Field Notes · No. 05 · September 2026
Four Kinds
of Root Rot
Nicole Segura
|
1,648 organizations
|
12 U.S. metros
|
IRS Form 990, 2022 to 2024
672
organizations carrying
a stress flag
68%
of them carry
exactly one
20% vs 50%
cash as the flag, Pioneer Pine
vs Plains Cottonwood
Most boards have one go-to financial question, and it is usually some version of how many months could we survive if the money stopped. It is a good question. It is quick, the treasurer can usually answer it from the last statement, and when the answer is bad, nobody has to argue about whether it is bad.
Where I see organizations actually struggle with it is programming. An organization that hasn’t looked closely at the fixed and variable costs sitting inside its program budgets, or at how those costs move across the season, is often working from a per-person cost to serve that doesn’t reflect much of the real picture, and that number gets quoted in grant applications and board reports for years before anyone goes back to it. When I work through this with clients it usually makes fundraising more specific, because a real figure lets you match a particular ask to a particular donor, and it gives requests for operational support a context they didn’t have before.
Even answered well, though, the question has a blind spot, and what sits in that blind spot is different for different organizations.
The four things this research looks at
A forester walking a stand of trees doesn’t just check one thing. Different species show distress in different places. Some drop needles first. Some hold a full crown right up until the roots give out.
This research flags an organization as stressed if any one of four things is true.
Fig. A · The four structural stress flags
| The flag | What triggers it | What it is really asking |
| Insolvency | Under 30 days of cash on hand | Could you make payroll through a bad month |
| Relevance | Revenue fell more than 15% over the period | Is the money still coming |
| Spiral | Operating margin below −5% and still declining | Is the gap getting wider |
| Deficit | Average operating margin below −10% | Have you been spending more than you bring in |
Revenue decline and sustained deficit cover all three filing years; the cash and widening-gap flags are measured at the most recent filing. Source: Segura Strategy Group | The Financial Forest
Any one of them is enough to get flagged, and across the 1,648 organizations in this study 672 carry at least one, which is the 40.8% figure this research keeps reporting.
Each of the four asks a different question, and which one an organization trips depends on how it is funded.
Most struggling organizations trip one flag out of four
68%
68% of the 672 organizations here carrying at least one warning sign carry exactly one. Fewer than one in ten carry three or more.
Financial trouble doesn’t usually arrive as a bundle. It feels like a bundle from the inside, but most of the organizations in difficulty here are doing fine on three of these four measures and are in real trouble on the fourth.
If your reports have mostly looked clean and something has still felt off, the data supports that it is worth leaning into the feeling and learning more about the "one thing not sitting right."
Which symptom shows up depends on what kind of organization you are
Reading across each row: among the organizations of that type that are carrying a warning sign, this is what the warning sign tends to be. An organization can carry more than one, so rows total to more than 100%.
Fig. B · Which flag, among organizations already carrying one (n=672)
| Archetype | Cash | Revenue decline | Gap widening | Sustained deficit |
| Pioneer Pine · young, donor-dependent | 20% | 50% | 27% | 37% |
| Gambel Oak · diversified generalists | 23% | 53% | 33% | 43% |
| Rocky Mtn. Juniper · property-owning | 29% | 48% | 24% | 47% |
| Serviceberry · fee-for-service | 47% | 33% | 18% | 37% |
| Plains Cottonwood · government contracts | 50% | 38% | 27% | 28% |
| Quaking Aspen · in-kind economy | 56% | 28% | 20% | 16% |
| Peachleaf Willow · large program-revenue | 83% | 13% | 9% | 4% |
Shares of flagged organizations within each archetype rather than of all organizations, which is why they run higher than the flag rates on the research page. Terracotta marks the leading flag in each row. Rocky Mountain Juniper carries two, because its top two sit one organization apart, 55 and 54 out of 115. Every other row is separated by at least seven. The tinted block is the four groups where cash is the leading flag. Source: Segura Strategy Group | The Financial Forest
The top three rows and the bottom four are telling different stories, and neither one is the story of a better-run group of organizations.
For young donor-funded organizations, diversified generalists, and property-owning reserve-holders, trouble most often shows up in the top line. Revenue slips. Sometimes a margin has been negative underneath it for a while, and for the property-owning group that is running just as often as the revenue slip itself. Cash is one of the flags these organizations are least likely to carry: more than eight in ten of the ones with falling revenue still clear the 30-day cash line. If you run one of these and the cash balance is your early warning, it may not be telling you much about the problem you are most likely to have.
For fee-for-service organizations, government contractors, and the in-kind and large program-revenue groups, it is close to the reverse. Cash is the leading flag, and it shows up while revenue still looks healthy, because in these models you often deliver the service and then wait to get paid for it. That is what a reimbursement calendar does to a bank balance, and it isn’t something a stronger finance committee would have prevented.
