Getting Acquainted: The Story Behind This Campaign

• What's the single most important reason your organization is considering a campaign right now? Options: New building/capital project, Endowment growth, Transformational program expansion, Responding to a major gift lead, Strategic plan requirement, Other
• How long has this idea been circulating internally—and who first raised it?
• What is your target public timeline for announcing or launching the campaign? Options: Within 6 months, 6–12 months, 12–24 months, More than 24 months, Undecided
• Who will be our everyday counterpart(s) during discovery and the feasibility phase? (select all that apply) Options: CEO/Executive Director, Board Chair, Chief Development Officer, Campaign Chair, Lead Staff (other), External volunteer leader, Other
• Tell us one story or moment that captures why this campaign matters to your stakeholders right now.

Who's Really Steering This Ship?

• If the board and senior leadership were perfectly aligned on a campaign, what would they be saying differently today?
• Which individuals or groups must explicitly sign off on campaign goals and why? Options: Full board, Executive committee, CEO only, Finance committee, Major donors/lead prospects, Other
• How confident are you that the board understands the time, role, and ask responsibilities required of them? Options: Very confident, Somewhat confident, Unsure, Not confident at all
• Have you identified a campaign chair or primary volunteer leaders? If yes, what motivates them to lead? Options: Yes—named and committed, Yes—identified but tentative, Not yet identified, Other
• Describe a recent board or leadership decision where politics, risk tolerance, or divergent priorities affected the outcome—what happened and what did you learn?

Where the Risk and Pressure Live Today

• What single outcome would cause the most reputational damage if the campaign falls short?
• Which of these risks keeps you awake at night about running a public campaign? Options: Insufficient lead gifts, Volunteer burnout, Donor fatigue, Operational disruption, Data privacy/reputational issues, Financial shortfall, Other
• How would a shortfall impact operations, staff morale, or future fundraising over the next 3–5 years?
• Have you previously started or paused a campaign or major capital effort? What caused that outcome and how long ago? Options: Yes—paused/failed (within 3 years), Yes—paused/failed (3–10 years), Yes—completed successfully, No previous attempts, Other
• Who on your team or board feels most worried about campaign risk, and what specifically are they worried about?

Are We Sure the Goal Matches Reality?

• What would you say to someone who insists the publicly stated goal is optimistic and not grounded in donor capacity?
• Which sources of evidence currently support the goal you’re considering? Options: Recent major gifts, Comparative campaigns in our sector, Internal donor metrics, Board/volunteer pledges, No concrete evidence yet, Other
• Do you have a current gift table or high-level prospect segmentation—if so, how recent and how complete is it? Options: Comprehensive and recent, Partial and needs work, Outdated, None exists
• Who do you believe are the 10–25 prospects most likely to provide leadership gifts, and what makes them likely?
• How would you prioritize: absolute dollar certainty, timeline speed, or broad volunteer engagement? Rank or describe your preference. Options: Dollar certainty first, Timeline speed first, Volunteer engagement first, Balanced approach

How Would Success Feel—Beyond the Dollars?

• Imagine the campaign exceeded its goal—what tangible institutional changes would you expect to see one year later?
• Which of these non-financial outcomes matter most to you? Options: Stronger volunteer leadership, Improved donor relationships, Elevated institutional reputation, Sustainable programs/endowment, Improved staff capabilities, Other
• How would achieving the campaign change the organization’s strategic posture or choices for the next decade?
• What would success look like to your board chair or CEO—describe how they would talk about it at a public event.
• If you had to name one legacy outcome you want donors and volunteers to remember, what would that be?

What Would Make You Confident to Move Forward?

• What would have to be different in our first 60–90 days together to change any lingering doubts about launching a campaign?
• Which deliverables from a feasibility study would convince you the public goal is attainable? Options: Validated lead commitments, Revised gift table, Prospect interview summaries, Board readiness memo, Volunteer recruitment plan, Other
• How do you prefer feasibility findings to be presented—highly candid with risk-first framing, optimistic plus mitigations, or strictly data-driven summaries? Options: Candid risk-first, Optimistic with mitigations, Strictly data-driven, Balanced narrative
• Who must be present or consulted during feasibility interviews to ensure candid responses from prospects? Options: CEO only, CEO + CDO, Board chair present, Independent counsel, No internal staff present, Other
• What would constitute an unacceptable outcome from our engagement or a reason to pause the campaign planning?

