Business Alignment

1. What problem does this tool solve, and how does it align with our business goals?

2. Are we sure we don't already have a tool that does this?

3. What alternatives have we explored?

4. Have we actually tested it, not just watched a demo?

Gartner separately estimates that 20-30% of SaaS budgets are wasted specifically on duplicate or unused subscriptions. Most of that is avoidable with a proper stack audit before procurement moves.

Pricing, Contracts and Scalability

5. What contract length are we comfortable committing to, and what do we get for locking in longer?

6. What is the total cost of ownership, including onboarding, training, and scaling?

7. Is this tool and its contract structure scalable as we grow?

8. How flexible is the pricing model for variable or seasonal usage?

Deloitte found hidden costs pushed TCO up by 50% in year one. In 2026, AI usage-based pricing makes this worse. If you don't have real-time visibility into token spend, the bill will surprise you every quarter.

Implementation, Customization and Support

9. What does implementation actually require from our team?

10. How does this tool handle future customization needs?

11. What does vendor support look like post-purchase?

Forrester found post-purchase customizations push companies 30% over initial budget. The pattern is always the same: works in the demo, falls short in production.

Compliance, Reliability and Exit

12. What data security and compliance standards does this tool meet?

13. What are the SLAs on uptime and issue resolution?

14. What are the renewal terms and exit options?

15. Is there an auto-renewal clause, and how far out do we need to cancel it?

GDPR violations can cost up to 4% of global annual turnover. Auto-renewal clauses and opaque exit terms are how vendors keep you paying for tools you've already moved on from.

Pre-Renewal Checklist

Before any signature:

• Pulled actual 12-month spend, including overages
• Checked utilization data for the last 90 days
• Identified at least one competitive alternative
• Confirmed no redundant capability exists elsewhere in the stack
• Reviewed updated contract terms, especially AI data and training clauses
• Calculated fully loaded cost, including admin and integration time
• Initiated the renewal conversation at least 90 days out
• Looped in finance and procurement before the vendor call, not after

Stop scoring tools on features. Evaluate them on whether they solve a documented problem, what they actually cost over three years, and whether you can exit cleanly if they stop working.

Do the work now. It's a lot cheaper than explaining the overrun to your board later.

Want to know what your AI stack is actually costing you? ELI tracks spend in real time, before the invoice does.