Opening the Book on Your Major Gifts Program

• Tell me briefly about your major gifts program and what success looks like this year
• How many full-time gift officers does your team have, and which range best describes a typical portfolio size per officer Options: 1–3 officers, 4–7 officers, 8–12 officers, 13+ officers
• Which type of system holds your canonical donor records today Options: Institution-wide CRM (single source of truth), Specialized advancement/donor database, Homegrown or custom database, Spreadsheets and shared drives, No consistent system / unsure
• When a gift officer prepares for weekly portfolio review, what reports or artifacts do they actually bring or reference
• Describe your current manager coaching cadence and the specific reports or signals you use to decide when to intervene Options: Weekly 1:1s with dashboards, Biweekly team portfolio reviews, Monthly reporting review, Ad hoc / informal, We do not have a defined cadence
• What single data or reporting gap would make you walk away from a proposed platform

Where Your Process Is Losing Momentum

• What single recurring issue causes your gift officers to spend time on low-probability prospects instead of the right ones Options: Poor prospect identification, Lack of visibility into moves, No standardized cultivation plan, Proposal tracking failures, Data quality issues, Other
• Walk me through the last time a major cultivation plan stalled, who noticed first, and what sequence of events followed
• How often do prospects move from identification to solicitation within the timeframe you consider healthy Options: Most move on time, About half do, A minority do, Almost none do, Unsure
• Which specific stage of the proposal pipeline creates the most handoffs or missed follow-ups Options: Identification / research, Assignment and ownership, Cultivation action tracking, Proposal drafting and approvals, Solicitation and stewardship, Other
• When proposals fail to progress as expected, what downstream impact do you see on this year's revenue and forecasting
• If this problem continued through the next fiscal year, which revenue band would you expect the program to fall into compared to plan Options: Within 0–2% of plan, Short 3–7% of plan, Short 8–15% of plan, Short 15%+ of plan, Unsure

Who's Holding the Keys and Who Needs Convincing

• Who on your leadership team will need to be convinced that changing systems is worth the disruption Options: VP of Development/Advancement, Chief Advancement Officer, CFO or Finance, Director of IT, Campaign or Board leadership, Other
• List the internal roles who will require user access, integrations, or training for this platform to succeed Options: Gift officers, Advancement operations, Research team, Development leadership, IT / integrations, Data analytics, Stewardship/Events team, Other
• Do you have a single owner who can coordinate data access, integrations, and final acceptance testing Options: Yes, a dedicated owner, Yes, shared between teams, No single owner today, Unsure
• Within a typical week, approximately how many active prospect updates or cultivation actions are recorded across the team Options: 0–50, 51–150, 151–300, 301–600, 600+
• Name the stakeholder whose objection would stop this project immediately

Can Your Data and Systems Support a Cutover

• If critical CRM connectors are not available, how would that affect your planned timeline Options: Delay by weeks, Delay by months, Require manual workarounds but proceed, Force re-evaluation of the project, Cancel the project
• Please identify your primary donor database, your wealth-screening or research source, and any secondary systems we must consider for integration
• Who currently owns API access and integration work, and will that person or team have capacity in the next 60 days Options: In-house IT with capacity, In-house IT but low capacity, Third-party consultant, Vendor-managed, No clear owner / unsure
• Do you store prospect research and proposal documents in a single repository that can be migrated Options: Yes, single repository, Partially centralized, Mostly decentralized across drives, No, scattered and inconsistent, Unsure
• Describe the cleanliness of your giving and interaction history, noting known issues like duplicates, missing contact fields, or inconsistent gift coding
• Name any technical, legal, or compliance constraint that would force a deployment delay or cancellation

The Other Paths You're Considering

• Imagine you chose to stay with your current approach; what problem would keep recurring and likely worsen over time
• Under which conditions would you choose to remain with your incumbent system instead of switching Options: No additional budget required, No implementation downtime, Vendor can meet all integration needs, Internal project promises same outcomes, Other
• Has anyone on your team proposed solving this problem internally without an outside partner, and if so who would lead that effort Options: Yes, Advancement Operations, Yes, IT / Engineering, Yes, Data Analytics, No internal proposal, Unsure
• If an internal option exists, please describe that proposal and the proposed timeline
• Select your top three evaluation priorities from the list below Options: Donor research quality, Portfolio management workflow fit, CRM integration ease, Analytics for manager coaching, Price and TCO, Implementation timeline and risk, Training and change management
• Identify the one evaluation finding that would make you sign and onboard within 90 days

