Accounting Software Evaluation: 40 Questions to Avoid $50k Implementation Disasters
Weighted evaluation checklist with 40 specific questions. Test real scenarios before you buy and avoid hidden costs.
Scoring Framework
Score each question 1-5 based on vendor capability demonstration. Require live demos for technical questions – don't accept promises or documentation. Weight scores by criteria importance to get objective vendor comparison.
Evaluation Criteria
Core Financial Operations
30% weightDaily accounting workflows, month-end close processes, and financial reporting capabilities that directly impact your team's productivity and close timeline.
Sample Questions
- Demonstrate closing a month with 2,500+ transactions including automated bank reconciliation, accrual entries, and financial statement generation
- Show exception handling for cross-period adjustments, duplicate payments, and account reclassifications with complete audit trails
- Create custom financial reports with drill-down to transaction detail and automated distribution to board members
- Configure approval workflows for invoices over $5,000 requiring CFO sign-off while allowing recurring payments to bypass approval
- Display real-time financial dashboard updates when posting journal entries, payments, and invoice transactions
Multi-Entity and Consolidation
25% weightIntercompany transaction handling, consolidated reporting, and elimination entries for companies with multiple subsidiaries or business units.
Sample Questions
- Process intercompany sale from Entity A to Entity B with automatic elimination entries and consolidated P&L generation
- Show multi-currency consolidation with EUR subsidiary, USD parent, and automatic translation adjustments
- Create consolidated cash flow statement eliminating intercompany transfers and shared expense allocations
- Configure dimension-based reporting allowing analysis by entity, department, project, and customer segment
- Demonstrate intercompany journal entries with automatic reversing entries and compliance documentation
Integration and Data Management
20% weightAPI capabilities, third-party system connections, data migration tools, and backup/recovery procedures for business continuity.
Sample Questions
- Import 5,000 Shopify orders in one hour showing API rate limit handling and error processing
- Demonstrate Salesforce integration syncing opportunity data with custom fields and revenue recognition automation
- Show Avalara tax integration handling multi-state transactions with exemption certificates and address validation
- Execute point-in-time backup restoration showing maximum data loss and recovery time for accidental deletions
- Import existing chart of accounts with 40+ custom fields maintaining all relationships and historical data
User Management and Security
15% weightRole-based access controls, audit trails, compliance documentation, and security features for financial data protection.
Sample Questions
- Configure granular permissions allowing AP clerk to post payments while restricting access to profit margin data
- Provide SOC 2 Type II report and explain data encryption methods for financial information at rest and in transit
- Show user activity audit trails with IP tracking, login history, and transaction modification logging
- Demonstrate automated user deprovisioning when employees leave with session termination and access reviews
- Configure IP restrictions limiting financial data access to office locations and approved remote connections
Implementation and Support
10% weightProfessional services requirements, customization capabilities, training resources, and ongoing support quality for successful deployment.
Sample Questions
- Detail implementation scope including data migration, custom reporting setup, and integration configuration with fixed-price quotes
- Show customization preservation through software updates including custom fields, reports, and workflow modifications
- Provide implementation partner credentials with specific industry experience and customer references
- Demonstrate support ticket prioritization during month-end close periods with guaranteed response times
- Explain training program including user certification, ongoing education, and new feature rollout communication
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