Practical Readiness: Systems, People, and Data

• If I asked your development team to produce a clean prospect list and recent giving history within two weeks, how feasible would that be? Options: Easily feasible, Possible with support, Would take significant time, Not feasible currently
• Which systems and data sources will we rely on during discovery (select all that apply)? Options: CRM (Raiser's Edge/Altru/Other), Finance/pledge systems, Board records, Legacy prospect research files, Volunteer tracking tools, None of the above/unknown
• What percentage of your major-donor prospect records do you estimate are complete and contact-ready? Options: 75–100%, 50–75%, 25–50%, Less than 25%, Don't know
• Who on staff will be the primary liaison for data access, interview coordination, and volunteer prep? Please include role and availability constraints.
• Have you got any outstanding compliance, gift restriction, or reputational issues that could surface during prospect conversations? If yes, please explain. Options: No known issues, Minor issues we can manage, Material issues we need to disclose, Prefer to discuss privately

Commitment, Timeline, and Deal-Breakers

• What would cause you to walk away from a consulting partnership before the campaign launches?
• Which engagement model feels most acceptable to you for the feasibility and campaign design phase? Options: Fixed-fee discovery + retainer, Milestone-based payments, Percentage-fee on dollars raised, Hybrid model, Undecided
• What timeline constraints are non-negotiable (e.g., fiscal year, capital project start, donor-driven dates)? Please list deadlines and consequences.
• Which governance structure do you expect for campaign decisions and approvals? Options: Executive committee oversight, Full board approvals at key milestones, Independent campaign oversight board, Other
• How would you like us to surface difficult trade-offs—directly in meetings, via written recommendations, or through a neutral third-party mediator? Options: Directly in meetings, Written recommendations first, Neutral mediator, Combination

Quick Snapshot: Where We Stand Today

• Which best describes your organization's current campaign posture? Options: No campaign planned, Exploring a campaign, Preparing feasibility study, In feasibility study now, Moving to quiet phase, Public campaign live, Campaign recently closed
• What is the target size (or range) you're contemplating for a capital or transformational campaign? Options: $5–10M, $10–25M, $25–50M, $50–100M, Over $100M, Undecided
• What is your ideal public launch timeline (months from now)? Options: 0–3 months, 3–6 months, 6–12 months, 12–18 months, More than 18 months, Undetermined
• Who are the primary internal stakeholders on this—select all who will drive decisions or need to be deeply involved. Options: CEO/President, Board Chair, Development Director/CDO, Finance Officer/CFO, Program Director, Institutional Advancement team, External counsel/consultant, Other
• Briefly name one recent campaign or major fundraising effort (internal or external) you consider comparable and why it felt similar.

If We Went Public Tomorrow, Who Would Lead the Giving?

• If we announced a campaign today, how confident are you that lead gifts sufficient to anchor the campaign would materialize? Options: Very confident, Somewhat confident, Unsure, Probably not, Not at all confident
• List the top 5 prospective lead donors (roles or names) and the relationship strength for each (e.g., active board champion, previously donated major gift, new prospect).
• How many ‘likely lead’ prospects do you believe exist inside your network today (people or institutions who could give $250k+)? Options: 0, 1–3, 4–7, 8–12, 13+
• Describe the most recent example where a major gift was won—what led to it and how long did it take from first contact to close?
• What internal fundraising capacity will be dedicated to major gifts (roles and approximate % of their time)? Options: Dedicated full-time campaign director, Part-time campaign lead, CDO shared across duties, Mostly volunteer-led, External consultant-led, Other

Where the Money Has Actually Come From

• Looking back, which source(s) have produced the majority of your largest gifts—and what does that pattern tell you? Options: Individual major donors, Board members, Foundations, Corporations, Planned giving/estate gifts, Earned income or program revenue, Other
• What was the average size of your top 10 gifts over the past 5 years? Options: Under $25k, $25k–$100k, $100k–$250k, $250k–$1M, Over $1M, Don't know
• What is your best estimate of donor retention for mid-to-major donors year-over-year? Options: Over 80%, 60%–80%, 40%–60%, Under 40%, Don't track
• Which donor segments have shown growth or decline in giving the past 3 years? Please name the segment and the trend.
• Tell us about one donor segment we should not ignore—who they are and why they matter.

Volunteer Heartbeat: Who Will Ask?

• If your most influential volunteer stepped away tomorrow, would someone else step into a solicitation role without losing momentum? Options: Yes, immediately, Yes, with short ramp-up, Maybe, but slow, No
• How many volunteers currently have both the interest and the relationship to make a six-figure ask? Options: 0, 1–2, 3–5, 6–10, 10+
• Describe the typical volunteer engagement rhythm—recruitment, training, solicitation frequency, and coaching cadence.
• Which volunteer-led asks in the past five years went especially well or poorly, and what caused that outcome?
• What support would volunteers need to confidently make major donor asks? Select all that apply. Options: Ask scripts and role-plays, Research on prospects, Joint visits with staff/counsel, Recognition and milestones, Clear solicitation timeline, Other

Reputational Thermometer: Risks and Sensitivities

• What single reputational risk would most likely make a top prospect pause or withdraw their support? Options: Leadership instability, Program controversies, Financial irregularities, Community opposition, High-profile litigation, None/Unsure
• Have there been recent media stories, audits, or controversies that affected donor confidence? If yes, summarize. Options: Yes—major impact, Yes—some impact, Minor or no impact, No
• How quickly and effectively has your organization responded to past reputational issues? Provide one example.
• Are there stakeholder groups (alumni, community partners, government entities) who could object to aspects of the campaign? Name them and the concern.
• What mitigation or communication strategies are in place or would you be willing to deploy? Select all that apply. Options: Transparent public statements, Targeted donor briefings, Independent audit or review, Adjusted project scope, Pause or reframe campaign elements, Other

Data, Systems & Access: Can We Run the Engine?