Defining Measurable Success

• Imagine a pilot shows a measurable lift in average giving per officer, what minimum percentage improvement would justify a purchase for you Options: 2–5%, 5–10%, 10–20%, 20%+, Depends on cost, Unsure
• Provide the short-term (0–6 months) and long-term (6–24 months) metrics you would use to judge whether the platform is delivering value
• Tell me how manager coaching and weekly reviews would change if those metrics improved as expected
• State the person, role, or committee that would approve a full rollout if the pilot meets your targets, and the timeline they would require

The Deployment Roadblocks That Stop Deals

• Point to the single vendor-related or internal constraint that would force you to pause a deployment
• Identify the person or role who would handle day-to-day data migration, integrations, and initial user support after go-live Options: Advancement operations manager, Data migration lead / analyst, IT integration lead, External implementation consultant, No one identified yet, Other
• Is there a preferred window for go-live that aligns with gift cycles, campaign milestones, or fiscal events Options: Start of fiscal year, After major giving season, Between campaign milestones, Anytime / flexible, Unsure
• Specify how many historical years of donation and engagement history must be migrated to meet reporting and stewardship needs Options: Last 2 years, Last 3–5 years, Last 6–10 years, All historical data, Unsure
• Provide the role or title required to sign off on a pause decision if migration or integration risk emerges during cutover

• Solution Experience Session

• Confirm the current state and its cost
• You confirm the demonstrated workflow eliminates time spent on low-value prospects by prioritizing work and makes progress toward solicitation visible.
• Run a sample portfolio prioritization using two provided gift officer portfolios and deliver the prioritized lists with short rationale before the follow-up session.
• Run an end-to-end portfolio prioritization using your data
• You confirm the analytics shown will enable managers to identify coaching opportunities and measure which activities move prospects toward solicitation.
• Provide two anonymized gift officer portfolios exported from your current CRM and a list of CRM fields used for portfolio tracking.
• Walk the proposal tracking and stewardship flow with a live prospect
• Provide the decision timeline and list of stakeholders who must sign off on scope and integrations.
• Agreement on the remaining integration and data evidence required to finalize scope and timeline.
• Schedule a technical discovery to validate integration endpoints and data access requirements after the sample prioritization is reviewed.
• Demonstrate manager analytics and coaching prompts
• Confirm integration and data gaps for your CRM and workflows
• Validate the future state

• Solution Experience Session
• Solution Experience Deck
• Solution Brief

• meeting
• slides
• document

• Import and Normalize Donor Records
• Wealth and Prospect Research Dossiers
• Assign and Configure Gift Officer Portfolios
• Configure Cultivation Activity Tracking
• Migrate Historical Engagements and Notes
• Create and Track Proposal Pipeline
• Setup Stewardship Workflows and Reminders
• Integrate with Source CRM and Sync
• Relationship Mapping and Network Charts
• Manager Dashboards and Goal Tracking
• Analytics Calibration and Custom Reports
• Train Gift Officers and Managers on Platform

Import and Normalize Donor Records

• Do you need import of constituent records from your current CRM (constituent table, contacts, households)? Options: Yes, No
• How many constituent records need to be migrated from your current CRM? Options: Less than 1,000, 1,000–10,000, 10,001–50,000, More than 50,000
• Which export method will you provide for donor records (CSV export of constituents, API access to constituent endpoint, database dump)? Options: CSV export, API endpoint, Database dump, Other
• Who on your team will be the single point of contact for field mapping of primary gift officer, constituent ID, and giving history?
• When should we perform the initial normalization pass (for example during migration or as a separate iteration)? Options: During migration, Separate normalization phase, Parallel with migration
• Define the import acceptance criteria for donor records (for example: 99% deduplicated, <1% unmapped records, key fields populated such as constituent ID, primary gift officer, email).

Wealth and Prospect Research Dossiers

• Describe the dossier template you want for each major prospect (wealth screen summary, giving history, biographical note, board affiliations, recent activity).
• List the data sources you expect in each dossier (public filings, screening vendor report, your CRM giving history, news alerts). Options: Public filings, Screening vendor report, CRM giving history, News and media, Other
• Specify the minimum elements a prospect capacity estimate must include (estimated capacity range, citation, last-screened date).
• Indicate how many prospects should receive full dossiers in phase 1 versus ongoing enrichment. Options: Phase 1: up to 100, Phase 1: 101–500, Phase 1: 501+
• Identify who on your team will review and approve each dossier's research notes before they are available to gift officers.
• Provide any donor privacy rules or suppression lists we must enforce when including capacity estimates or sensitive biographical details.

