We Digitized the Form and Threw Away the Envelope
by Tom Rossi
Note: This article originally appeared in ASBO International's School Business Now magazine in October 2026 and is reprinted with permission of the Association of School Business Officials International.
The club advisor has a prep period, so they bring the payment request to the principal for
approval. The principal is in a meeting. The school clerk is at lunch. Three days later the request is still unsigned, the vendor still hasn’t been paid, and the advisor is deciding whether to cover it personally.
This is what happens when student activity fund standards meet a school schedule. The
standards are clear, and none of them are difficult, not individually. Two signatures on every check. An observer for every cash count. Approval before money can be spent. You probably know most of them.
But what do these things have in common? Everything requires more than one person. That’s where the difficulty comes in. The club advisor tried.
The second person wasn’t available. In most buildings, in most weeks, that isn’t the exception. It’s the schedule.
My brother was a school principal for many years, and we’ve had this conversation. He said it plainly: “Schools are designed to manage students, not money.”
He was right about the design. But when a single building is holding tens of thousands of
dollars, design stops being an excuse.
The Interoffice Envelope
When I was in school, all of the approvals were handled with paper. Interoffice envelopes were everywhere. If you’ve never seen one, an interoffice envelope is a large manila envelope with a string tie and a grid of names printed on the front. It was a routing system. You crossed off your name, wrote the next one, and sent it on. It moved, and you could see where it was. It was also the only copy, so it never got buried. The last person in the process crossed off their name, and the contents came out and went into a filing cabinet.
Today, very little has changed. Many districts still use paper forms, scanned and emailed to whoever is supposed to approve them. The difference is that the email lands in a stack of other emails, and a year later nobody can find it.
Have you ever tried to find an email from a year ago?
That is not the fault of the schools or the school district. Accounting software is built for an
organization with a finance department, with people at desks, in one office, working the same hours. That’s the district office, not the school building.
We used technology to go backwards. The form was the least valuable part of the system, and that’s what’s in the email.
The envelope was the control. Strip it down and the envelope did four things:
Declared the path. The grid of names was the approval sequence, printed on the object itself. Nobody had to ask who’s next.
Kept one copy. What you held was the record. No version question, ever.
Showed custody. You could find out whose desk it was sitting on. Delay had an address.
Carried history. The crossed-off names were the audit trail, and they traveled with the document instead of being reconstructed later.
Every step of the interoffice envelope was a control.
Taking Back the Control
So what’s the answer? How do we get back to the control that the interoffice envelope gave us? To get there, your process, paper or digital, has to do four things.
Declare the path. Who can submit, who approves, and in what order, in the request, not in a manual on a shelf.
Keep one copy. Paper or digital, there is one record that holds everything. It can be found in the same place as all the other like requests.
Show custody. Everyone knows where the request is in the process.
Carry history. Who asked, all who approved, who processed. All with date and time stamps.
Does your current process give you this information? If it doesn’t, you might want to consider going back to interoffice envelopes. It might give you more control than you have today.
They still sell them. I checked.
Where Account Tree Fits
Account Tree is built for the work that happens before the money moves, and for the accounting that follows.
In Account Tree, the payment request is the envelope. The approval path is set by the district and travels with every request, so nobody has to ask who’s next. The invoice, the request and every approval live in one record, filed with every other request like it. Anyone in the process can see whose desk it’s sitting on. And the history builds itself: who asked, who approved, who processed it, each with a date and time. A year from now, you won’t be searching an inbox for it.
Control the process. Then account for the result.
Tom Rossi is the co-founder of Account Tree and the author of two books, and is a regular contributor to ASBO International’s School Business Now Magazine. He has a degree in accounting and has worked as an auditor, a controller, and a business owner. Email me tom.rossi@accounttree.com
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