How to Upskill Legal Teams and Modernize Legal Operations

The pressure on legal departments to modernize isn’t new. What has changed is the visibility and consequence of the skills gaps that departments must address. To succeed in this environment, leaders must find ways to upskill legal teams and bridge the divide between current capabilities and future needs.

Many legal departments currently lack the talent, structure, and tools needed to meet rising modernization expectations, according to Robert Half research of more than 140 in-house legal leaders in the U.S. Artificial intelligence (AI) and legal tech integration, and legal operations and efficiency, are priorities for many in-house legal leaders this year. But they face challenges in delivering these initiatives—57% say their team struggles to adopt and execute legal operations practices and 53% lack sufficient legal tools and technology to do their jobs.

What’s more, 84% of in-house legal leaders report skills gaps in their department, with legal operations and workflow efficiencies as the most significant gap, closely followed by legal technology proficiency. While distinct, both gaps point to the same underlying issue: Modernization for legal teams requires legal ops to design the process, and technology to execute it at scale.

As legal leaders strategize how to operate with greater agility, efficiency and long-term resilience, the path forward requires a talent-first approach to close critical skills gaps and redesign team structures that blend legal, technical, and process expertise.

The modernization mismatch

Legal technology falls squarely within the legal ops function, but many professionals are concentrating on the process side of legal ops rather than the tech capabilities where employers are feeling the pinch. Nearly half of legal professionals surveyed by Robert Half are building legal research and analysis skills, and a third are working on legal operations proficiency. Only 28% are developing legal technology fluency—including AI, eDiscovery, Contract Lifecycle Management (CLM) and matter management platforms—the very areas leaders flag as the biggest deficit.

Your department can address that mismatch by making technology upskilling easier to access and harder to ignore. Pilot projects that let people see firsthand how AI or automation can improve their daily work are more persuasive than any training manual. Reverse mentorship programs that pair senior lawyers with tech-fluent junior staff can build confidence where it’s most needed. The goal is to make technology fluency feel like a natural extension of legal work, not a separate skill set bolted on from the outside.

Rethinking team structure

Closing the skills gap also includes rethinking how legal teams are staffed. A blend of permanent and contract professionals gives you the flexibility to respond to what’s changing without overcommitting to resources you may not need long term. Contract hires are particularly useful for short-term needs like technology rollouts, system migrations or building out new workflows—and the knowledge transfer that happens during those engagements often outlasts the engagement itself.

Bridging the gap also means broadening the talent pool. Legal operations professionals are in demand—and can be difficult to recruit. The strongest legal ops teams don’t recruit exclusively from traditional legal pipelines. People with backgrounds in project management, IT, process design or data analysis bring skills that are hard to develop through legal training alone. Hiring for adjacent expertise and upskilling those professionals in legal concepts and workflows can close gaps faster than waiting for the perfect candidate to appear.

Developing skills in a moving target environment

One of the biggest challenges with helping your team become more tech-savvy is that technology is constantly changing, and that includes new tools that assist legal functions. Continual learning is critical because the pace of change won’t slow down to let your team catch up.

Agentic AI is a good example. Much of the conversation around AI in legal has focused on tools that help with targeted tasks such as reviewing a contract clause or summarizing a deposition. The next shift is likely toward agentic AI: systems that don’t just respond to individual prompts but independently execute multi-step workflows with minimal human direction.

In an in-house setting, this could look like a contract moving through its entire lifecycle with AI orchestrating each stage. A new agreement arrives through intake, gets classified by type and risk level, is compared against the department’s own precedent terms, receives initial redlines, and gets routed to the right reviewer. The lawyer still makes the judgment calls. But the process surrounding those calls is handled end-to-end by AI.

Keeping pace also means breaking down the walls between legal ops and the rest of the business. As legal technology tools become more embedded in workflows, decisions about what to automate and where to invest require input from beyond the legal department. That means collaborating with IT on implementation, with finance on spend management and with procurement on vendor evaluation. Legal departments that continue to operate in isolation will struggle to absorb the changes ahead, regardless of how much they spend on tools.

Start on Monday, not next quarter

Building a more tech-fluent, adaptable legal ops team doesn’t require a multi-year roadmap. Here are five moves legal operations leaders can make right away.

• Assess your team’s technology fluency. Find out which skills your employees possess, not what you assume they have. Start conversations about their current skills and their professional development goals or send out a survey to the team. This assessment can help identify upskilling opportunities and guide the development of a practical roadmap forward.
• Conduct pilot projects with new technology. The results of the skills gap assessment above can also tell you where pilot projects will have the most impact. Pick one workflow, such as contract intake or document review, and run a small-scale test with an AI or automation tool. Let your team learn by doing rather than sitting through a training deck.
• Launch a reverse mentorship program. Match senior lawyers who bring deep legal judgment with junior team members who may generally be more comfortable using new legal tools and technology. Both sides benefit, and it builds the kind of cross-generational trust that makes adoption stick.
• Adopt a flexible staffing model. If your team lacks the technical expertise for an upcoming rollout or migration, a contract professional can quickly meet that need while transferring knowledge to your permanent staff. And when you’re hiring for permanent roles, widen the search beyond traditional legal backgrounds. People with experience in project management, IT, or process design can bring the skills your team is missing.
• Talk to your counterparts in IT, finance, and procurement. When making technology decisions, partnering with the teams that manage implementation, budgets, and vendor relationships can streamline processes and integration—so your tools deliver impact faster.

What comes next

The gap between what legal operations needs to keep pace with modernization and what teams can deliver today is real—but it is manageable. Leaders who invest in technology fluency, strengthen workflows, and build cross-functional partnerships will narrow it deliberately and sustainably. Modernization isn’t a one-time initiative. It’s an operational capability, and developing the right talent is what makes that capability durable.