Assign and Configure Gift Officer Portfolios

• Confirm your target portfolio size per gift officer (for example 100–200 active prospects) and whether that target varies by fund or geography. Options: 100–200, 200–300, Custom
• Estimate how many active portfolios will require balancing during implementation. Options: 1–5, 6–20, 21–50, 50+
• Designate the CRM field name that should map to 'primary gift officer' on prospect records (please provide the exact field name used in your current CRM).
• Define the rules for automatic portfolio reassignment (trigger events such as officer departure, territory change, or workload imbalance).
• Include any constraints for portfolio assignment such as donor affinity groups, geography, or prospect dollar thresholds.
• Are team managers permitted to view and edit all portfolios or only those within their management hierarchy? Options: View/Edit all portfolios, View/Edit only managed portfolios, Custom permission model

Configure Cultivation Activity Tracking

• Should activity types be standardized across teams (visit, phone call, proposal sent, stewardship touch) or customized per gift officer? Options: Standardized across teams, Customized per officer, Hybrid
• Would you like pre-built cultivation templates for common donor segments (major donor, planned giving, alumni)? Options: Yes, No
• Select default reminder intervals for cultivation tasks (for example 7 days before event, 3 days follow-up). Options: 1 day, 3 days, 7 days, Custom
• Name the required fields on each activity record (for example: activity type, outcome, ask amount, next steps, contact date).
• Attach or link any existing cultivation plan documents or sample activity templates you want replicated in the platform.
• State how activity data should be surfaced in manager reviews (for example aggregated move-rate, overdue tasks, time-on-portfolio metrics).
• Define the acceptance evidence for activity tracking to confirm solicitations and asks are captured correctly (for example: sample of 30 tracked asks matched to CRM gifts, <5% missing ask amounts).

Migrate Historical Engagements and Notes

• Detail which historical note types must be migrated (meeting notes, call logs, pledge terms, acknowledgment notes) and any types to exclude.
• Share the volume of attachments associated with engagements (for example number of PDFs, pledge letters) and average file size. Options: None, <1,000, 1,000–10,000, 10,000+
• Outline whether original timestamps and authorship should be preserved for each migrated note. Options: Preserve timestamps and authorship, Preserve timestamps only, Do not preserve
• Assign an owner in your organization who will approve a migration sample set and resolve mismatches.
• Approve the migration success threshold you require for engagements (for example: 95% of notes migrated with intact key fields and attachments). Options: 90%, 95%, 99%, Custom
• Measure any data quality metrics you require post-migration (duplication rate, missing ask amounts, corrupted attachments) and provide thresholds.

Create and Track Proposal Pipeline

• Report the proposal types you currently track (solicitation, grant proposal, major gift ask, pledge renewal) and any custom categories.
• Choose which proposal fields must be required (ask amount, decision date, assigned officer, fund designation). Options: Ask amount, Decision date, Assigned officer, Fund designation, Other
• Set the approval workflow for proposals that exceed defined ask thresholds (who must approve asks above $X and what documentation is required).
• Rate the expected win probability methodology for proposals (manual salesperson estimate, historical win rates by segment, algorithmic model). Options: Manual, Historical average, Algorithmic model, Hybrid
• Clarify whether a proposal record should create a follow-up stewardship workflow upon closure and what that workflow should include. Options: Yes, standard stewardship, Yes, custom per proposal type, No
• Supply sample pipeline reports or spreadsheets used today for forecasting so we can map fields and KPIs.

Setup Stewardship Workflows and Reminders

• Indicate the stewardship touchpoints you require after a gift closes (thank you call, recognition event, impact report).
• Within what timeframe should first stewardship contact occur after gift receipt (for example 7 days)? Options: Within 7 days, Within 30 days, Other
• Should recurring reminders be configured for multi-year pledges and, if so, at what cadence? Options: Yes, annual reminders, Yes, quarterly reminders, No
• Identify who will maintain stewardship content templates and schedule impact reports.
• Select the metrics that will demonstrate stewardship effectiveness for managers (donor retention, repeat gift rate, timeliness of acknowledgments). Options: Donor retention, Repeat gift rate, Timely acknowledgments, Other
• Detail any donor acknowledgment language or recognition tier rules that must be enforced in templates.

Integrate with Source CRM and Sync

• Specify the source CRM platform and API endpoints we will use to sync (please provide API docs or connector details if available).
• Provide the list of CRM object mappings required at go-live (constituent, gift, opportunity/proposal, activity, attachment). Options: Constituent, Gift, Opportunity/Proposal, Activity, Attachment, Other
• Confirm the desired sync cadence for each object type (real-time webhook, hourly, daily) and whether bidirectional sync is required. Options: Real-time/webhook, Hourly, Daily, One-way only
• Designate the team that will provide API credentials and test accounts for the source CRM.
• Are there custom CRM fields or computed fields we must respect or recreate in the platform (for example institution-specific giving codes)? Options: Yes, No
• State any SLA or uptime requirements for the integration endpoints and the acceptable window for sync failures.

