Looking for the best contract management software in 2025? Discover the 10 essential questions to ask before choosing a CLM solution that ensures security, scalability, and ROI for your business.
Choosing the right contract management software in 2025 is overwhelming. Dozens to select from, all with automation, compliance, and efficiency, how do you choose the one that will fit your company's needs?
The key is to ask the right questions.
A cloud Contract Lifecycle Management (CLM) solution today can be highly customized; with industry-specific functionality, compliance capabilities, and integration possibilities. But not all tools are created equal.
To help you make your decision, here are 10 questions that you should ask before selecting your next contract management system.
1.What Security Features Does the Software Use?
Security is the backbone of any web-based system, especially one that handles sensitive legal documents. In 2025, businesses handle more advanced privacy regulations like GDPR, HIPAA, and local data protection regulations.
Ask your potential vendor:
- Is it hosted in a secure, stable server environment?
- Does it meet industry-sector-specific regulatory environments?
- What access control, audit trails, and data encryption are used?
A leading solution should offer multi-factor authentication, role-based access, and automated data back-up.
For instance, SharePoint-based and Microsoft 365 solutions usually employ native security layers like SharePoint Backup and Restore to ensure that no critical contract information will ever be lost. When buying CLM software, make sure that it offers repeatable, automated data protection mechanisms that reduce risk and maintain compliance at all times.
2.Can I Easily Transfer My Current Contracts into the Platform’s Repository?
One of the most exciting advantages of using CLM software is a centralized contract repository. But getting existing contracts migrated tends to be the most daunting part.
Ask:
- Does the platform have bulk upload and all mainstream file types (PDF, Word, Excel, etc.) accepted?
- Will the vendor migrate your existing documents?
- Are there storage or user access limits?
The best systems allow you to store, categorize, search, and recover files in seconds. In Dock 365, for example, we migrate on your behalf-all your contracts nicely relocated to your new virtual headquarters seamlessly with no downtime or interruption.
3.Are There Advanced Search and Reporting Capabilities?
Having the correct contract or clause at the correct moment can make or break productivity. That's where sophisticated search and custom reporting functionalities come into the fore.
Check for:
- Text-based and metadata search across all the documents.
- Custom filters (such as by vendor company name, contract type, or renewal date).
- Dashboard analytics and reporting tools.
A clear CLM dashboard should allow you to view contract performance, track renewals and commitments, and generate reports that you can export and share.
These insights maximize accountability, reduce missed deadlines, and allow you to forecast risk and opportunity-based business decisions.
4.Is the Platform Scalable and Future-Ready for My Business?
Perhaps the greatest advantage of a cloud-based contract management solution is that it is scalable. If your business expands, your application should be able to expand with it, seamlessly and without downtime, or expensive upgrades.
Ask:
- Are new departments or users easily added?
- Is there multi-location visibility under one platform?
- Are there hidden costs for growth, support, or data storage?
A CLM solution that is scalable should enable your company to process growing numbers of contracts as well as collaborate both across teams.
Ensure that you also know how long-term pricing models-upgrades, user training, and maintenance-are managed. Solutions that are future-proof should evolve seamlessly as the business objectives and regulations evolve.
5.Can the Solution Integrate with My Existing Tools?
In 2025, the typical business employs over 100 software pieces for running business operations, HR, finance, and law. A CLM solution that naturally integrates into your current setup saves time and minimizes manual labor.
Ask:
- Does it integrate into Microsoft Teams, Dynamics 365, Power BI, Outlook, or other key applications?
- Does it have eSignature integrations such as DocuSign, Adobe Sign, or Sertifi?
A CLM platform that's built into your current tools unified workspace-more productivity, less data silos, and less mistake.
At Dock 365, our CLM solution integrates seamlessly with Microsoft's productivity toolset and top eSignature tools, allowing teams to close deals faster and work together confidently.
6.How Smooth Is the Implementation Process and Is Training Included?
Regardless of how well-featured the software is, it can still fail if users struggle to accept it. A good vendor smooths the implementation process, makes it clear, and gives solid support.
Ask:
- Is there a guided onboarding process?
- Do they offer user training sessions or tutorials?
- Will they provide ongoing customer support post-launch?
Your vendor should be more of a partner, not just a vendor-offering support with data migration, system configuration, and user configuration.
Look for vendors offering webinars, documentation, and live support free of charge. This will make your staff feel at ease using the platform right from day one.
7.How Does This Solution Compare to Other Options?
Not all CLM solutions are created equal in the marketplace today. What distinguishes it is often how much the solution aligns with your business needs.
Ask yourself:
- Does it shorten contract turnaround time through automation or eSignatures?
- Does it automate negotiations with redlining, commenting, and version comparison features?
- Can workflows be customized for reviews and approvals?
Experimenting with several platforms enables you to identify what must-haves versus nice-to-haves are.
For instance, if your biggest challenge is slow approvals, head for solutions with automated approval flows. If compliance is paramount, look for one that has audit trails and clause libraries. Your proper comparison allows you to acquire the most value-driven solution for your own specific requirements.
8.Does the Solution Save Time and Money?
Finally, any software investment has to deliver real ROI. A great CLM product has to save you time, reduce costs, and increase contract value.
Ask:
- Does it automate contract creation, approval, and renewal reminder processes?
- Does it help minimize legal risks using pre-approved libraries of clauses?
- Does it provide you with real-time visibility into contract performance?
With the right solution, you'll eliminate duplicate manual processes, prevent mistakes, and enhance overall compliance.
A tool like Dock 365 CLM, for example, streamlines contract operations, integrates data, and improves negotiation turnaround-with quantifiable savings and productivity gains across departments.
9.Can the Software Be Customized to Fit My Business's Branding and Needs?
Every organization has unique workflows and compliance requirements. Your CLM platform needs to adapt to these, rather than the other way around.
Request:
- Can the dashboard be customized with logos and preferred layouts?
- Are configurable user permissions and role-based access controls supported?
- Does the vendor allow custom modules or reports?
Customization makes your platform reflect your company's spirit and enable your operational goals.
The top systems allow administrators to customize user access, alerts, and dashboards by department. In this way, every user receives the most pertinent information and tools, without risking security.
10.Does the Solution Provide Good Version Control and Audit Trails?
Edits, revisions, and negotiations are ongoing in contracts. Without good version control, teams are at risk for confusion, mistakes, and compliance failures.
Ask:
- Does the platform record all document updates with timestamps?
- Can you see or restore previous versions?
- Is there a digital audit trail to hold someone accountable?
Strong version control grants you complete visibility across your contract lifecycle. Every single change, from redline to approval-is captured automatically.
Not only does this promote improved collaboration across business and legal groups, but compliance and data integrity are also improved. The best CLM solutions maintain an immutable history of every single contract available even after signing.
Get the Most Value Out of Your Contracts in 2025 with Dock 365
Choosing the right contract management platform in 2025 entails a balance of security, scalability, usability, and value. Knowing the correct questions to ask enables you to find a platform that not only simplifies your contracting process but also drives measurable business growth.
A cloud-based CLM system offers:
- Unmatched scalability and security
- End-to-end contract visibility
- Automated workflow for faster execution
- Compliance management and audit trails
- Deep integration with business applications you already use
At Dock 365, we have created a SharePoint-based contract management system that leverages your existing Microsoft 365 environment for maximum efficiency and cost savings. From creation to renewal, Dock CLM enables your teams collaborate smarter, close deals faster, and stay compliant effortlessly.
Ready to take the next step?
Unlock the potential of smarter contract management with Dock 365 today.
Schedule a free demo with Dock 365 and learn how Dock's CLM platform can transform your business in 2025.
