Selecting CapEx management software is a significant decision. The wrong choice means months of implementation pain, workarounds for missing features, and eventually starting over with a different solution. These eight questions help you evaluate vendors thoroughly and avoid costly mistakes.
Questions without context produce generic answers. Before vendor conversations, document:
With requirements documented, you can ask pointed questions and evaluate answers against your specific needs.
Why this matters: Every organization has unique approval hierarchies—dollar thresholds, role-based approvals, multi-level sign-offs, conditional routing. Generic demos show ideal scenarios. Your reality is messier.
What to probe:
Red flags: Vague answers about "configurable workflows" without demonstrating your specific scenario. Suggestions to "adjust your process" to fit the software.
Good signs: Vendor asks detailed questions about your approval process before answering. Demonstrates configuration for your specific rules, not generic examples.
Why this matters: CapEx software must exchange data with accounting, property management, and document systems. Poor integration means manual data entry, reconciliation headaches, and duplicate sources of truth.
What to probe:
Red flags: Claims of "easy integration" without specifics. No existing customers using your systems. Integration requires expensive custom development with unclear timelines.
Good signs: Documented integrations with your specific systems. Reference customers using similar integration patterns. Clear API documentation and support resources.
Why this matters: Software demos show finished products. Implementation determines whether you get there—and how painful the journey is.
What to probe:
Red flags: Unrealistically short timelines (complex implementations take 3-6 months minimum). Vague answers about your responsibilities. No mention of change management challenges.
Good signs: Realistic timeline with clear milestones. Detailed implementation plan showing your team's required involvement. References to common challenges and how they're addressed.
Why this matters: License fees are just the beginning. Implementation, integration, training, and ongoing administration add up. You need the full picture to make apples-to-apples comparisons.
What to probe:
Red flags: Reluctance to provide detailed pricing. Significant costs hidden in "optional" modules you'll definitely need. Pricing that increases dramatically with scale.
Good signs: Transparent pricing with clear documentation. All-inclusive models without hidden fees. Predictable costs as you grow.
Why this matters: Vendors show their best customers. You need to talk to customers similar to you—same industry, similar scale, comparable complexity.
What to probe:
Red flags: Only offering references from different industries or vastly different scales. References who implemented years ago on older versions. Reluctance to provide references at all.
Good signs: Multiple references matching your profile. Recent implementations you can learn from. Vendor proactively suggests relevant references.
Why this matters: You're buying for the future, not just today. Understand where the product is headed and whether it aligns with your evolving needs.
What to probe:
Red flags: No clear roadmap or reluctance to share it. Features you need are "planned" but with no timeline. Roadmap driven entirely by largest customers, not customer base broadly.
Good signs: Published roadmap with realistic timelines. Customer advisory board or feedback mechanisms. Track record of delivering planned features.
Why this matters: Every system has problems. What matters is how quickly and effectively they're resolved.
What to probe:
Red flags: Vague SLAs or resistance to contractual commitments. Support only via email with no urgency tiers. No clear escalation path.
Good signs: Specific, contractual SLAs with teeth. Named support contacts, not just a queue. Transparent communication about incidents and resolutions.
Why this matters: Every product has weaknesses. Vendors who acknowledge them are more trustworthy than those claiming perfection. Understanding limitations helps you plan for workarounds or decide if they're dealbreakers.
What to probe:
Red flags: Claims that customers love everything and have no complaints. Defensive responses to questions about limitations. No acknowledgment of areas for improvement.
Good signs: Honest acknowledgment of limitations with context. Clear explanation of why certain features aren't prioritized. Workarounds documented for known gaps.
If possible, run a limited pilot before full commitment. Use a real project or property to test the system with actual data and workflows. Pilots reveal issues that demos and references cannot.
Include future users in evaluation, not just decision-makers. The people who will use the system daily often spot usability issues and missing features that executives miss.
Review terms for:
If something feels off during the sales process—pushy tactics, evasive answers, unrealistic promises—that's data. Vendors who are difficult during sales rarely improve after you've signed.
How many vendors should we evaluate?
Three to five vendors provides enough comparison without overwhelming the evaluation team. Start broad with research, then narrow to serious contenders for detailed evaluation.
How long should the evaluation process take?
Plan for 6-12 weeks from initial research to selection. Rushing leads to missed requirements and poor decisions. Taking too long leads to analysis paralysis.
Should we use an RFP process?
Formal RFPs work well for large organizations with procurement requirements. Smaller organizations often get better results from direct conversations and demonstrations. Either way, document requirements before engaging vendors.
What if no vendor meets all our requirements?
Prioritize ruthlessly. Separate true must-haves from nice-to-haves. No solution is perfect—choose the one that best addresses your critical needs with a credible plan to address gaps.
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