Overcoming CLM Implementation Challenges

Contract management software implementations take effort, and Gartner predicts that almost 50% of CLM implementations fail. Don’t let that number scare you off, though, because there are plenty of teams who realize the full potential of a contract management system.

The trick is knowing which challenges to look out for and how to avoid them.

Successful CLM implementations have a lot of moving parts, and the common challenges in contract lifecycle management implementation fall into five categories: people, process, platform, performance, and planning.

People

You can choose the best CLM platform in the world, but if nobody uses it, you’re back to square one.

• Resistance to change. Even the most eager innovators can face friction from their organization. The key is figuring out how to position and handle the change to make others care, too.
• Lack of buy-in from leadership. You need support from people with influence (and budget) to kickstart and maintain your CLM efforts.
• Training gaps. People learn in different ways and at varying paces. If someone isn’t comfortable with the new CLM, they may not use it.

Avoid these challenges by planning for change management and learning from winning user adoption strategies.

Process

Put good in, get good out. You need to organize your legal workflows before you set them up in a contract management system.

• Lack of clarity into the contracting process. If you aren’t clear on what steps a contract needs to pass through, you can’t program them into an automation. If you don’t have everything figured out, that’s okay. You can always start with a single, simple automation.
• Messy documentation. Contract automation consolidates, but you need to have good documentation, templates, and clauses to plug into it.

Avoid these challenges by laying the groundwork to make integrations easier.

Platform

The platform you choose can contribute to contract lifecycle management implementation difficulties.

• Complex tools. Not all contract automation platforms are created equally, and some have a steeper learning curve. Read customer reviews, ask for demos, and be realistic about your team’s willingness to learn new platforms.
• Lack of integrations. Your contract management implementation should make workflows simpler, not more complex, so missing or cumbersome integrations are a problem.
• Limited customization and support. If editing a workflow in your CLM is a big lift, you’ll fatigue your people or the goodwill of your tech team. An unresponsive CLM support department also adds frustration.

Avoid these challenges by carefully evaluating contract automation solutions.

Performance

Before you consider a contract management software implementation successful, you have to know what ‘success’ looks like.

• No ROI tracking. Without hard data or at least compelling stories to share with leadership, people’s opinions can color the perception of your CLM.
• Missing benchmarks. Not having a ‘before’ picture to compare your CLM implementation to makes it hard to grasp workflow improvements.

Avoid these challenges by deciding on CLM implementation benchmarks and measuring ROI.

Planning

Whether it’s your first or fifth CLM implementation, you need to create a clear plan.

• Lack of implementation resources. If your implementation goals—whether timeline or scope—don’t match your actual availability, you’ll fall short.
• No implementation priority. Will you start with low-hanging fruit or start by centralizing existing contracts? Without a priority list of projects, it’s easy to get distracted by all the bells and whistles of your new CLM.

Avoid these challenges by assessing your implementation requirements.

There are plenty of contract automation success stories to learn from and entire communities dedicated to helping legal professionals improve their work.

We’ve compiled tips, stories, and stats from successful CLM implementations to avoid common contract lifecycle management implementation difficulties.

Plan for change management before, during, and after implementation

Adding a new contract automation platform to your workflow is just as much an organizational and mindset shift as it is a tech stack update. Here’s what to keep in mind before, during, and after implementation to make lasting change.

Before implementation: Lay the groundwork by collaborating across teams and making sure everyone has clear and relevant expectations. Aim for executive buy-in, talk to other departments to prioritize use cases, and share the why, what, and how of contract automation.

During implementation: Build momentum with quick wins, encouragement, and feedback channels. Launch workflows or templates one at a time, use regular check-ins to catch friction points early and celebrate team and individual efforts. You can also use an implementation consultant, which the Calm team worked with on their road to nearly 100% tool adoption.

“By partnering closely with our implementation consultant, we stayed accountable throughout the process. We picked the two most used and complex workflows and worked on them together, which helped me understand the intricacies of the product and build from there.”
Lauren Healey, Manager, Deal Desk, Calm

After implementation: Continue engagement and refinement to expand contract automation across workflows and teams. Track and share impact, share stories, and take what you learned from the first phase to expand further.