• Do your current systems (CRM, finance, data) let us reliably track prospect engagement, gift commitments, and pipeline forecasting? Options: Yes—well integrated, Partially—workarounds required, No—significant gaps, Unsure
• Which CRM or donor database do you use, and how complete is your historical gift and contact data? Options: Raiser's Edge/Blackbaud, Salesforce, Bloomerang/Other small CRM, Homegrown/Excel, Multiple with sync issues, Unsure
• Estimate the percentage of major-donor engagement notes and gift history that are digitized and accessible. Options: 90–100%, 70–89%, 50–69%, Under 50%, Not tracked
• What access or approvals would our embedded counsel need to operate effectively (data, system logins, donor contact permissions)?
• Do you have dedicated capacity for prospect research and wealth screening, or would that need to be provided externally? Options: In-house research team, Shared staff with limited time, Outsourced currently, No capacity—need support

What Success Actually Feels Like — and Are We Willing to Change?

• If we set an ambitious goal and then fell short publicly, what would that cost your organization emotionally and operationally? Options: Severe reputational/financial harm, Meaningful setback but recoverable, Manageable with adjustments, Minimal impact
• Which internal changes would leadership be willing to make to secure success (select all you would consider)? Options: Reprioritize staff time, Hire dedicated campaign staff, Increase board solicitation expectations, Adjust project scope or phasing, Delay public launch until secure, Other
• What are the non-negotiables—things leadership will not change even if asked?
• How do you define an acceptable feasibility study outcome—what thresholds or signals would you need to move forward? Options: Lead gifts identified meeting X% of goal, Strong volunteer bench committed, Clear public support indicators, Multiple criteria must align, Unsure—want guidance
• Looking ahead, what immediate internal barriers (people, process, politics) could stop this readiness work from progressing in the next 90 days? Options: Board availability, Leadership turnover, Data access, Funding to start study, Volunteer recruitment, No immediate barriers
• What would make you feel ready to invite an external campaign partner to begin a feasibility study within the next month? Options: Clear board mandate, Preliminary donor interest, Committed interim staff, Budget for study, Agreement on timeline, Other

• Construct campaign gift table and solicitation pyramid
• Create individualized solicitation briefs for priority prospects
• Draft personalized solicitation scripts and email templates
• Coach and rehearse volunteer solicitors with role‑play sessions
• Lead consultant‑accompanied major donor solicitation visits
• Design and produce campaign case‑for‑support collateral
• Develop and deploy campaign website pages and donation forms
• Set up campaign pipeline and import prospects into CRM
• Create gift agreement and pledge documentation templates
• Prepare donor recognition and naming proposal materials
• Produce solicitation assignment packets for board volunteers
• Build campaign gift tracking dashboard and weekly reports

Construct campaign gift table and solicitation pyramid

• Do you want a full gift table and solicitation pyramid built for the campaign? Options: Yes, No, Unsure
• What is the public campaign goal (numeric)?
• By when do you need the completed gift table? Options: 2 weeks, 4 weeks, 6-8 weeks, Flexible
• How many prospect records should be modeled into the pyramid? Options: Under 200, 200-1,000, 1,000-5,000, More than 5,000
• What historical giving data is available to inform capacity modeling? Options: Full giving history (10+ years), Partial giving history (3-10 years), Major gift history only, No usable giving history
• Which output formats do you need for the gift table? Options: Spreadsheet (CSV/XLSX), Printable report (PDF), CRM import file, Interactive dashboard
• Are there internal stakeholders who must approve the gift table tiers before rollout? If yes, list them and their approval timeline.

Create individualized solicitation briefs for priority prospects

• How many priority prospects should receive individualized solicitation briefs? Options: Under 25, 25-50, 51-100, More than 100
• What information must each brief include (select all that apply)? Options: Giving history, Affinity/engagement notes, Capacity and recommended ask, Suggested solicitors and approach, Key stewardship points
• Do you have research profiles or wealth screening results for these prospects? Options: Comprehensive profiles, Partial research, Basic contact info only, No research available
• Who will own distribution and updates to solicitation briefs (role/title)?
• Do the briefs need segmentation by donor type (e.g., major donor, foundation, corporate)? Options: Yes, No, Only for some prospects
• Are there privacy or stewardship sensitivities to reflect in briefs (e.g., anonymous donors, naming prospects)? Options: Yes, No
• Preferred delivery format for briefs? Options: One-page PDF, Two-page PDF, CRM record with attachments, Printed packet

