This Week: Finance pillar focus — Inbound infrastructure + UNO delivery prep + workflow mapping
Sprint: Mar 16-22 | Active: Cold outreach + UNO delivery
Discovery Framework
Pre-call prep, diagnostic questions, segment assessment, call framework.
Pre-Call Prep (15 min)
| Source | What to Look For |
|---|
| Prospect DB | Readiness score, revenue, growth %, subsector, geo |
| Website | Team page (ED? Dev Dir?), events, programs, CRM signals (donation forms, event reg) |
| 990 Data | Revenue trend, expense breakdown, officer names + comp, grant ratio |
| LinkedIn | ED profile (tenure, past orgs), org page (posts, headcount) |
Goal: Diagnose maturity stage (1-5), identify buying trigger, understand decision process, qualify budget.
Call Framework (15-20 min)
"Thanks for taking the time, [First Name]. Before I say anything about what I do, I'd love to hear from you -- what prompted you to take this call? What's the thing that's top of mind when it comes to your data or technology?"
Let them talk first. Their answer tells you everything about their trigger, pain, and emotional state. Don't interrupt.
Ask in order -- they map to the 5-stage maturity model:
1. "Where does your donor/client data live today?"
Spreadsheets = Stage 1
CRM + spreadsheets = Stage 2
Centralized CRM = Stage 3+
2. "Can you pull a report showing total giving by donor for the last 3 years in under 5 minutes?"
No = Stage 1-2
Yes, manually (export) = Stage 2-3
Yes, dashboard = Stage 3+
3. "When someone donates or registers for an event, what happens automatically?"
Nothing, manual = Stage 1-2
Goes into CRM = Stage 2-3
Triggers emails + updates + notifies = Stage 4
4. "Who is responsible for data quality in your organization?"
Nobody / "everyone" = Stage 1-2
One person = Stage 2-3
Defined roles + routine = Stage 3+
5. "Have you used any AI tools in your work?"
No = Below Stage 5
ChatGPT informally = Below Stage 5
Specific tools + strategy = Stage 5
Based on their answers, dig into the pain:
- "You mentioned [the manual process]. How much time does that take your team per week?"
- "When the board asks for [report they can't produce], what happens?"
- "Has that ever caused a problem with a funder or donor?"
- "What would change for you if that just... worked automatically?"
Key: Get them to say the cost out loud. "We spend about 15 hours a month on that" = ammunition for your proposal.
- "If we figured out the right fix, what would the process look like on your end to move forward?" (who decides, approval process)
- "Is there a budget set aside, or would this be something you'd need to build a case for?" (budget exists or not)
- "What's driving the timing? Event, grant deadline, board meeting?" (urgency)
- "Have you worked with an outside consultant on technology before?" (trust level, what NOT to do)
If Stage 1-2 (most common)
"Based on what you've described, [Org Name] is sitting at what I call Stage 2 -- you have a CRM, but it's not configured for what you actually need, and your other systems aren't connected to it. The fastest path forward is a Data Health Check -- it's $500-$1,500, takes about a week, and gives you a clear picture of what's working, what's broken, and what to fix first."
If Stage 3
"You're in good shape -- your systems are connected, but there's a layer of automation that would save your team significant time. I'd recommend scoping a targeted automation project -- usually $3K-$5K -- focused on the 2-3 workflows that are still manual."
If Stage 4+
"You're ahead of most nonprofits your size. The opportunity now is to start leveraging AI tools -- donor prediction, automated grant writing assistance, personalized outreach. I'd recommend an AI Readiness Assessment first, then we scope a pilot."
"Here's what I'd suggest as a next step: I'll put together a one-page summary of what we discussed -- your current state, the specific recommendations, and what the first project would look like with pricing. I can have that to you by [2 business days]. Does that work?"
If board approval needed: "I'll include an ROI summary designed to share with your board. And if it would help, I'm happy to join a brief call with [ED / board committee] to answer questions directly."
5-Question Segment Assessment
Ask these to diagnose which donor segments they're tracking. Most EDs say "no" to 3-4. Each "no" = a gap you can fill.
1. "What happens when someone gives for the first time?"
Tests: welcome series, 90-day second ask (First-time donor segment)
2. "How do you identify donors who gave last year but haven't given yet this year?"
Tests: LYBUNT tracking -- highest-ROI re-engagement segment
3. "Do you have a different communication plan for $500+ donors vs. $25 donors?"
Tests: major/mid-level segmentation
4. "How many recurring monthly donors do you have? When did you last invite one-time donors to go monthly?"
Tests: recurring program (90% annual retention)
5. "Can you pull a list right now of everyone who gave 2+ years ago but not since?"
Tests: SYBUNT capability and CRM literacy
Post-Call Checklist
- Send thank-you email with 1-page summary (within 24 hrs)
- Log interaction in prospect database
- Update prospect status
- If proposal requested, start drafting
- Set follow-up reminder for 3 business days