Ten questions to ask before buying CLM software

Contracts are the lifeblood of most in-house legal teams, but they’re also the biggest bottleneck. Manual processes, scattered templates, and inconsistent workflows result in slow deal cycles, missed renewals, and limited visibility of contractual value and risk. These challenges only compound as organizations scale up, placing pressure on legal teams to move faster without sacrificing compliance or quality, which is a near impossible task.

Contract lifecycle management (CLM) software has emerged as a savior for the legal function, helping to standardize processes, automate routine work, and provide the business with much-needed transparency. However, choosing the right CLM software to suit your team is not so simple. As we discussed in our article “Five questions to ask when choosing a CLM for your in-house legal team”, there are myriad software solutions posing as the perfect fit when not all of them are.

With vendors offering a wide range of features, pricing models, and levels of sophistication, choosing the right CLM can feel overwhelming. We recommend searching for a tool that aligns with your team’s maturity and goals. This guide gives you a buyer-enablement checklist of the top 10 questions to ask before buying CLM software, helping you confidently assess suitability, capabilities, and long-term value, and ensuring you select a system that genuinely accelerates your contract lifecycle from request to renewal.

The 10 questions to ask before investing in CLM software

1. Does it cover the full contract lifecycle (from request to renewal or termination)?

A robust CLM system should support every stage of the contract journey: intake, drafting, negotiation, approval, signature, storage, obligation management, and renewal or termination. Many tools on the market only focus on document storage or e-signature, creating a fragmented process for legal teams.

Full contract lifecycle visibility enables organizations to capitalize on value opportunity and achieve efficient deal cycles that satisfy internal and external stakeholders, especially regarding renewals and obligations.

You want a CLM system that centralizes and streamlines the legal team’s workstream, creating strategic insight and removing bottlenecks.

2. Is it easy to use for both legal and business users?

CLM adoption, and in fact all tech adoption, hinges on usability. There’s a reason why Apple products are beloved for their fantastic UX Design; they’re intuitive to use. If you adopt a CLM software with a complicated interface, it’s likely team members will revert to old habits, such as emailing Word documents, undoing the entire purpose of the software.

It’s critical you factor in the usability of your CLM tool for both legal and the wider business. Look for intuitive dashboards, simplified request portals, and workflows that businesspeople can follow without constant legal involvement.

The reality is that adoption equals impact; a CLM will only be effective if people use it. Our article, Why contract management software for in-house counsel needs to delight the business, further explores the psychology of adoption and how the right CLM fosters true engagement and drives meaningful collaboration between legal and the wider business for the best ROI.

Nicola Gannon is the Deputy Chief Legal Counsel at Craveable Brands, who recently adopted LawVu and reaped many benefits from business users. “From the business perspective, they have really appreciated having a platform that tracks what they are giving to the legal team,” she says. “Previously, they would email us and then have no visibility and understanding of where their matter was at. We are now getting really good feedback from the business about them being able to see the list of their work on their Business Portal interface and the status updates. At any point, they can see who it is with, where it is at, and they don’t have to be coming back and emailing us constantly for updates.”

3. Does it integrate with our existing tools (Salesforce, e-signature, email, Microsoft 365, matter management)?

Integration is one of the biggest differentiators between a fantastic CLM solution and an average one. You want a CLM system that reduces “toggle tax” by pushing and pulling contract data automatically into the tools your teams already use. The right integration will also help to centralize contract intake into one place for visibility, reducing the risk of tool sprawl or jumping between systems. Common high-value integrations we recommend looking for are:

• Salesforce for sales-driven contracts
• Docusign or Adobe Sign for e-signatures
• Microsoft 365 or other tools for drafting
• Matter management for linking contracts to legal work and capturing legal requests from the business
• Email for notifications and communications

The whole point of CLM adoption is to drive efficiency, so it’s crucial that this system integrates with your existing tools, reducing manual data entry and overwhelm from using multiple tools to get a holistic view of all legal work.

4. What workflows and automation are built in?

ROI is a priority when investing in new software, and there’s no doubt the business expects to see it on your CLM. The 2025 ACC Chief Legal Officers Survey shows that CLOs rank operational efficiency as their top strategic initiative, so it’s no surprise that automation should be a focus for your new CLM.

Efficient, effective systems demonstrate ROI, largely thanks to automation and AI which has the power to identify patterns in large datasets, making it ideal for the density of contract workflows.

Look for features like:

• Automated approval routing
• Template-based drafting
• Self-serve contract creation for the business
• Playbooks and clause libraries
• Auto-generated audit trails
• Contract summarization
• Clause extractions

These reduce repetitive work and increase compliance by ensuring processes are followed consistently. Freeing the legal team from time-consuming manual tasks is pivotal to creating a team that is scalable and able to lead a business through a period of growth. If the technology handles routine BAU tasks, legal can focus on high-level, value-enabling work.