Draft personalized solicitation scripts and email templates

• Which solicitation channels should templates cover? Options: In-person ask, Phone script, Email outreach, Letter / mailed packet
• How personalized should scripts be (select one)? Options: Highly personalized per donor, Segmented templates by donor tier, Standard templates with small personalization fields
• Do you require templates for multiple stages (initial ask, follow-up, stewardship)? Options: Yes, all stages, Initial ask only, Ask + follow-up only, No
• Are there organizational language or compliance requirements to include (e.g., legal wording, affiliation statements)? Options: Yes, No
• Who will approve final script and email language (role/title)?
• Do you want A/B variations for email templates to test messaging? Options: Yes, No
• List any key messages or donor motivations that must be emphasized in scripts (brief).

Coach and rehearse volunteer solicitors with role‑play sessions

• How many volunteers will require coaching sessions? Options: Under 10, 10-25, 26-50, More than 50
• What format do you prefer for rehearsals? Options: Group workshops, One-on-one coaching, Virtual role-play sessions, Hybrid (mix)
• How many coaching sessions per volunteer do you anticipate needing? Options: 1, 2-3, 4-6, Ongoing/As-needed
• Do volunteers have prior solicitation experience? Options: Experienced, Some experience, No experience
• Are you requesting training materials and practice scripts to be provided? Options: Yes, full materials, Yes, summary only, No
• Any scheduling constraints for volunteer rehearsals (days/times/season)?
• Who will coordinate volunteer attendance and track readiness?

Lead consultant‑accompanied major donor solicitation visits

• Do you expect the lead consultant to attend asks for top-tier prospects? Options: Yes, top-tier only, Yes, for top and mid-tier, No, consultant will prepare not attend
• How many consultant-accompanied visits are anticipated during campaign? Options: 1-5, 6-15, 16-30, 30+
• Which roles should join consultant on visits (select all that apply)? Options: CEO/ED, Board Chair, Development Director, Volunteer lead, Other
• Do you require the consultant to handle scheduling and logistics for visits? Options: Yes, full coordination, No, client will coordinate, Partial support
• Will consultant be asked to debrief and provide written visit reports? Options: Yes, written reports after each visit, Yes, summary reports weekly, No, verbal debrief only
• Are there travel or security considerations for consultant visits? Options: Yes, No
• What authorization or confidentiality agreements (if any) must consultant sign prior to visits?

Design and produce campaign case‑for‑support collateral

• Which collateral pieces are required? Options: Case brochure (print), Case one-pager, Campaign slide deck, Prospect packet, Video/Multimedia
• Do you have existing brand and messaging guidelines to follow? Options: Yes, full brand guide, Partial guidelines, No brand guide
• What is the preferred production quality and format for collateral? Options: High-end print, Standard print, Digital-first (PDF/slide), Web-optimized assets
• Who will provide images, donor stories, and program content? Options: Client provides all, Client provides some, consultant sources remainder, Consultant to source content
• Do materials require translation or alternative language versions? Options: Yes, No
• What is the timeline for first drafts and final production? Options: 2 weeks for draft, 4 weeks for draft, 8+ weeks needed
• Are there regulatory or acknowledgment requirements to include in collateral? Options: Yes, No

Develop and deploy campaign website pages and donation forms

• Do you want new campaign web pages, updated site sections, or microsite? Options: New campaign pages, Microsite, Update existing pages, No web work needed
• Which donation form capabilities are required? Options: One-time gifts, Recurring gifts, Pledge payment schedule, Tribute gifts, Matching gifts
• Which payment processors/CRM integrations must forms support? Options: Stripe, PayPal, Blackbaud/Luminate, Raiser's Edge, Other
• Do you have hosting, domain, and technical admin access available? Options: Yes, full access, Limited access, No access — need assistance
• Are accessibility (WCAG) or language requirements needed for pages/forms? Options: Yes, WCAG required, Yes, multi-language, No
• Do you require analytics and conversion tracking to be set up? Options: Yes, No
• Desired timeline for web pages and live donation form? Options: 2 weeks, 4 weeks, 6-8 weeks

Set up campaign pipeline and import prospects into CRM

• Which CRM are you using for campaign pipeline? Options: Raiser's Edge / NXT, Salesforce, Bloomerang, Other, No CRM
• How many prospect records will need to be imported? Options: Under 500, 500-2,000, 2,000-10,000, Over 10,000
• Do imported records include historical giving, notes, and contact history? Options: Yes, complete history, Partial history, Only contact info
• What pipeline stages do you want configured (select all that apply)? Options: Prospect identification, Qualification, Cultivation, Solicitation/Ask, Pledged, Closed
• Do you need automated triggers, tasks, or reminders tied to pipeline stages? Options: Yes, No, Some stages only
• Who will be the primary CRM admin and what access level do they have?
• Are there data privacy or donor consent fields that must be preserved during import? Options: Yes, No

