing workflows making it easier to coach gift officers — or are they creating noise that hides who is actually moving prospects? Options: They enable clear coaching and visibility, They mostly help but have gaps, They create noise and confusion, They obscure real progress entirely, Unsure
      • Which day-to-day tools do gift officers rely on for managing activities and next steps? Options: CRM (e.g., Raiser's Edge, Salesforce), Spreadsheets, Email/Calendar, Portfolio management platform, Paper/handwritten notes, Other
      • Do managers have reliable, timely visibility into which prospects are progressing toward solicitation? Options: Always, Mostly, Sometimes, Rarely, Never
      • Describe a time when a dashboard or report error led you to coach the wrong priority or miss an opportunity.
      • Which automation gaps slow your soliciting cadence the most? Options: Data sync delays with CRM, No activity→proposal linkage, Manual proposal tracking, Poor task assignment routing, Lack of alerts for critical moves, Other
      • How important is near-real-time dashboard visibility to your regular coaching and review cadence? Options: Critical — we need it live, Very important, Somewhat helpful, Not important

      What Would Hitting Your Targets Actually Feel Like?

      • Imagine your team consistently meets or exceeds major gift targets — what would that change inside the organization?
      • Which metrics do you treat as the clearest indicators of success for major gifts? Options: Total dollars raised, Number of major gifts closed, Average gift size, Proposal win rate, Time-to-close, Gift officer activity per successful solicitation
      • How often do you formally review progress against those metrics with gift officers? Options: Weekly, Biweekly, Monthly, Quarterly, Annually, Ad hoc
      • What cultural or behavioral changes would need to stick for those results to be sustainable? Options: Stronger data discipline, Regular coaching cadence, Shared accountability across team, Centralized research & portfolio rules, Incentive alignment, Other
      • Which stakeholders must be visibly aligned and engaged to sustain that level of performance? Options: Gift Officers, Major Gifts Managers/VP Development, Advancement Services/CRM, Executive Leadership/CDO, Board/Trustees, Finance

      What’s Blocking Change — and Who's Holding the Keys?

      • If this needs to change, why hasn't it already — is it budget, politics, lack of clarity, fear of disruption, or something else? Options: Budget/cost concerns, Internal politics and turf, Data complexity or quality, Staff bandwidth and time, Lack of frontline buy-in, IT/Integration risk, Unclear ROI, Other
      • Which single barrier feels most likely to block a decision to adopt a new platform? Options: Budget/cost, Internal politics, Data/integration complexity, Staff bandwidth, Gift officer resistance, Procurement/IT constraints, Other
      • How does your organization typically make procurement decisions for advancement technology? Options: Development-led, with IT support, Centralized (IT/Procurement-led), Committee or Board approval required, Ad-hoc/user-led pilot to scale, Other
      • Who inside the organization would need to champion this project for it to succeed? Options: VP/Director of Development, Major Gifts Director, Advancement Services/CRM Lead, Chief Development Officer, IT/CRM Manager, Board member/specific trustee, Other
      • Tell us about a previous technology or process change effort that stalled—what specifically caused it to stop?
      • How tolerant is leadership of short-term disruption during implementation (e.g., weeks of reduced efficiency)? Options: High tolerance, Moderate tolerance, Low tolerance, Depends on ROI proof

      What Small Early Wins Would Prove This Works?

      • What minimal, early outcomes would convince you this platform is delivering value within 90 days? Options: Reliable data sync with CRM, Gift officer adoption/logins, Accurate proposal tracking, Increase in qualified moves, Manager dashboard usage, Positive frontline feedback, Other
      • Which acceptance criteria must be met before you consider an initial deployment successful?
      • Which CRM(s) do we need to integrate with as part of the initial deployment? Options: Raiser's Edge / Blackbaud, Salesforce (NPSP or Custom), Blackbaud CRM, Microsoft Dynamics, Other, None / standalone pilot
      • What sample data sets or reports do you want validated during pre-deployment (select all that apply)? Options: Constituent/donor records, Prospect scoring/wealth data, Active proposals pipeline, Recent activity logs and tasks, Gift officer assignment lists, Stewardship commitments
      • Who will be responsible for signing off on go-live acceptance criteria and for ongoing success checkpoints? Options: VP/Director of Development, Chief Development Officer, Major Gifts Director, Advancement Services / CRM Lead, Gift Officer Manager, IT/Integration Lead, Other
      • Realistically, how quickly could your team commit to a short pilot or proof-of-value? Options: Immediately, Within 30 days, Within 60–90 days, Longer than 90 days, Unsure
  6. Success

    Review outcomes vs. success signals, capture learnings, and maintain a shared channel for issues and feature requests.