Read More: Key Strategies to Ensure a Successful CLM Implementation

Lay the groundwork to make integrations easier

In theory, one of the major perks of contact automation platforms is integration with the tools your organization already uses, which means less manual data entry or information shuffling.

In practice, some integrations are easier than others.

Contract automation integration is easier if the tool you choose has built-in integrations with strong documentation and support. It’s always a bonus if your internal technology teams can help, too.

Tip: Prioritize critical integrations first, such as syncing contract data with Salesforce or routing signed contracts to a shared drive like Google Workspace or SharePoint.

Tip: Choose a platform with robust APIs or prebuilt integrations for commonly used tools like DocuSign, Coupa, Workday, SAP, or NetSuite.

Tip: Use low-code or no-code integration options so operations or legal teams can build connections without deep technical support.

Contract automation integration is more difficult if your team needs to build integrations or work with complicated connections.

Tip: Talk to your tech team before you choose a contract automation system to discuss your need-to-have connections vs. nice-to-haves and to let them explore integrations and APIs.

Tip: Map out data flows early to ensure you capture contract metadata, approvals, and obligations across systems.

Learn from winning user adoption strategies

We’ve covered the organizational shifts and tech requirements of contract automation implementation, but we can’t forget about the people. Here are tips from people who’ve successfully implemented legal tech.

Choose an automation champion

Getting clear on who will manage the change, what they’ll do, and what support they need avoids confusion down the line. Having an automation champion also creates excitement that can ripple outward.

Read More: How Legal Ops Pros Roll Out Their CLM Across the Org

Communicate and educate—early and often

Learning a new tool can take time, even if it has the most intuitive design in the world—plan for upfront and ongoing training time with anyone who will interact with the contract automation software. Consider using different teaching methods, like lunch and learns, office hours, recorded walkthroughs, and one-on-one training, to help people who learn differently.

Choosing an easy-to-use tool and then being hands-on with education helped Cofense achieve 100% adoption of their CLM.

“We really work to make sure our Sales and Procurement teams are sticking with the Ironclad platform. I’m on Ironclad all the time, and I regularly train our teams to ensure the right approaches and steps are being taken. Today we have 169 active workflows. And we don’t have a problem with adoption anymore,” said Heather Quinn, contracts administrator at Cofense.

Tip: Help people with something they hate

One valid strategy to get people excited about new legal tech is listing all the potential benefits and upsides that other organizations have gained. Or, you can help them avoid something they hate. Ask your coworkers what tasks aggravate them the most, like hunting for the latest version in an email thread. Then, show them how contract automation can make those to-dos go away.

Do legal pros trust AI? Learn about how teams are (and aren’t) using GenAI in our State of AI in Legal Report.

Decide on CLM implementation benchmarks

Knowing how you’ll measure the success of your contract management system implementation before you start guarantees you can collect the info you need as it happens.

CLM implementation benchmarks like time to set up your first automation, number of contracts put into the repository, and timeline of tools integrated.

CLM adoption and engagement metrics like user adoption rate, number of people onboarded, and satisfaction survey scores or feedback from stakeholders.

Operational efficiency metrics like average contract turnaround time and number of manual tasks eliminated.

Data hygiene benchmarks like the percent of legacy contracts uploaded and tagged or the number of standardized contract templates created.

Measure ROI and tie your work to business cases

Money talks. If you want to gain or keep buy-in for contract automation software, you need to understand organizational goals and fears and validate your work via measurement.

Tying your work to wider business cases can also make your CLM implementation more successful in the long run. McKinsey research found that 76% of transformation initiatives were successful if they fit with organizational goals and used multiple approaches to shift mindsets and behaviors.

Executives care about accelerating revenue, minimizing risk, and doing more with the same (or less) resources. If you can tailor your pitch to those outcomes, you’re more likely to get people on your side.

Legal team ROI

What it is: Comparison of legal input to company revenue to track the impact and efficiency of the legal team.