Create gift agreement and pledge documentation templates

• Do you require legally vetted pledge and gift agreement templates? Options: Yes, attorney-reviewed, Standard templates only, No templates needed
• What pledge types must templates support? Options: Multi-year pledges, Matching gift pledges, In-kind gifts, Naming/Restricted funds
• Do you need digital signature and e-sign workflows integrated? Options: Yes, No
• Which approval or authorization fields are required on agreements? Options: Board authorization, CEO signature, Finance approval, Donor contact info

• Construct campaign gift table and pledge schedule
• Produce case for support and messaging collateral
• Create top-200 major donor profiles with ask packages
• Draft personalized donor proposals and solicitation letters
• Recruit and orient volunteer campaign leadership
• Deliver volunteer solicitation coaching and role-play sessions
• Train development staff in major gift solicitation tactics
• Accompany and lead face-to-face donor solicitation meetings
• Design and launch campaign microsite and donation portal
• Produce multi-channel fundraising communications content
• Manage gift processing and pledge fulfillment operations
• Host donor stewardship events and executive briefings
• Build and maintain campaign pipeline dashboard and forecasts

Construct campaign gift table and pledge schedule

• Do you want us to construct the campaign gift table and a formal pledge schedule? Options: Yes, No, Unsure—need recommendation
• What is your tentatively targeted campaign goal (select range or specify)? Options: $10M–$25M, $25M–$50M, $50M–$100M, More than $100M, Specify amount
• What pledge fulfillment timeframe do you plan to use? Options: 3 years, 4 years, 5 years, Custom—specify
• Do you have existing donor giving data that can be used to model capacity (e.g., last 5 years of gifts)? Options: Yes, No, Partial—some data available
• Preferred approach for gift table construction? Options: Standard gift pyramid by percentage, Customized segmentation by donor capacity, Hybrid—standard + custom adjustments
• Who must approve the final gift table and pledge schedule (list roles/names)?

Produce case for support and messaging collateral

• Do you need a full written case for support or a brief messaging packet (or both)? Options: Full case for support, Brief messaging packet, Both
• Are there existing brand guidelines, tone, or key messages we must follow? Options: Yes, No, Partial—style guide available
• Which collateral formats do you require? Options: Print/leave-behind, One‑page ask memos, Slide deck for volunteers, Donor-facing microsite content, All of the above
• Who is the primary audience for the case (lead prospects, board, general donors, all)? Options: Lead prospects & major donors, Board and volunteer leaders, General donor base, Multiple distinct audiences
• What approval cycle and turnaround time do you expect for drafts? Options: 3–5 business days, 1–2 weeks, Custom—specify
• Are there sensitivity or confidentiality constraints on messaging (e.g., naming, program details)? Options: None, Some restrictions—will provide guidance, High confidentiality—NDA required

Create top-200 major donor profiles with ask packages

• Do you want a top-200 prospect list built from your database and external research? Options: Yes, No, Start smaller (top 50/100)
• Do you have an existing prospect ranking or moves-management stage for these donors? Options: Yes—fully ranked, Partial, No—need us to assess
• Which data points should each profile include? Options: Giving history, Wealth indicators, Affinity/engagement notes, Relationship map, All of the above
• Should we prepare tailored ask packages (dollar ask, case highlights, solicitation strategy) per prospect? Options: Yes—every profile, Yes—for top tier only, No—profiles only
• Who will be the primary relationship holders for the top prospects (staff and volunteers)?
• Any prospects or households that must be excluded or handled differently (e.g., anonymity requests)? Options: None, Yes—will provide list

Draft personalized donor proposals and solicitation letters

• Do you require templated personalized proposals or fully bespoke letters for top prospects? Options: Templates with merge fields, Fully bespoke for top 20–50, Combination
• Which audiences need personalized materials (major donors, mid-level donors, institutional funders)? Options: Major donors (top), Mid-level donors, Foundations & corporations, All audiences
• Are there institutional/legal requirements for proposals to foundations or corporate partners? Options: Yes—specific language needed, No
• Preferred tone and length for donor-facing solicitation letters? Options: Concise (1 page), Detailed (2+ pages), Executive summary + appendix
• Do you need letters localized by donor geography, language, or affinity? Options: Yes—geographic, Yes—language, No
• Who will review and sign solicitation letters (CEO, Board Chair, Volunteer leader)?