    Success Reviews

    • Success Review — Outcomes vs Success Signals
    • Lessons Learned & Process Optimization Workshop
    • Issue & Feature Request Triage — Shared Channel Handoff
    • Adoption & Coaching Check-in
    • Executive Readout & Renewal/Expansion Planning

    Issues & Enhancements

    • Agree on adoption KPIs and a short cadence for follow-up measurement.
    • Channel Rules & Definitions
    • Maintain a single source of truth for issues and feature requests tied to business impact.
    • Assign severity and SLAs so customers know expected response/resolve timelines.
    • Ensure transparency by linking channel items to product/ops tickets and owners.
    • Create and link tickets in the product tracker for all prioritized items and assign owners.
    • Publish an updated triage summary in the shared channel with expected SLAs and next update date.
    • Configure channel subscriptions and notification rules so relevant stakeholders receive updates.
    • Adoption Snapshot
    • Increase measurable adoption among gift officers and managers tied to specific behaviors.
    • Define and assign targeted coaching and enablement actions to address blockers.
    • Welcome & Objectives
    • Generate a list of low-adoption users and assign coaching leads with dates for outreach.
    • Schedule targeted refresher trainings and publish playbooks for common tasks (portfolio review, proposal tracking).
    • Set up manager alerts/dashboards for early visibility of at-risk portfolios.
    • Executive Summary of Outcomes
    • Secure executive alignment on the value delivered and the decision path for renewal or expansion.
    • Agree on the commercial option and timeline for next-phase work or contract renewal.
    • Assign executive owners for any strategic investments and confirm governance for the next period.
    • Prepare and distribute an executive one-pager summarizing outcomes, ROI, and recommended next steps.
    • Deliver proposed commercial options and timelines to procurement/legal for fast-tracked review.
    • Schedule the kickoff for the renewal/expansion implementation upon executive sign-off.
    • Confirm which success signals were met, missed, or exceeded and by how much.
    • Quantify the operational and financial consequence of gaps in outcomes.
    • Assign owners and deadlines for corrective actions with clear acceptance criteria.
    • Establish cadence for progress checks and reporting format.
    • Publish the outcomes report comparing each success signal to baseline and targets, with owners noted.
    • Create action trackers for each gap with owners, deadlines, and acceptance criteria.
    • Schedule the follow-up progress checkpoint and dashboard refresh dates.
    • Document workshop findings and publish a prioritized optimization backlog.
    • Update SOP/training materials to reflect agreed quick wins.
    • Kick off pilot(s) for at least one high-impact experiment with defined metrics and a 30/60/90 day check.
    • Context & Recap
    • Capture actionable lessons tied to specific processes or behaviors.
    • Define 2–4 prioritized experiments or process changes with measurable acceptance criteria.
    • Assign owners and timelines for pilots and updates to standard operating procedures.
    • Root Cause Breakout (by role)
    • ROI & Strategic Impact
    • Success Stories & Blockers
    • Review Open Items
    • Success Signals Recap
    • Triage & Prioritize
    • Risks & Mitigations
    • Coaching Plan Review
    • Synthesize Findings
    • Data Walkthrough
    • Renewal/Expansion Options
    • Gap & Consequence Analysis
    • Scope & SLA Assignment
    • Targeted Enablement Actions
    • Design Experiments & Quick Wins
    • Create/Link Tickets & Confirm Communication Plan
    • Decision & Next Steps
    • Agreement on Next Steps
    • Prioritize & Assign
    • Measurement & Follow-up
    • Close & Confirm Owners
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