If you are a government contractor who has been told your cash management needs work, the data suggests your cash is doing what your funding structure makes it do. The next step is likely a mix of setting realistic goals and seeking cash flow specific services to bridge the gap. And if you run a young donor-funded organization with a comfortable cushion, that cushion isn’t the reassurance you have been treating it as, because it isn’t where your kind of organization tends to get sick.
Neither of those is a verdict on anyone’s competence, they are just two different trees showing distress in two different places.
What I would not read into this
The bottom two rows come from 23 and 25 organizations, which is small enough that Peachleaf Willow’s 83% could reasonably sit anywhere from about 63% to 93%, so the shape of those rows carries more than the decimal does.
There is also a size effect sitting inside the cash column. Peachleaf Willow holds the largest organizations in the study, a median of $36M in revenue, and the cash flag rises steeply with size, from about one in ten organizations under $250K to more than a third above $30M. A $36M operation doesn’t sit on a year of expenses and doesn’t need to. The flag is still picking up something real, because the large organizations tripping it carry thinner margins than their peers who don’t and hold less outside of cash, though above $30M those margins are still positive, so the flag is a weaker signal at that size. It is easier to trip if you are large, and I am re-examining that 30-day line for bigger organizations ahead of the next data release.
The differences between the groups themselves are not a small-sample story. Set the two smallest groups aside entirely and the remaining five still differ from chance at about one in 260,000. The specific gap this piece leans on, a young donor-funded organization at 20% on cash against a government contractor at 50%, is about as firm as anything in this dataset.
Start with which of these four is the relevant warning sign for an organization built the way yours is built. Which one organizations built like yours most often carry, which isn’t always the one that looks worst on the current statement. If you run on government contracts or reimbursement, it is most often cash. If you are young and donor-funded, it is most often the top line, and your cash balance or reserves can look fine while revenue is falling.
Then work out where that measure lives, and whether it is presented in a way that lets you nudge the ship rather than announce the crash. Those are two different instruments built from the same number. Days of cash reviewed at the quarterly meeting against a 30-day line is an alarm: by the time it sounds, the decision has largely been made for you. The same figure charted month over month, with the direction and the slope visible, is something you can steer by, because six months of gentle decline is legible long before any threshold gets crossed.
None of this adds a line to the report. Pick the one organizations shaped like yours most often trip. Put it on the monthly report next to whatever came with the template. Show it as a trend line over twelve or twenty-four months instead of a pass-fail against a threshold. Then agree in advance what size of move gets a conversation, so that the conversation happens while it is still a course correction.
And if the answer isn’t obvious, that isn’t a gap in your financial literacy. Your funding structure determines it, and funding structure is easier to see from outside an organization than from inside it. This might be an opportunity to reflect on who from the community with institutional knowledge or high level financial leadership experience at organizations structured like yours might be a great board member addition or contracted staff support, depending on scope of work and immediate needs.
Questions to sit with
For executive directors
Think back to the last hard stretch here. What was the earliest number that had already turned, and how was it, or how could it have been, tracked?
For board members
Of the financial measures this board reviews, which are early warnings, which are red flags for something that has already happened, and which are just noise?
For funders
Are you defining organizational stress the same way for every grantee, and where that definition feeds a capacity-building intervention, which financial markers are actually driving the decision?
Finding the ones that are yours
If you don’t know which of the seven you are, the research explorer at thefinancialforest.com/research walks through all of them and takes a few minutes. Classify, the free plan in Bearings, will confirm it from your own Form 990.
If you already know, there is a workbook for each of the seven. Each one takes a single archetype and lays out the pressures built into that business model, what the data shows for organizations shaped like yours, and a set of prompts to work through with your team. A workbook won’t score you and it won’t rank you against a universal standard. It gives you and your board language for the shape you’re already in, which is why there are seven of them. thefinancialforest.com/workbooks
Archetype Workbooks
One workbook for each of the seven archetypes: the pressures built into that business model, what the data shows for organizations shaped like yours, and prompts to work through with your board.
See the workbooks
A note on method: revenue decline and sustained deficit are computed across all three filing years, while the cash and widening-gap flags are measured at the most recent filing. None of the four shows which problem arrived first. The percentages in Fig. B are shares of flagged organizations rather than of all organizations, which is why they run higher than the flag rates published on the research page. Both are correct and they answer different questions. The four thresholds are this framework’s own choices rather than sector standards.
The study covers organizations that filed a full Form 990 in all three years, roughly $200K in revenue and up. Organizations below that line, and those that closed or shrank out of the sample, are not in here, so every rate in this study is best read as a floor. These are patterns across groups rather than verdicts about any organization, and nothing here establishes that one flag causes another or predicts what happens next.
The full methodology is at thefinancialforest.com/research.
Forest Ranger
To ask clarifying questions or explore other Financial Forest findings, the Forest Ranger query tool is live at thefinancialforest.com.
Ask Forest Ranger
Get Field Notes in your inbox.
Subscribers receive each issue before it opens in the archive. No pitches, no fluff, just the research.
Follow the Research