Recruit and orient volunteer campaign leadership

• Do you want consultant support to recruit volunteer leadership (chairs, campaign cabinet)? Options: Yes—full recruitment support, Advisory support only, No—internal team will lead
• How many volunteer leaders do you plan to recruit (campaign chair, co-chairs, cabinet size)? Options: 1–2 (chair/co-chairs), 5–10 (small cabinet), 11–30 (large cabinet), Custom
• What selection criteria are most important for volunteer leaders? Options: Giving capacity, Network & access to prospects, Board leadership experience, Public profile/credibility
• What orientation format do you prefer for volunteers? Options: In-person workshop, Virtual orientation, Hybrid
• Do volunteers require formal role descriptions and commitment agreements? Options: Yes—detailed role descriptions, Basic expectations only, No
• What is the timeline for recruiting and confirming volunteer leadership? Options: Immediate—within 4 weeks, 1–3 months, Custom

Deliver volunteer solicitation coaching and role-play sessions

• Do you want structured coaching and role-play sessions for volunteers before solicitations begin? Options: Yes—multiple sessions, One session per leader, No—optional resources only
• Preferred coaching delivery method? Options: In-person workshops, Live virtual sessions, Recorded modules + live Q&A, Hybrid
• How many volunteer participants should each coaching cohort include? Options: 1–5, 6–15, 16–30, 30+
• Which topics should coaching cover (select all that apply)? Options: Asking language & scripts, Handling objections, Prospect briefing & research, Post-ask follow-up/stewardship
• Are there high‑profile volunteer scenarios requiring bespoke rehearsal (e.g., CEO + Chair joint asks)? Options: Yes—will specify, No
• What measures will indicate coaching readiness (e.g., mock ask success criteria)? Options: Comfort with script, Successful role‑play, Volunteer commitment to ask, Other—specify

Train development staff in major gift solicitation tactics

• Do you require formal training for internal development staff on major gift tactics? Options: Yes—comprehensive program, Targeted refreshers, No—not necessary
• Which staff roles should be trained (CDO, gift officers, front-line staff, data team)? Options: CDO/executive, Gift officers, Front-line development staff, Database/operations
• Preferred training format and cadence? Options: One-day intensive, Series of shorter modules, Ongoing coaching & shadowing
• Do you want role-based competency assessments before and after training? Options: Yes—pre/post assessments, No—training only
• Any internal policies or cultural considerations training should reflect? Options: Yes—will provide guidance, No
• Will staff be expected to co-solicit with volunteers or lead independent asks? Options: Co-solicit with volunteers, Lead independent asks, Both

Accompany and lead face-to-face donor solicitation meetings

• Do you want consultant-led attendance at face-to-face donor solicitations? Options: Yes—for top prospect visits, Advisory presence only, No
• How many solicitation visits do you anticipate needing consultant accompaniment for? Options: 1–5, 6–15, 16–30, More than 30
• Who will participate in each visit (CEO, Board Chair, volunteer, gift officer)? Options: CEO + volunteer, Board + CEO, Staff + volunteer, Custom—specify
• Are there geographic or travel constraints for in-person solicitations? Options: Local only, Regional travel, National/international travel
• Do you need post-meeting briefings and standardized visit reports? Options: Yes—standardized templates, No—informal notes only
• Are there legal or institutional protocols for who may solicit (e.g., public officials, corporate reps)? Options: Yes—restrictions apply, No

Design and launch campaign microsite and donation portal

• Do you require a campaign microsite and integrated donation portal? Options: Yes—full site + portal, Microsite only, Portal only, No
• Do you have brand assets, photography, and content ready for the site? Options: Yes—ready, Partial—need support, No—need full content creation
• Which payment methods and pledge types need to be supported? Options: Credit card, ACH/eCheck, Pledge/recurring gifts, Stock/transfer instructions, All of the above
• Do you need donor login/pledge management or anonymous giving options? Options: Donor login required, Anonymous giving enabled, Both, Neither
• What integrations are required (CRM, donor database, finance systems)? Options: CRM integration, Finance system, Email platform, All of the above, Other
• What timeline do you expect for site launch? Options: 2–4 weeks, 4–8 weeks, 8+ weeks

Produce multi-channel fundraising communications content

• Which channels should be included in the campaign communications plan? Options: Email, Direct mail, Social media, Paid media, Events, All of the above
• Do you require segmentation of messages by donor tier or audience? Options: Yes—by tier, Yes—by audience (alumni, parents, patients), No—one message fits all
• Do you have an existing communications calendar we should align to? Options: Yes—will provide, No—need us to create
• Are there compliance or approval workflows for donor communications? Options: Yes—legal/PR approval needed, No
• What performance metrics should we track for communications (open rates, conversion, ROI)? Options: Open/click rates, Donation conversion, Event RSVPs, All of the above, Other
• Do you need design and production support for print/mail pieces? Options: Yes—design + production, Design only, No

Quick Win: What’s Already Locked In?

• What single element are you most confident is already ready for launch?
• Which of these core launch elements are already complete? Options: Campaign goal announced, Lead gift committed, Feasibility study closed, Gift table drafted, Volunteer cadre recruited, Solicitation calendar created, Communications plan approved, None of the above
• Who will be our primary day‑to‑day partner inside your organization during the launch phase? Options: CEO, Board Chair, Chief Development Officer, Development Director/Manager, Volunteer Chair, Operations Director, Other
• What is the target public announcement date (if any)?
• What is the single biggest reason you believe that date is achievable?