Relationship Mapping and Network Charts

• Describe the relationship types to surface in network charts (board membership, family ties, event co-attendance, corporate affiliations).
• List the data sources that should feed relationship graphs (CRM relationship links, LinkedIn/biographical data, board lists). Options: CRM relationship links, Public biographical sources, Board lists, Other
• Specify whether relationship graphs should expose inferred relationships from donations and address overlaps and what inference rules to apply.
• Identify any sensitivity rules for hiding or redacting relationships for privacy or compliance reasons.
• Provide expected network sizes for typical prospects (for example leaders with 10–50 connected nodes) so we can size visualizations. Options: Small (1–9), Medium (10–49), Large (50+)
• Confirm whether exportable network reports (PDF/CSV) are required for gift officer briefings. Options: Yes, No

Manager Dashboards and Goal Tracking

• Indicate the KPIs managers must see on a portfolio review dashboard (moves, asks, proposals, pipeline value, close rate). Options: Moves, Asks, Proposals, Pipeline value, Close rate, Other
• Provide the target goal structures managers use today (individual gift officer targets, team targets, fund-specific targets).
• Specify required drill-downs from dashboard tiles (for example see contributing prospects, recent activities, and closed gifts by officer).
• Identify who should receive scheduled dashboard reports and at what frequency (daily summary, weekly review, monthly executive report). Options: Daily, Weekly, Monthly, Quarterly
• Select which alert thresholds managers require (for example portfolio move-rate below X, ask pipeline below Y).

• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Order Form / Subscription Agreement
• Data Processing Agreement (DPA)
• Acceptance Certificate
• Payment Schedule Agreement
• Change Order Agreement
• Readiness & Dependencies Confirmation
• Service Level Agreement (SLA)
• Security & Compliance Addendum

• Go-Live Health Check
• First Measurement Review
• Acceptance Gate Review (Day 90)
• Quarterly Success Review

• Schedule recurring manager coaching checkpoints and a training refresh if adoption or performance metrics decline.
• Produce a root-cause analysis for each metric that is off-target and circulate for comment.
• Update the training and adoption plan to address identified gift officer workflow gaps.
• Publish a short remediation timeline that maps each corrective action to a verification step before the acceptance gate.
• Restate acceptance criteria and numeric targets
• Produce a documented pass/fail table for each acceptance criterion recorded in Solution Scope.
• Capture a formal buyer acceptance decision or conditional acceptance with remediation timelines and verification steps.
• Confirm the incumbent system wind-down status or a documented retention plan to prevent dual-system fallback.
• Publish the acceptance decision and the pass/fail table to the shared workspace for archival.
• If remediation is required, log remediation tasks with completion dates and verification criteria and circulate to stakeholders.
• Execute the agreed final steps for incumbent decommissioning or produce the retention-read-only plan with dates for completion.
• Review current period outcomes vs targets
• Confirm whether rep adoption rate and pipeline coverage ratio remain at or above the targets in Solution Scope or require adjustment.
• Maintain a sustainable manager coaching cadence that demonstrably improves gift officer focus and pipeline movement.
• Agree which enhancement requests will be scheduled for the next quarter and which will remain in backlog.
• Prioritize enhancement requests for the next quarter and publish the scheduled items with expected delivery windows.
• Publish the quarter's action log with verification steps and expected completion dates.
• Re-confirm success criteria and owners
• Confirm the deployment components listed in Solution Scope are live and functioning to allow normal user activity.
• Identify and document any high-priority blockers with clear resolution steps and timelines.
• Confirm initial user onboarding status and any short-term training needs for gift officers and managers.
• Validate data migration completeness against the migration checklist in Solution Scope and report discrepancies.
• Produce a short issue log with remediation steps and target resolution dates for all high-priority defects.
• Schedule targeted training sessions for any user group showing adoption gaps in the first-week analytics.
• Present first-period outcomes vs targets
• Determine whether rep adoption rate and CRM data completeness rate are on a trajectory to meet the targets in Solution Scope.
• Document root causes for any shortfalls and commit to specific corrective actions with target dates.
• Confirm readiness timeline to proceed to the acceptance gate meeting.
• Deployment and migration validation
• Manager coaching cadence and effectiveness
• Present outcome data against each criterion
• Diagnose root causes for gaps
• Review pipeline coverage ratio and proposal movement
• Early adoption signals and usage patterns
• Document pass/fail per criterion
• Open issues and enhancement request review
• Update action log and next-quarter commitments
• Agree corrective actions and timelines
• Buyer acceptance decision and attestation
• Blockers and open issues triage
• Agree immediate remediation actions
• Meeting efficiency check
• Confirm timeline to acceptance gate
• Remediation plan for unmet criteria
• Incumbent system wind-down confirmation