Top 10 Questions to Ask When Choosing a New CLM

Managing your contracts is a key part of running a successful business operation. How else do you keep track of whether all obligations (including your own) are met? Contract lifecycle management (CLM) solutions have rapidly become a mainstay in SaaS, and for good reason. 

With several established CLMs out there, it can be easy to feel overwhelmed. That’s where this article comes in. 

In our article, we’ve gathered a list of simple, practical questions to help you find a software that meets your goals — whether you need something that works seamlessly with existing tools, is easy to use, or can scale as your business grows. Docfield stands out to us as a clear winner in terms of price to value, and we’ll explore in more detail why.

Regardless of your role or department — be it legal, purchasing, or general management — these questions will help you steer clear of common pitfalls and pick a solution that truly works for you.

Choosing the Right CLM: 10 Must-Ask Questions

1. How does this CLM system connect with your existing stack?

If you’re reading this article, chances are some tech stack precedes your CLM implementation. You might already be in the process of implementation or have a tool in place. 

Without going into detail on the many use-cases for a CLM, you’ll generally want to consider how a CLM integrates with your other key systems, mainly your ERP (like SAP or Oracle) and CRM (like Hubspot or Salesforce). Additional ones include e-signature solutions, compliance tools, and collaboration platforms, though many CLMs have this functionality built-in. 

Looking at integrations ensures that data flows efficiently between systems, reducing manual entry and the risk of errors. Tools like Docfield are sure to offer these key integrations. 

2. What security protocols are in place?

Contracts contain sensitive information, which must be protected. Ask your supplier about the security features offered by the system itself, such as data encryption, multi-factor authentication, SSO, and compliance with standards like ISO27001 and GDPR. 

You can also request a recent pen-test to understand whether the supplier is prone to breaches. If you are based in the EU or UK, you may want to ask whether any data is transferred to the US, which exposes it to different regulations. It is important to not only protect the data in your contracts, but also that of its users. 

3. Does the system harness automation and AI?

AI is the name of the game in 2025, but in many ways, it overlaps with automations that pre-exist the term. Automations are great because they eliminate repetitive tasks like sending renewal reminders or generating standard contract clauses. 

Having these built-in is a great asset to your team. Additionally, AI capabilities like summarizing contracts and providing insights will undoubtedly free up your team to focus on more strategic tasks, enhancing overall productivity.

MORE: Ultimate guide to Sora.

4. Is the platform scalable for your future needs?

Generally, the goal of all organizations is to grow over time. Companies can subscribe to different philosophies, which means they attach value to different metrics. Whether this implies growth in revenue, customer count, team size, or product features – effectively all of them lead to an increase in contract volume and complexity. So, regardless of how you want to grow your company, you should seriously consider a CLM. 

To be more specific, you can search for a CLM solution that can support your growth path, such as more users, larger datasets, or evolving workflows, without compromising performance. Scalability is crucial for ensuring long-term success.

5. How reliable is the vendor’s customer support?

Good support is what separates a good CLM from a great CLM. This is especially important during the implementation of the platform, but the ongoing use is just as important. More on this in point 7. 

Inquire about the types of support available. However, don’t just ask your suppliers; do look at reviews on different websites. Knowing you have reliable support is like a proxy for minimal downtime and quick resolution to issues. Docfield has been praised time and time again for its outstanding support – both in terms of timeliness and effectiveness. 

6. Can this solution be tailored to your processes?

Every organization has unique processes and compliance needs. Look for a CLM system that offers customization options, such as configurable dashboards, adjustable workflows, and flexible templates. A tailored solution can align more closely with your internal practices, making it more effective from day one.

MORE: Software buying process.

7. What is the implementation journey like?

Transitioning to a new CLM system requires some planning. Usually, for more mature companies, it can lead to a noticeable overhaul in processes, workflows, and systems. Ultimately, this is why CLMs are so transformative to organizations. The implementation process will likely kick-off with an audit of processes and inventory of all important documents and systems, which will be transferred over to the new CLM. 

Ask your vendor about the implementation timeline, training programs, and any support provided during the rollout. Understanding these details helps set clear expectations and reduces potential disruptions during the transition.

8. How intuitive is the user interface?

A user-friendly interface encourages your team to quickly adopt the new tool and reduces time spent on training. Evaluate the system’s design and navigation to ensure it is straightforward and easy to use. 

9. What is the pricing structure and expected ROI?

We saved the best for last. Of course, the pricing structure is immensely important in making the right choice for your company. Clearly understanding the pricing structure, and being able to off-set this against expected return on investment (ROI) is critical in defining whether the decision to implement a new tool was a success or not. 

CLMs use various pricing models; clarify whether pricing is based on a flat subscription model, per user, or per contract volume. What about add-ons? Compare the costs to the expected improvements in efficiency and potential cost savings. A transparent pricing model, along with a clear return on investment, supports sound financial decisions.

Usually, you can ask your vendor for help on this, as they are keen to close a deal and express to you just how much value they can bring.

10. What other developments can you expect from the vendor?

Within a rapidly changing business environment, you want a vendor that stays on top of the latest requirements and developments. Ask about the vendor’s product roadmap, including how often the software is updated and what new features or security enhancements are planned. 

A vendor focused on continuous improvement will ensure that your CLM solution remains relevant and effective over time, giving you the best value for your money. For this reason, solutions like Docfield publish their roadmap on their website, alongside a product change log of recently rolled out features.

MORE: How to build a project roadmap.

Conclusion

Choosing the right CLM solution is about much more than checking off features, it’s about selecting a partner that will support your organization’s growth, security, and efficiency. 

By asking these 10 key questions, you’re equipping yourself with a practical checklist to assess how well a system integrates with your current tech stack, safeguards sensitive information, leverages automation and AI, scales with your business, and delivers reliable support. 

Ultimately, a great CLM like Docfield will streamline your contract management process without hindering other workflows. Use these insights to navigate the market confidently, ensuring you select a solution that not only meets your current requirements but also paves the way for long-term success.