Selecting Contract Lifecycle Management (CLM) software is a significant decision. It requires input from Legal, Procurement, IT, Finance, and business leaders, and it often involves evaluating dozens of vendors, defining requirements, and building consensus before a purchase is approved.
Many organizations are now using ChatGPT (and other AI Agents) to help streamline that process.
It can summarize research, generate first drafts of RFPs, organize requirements, compare vendors, and prepare executive presentations. Used well, it saves time and helps teams approach software evaluations with greater structure.
What it can't do is tell you which solution is right for your organization. That still requires an understanding of your business processes, governance requirements, technology environment, and long-term objectives.
The prompts below are designed to help you get more value from ChatGPT throughout your contract lifecycle management (CLM) evaluation. Think of them as starting points that can help your team ask better questions, organize information, and make more informed decisions. 
Prompt 1: Build a Business Case for Contract Lifecycle Management
"Act as a Contract Lifecycle Management consultant. Help me build a business case for replacing manual contract management. Our organization has 1,200 employees, uses Microsoft 365 and SharePoint, and manages approximately 15,000 contracts.
Estimate the operational savings, compliance improvements, revenue acceleration, and risk reduction we should expect."
Why this matters
A CLM software project rarely moves forward based on features alone. Executive sponsors want to understand the business impact. How much time can be saved? Where can risk be reduced? How will the investment improve productivity or accelerate revenue?
ChatGPT can help organize those ideas into a structured business case and tailor the messaging for different audiences, whether you're presenting to Legal, Finance, IT, or executive leadership.
Treat the results as a starting point, not a finished analysis. Replace generic assumptions with your own contract volumes, cycle times, and business metrics to build a case that reflects your organization's priorities.
Learn More
If you're still deciding whether it's the right time to invest in Contract Lifecycle Management software, our Demonstrating the Value of Contract Management eBook explains how organizations calculate ROI, identify hidden costs, and build executive support for a CLM software initiative. It's an excellent companion before you begin evaluating vendors.
Prompt 2: Identify Every Stakeholder
"List every department that should participate in selecting enterprise Contract Lifecycle Management software. For each department, explain its goals, concerns, required functionality, and the questions it should ask prospective vendors."
Why this matters
Contract management affects far more than the Legal department. Procurement, Sales, IT, Finance, Compliance, and business operations all have different priorities and expectations.
ChatGPT can help identify those stakeholders early and summarize what each group should contribute to the evaluation. That often leads to better requirements, fewer surprises during implementation, and broader organizational support once a solution is selected.
Prompt 3: Create a Requirements Checklist
"Create a comprehensive requirements checklist for enterprise Contract Lifecycle Management software. Organize the requirements into Must Have, Nice to Have, and Future Phase categories.
Include AI capabilities, reporting, workflow automation, approvals, repository management, Microsoft integration, security, obligation management, analytics, and contract lifecycle governance."
Why this matters
Every software evaluation begins with a list of requirements. The challenge is deciding which capabilities are essential today and which can wait until later phases.
Organizing requirements into priorities helps the evaluation team stay focused and makes vendor comparisons more meaningful. It also encourages conversations about governance, reporting, security, and long-term scalability instead of concentrating solely on individual features.
Remember that a successful CLM implementation is about more than functionality. It should support consistent business processes and create trusted contract data that the organization can rely on over time.
Prompt 4: Write a Better RFP
"Write a professional Request for Proposal (RFP) for enterprise Contract Lifecycle Management software.
Include the following:
- Company background
- Business objectives
- Functional requirements
- Technical architecture
- Security requirements
- Implementation methodology
- Support expectations
- Pricing
- Vendor qualifications
- Project timeline
- Evaluation criteria for vendors"
Why this matters
Writing an enterprise RFP from scratch can take weeks. ChatGPT can produce a well-structured first draft in minutes, giving your team more time to refine the requirements that are unique to your organization.
Use the draft as a framework, not the final document. The strongest RFPs clearly describe your business processes, governance requirements, security expectations, and implementation goals. Those details ultimately determine whether a solution is the right fit.
If you're new to the process, a detailed CLM RFP guide can also provide useful examples of evaluation criteria, implementation questions, and vendor qualifications to include in your final document.
Learn More
Our How to Write an Effective Request for Proposal for Contract Lifecycle Management Software eBook walks through each section of a successful CLM RFP in detail, including company information, functional requirements, solution architecture, implementation methodology, support expectations, pricing, and vendor relationship considerations. It also includes a downloadable RFP worksheet to help organize your evaluation.
Prompt 5: Compare Contract Management Software Vendors
"Compare the following Contract Lifecycle Management vendors: Vendor A, Vendor B, and Vendor C.
Evaluate each solution's capabilities on the following criteria and summarize the strengths and potential limitations of each.
- AI capabilities
- Microsoft integration
- Ease of implementation
- Reporting
- Security
- Scalability
- Contract authoring
- Negotiation
- Repository management
- Customer support
- Implementation methodology"
Why this matters
ChatGPT can quickly summarize publicly available information about CLM vendors, making it easier to understand how products compare before scheduling demonstrations.
Keep in mind that public information only tells part of the story. Product demonstrations, customer references, and conversations with implementation teams often reveal important differences in usability, deployment approach, and long-term support. Use ChatGPT to narrow your research, then validate its findings through your own evaluation.
