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Streamline and Simplify: 6 Expert Tips for a Smooth CLM Software Implementation

To help legal leaders unlock the value they’re looking for, we asked experienced legal teams to share their top tips for implementing contract lifecycle management (CLM) software.

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Streamline and Simplify: 6 Expert Tips for a Smooth CLM Software Implementation
Tip 1: First, do no harm. What’s true in the Hippocratic Oath must also be true during CLM implementation. While most roll-out playbooks encourage project champions to start small, they often overlook risk management. “When deploying in phases with subsets of users, leaders are usually thinking primarily about adoption,” shares Shawn Hoyt, legal vice president, commercial at OutSystems. “While adoption is critical for success, I also think about what speed bumps we might hit early and what impact those could have on our operations.” A bite-sized beginning lets legal prove out the new technology – “but if you hit your first speed bump in a high-stakes area, you may still expose your business to significant disruption,” guides Hoyt. “By deploying first to lesser-stakes areas, you can recover easily from those first speed bumps and avoid them by the time you get to the higher-stakes areas.”
Tip 02: Define stakeholders and their role. Before implementation, project leads must identify impacted stakeholders. According to Harvard Business Review, resistance or reluctance from impacted parties is the primary culprit of stalled or failed projects. Ideally, an executive sponsor or champion meets with department leads and/or assembles a cross-sectional leadership team. Participants should represent key stakeholders from affected departments – including technical specialists, finance or procurement representatives, legal, sales, and customer- facing end users. While looping in stakeholders eases reluctance, defining role specifics is arguably more important. “Make it clear what everyone’s roles are, but don’t bog yourself down assuming everyone needs the same level of participation,” guides Hoyt. He encourages legal teams to lean on a responsibility assignment matrix (e.g., RACI) or another participation model to assign role types to those who are Responsible or Accountable versus those who need to be Consulted or Informed.
Tip 03: Provide distinct training to different users. Training is a must to ensure that end users are comfortable with your new platform. Inside global or dispersed enterprises, however, trainings tend to be held live once, then recorded and provided on-demand in asynchronous form. Meg Cavanaugh, deputy general counsel at Commvault warns against this. “Even if your company spans multiple time zones, don’t scrimp on interactive, live training. Make your training a two-way street – include Q&A and, where possible, ask users to prove proficiency.” Cavanuagh also notes that trainers should tailor sessions to specific workflows and use cases. “Break out educational sessions by role type. Have teams highlight pain points in the previous software, and show them how to solve these with the new tool. You have to speak their ‘language’ to keep them excited.” “Your new CLM is a cross-functional tool. Prove it by customizing training for various user groups. One-size-fits-all experiences won’t boost users’ skills or adoption.” -Meg Cavanaugh Deputy General Counsel at Commvault
Tip 04: “Adoption” is a general outcome — plan specific ones. For legal operations leaders looking for an efficiency edge, an AI-powered contract review and reporting tool (like LinkSquares Finalize) generates buzz. But when teams bring their contracts, clauses, and templates into a solution, they need to drill into what outcomes are most compelling. “Using a tool and maximizing benefits are two different things,” notes Hoyt. He encourages project champions to specifically define success measures, perhaps starting with robust, targeted reporting. “Partner with your solution provider and think through the dimensions and critical data points you may want to report on or take advantage of. While this may require some upfront work – like tagging or evaluating existing contract text – you’ll be more confident in the accuracy and usability of your reports and have impactful success metrics to point to.” The specific, measurable, wins become part of the ‘story’ as legal operations builds the case for further tool integration or wider platform expansion.
Tip 05: Prioritize Progress, not perfection. Many who have led enterprise software implementations highlight the importance of a data or document migration strategy. This phase involves extracting, transforming, loading, and validating data from multiple systems. Naturally, each of these may include different formats or obsolete and unused data. While attention to data migration is wise, Hoyt encourages project leaders to strike a balance: “Get moving early by batching your data migration and contract uploads as resources and timeframes permit instead of holding everything up until all of the data is perfect or vetted.” Nobody wants irrelevant files or dirty data, but teams must avoid wasting too much time cleaning up. As this phase drags on, your once-eager stakeholders lose enthusiasm waiting through the rationalization effort. “Even if you start with 20% of your contracts, your organization is unlocking business insights you didn’t have before. Take these wins – even if in phases.” - Shawn Hoyt Legal Vice President, Commercial at OutSystems
Tip 06: Remember: All you have to do is ask. Every enterprise implementation has sticking points. But the real problems arise when teams wait until they’re stuck to ask for help. Even the most efficient teams bump into issues, but what separates them is the readiness to invite resources to troubleshoot alongside them. When you’re staring down a huge milestone – like figuring out how to migrate 50,000 contracts or strategizing key clauses to extract – it’s scary,” acknowledges Cavanaugh. Don’t allow inertia, fear, or unnecessary self-reliance to take over. “Project leaders often underestimate just how helpful and competent support teams are. Don’t hesitate to lean on the implementation resources your vendor provides.” Confidence in navigating hurdles can be empowering, but it’s possible to go too far. Your provider wants to help – and while they do their best to anticipate your needs, “if you don’t ask, they can’t help,” reminds Cavanaugh.
ABOUT LINKSQUARES LinkSquares helps legal department leaders drive innovation, reduce backlog, lower costs, increase revenue, and minimize loss. If you’re ready to adopt the most effective solutions for the legal function – and harness cutting-edge artificial intelligence to improve every aspect of your department – then contact LinkSquares today.
ABOUT LINKSQUARES LinkSquares helps legal department leaders drive innovation, reduce backlog, lower costs, increase revenue, and minimize loss. If you’re ready to adopt the most effective solutions for the legal function – and harness cutting-edge artificial intelligence to improve every aspect of your department – then contact LinkSquares today.