• Legal team ROI = (Annual recurring revenue) / (Annual legal team cost)

Why it matters: Understanding the ratio of legal effort to business results helps you understand workload demands and advocate for more resources.

Percent legal involvement

What it is: How often the legal team is required for an end-to-end contracting process. You can use a single equation to measure overall legal involvement, or break it down by type of involvement or contract.

• Percent legal involvement (PLI) = (Number of contracts that involved legal / Total contracts processed) x 100

Why it matters: Legal teams often get bogged down with low-risk contract reviews, but they provide the most value when using their expertise to work through complex legal scenarios. It’s advantageous to only pull them in for review when it’s truly needed. Once you have workflow rules in place, this data also signals the complexity or importance of the contracts you work on.

Contract value leakage

What it is: Value of revenue or cost leakage identified with clause monitoring

• Contract value leakage = Cost leakage + Revenue leakage
  • Cost leakage = Projected cost – Actual cost
  • Revenue leakage = Projected revenue from contracts – Realized value

Why it matters: Contract value leakage directly impacts a company’s financial performance, with organizations typically losing 5-9% of annual revenue due to poor contract management. Identifying and addressing these leakage points enables legal teams to transform from cost centers into strategic value creators by improving contract terms, negotiation strategies, and compliance monitoring.

Tip: Get more legal benchmark equations in the 2025 Legal Ops Field Guide

Carefully evaluate contract automation solutions

Ready to make a change? Check. Excited for the possibilities? Double check. Now, onto the more intimidating step of evaluating and choosing a contract automation tool. Here’s what to keep in mind.

Key factors to consider when assessing solutions

• Usability. If a tool is difficult to use, adoption will be low, and your investment will be wasted. You can learn a lot about usability from demos and customer reviews.
• Customization. Your work will be easier and more organized if the contract automation solution lets you create different contact templates, set up user parameters, and send negotiable and non-negotiable contracts.
• Integrations. Built-in integrations with your other software save time and reduce errors from shuffling information. The tools you might want to connect with include:
  • Customer relationship management (CRM)
  • Cloud storage
  • E-signature
  • Business spend management (BSM)
  • Data visualization
• Support. Strong onboarding and responsive support teams make a huge difference in long-term success. Ask about dedicated customer success managers, implementation resources, and how quickly support responds when issues arise.
• Pricing and scalability. Your needs will evolve—your contract solution should, too. Make sure pricing aligns with your usage and that the platform can scale across departments and contract volumes without hidden costs or feature restrictions.
• Artificial Intelligence (AI). Even if you’re new to legal AI right now, you might want to incorporate it in the future. Look for a tool focused on innovation and security—here’s a guide to selecting the best AI tool for contract review.

Essential features vs. nice-to-have features

Feature wish lists will vary between organizations, so you need to understand where you are and where you want to go. For example, you might be willing to sacrifice customization for price because you only have simple workflows. Or, you might want easy-to-use reporting to make sense of efforts across a big company.

Figure out where you are. Start by mapping your current contract processes. How complex are your workflows? Who’s involved? Where do bottlenecks occur? Identify the minimum functionality you need to solve today’s problems—such as self-service templates, version control, or basic approval routing. These are your essential features.

Consider where you want to go. Next, think ahead. As your volume grows or your contracts become more complex, you may need more automation, integrations, or robust analytics. Features like clause libraries, advanced reporting, or AI-assisted review might not be urgent now—but could be critical in 6–12 months. These are your nice-to-have (or soon-to-need) features.

Questions to ask potential contract automation vendors

New to contract automation? Here’s how to vet your potential vendors.

Usability

• What feedback have you received from similar companies about usability?
• Can you walk us through a typical user flow for creating, reviewing, and approving a contract?
• Are there in-app tips, guided actions, or help resources available?

Customization

• Can we create and manage our own contract templates and clause libraries?
• How easy is it to modify workflows or templates once they’re live?
• Are custom approval routes or conditional logic supported?