Prompt 6: Create a Vendor Evaluation Scorecard
"Create a weighted evaluation scorecard for selecting Contract Management software. Assign percentage weightings totaling 100% across:
- Implementation approach
- Ease of use
- Microsoft integration
- AI capabilities
- Security
- Reporting
- Vendor support
- Scalability
- Total Cost of ownership"
Why this matters
Without a consistent scoring model, software evaluations can become highly subjective. Different stakeholders naturally prioritize different capabilities, making it difficult to compare vendors fairly.
A weighted scorecard gives everyone the same framework. More importantly, it encourages your team to agree on priorities before demonstrations begin, helping ensure that every solution is evaluated against the same business objectives.
Prompt 7: Challenge Your Assumptions
"Assume the role of a CIO reviewing our Contract Lifecycle Management evaluation. Based on our requirements, what important questions have we overlooked? Where are the biggest implementation, governance, security, or adoption risks?"
Why this matters
One of the best ways to use ChatGPT is to ask it to look for gaps instead of confirmation.
Whether you ask it to think like a CIO, General Counsel, Procurement leader, or Information Security team, it can introduce perspectives your evaluation team may not have considered. That often leads to stronger requirements and more thoughtful conversations with prospective vendors.
Prompt 8: Evaluate Microsoft 365 Integration
"Our organization has standardized on Microsoft 365. Generate 30 questions we should ask every Contract Lifecycle Management vendor about Microsoft 365 integration, including SharePoint, Microsoft Word, Outlook, Microsoft Teams, Power Automate, Power BI, Dynamics 365, Microsoft Entra ID, Microsoft security, and governance."
Why this matters
For organizations that rely on Microsoft 365, integration deserves a dedicated part of the evaluation. Many vendors advertise Microsoft integration, but the depth of that integration varies significantly. Understanding those differences early can prevent costly surprises later.
Ask questions such as:
- Where are contracts stored? In SharePoint or a separate repository?
- Are permissions managed through Microsoft Entra ID?
- How do Outlook notifications, Power Automate workflows, and Power BI reporting fit into the overall solution?
- How easily does the platform integrate with Dynamics 365 or other Microsoft business applications?
- Can users negotiate agreements directly in Microsoft Word?
These aren't simply technical questions. They influence security, governance, user adoption, implementation effort, and the long-term value of your Microsoft investment.
Prompt 9: Build an Executive Presentation
"Create a 10-slide executive presentation recommending investment in Contract Lifecycle Management software.
Include current challenges, business risks, projected ROI, implementation approach, timeline, expected business outcomes, and an executive summary suitable for senior leadership."
Why this matters
By the time a software evaluation reaches executive leadership, months of research often need to be distilled into a concise business recommendation.
ChatGPT can help organize that information into a clear presentation, but the strongest presentations rely on your organization's own data and priorities. Focus less on product features and more on business outcomes, implementation strategy, risk reduction, and measurable value.
Prompt 10: Turn ChatGPT into an Interactive CLM Consultant
"You are an enterprise software selection consultant. Interview me one question at a time to help select the best Contract Lifecycle Management solution for our organization. We use Microsoft 365, including SharePoint, Outlook, Microsoft Word, Dynamics 365, and Power Automate.
After gathering the necessary information, help us:
- Build our requirements
- Recommend evaluation criteria
- Create an RFP
- Develop a weighted scorecard
- Identify implementation phases
- Highlight potential risks
- Prepare questions for vendor demonstrations"
Why this matters
Many organizations begin a software evaluation without knowing exactly what they need. That's normal. Requirements evolve as stakeholders become more involved and the evaluation progresses.
Instead of generating individual documents, this prompt turns ChatGPT into a collaborative planning tool. By asking questions one at a time, it helps organize your thinking before recommending requirements, evaluation criteria, and implementation priorities.
Used this way, ChatGPT becomes a practical research assistant throughout the buying process—not a replacement for demonstrations, implementation planning, or conversations with experienced vendors.
ChatGPT Can Help You Evaluate CLM Software. It Shouldn’t Make the Decision.
ChatGPT has quickly become a valuable tool for enterprise software buyers. It can organize research, build business cases, draft RFPs, compare vendors, and prepare executive presentations in a fraction of the time those tasks once required.
Its greatest value, however, isn't making decisions, it's helping your team ask better questions.
The prompts in this guide are designed to support every stage of a Contract Lifecycle Management software evaluation. They can help uncover blind spots, bring stakeholders together, and create a more structured buying process. Used well, they allow your team to spend less time creating documents and more time evaluating the factors that truly matter.
The final decision still depends on understanding your organization's contract processes, governance requirements, technology strategy, and long-term business goals. Product demonstrations, implementation planning, conversations with customer references, and discussions with prospective vendors remain essential parts of selecting the right solution.
For organizations that have standardized on Microsoft 365, it's equally important to understand how a contract lifecycle management system fits within your existing environment. Ask how contracts are stored, how users collaborate, how security is managed, and how contract data supports reporting, automation, and future AI initiatives. Those architectural decisions have a lasting impact on adoption, governance, and long-term success.
ChatGPT can make your evaluation more efficient. Experience, planning, and thoughtful vendor selection are what ultimately make it successful.
Continue Your Evaluation
If your organization is evaluating Contract Lifecycle Management software for Microsoft 365, we'd welcome the opportunity to help.
Schedule a demo to see how Contracts 365 supports the complete contract lifecycle, from request and authoring through negotiation, approvals, repository management, reporting, AI-assisted workflows, and post-signature governance. All while extending the Microsoft 365 environment your teams already use every day.
And if you've used the prompts in this article to build your evaluation criteria, bring them with you. We'll walk through your questions together and show you how Contracts 365 approaches each one in a real-world implementation.
