Why This Article?

AMS demos are exciting. You hear words like automation, integration, intelligence, and workflow. But once the excitement fades, your team has to live inside that AMS for years.

Small things that didn’t get asked can turn into big frustrations.
Costly surprises show up post-contract.
And sometimes… what was promised doesn’t match what gets used.

This guide is your last-mile checklist — a set of strategic, reflective questions to help you evaluate not just what the AMS can do, but how well it will work in your real-world environment.

1. How does the AMS help non-technical staff do better, faster, or more accurate work—without IT support?

“Automation” is a popular promise—but automating an inefficient process only magnifies inefficiencies.

Instead of asking, “Does your system support automation?”, ask:

“Can you show how a non-technical team member might optimize a daily task using the AMS, with automation or workflows—without needing IT?”

Why this matters:
Tools shouldn’t just replace effort—they should improve how work is done. The real ROI comes when staff can independently create, trigger, or adjust workflows to be more effective in less time.

2. Which features create the most day-to-day value—and which tend to sit unused?

Feature-rich systems often come with long menus and complex configurations. More isn’t always better.

Ask your vendor:

“Which features do your clients use most often, and which tend to get overlooked or disabled?”

Why this matters:
Unused features still carry a cost—licensing, training, maintenance, cognitive overload. Clutter slows adoption, especially for new staff. Ask your vendor to help break down how they keep the system focused and usable.

3. How do you handle integration issues—especially when things unexpectedly break?

Integrations are often the lifelines between your AMS and tools like Zoom, Mailchimp, Stripe, or your finance system. But even “working” integrations can be fragile.

Examples:

• An email platform fails to sync after a security update
• Financial data doesn’t reconcile after an API change
• A webinar registration doesn’t push into the AMS correctly

Ask your vendor:

“Can you share how your team responds when an integration fails unexpectedly—especially with widely-used platforms—and how quickly those issues are typically resolved?”

Why this matters:
Many associations report that integration hiccups lead to delays in renewals, event registrations, and reporting—sometimes for days. Proactive vendors should have not just uptime stats but also real-world recovery plans.

4. How does the AMS support accurate, clean data—during migration and beyond?

Think of your data as the fuel—and the AMS as the lantern. Without clean, structured data, the system can’t illuminate the insights you need.

Ask your vendor:

“How does your platform support data integrity during migration, and what ongoing tools exist to maintain data hygiene (e.g. deduplication, validation, smart merges) over time?”

Why this matters:
Migration isn’t just a tech job—it’s a strategic opportunity to clean house. But the need for clean data doesn’t stop at launch. Your AMS should actively support the maintenance of high-quality data without IT intervention.

5. What’s your fastest and slowest implementation in the last 12 months—and what made the difference?

This question isn’t about speed—it’s about uncovering variables that affect success.

Ask:

“Can you walk me through one of your fastest and one of your slowest implementations from the past year? What contributed to the outcomes in each?”

Why this matters:
You’re fishing for unknown unknowns—things that don’t show up in contracts, but show up in reality. You’ll learn how much is in your control, and how proactive the vendor is in managing client-side risks (e.g. unclear requirements, staffing issues, decision-making delays).

6. What signals do you watch for that an implementation is going off-track—and how do you course-correct?

“Off-track” might mean missing deadlines, overrun budgets, stalled decisions, or reduced scope.

Ask:

“What early signs do you look for that an implementation is off-track in terms of timeline, scope, or client readiness—and how do you get it back on track?”

Why this matters:
No project is immune to hiccups. But vendors who track health indicators (like missed approvals or training attendance) and have playbooks to correct course are more likely to protect your investment.

7. What types of additional costs have surprised clients after going live—and how do you help them prepare for those?

Most unexpected costs aren’t “hidden”—they emerge as your needs evolve. Post-launch, associations often realize they need more training, support, or features than expected.

Ask:

“What types of costs have clients encountered post-launch that weren’t fully anticipated during the initial proposal? And how do you typically help clients prepare for or manage those scenarios?”

Why this matters:
Licensing changes, training expansions, or extended support hours often surface later. Asking this way keeps the conversation collaborative, not confrontational—and gives you visibility into realistic budgeting.

🚀 Final Thought: Smart Questions Build Smart Partnerships

You’re not just buying a product—you’re starting a long-term partnership. The best vendors won’t be rattled by these questions. In fact, the right partner will welcome them because they show you’re serious about getting the most from your investment.