5. Does it provide obligation and renewal tracking?

One of the most common and costly failures in contract management is losing track of a contract’s obligations, renewal dates, termination windows, and performance windows once it has been signed. Many organizations store executed agreements but lack a reliable way of tracking these milestones, creating risk long after negotiation is complete. Picture these common scenarios: a vendor contract automatically renews with a 60-day notice period, but without tracking the renewal passes unnoticed, locking the business into unfavorable pricing for another year. Alternatively, a missed customer obligation could result in penalties or strained commercial relationships.

CLM software should prevent these issues by turning static contracts into living, monitored assets by automatically flagging upcoming deadlines and obligations such as payment terms, notice periods, SLAs, exclusivity clauses, and renewal conditions. These obligations should be kept in a centralized dashboard, with alerts notifying legal and business stakeholders well before action is required.

6. What reporting and analytics capabilities does it offer?

As Shaun Plant, LawVu’s Chief Legal Evangelist, says, “Executives respond to data, and data proves the value of legal.” Harnessing data to report on specific metrics is essential to an informed legal team that can have data driven conversations that inform strategic decisions that allow the function to be a better partner to the business. Businesses expect insights on contract cycle times, contract volume, legal spend, negotiation friction points, and contract value.

When choosing a CLM software, we recommend looking for dashboards with customizable key metrics that legal often report on, allowing the team to generate reports faster. These should include:

• Time spent in each stage
• Bottlenecks
• Renewal forecasts
• Contract types and volumes
• Department usage patterns

A report from Deloitte UK reveals that legal teams harnessing data to their advantage can establish a competitive edge through more efficient operations, better compliance, greater risk management, and anticipating client needs.

7. How does it handle security, compliance, and audit trails?

Contracts store sensitive and highly confidential client and business information, from IP to personal data, and pricing to regulatory commitments. It’s imperative that your CLM has a rigorous security system that protects your organization and doesn’t introduce any new risk.

At a minimum, legal teams should look for CLM vendors that offer industry-recognized certifications such as SOC 2 Type II and ISO 27001, alongside compliance with data protection regulations like GDPR. These certifications signal that the vendor has mature controls around data handling, access management, and incident response. Practical security features are also important, from granular user permissions, encryption of data both at rest and in transit, and secure authentication methods.

Audit trails are equally critical, as incomplete trails can create significant legal and compliance exposure, especially in regulated industries. A robust CLM should automatically log every action taken on a contract: edits, approvals, signatures, and access history. This is essential for internal governance, regulatory audits, and dispute resolution.

8. Can it support AI-driven insights (now or in the future)?

AI in CLM is evolving quickly, from automated drafting to clause extraction, risk scoring, and renewal predictions, as detailed in our article on AI powered contract management. It’s obvious AI is here to stay in the modern legal team, with Gartner reporting that evolving or implementing AI governance was a priority for 58 percent of legal leaders in 2025, and that number is increasing. It’s safe to say that AI is the way of the future.

When choosing a CLM tool, look for a system with built-in AI capabilities or a clear roadmap for scalable AI adoption. Ask vendors how their AI works, what models they use, and where your data goes during processing. It’s important that the AI be user friendly, and to promote user adoption we recommend prioritizing practical AI tools that fit into the legal workflow, not the latest AI trends and features.

9. What implementation, onboarding, training, and support are included?

CLM success depends heavily on the strength of implementation and early adoption from business users. As such, you want to ensure your vendor will support your team through the implementation process and beyond, and won’t abandon you to drown in a sea of new tech. Look for vendors that provide:

• Dedicated onboarding specialists
• Clear timelines and milestones
• Change-management support
• On-demand training resources
• Live customer support

Poor implementation processes lead to low adoption and unrealized ROI, with users adhering to old manual habits. You can have a great CLM, but if the onboarding process goes badly, or the support it provides is lacking, it will ultimately be a bad investment and increase friction between legal and the business due to usability issues.

10. What ROI can we expect, and how quickly?

Seeing ROI on a new CLM tool as quickly as possible is a priority for many legal leaders, who have to report back to the business on the success of their investment. The most common drivers of ROI are reduced cycle times, improved compliance, fewer missed renewals, reduced legal workload, or increased revenue velocity.

Before signing onto a CLM, ask vendors for case studies, benchmarks, and estimated payback periods (typically 6–18 months for mid-sized to enterprise teams), so you can be confident you will have positive news to report to the business powers that be.

Craveable’s Nicola Gannon saw ROI very quickly after adoption. “The biggest benefit for the legal team has been the time saving with our franchise documents,” she says. “We were creating them manually and copy and pasting information into each document. It would take 90 minutes to two hours to create a suite of franchising documents. Because we’re now using the contracts wizard, this has come down to 20-25 minutes to create.”

CLM should deliver measurable business value, not just operational improvements. Read our article for more information on how to measure ROI and communicate it to the business.