What Could Blow Up the First 90 Days?

• If the launch goes sideways in month one, what is the most likely cause?
• Which of these failure modes worries you most right now? Options: Key volunteer withdraws, Major prospect declines, Data errors exposed, Communications misfire, Timing conflict with another event, Internal governance delay, Other
• For the top risk you selected, describe the scenario you fear and who would need to act to prevent it.
• How would an early setback affect board confidence and volunteer momentum? Options: Severely, Moderately, Minimally, Not sure
• What early warning signs should we monitor in weeks 1–4 and how should they be reported?

Is Your Data the Backbone—or the Weak Link?

• What piece of your donor data would embarrass you if it appeared in a public audit?
• Which donor and prospect data sources can our team access right away? Options: CRM (e.g., Raiser’s Edge, DonorPerfect), Legacy/departmental spreadsheets, Finance/gift accounting system, Event/attendance lists, Volunteer/prospect lists, Third‑party research vendors, Other
• How would you rate the cleanliness of key donor fields (gift history, contact info, capacity indicators)? Options: High quality, Moderate (some cleanup), Poor (significant cleanup), Unknown
• Do we currently have permission and access to run wealth and capacity research on major prospects? Options: Yes — full access, Yes — restricted access, No — need approvals, Unknown
• Who owns donor data inside your organization and how quickly can they respond to cleanup or access requests?
• Are there privacy, legal, or donor‑requested restrictions we must honor before outreach? Options: Yes — donor anonymity requests, Yes — legal/compliance constraints, No known restrictions, Unknown

Who Will Actually Do the Asking?

• Which volunteer, if they stepped away tomorrow, would create the largest hole in our solicitation plan?
• Which volunteer roles are currently committed and named for soliciting prospects? Options: Campaign Chair, Honorary Chair, Major Gifts Committee members (named), Steering Committee members, Named volunteer solicitors, Alumni/Parent ambassadors, Corporate/Institutional champions, None yet
• How confident are you in volunteers’ ability to make a direct major‑gift ask without staff present? Options: Very confident, Somewhat confident, Not confident, Don't know
• Tell us about one volunteer who can open a lead gift conversation today—what makes them effective?
• What specific coaching, rehearsal, or briefing do volunteers still need before their first solicitations?
• If a volunteer drops out, how fast can you replace or reassign their asks? Options: Within 1 week, 1–4 weeks, 1–3 months, Longer/uncertain

Do Our Timelines Match Reality—or Wishful Thinking?

• Which timeline assumption are we inventing because it simply 'sounds right'?
• Which milestones are scheduled and confirmed in your calendar? Options: Feasibility final report, Gift table approval, Volunteer training sessions, Public launch announcement, Major donor visits, Stewardship/thank‑you events, None confirmed
• How firm are those dates: confirmed, tentative, or aspirational? Options: Firm (booked/confirmed), Tentative (being scheduled), Aspirational (no logistics), Unknown
• Which internal or external dependencies could force a launch date change?
• If we postponed launch 6–8 weeks, which area would be most affected? Options: Volunteer momentum, Major gift pipeline, Public announcement timing, Board patience, Operational budget windows, Other

Will Our Messages Land with Donors?

• What part of the campaign case are you least comfortable defending in a private donor conversation?
• Which audiences need bespoke messaging before we solicit them? Options: Major donors, Board members, Corporate partners, Foundations, Alumni, Community leaders, Staff/donors with legacy concerns, Other
• Do one‑minute and five‑minute donor pitches exist and have they been rehearsed? Options: Both exist and tested, Drafts exist but untested, Not developed, Unknown
• Who is responsible for preparing donor‑facing materials (case statements, FAQs, briefing notes) and what is their revision turnaround?
• What top objections do you expect from your largest prospect segment and how have we prepared to respond?

Access & Approvals: Who Holds the Keys?

• If a major ask needs immediate CEO sign‑off, who can provide it without routing through multiple layers?
• Which gatekeepers currently limit rapid access to donor records or calendars? Options: IT/data security, CEO/executive approval, Board Chair, Legal/Compliance, Development operations, Executive Assistant/Calendar control, Other
• What approvals are required before a volunteer or staff member may meet a prospect (select all that apply)? Options: No approvals required, CEO approval, Board approval, Development manager approval, Legal sign‑off, Other
• How quickly can we obtain written authorization for a personalized solicitation or naming conversation? Options: Same day, 1–3 days, 1 week, Longer/uncertain
• Are there upcoming board meetings, public events, or external timelines that will constrain solicitation windows?

