10 Questions to ask your Contract Lifecycle Management (CLM) provider before you buy

Choosing the right Contract Lifecycle Management (CLM) solution is a powerful technology decision. Contracts are the source of truth at the heart of business, governing revenue, vendor relationships, compliance obligations, and risk exposure. Yet too many companies still rely on outdated, manual processes or legacy tools that create contract bottlenecks instead of removing them.

Modern CLM platforms, especially those powered by artificial intelligence, are transforming how legal, procurement, and sales teams work with contracts. From streamlining review cycles to surfacing actionable insights, AI-powered CLM delivers faster deal velocity, higher levels of compliance, and better decision-making.

But not all CLM providers are created equal. To make sure you select a platform that truly supports your business, it’s essential to ask the right questions during your evaluation process. Below, we’ve outlined 10 critical questions every CLM buyer should bring to the table, along with insights on why they matter and what you should look for in a best-in-class provider like LinkSquares.

1. How does your AI improve contract review and analysis?

“AI-powered” is no longer a novel offering. AI’s scope and capabilities range from predictive text to advanced statistical reasoning and comprehensive agents. A modern CLM should do more than just store documents; it should help you understand them. Ask how the provider’s AI extracts key terms, identifies risk, and supports faster review cycles. With LinkSquares, AI isn’t an add-on -- it’s built into the platform, providing real-time insights into obligations, renewal dates, and compliance risks so teams can act with confidence.

2. Can your platform integrate with my existing tech stack?

Contracts touch every corner of the business, so integrations across team tools are critical. Depending on your unique tech stack, your CLM must connect to the tools you already use. Sales will likely need a Salesforce integration to keep New Logo deals timely, Procurement will need redlining capabilities via Microsoft Word to adjust contracts to their unique needs, all teams will need Slack capabilities for prompt communication… all while appropriately meeting your legal team’s everyday CLM needs. LinkSquares offers robust integrations that reduce friction and keep workflows smooth across departments.

3. What reporting and analytics features are available?

Data-driven insights are the difference between reactive contract management and strategic decision-making. Ask about dashboards, customizable reporting, and analytics capabilities. LinkSquares empowers leaders with contract intelligence -- helping you spot trends, forecast renewals, and make smarter business decisions in minutes.

4. How does your solution handle compliance and risk management?

With ever-changing regulations, compliance is a moving target. A CLM should flag risky clauses, help enforce policy, and maintain audit-ready records. LinkSquares provides proactive risk detection and compliance monitoring, giving legal teams peace of mind and reducing exposure.

5. What is your implementation timeline and support process?

Some CLM providers take months -- or even years -- to get up and running. Ask about deployment speed and the type of support you’ll receive. LinkSquares prides itself on fast implementation with white-glove onboarding and ongoing support that ensures your team is successful from day one and onboarded in 90 days.

6. Does your solution support the full contract lifecycle?

Drafting, negotiation, approval, execution, and renewal management -- your provider should cover it all. Many platforms focus heavily on one phase while neglecting others. LinkSquares delivers end-to-end CLM so your teams can manage every step of the process in a single, AI-powered platform.

7. How user-friendly is the platform for non-legal teams?

Your CLM will be used by more than just lawyers. Instead it should strike an appropriate balance between the lofty expectations of legal teams and the accessibility required for non legal entities. Sales reps, procurement managers, and finance leaders all need to interact with contracts. LinkSquares is designed with intuitive, user-friendly interfaces that make adoption easy across the organization, not just in legal.

8. What security and data privacy measures are in place?

Contracts contain sensitive data – sensitive data that flows within your organization and back and forth with your vendors. Ensure your provider offers enterprise-grade security, compliance certifications, and strict access controls. LinkSquares safeguards your contracts with industry-leading security standards so your data is always protected.

9. How does your platform enable collaboration across departments?

Contract management is a team sport. Look for features that enable shared visibility, real-time collaboration, and seamless communication. With LinkSquares, stakeholders can work together in one centralized platform, reducing email back-and-forth and keeping everyone aligned.

10. What is your product roadmap and commitment to innovation?

Your CLM solution should evolve with your business. Ask about the provider’s roadmap, investment in AI, and commitment to innovation. LinkSquares consistently delivers enhancements that keep customers ahead of the curve -- ensuring your investment pays off for years to come.

Conclusion

Checking the right boxes is important, but selecting the right CLM is about finding a solution that transforms contracts into a source of strategic value. By asking the right questions, you can separate providers who simply digitize documents from those who deliver real intelligence and efficiency.

LinkSquares is built to empower legal and business teams alike, with AI at the core, seamless integrations, robust reporting, and a proven commitment to customer success. Don’t settle for outdated tools or limited functionality -- choose a CLM that helps your business move faster, manage risk smarter, and drive growth.

Ready to see the power of AI-driven CLM? Schedule a demo with LinkSquares today.