Every week, organizations sign contracts for software they won't fully use, kick off migrations they haven't adequately planned, and make technology decisions based on a vendor's polished demo rather than their own reality.
I've seen it happen at human services nonprofits with $10M budgets and at two-person consulting firms with $200K revenues. The dollar amounts differ; the pattern is the same.
Before your organization commits to any significant technology investment whether it's a new CRM, a cloud migration, a collaboration platform, or a custom application, you should be able to answer five questions with confidence.
1. What specific problem are we solving?
This sounds obvious. It isn't.
"We need a better CRM" is not a problem statement. Neither is "our current system doesn't work" or "we want to modernize."
A real problem statement looks like this: "Our development team is manually reconciling three spreadsheets before every board meeting because our current database doesn't produce reliable gift reports, and it takes four hours each month that we don't have."
The specificity matters. It tells you exactly what the new system needs to do, gives you a way to measure whether the new system is working, and helps you avoid scope creep during implementation.
If you can't write a clear, specific problem statement before evaluating software, you're not ready to buy.
2. Who will actually use this, and are they on board?
Technology doesn't fail because of technology. It fails because the people who are supposed to use it don't use it or use it incorrectly.
Before committing to any system, identify the five to ten people who will interact with it most. Talk to them. Not just their managers them. Find out what frustrates them about the current process, what their daily workflow looks like, and whether they've seen anything that might solve the problem.
Their buy-in is not a nice-to-have. It's the difference between a successful implementation and an expensive shelf ornament.
Also consider: who is going to own this system after implementation? Who will troubleshoot it, update it, onboard new staff, and manage vendor relationships? If you don't have a clear answer, you have a staffing problem that technology won't solve.
3. What will this cost all in?
The license fee is never the whole number.
When evaluating a technology investment, budget for all of the following:
- License fees (per user, per record, per feature tier)
- Implementation costs (vendor services, internal staff time, consultant fees)
- Data migration (often underestimated by 2–3x)
- Training (initial and ongoing as staff turns over)
- Integration work (connecting to your other systems)
- Ongoing administration (someone's time, every month)
- Year 2+ price increases (check the contract carefully)
A platform that costs $300/month in licenses might cost $40,000 to implement properly. That's not a bad deal if it's worth $40,000, but you need to know that going in.
4. What happens to our data?
This question has two parts.
Before you start: Where is your data now? How clean is it? What will it take to get it into the new system? A poor data migration can undermine an otherwise solid implementation, garbage in, garbage out.
After you commit: Who owns your data in the new system? Can you export it in a standard format? What happens to it if you cancel the subscription or the vendor goes out of business? These are contractual questions worth reviewing before you sign.
For nonprofits in particular: if your data includes client records, donor information, or health data, you may have compliance obligations (HIPAA, state privacy laws) that affect your vendor selection.
5. What does success look like in 90 days?
If you can't describe what the system should be doing, for whom, at 90 days post-launch, you don't have a clear enough picture of what you're buying.
A good 90-day success definition might look like:
- All development staff are entering gift acknowledgments in the new CRM within 24 hours of receipt
- Monthly reports are being generated automatically without manual intervention
- Data from the old system has been imported and validated
These benchmarks give you a way to evaluate whether the implementation is working, and they give your vendor and implementation partner clear accountability.
The Bottom Line
None of these questions require technical expertise to answer. They require organizational clarity about your problems, your people, your budget, and your goals.
If you're working through these questions and finding the answers unclear, that's useful information. It means you're not quite ready to evaluate vendors yet. That's a much better place to be than discovering it six months into an implementation.
Have questions about an upcoming technology decision? Get in touch the first conversation is always free.