A Launch That Builds Trust — Not Panic

• What would have to happen in the first 30 days to make you feel proud of how the launch began?
• Which early success metrics should we report weekly to demonstrate progress? Options: Volunteer asks completed, Major donor meetings held, Gifts secured (count), Dollars secured, Prospect moves recorded, Data cleanup tasks completed, Volunteer training attendance
• How often and in what format would you like status updates, and who must receive them? Options: Daily brief (email/slack), Weekly digest, Biweekly summary, Monthly report, Ad‑hoc for issues
• What escalation path should we use if a major issue appears (who do we call first)? Options: Immediate call with CEO & Board Chair, Email to campaign director, Emergency steering committee meeting, Other
• Name one small, non‑financial milestone we can achieve in week 1 to build confidence with your board and volunteers.

Final Checklist: Are We Launch‑Ready?

• Gift table finalized? Options: Complete, In progress, Not started, Blocked, Unknown
• Solicitation calendar published and shared with solicitors? Options: Complete, In progress, Not started, Blocked, Unknown
• Volunteer assignments for top 50 prospects confirmed? Options: Yes — all confirmed, Partially confirmed, No, Unknown
• Communications materials (case, FAQs, briefing notes) approved? Options: Approved and distributed, Drafted, not approved, Not started, Unknown
• Donor/prospect data cleaned for top 100 prospects? Options: Clean and verified, Some cleanup needed, Major cleanup required, Unknown
• Access and permissions (CRM, calendars, research tools) granted to campaign team? Options: Fully granted, Partially granted, Not granted, Unknown
• What is your single biggest ask of our team before launch?
• Is there any additional context, concern, or history we haven’t asked about that would change how we prepare for launch?

• Mid‑Campaign Performance Review
• Top Prospect Re‑qualification Workshop
• Volunteer Leadership Calibration & Coaching
• Communications, Stewardship & Reputation Review
• Corrective Action Decision & Governance Meeting

• Assign backup leads for at‑risk solicitations and define escalation protocols.
• Schedule follow‑up checkpoint meeting in two weeks to review early indicators.
• Pre‑work Review & Rules of Engagement
• Update the gift table with revised, validated capacity and likelihood for top prospects.
• Lock in ask amounts, lead solicitors, and target dates for each priority prospect.
• Create a short list of high‑risk prospects and mitigation actions (alternate prospects, escalations).
• Update CRM/gift table entries with new capacity scores and next‑step dates within 72 hours.
• Assign and schedule tailored coaching sessions for each lead solicitor before the next ask.
• Commission two intelligence interviews for prospects flagged as high risk and report findings in one week.
• Performance Snapshot
• Increase volunteer readiness for imminent solicitations through targeted coaching.
• Resolve access or messaging blockers that inhibit volunteer asks.
• Recap of Diagnostic Findings
• Deliver individualized briefing packets and objection handling guides to each volunteer within 48 hours.
• Schedule one‑on‑one coaching calls for volunteers leading top five asks before their meetings.
• Publish a volunteer escalation contact list and protocol document.
• Current External Calendar
• Ensure donor communications remain consistent with campaign reality and do not jeopardize major prospects.
• Have contingency messaging pre‑approved for rapid deployment if campaign public posture must change.
• Confirm board/CEO briefing schedule and sign‑off process for external messages.
• Produce contingency talking points and a one‑page donor FAQ for immediate use.
• Schedule a briefing with the board chair and CEO to approve any public adjustments within five business days.
• Update stewardship calendar for top donors to ensure immediate touchpoints post‑decision.
• Obtain formal approval for the corrective course of action and confirm resource commitments.
• Document updated acceptance criteria that will be used to validate campaign recovery.
• Establish an explicit governance and reporting cadence to monitor corrective plans.
• Publish the approved corrective plan, updated gift table, and acceptance criteria to stakeholders.
• Assign a campaign recovery lead and publish a 30/60/90 day dashboard to the governance body.
• Schedule mandated governance checkpoints (e.g., 30‑day, 60‑day) to review progress and reauthorize actions.
• Opening & Objectives
• Ensure all stakeholders understand the exact gap between current results and the gift table.
• Agree on a prioritized corrective path with named owners and timelines.
• Establish measurable acceptance criteria to validate effectiveness of corrective actions.
• Document any immediate volunteer or staff reassignments required.
• Produce a one‑page variance report (gift table vs. commitments) and distribute within 48 hours.
• Assign owners for each corrective scenario and publish a 30/60/90‑day implementation plan.
• Present Recommended Corrective Plan(s)
• Donor Stewardship Status
• Feedback from Volunteers
• Prospect-by‑Prospect Deep Dives
• Current State Dashboard
• Coaching & Role Play
• Contingency Messaging
• Variance & Consequence Analysis
• Validation of Consequences
• Decision & Approval
• Reassignment & Escalation Plan
• Ask Strategy & Volunteer Match
• Board & Executive Alignment
• Root Cause Identification
• Revised Acceptance Criteria
• Volunteer Recognition & Retention
• Governance & Reporting Cadence
• Preliminary Strategy Options
• Risk Flags & Next Steps
• Approval & Distribution Plan
• Decision & Owners
• Wrap & Validation