Integrations

• Which tools do you integrate with out of the box?
• How are integration updates and maintenance handled?
• What integration methods are available—native, API, or third-party connectors like Zapier?

Support

• What does onboarding look like for a company of our size and structure?
• What support channels are available (email, chat, phone)? What’s your average response time?
• Are there help center resources or a customer community we can access?

Pricing and scalability

• How is your pricing structured?
• How do you handle usage spikes or growing contract volumes?
• Are there any limits on templates, workflows, or integrations?
• How have other organizations handled multiple languages, regulations, or currencies in your platform?

AI

• What AI capabilities do you offer today?
• How does your AI handle data security and privacy?
• How do you plan to expand or improve your AI functionality in the future?

Data security

• What data compliance accreditations do they have?
• Do they make it easy to self-assess and confirm?
• Which data security features are included?
• Can you manage permissions?
• What is their security score?

Implementation

• How long does a typical implementation take for an organization of our size or complexity?
• What levels of assistance do you offer?
• Can you walk us through a typical implementation process for a team like ours?

How contract automation software is priced

When you begin evaluating contract management software pricing, the first thing to know is that there are two structures—flat rate and custom. Within those two price structures, there are a handful of factors that determine the final cost:

• Number of users (a.k.a. “seats”)
• Number of contracts and workflows
• Integrations
• One-time fees
• Tools and features
• Contract length

Read More: How Much Does Contract Management Software Cost?

Total cost of ownership considerations

Anyone who has made a big purchase—like a house, car, or college degree—knows that the actual cost tends to go beyond what’s listed on the sticker. Buying contract automation software is no different.

Extra costs like additional licensing over time, on-premise infrastructure, and cloud data can all add to the all-in price of legal software.

Beware that a lower total cost of ownership isn’t always indicative of success. Organizations might–and should–be willing to accept a higher TCO if it means that every single one of their business requirements is not only met but exceeded, helping them achieve their long-term business goals faster. Recognizing that TCO analysis is actually a part of a broader ROI strategy is a key part of understanding its value.

Assess implementation requirements

Every legal tech implementation is different since your work volume, resources, and goals vary. How easy your new tool is to use and customize impacts your timeline, too. These are questions to ask to gauge your implementation requirements.

Ask yourself:

• What’s our current contract volume and complexity?
• Which contracts or workflows do we want to set up right away? Which can wait 3, 6, or 12 months?
• Who will lead implementation? What support will they have, and how much time can they dedicate upfront?
• How comfortable is our team with workflow configuration? Will we need IT resources?
• What integrations do we need to set up?

Tip: Choose a single project to start with. CallMiner ripped and replaced their CLM in just two weeks by using a no-code platform and a clear vision of the workflow they wanted to create.

Ask your contract automation software provider:

• How long does a typical implementation take for an organization of our size or complexity?
• What levels of assistance do you offer?
• Can you walk us through a typical implementation process for a team like ours?

Read More: How 3 Lean Teams Set Ironclad Up in Weeks – with $0 in Implementation Costs

Generally, legal teams face similar contract lifecycle management implementation difficulties like resistance to change, complicated tool setup, or unorganized processes. There’s always going to be some variability based on your unique circumstances, though.

Here’s how to get ahead of CLM implementation issues:

Spot potential problem areas. Ask other departments or teams who have rolled out tools about their experience. What went well and what didn’t? It’s not a one-for-one with CLM challenges, but it can give you a sense of the culture for change in your organization. Also, talk to stakeholders about what excites them or gives them pause about the upcoming change.

Prioritize the biggest challenges. Realistically, you might face a few different problems during contract management software implementation. In that case, you need to assess the intensity and scope of the challenge to choose what to focus on. For example, the entire sales team lagging on onboarding is a more pressing problem than finalizing a few contract templates.

• High impact, high risk = Solve first
• High impact, low risk = Solve next
• Low impact, low risk = Tackle later or park

Talk to people with CLM implementation experience. If you want help sorting through your implementation priorities or assessing what a realistic rollout could look like, schedule time to talk to a digital contracting specialist.