Deena Strategic Group · Philanthropy Sustainability Relationship System · Pilot
Know the people you fund, without chasing them.
A midterm report and a final report is a file, not a relationship. Design a year of better questions, shared dates and honest answers, where each grantee decides what you see. Built for small foundation staffs.
How a pilot runs
- 1A 30-minute conversation.What you want to know, how many grantees, what your staff can carry.Available now
- 2Design your year.Questions, dates, events and an optional survey. Start below, today.Planning tool works now
- 3Onboard your grantees.We load your plan, walk each grantee through it and answer their questions.Service by inquiry
- 4One full cycle, then review together.Shared accounts, reminders and dashboards for this step are in pilot design.Pilot design
You'll see notes marked The Underneath™. They name what the system tends to miss or punish, and what to do about it. They're part of every DSG tool, not an add-on. What The Underneath is.
Automated reminders, shared calendars, surveys, dashboards and integrations are not running yet. We will not say they are until they are built and tested.
Design your pilot
Nothing here is sent or saved. When you're done, download or print the plan and bring it to our conversation. No grantee or client information, please.
1. The basics
For the top of your plan.
Many pilots start with about ten. Your call.
2. Your questions 6 of 10
Plain and open. Something you'd ask over coffee.
3. Milestones and grant calendar
| DateWhen it happens. | What happensCheck-in, report, renewal, site visit. | Who takes partFunder, grantees, or both. | Remove |
|---|---|---|---|
Events
| DateWhen. | EventConvening, learning call, site visit. | Grantee time paid?Do you pay for their time? | Remove |
|---|---|---|---|
4. A short optional survey
5. What you're asking of each grantee
Ask a grantee. We won't guess for you.
Grantee time a year: Unknown until you enter minutes per answer
What a grantee sees
Your foundation · Round 1 of 2
- What went better than you expected since we last talked?
- What is getting in the way that money alone won't fix?
- What did the people you serve tell you this season, in their words?
and 3 more
Before anything is sent: Share with the foundation? Yes, No, or Share part of it.
A mockup of the planned screen. Not live.
A sample board brief
Fictional cohort for Harbor Family Fund (fictional). It shows how a brief reads when grantees control what's shared.
Harbor Family Fund (fictional) · Fall brief · Built only from what grantees chose to share
Northside Youth Table (fictional)
Shared by the grantee
Volunteer coaches doubled after a parent-led recruiting night. Asked: could the fund introduce them to the school district's after-school office?
Second Shift Meals (fictional)
Shared by the grantee
Reimbursement from a county contract is running 60 days late. They are covering payroll from reserves and asked about a bridge.
Kin Circle Caregivers (fictional)
Not shared
Chose not to share this round. That is their right, and nothing about the grant changes.
Sample only. Every name is fictional. No live dashboard exists yet.
What is built today
Status checked November 10, 2026. We change this table only when something is built and tested.
| Piece | Status | What that means today |
|---|---|---|
| This pilot designer | Working now | Plan questions, dates, events and a survey; count what you're asking for; download or print the plan. Nothing is sent or saved. |
| Sample funder brief | Demo only | Fictional cohort, to show how grantee-controlled sharing reads. Not a live dashboard. |
| Separate accounts | Pilot design | Grantees can already keep their own private account in Sustainability in a Box. Funder accounts are not built yet. |
| Reporting milestones and grant calendar | Pilot design | You set the dates that matter: check-ins, reports, renewals. |
| Events | Pilot design | Convenings and site visits on one shared calendar. |
| Two-way questions | Pilot design | You ask your ten questions. Grantees can ask you theirs. |
| Short optional surveys | Pilot design | A few questions, sent rarely, that grantees can skip. |
| Grantee-controlled sharing | Pilot design | Each grantee decides what you see. Nothing is shared without consent. |
| Foundation dashboard | Pilot design | What your grantees chose to share, in one place. |
| Exportable funder briefs | Pilot design | Today each grantee can download its own Sustainability Plan PDF and choose to send it to you. |
| Setup, onboarding and help desk | Service by inquiry | We load your questions and dates, onboard your grantees and answer their questions, so your small staff isn't chasing anyone by phone. |
Bring your plan to a conversation.
We'll tell you what we can run for your cohort now, what's still in pilot design, and what setup and help desk support would look like. Priced with you. No public price.
The structure, questions, guidance and examples in this tool were written by Deena Strategic Group. Your answers and your numbers belong to you. Free to use for your own organization's work. Do not resell, rebrand or teach it as your own paid product. Read the terms. © 2026 Deena Strategic Group · Fredericka Wallace Deena. All rights reserved.