A software demo is a sales presentation wearing the costume of a product tour. The vendor picks the data, picks the workflow, and picks the moment to change the subject. None of that is dishonest — it’s just how demos work. Your job is to redirect.
The organizations that end up regretting a purchase almost never say “the demo looked bad.” They say some version of: nobody told us it couldn’t do that. The questions below are designed to surface those gaps while you still have leverage — before the contract, before implementation, before you’ve migrated three years of grant history into a system that can’t produce your Schedule of Expenditures of Federal Awards.
Bring this list. Ask the awkward ones.
Before the Demo: Set the Terms
Send your funding profile to the vendor a week ahead — number of active grants, funders, whether you’re a pass-through entity, your reporting deadlines. Then ask for one thing:
1. Can you demo using our scenario instead of your sample data?
Sample data is engineered to make software look elegant. Your data is messy. A grant with three funding sources, a mid-year budget amendment, and a subrecipient will expose things a clean demo never will. Vendors who agree to this are usually the ones with something to show. Vendors who deflect are telling you something too.
2. Who is on this call, and will they be involved after we sign?
Sales engineers are often the most technically fluent people you’ll meet in the process — and often the last time you’ll meet them. Ask who owns your account post-signature.
Fund and Grant Accounting Fundamentals
Most systems marketed to nonprofits are commercial platforms with nonprofit vocabulary bolted on. The difference shows up in the accounting layer.
3. Is this true fund accounting, or a general ledger with tagging?
Tagging transactions with a “grant” label works until you need a balance sheet by fund. Ask them to produce one live. Purpose-built fund accounting handles restricted and unrestricted balances natively; workarounds require reconciliation you’ll be doing manually forever.
4. How does the system handle a single expense split across multiple grants?
Shared costs — a program director’s salary, rent, a shared vehicle — are where allocation logic either exists or doesn’t. Ask to watch someone code a payroll expense across four funding sources with different percentages, then change one percentage and see what happens downstream.
5. Can we track both grants we receive and grants we make?
Organizations that regrant or manage subawards need both sides. Many systems only do one. If you’re a pass-through entity with subrecipient monitoring obligations, this is a disqualifying question, not a nice-to-have. Dedicated grant management functionality should cover grantee and grantor roles in the same platform.
6. How are indirect cost rates applied?
Ask specifically: does it support multiple rates, rate changes mid-grant, and different bases for different funders? Manual indirect calculation is a quiet, permanent tax on your finance team’s time.
7. Show me the drawdown process.
Not a slide about drawdowns — the actual screens. How many clicks from expense recognition to a reimbursement request? Does it handle cost reimbursement and advance payment methods? Does it flag expenses already drawn against?
Budgets and Controls
8. What happens when someone tries to spend past a grant budget?
The answer you want is that the system stops or warns them at the point of entry. The answer you’ll often get is that it shows up in a report next month. There’s a large operational difference between prevention and discovery. Systems with real-time budget management check against available funds during data entry rather than after the fact.
9. Can we track committed-but-unspent funds?
A purchase order issued against a grant isn’t an expense yet, but it isn’t available money either. Encumbrance accounting closes that gap. Without it, your available balance is optimistic — sometimes expensively so.
10. How do we handle budget amendments and no-cost extensions?
Grant periods change. Ask whether amended budgets preserve the original for variance reporting, or overwrite it.
11. Can grant periods run on different fiscal calendars than ours?
A federal award running October–September inside an organization with a June fiscal year end is normal. Software that can’t model overlapping periods will force you into spreadsheet workarounds immediately.
Reporting and Compliance
This is where demos get vague. Push hard.
12. Build a funder report in front of me, right now.
Every vendor claims custom reporting. Ask them to construct a report you actually submit — a specific funder’s format, with your line items. Time it. If it takes the vendor’s own expert twenty minutes, imagine your program manager.
13. Can non-finance staff pull their own reports?
If every report request routes through your controller, you’ve bought a bottleneck. Ask about role-based dashboards and permissions.
14. What does this produce for our single audit?
If you spend $1 million or more in federal awards in a fiscal year, you need a Single Audit under Uniform Guidance. Ask directly whether the system generates a Schedule of Expenditures of Federal Awards, and how it tracks CFDA/Assistance Listing numbers.
15. Show me the audit trail on a modified transaction.
Change an amount. Then show me who changed it, when, what it was before, and whether that record can be deleted by anyone.
16. How do we document compliance requirements per grant?
Match requirements, reporting deadlines, allowable cost restrictions — can these live in the system attached to the grant record, or do they live in someone’s inbox?
Integration and Data
17. What does it connect to, and how?
Payroll, donor CRM, banking, time tracking. Ask whether integrations are native, via a documented API, or “we can build that.” The third answer means a services quote you haven’t seen yet.
18. Who owns our data, and how do we get it out?
Ask for the export format and whether historical grant detail exports intact. Every vendor relationship ends eventually.
19. What does migration actually involve?
How much history comes over? Who does the mapping? What’s the realistic timeline — and what’s their track record against that timeline for organizations your size?
Cost, Implementation, and Support
20. What is the total first-year cost, itemized?
License, implementation, data migration, training, integrations, and any per-user or per-module fees. Get it written.
21. How does pricing change as we grow?
Per-user pricing punishes organizations for giving staff access to the information they need. Ask what happens when headcount grows 40% or you add three programs.
22. What is the implementation timeline, and what do you need from us?
Implementations fail on client-side capacity more often than vendor capability. Ask how many hours per week they expect from your team.
23. What is support like — hours, channels, response times?
Then ask: is support included, or a paid tier? And is it staffed by people who understand nonprofit accounting, or generalists reading a script?
24. Can I speak with two customers who look like us — including one who had a hard implementation?
The second half of that question is the one that matters. A vendor who can honestly discuss a difficult rollout is more trustworthy than one with only glowing references.
25. What can this software not do well?
Ask it plainly and sit through the silence. Good vendors have an honest answer. If they claim there isn’t one, you’ve learned something about how the rest of the relationship will go.
After the Demo
Score vendors on the same criteria while it’s fresh — a simple weighted matrix with your must-haves and nice-to-haves will do. Involve the people who’ll live in the system daily, not just the executives who sign. And insist on a sandbox with your own data before final commitment.
The best-fit system isn’t always the one with the most features. It’s the one that handles your funding complexity without workarounds — because workarounds compound, and three years from now they become the reason you’re shopping again.
If you’d like to see how these questions get answered in practice, request a demo and bring your hardest scenario. That’s the one worth testing.
