Legal tech that works

The legal technology landscape

Not that long ago, legal department technology consisted of a phone, a filing cabinet, and maybe a shared drive if you were progressive. Fast forward a few decades, and we have artificial intelligence, contract lifecycle management, e-signatures, dashboards, and data analytics. The pace of technological change has been breathtaking, and for many corporate legal departments, overwhelming.

Legal departments are also under more pressure than ever to perform multiple functions. Matter volumes continue to rise, regulatory obligations expand across industries and jurisdictions, and budgets are flat or shrinking. At the same time, general counsel is expected to operate as strategic business partners, not simply as “risk spotters” or contract drafters. This combination forces us to conclude that legal departments must work differently than in the past, and technology is a critical part of the solution.

Previously, we discussed how to build a compelling business case for obtaining legal tech. Now we tackle the other side of the coin — a practical roadmap for selecting and implementing legal tools that work, and ones that solve problems instead of creating more. Done right, legal technology can materially improve efficiency, reduce costs, and help legal teams spend more time on higher-value work. Done poorly, the technology becomes another expensive misstep, gathering dust on the Island of Misfit Legal Tech.

This paper addresses the core pain points facing legal departments today, reviews the major categories of legal technology solutions, and lays out a step-by-step process for selecting and implementing tools that align with business priorities, deliver measurable results, and — most importantly — are used by the department daily.

Key pain points facing corporate legal departments

Before talking about solutions, it is important to understand the problems. Technology, legal or otherwise, only adds value when it addresses real pain points. Choosing to buy software without understanding the problem you are trying to solve almost always leads to wasted time, wasted money, and wasted opportunity.

Manual and inefficient processes

Believe it or not, many corporate legal departments still rely on manual processes to manage core work. Spreadsheets track matters and budgets. Email drives approvals. Shared drives hold contracts with inconsistent naming conventions. Lawyers spend a surprising amount of time on administrative tasks that do not require legal judgment, like finding all the amendments to a critical agreement or looking for standard clauses to add to a contract.
Manual processes create predictable challenges and problems:

• They consume valuable lawyer time that could be spent on strategic work.
• They introduce errors through inconsistent data entry.
• They make reporting slow, incomplete, or impossible.
• They cannot scale as matter volumes increase.

While technology cannot replace legal reasoning, it can eliminate friction against lawyer time created by repetitive, low-value tasks.

Regulatory complexity and risk management

Regulatory obligations continue to grow in both scope and complexity. Data privacy, cybersecurity, environmental, social, and governance (ESG), artificial intelligence, employment, consumer protection law — such as TCPA — trade, antitrust, and anti-corruption requirements all compete for limited attention and resources.

Managing such risks manually makes it harder to track regulatory change, monitor compliance consistently, identify emerging issues, and demonstrate compliance to regulators, auditors, and boards. Legal technology does not eliminate risk, but it improves visibility, consistency, and documentation in ways that manual processes cannot. Technology also works at speeds that cannot be matched by manually performing the same task.

Outside counsel spend and lack of visibility

Outside counsel spend remains one of the highest controllable costs for many legal departments. Yet many teams struggle to answer basic questions about where money is going, which matters drive the most spend, average costs, outside counsel guideline compliance, forecasting, spending accruals, whether work is being staffed efficiently, or even generating basic reporting and dashboards.

Without reliable data, legal leaders manage spend reactively — relying on spreadsheets and the goodwill of outside firms to do the right thing. With the right technology, they can manage it proactively, making informed decisions about sourcing, staffing, and budgeting — while keeping outside counsel on their toes.

Major categories of legal technology solutions

The legal technology market is crowded, hot, and noisy. Vendors often describe very different products using the same buzzwords. Every product has AI, and every product solves all your problems. In-house lawyers should focus on core categories of technology that solve critical pain points, and not just the newest shiny bauble that looks cool but doesn’t do what you need.

E-billing, spend, and matter management systems

If legal technology has a foundation, this is it. E-billing and matter management systems create a centralized way to track matters, manage invoices, and analyze legal spend. For many departments, this is the first technology investment that delivers immediate and measurable value.

One common mistake to avoid is treating e-billing as a “finance-only” tool. When lawyers are hands-off and not involved in matter setup, guidelines, and reporting, an e-billing system becomes a back-office exercise instead of a strategic asset. With the right focus and attention, however, these systems replace disconnected spreadsheets and email-based invoice reviews with structured data and consistent workflows. They give legal leaders visibility into how work flows through the department, who the big users of legal resources are, what types of matters are most prevalent, and where money is actually spent.

What these tools do well:

• Capture matter data in a consistent, searchable format
• Enforce billing guidelines automatically
• Reduce invoice review time through rules-based automation
• Provide real-time reporting on spend, firms, and trends
• Support budgeting and forecasting with reliable data

Here’s what this looks like in practice. A general counsel preparing for a budget review can quickly answer questions about top-spend firms, matter mix by business unit, and cost drivers with access to a state-of-the-art e-billing system. Invoice review that once took hours now takes minutes, with lawyers focused only on true exceptions.

Key evaluation criteria:

• Ease of use for lawyers, not just administrators
• Flexibility in matter types and data fields
• Quality and usability of reporting tools
• Integration with finance and procurement systems
• Vendor experience with similarly sized legal departments
• Integration of artificial intelligence capabilities

Legal research and know-how solutions

When it comes to legal research tools, a common mistake to avoid is assuming lawyers will naturally adopt a new research tool. Without training and clear expectations, teams default to old habits, even when better resources exist.

Every in-house lawyer does research. The question is how quickly and confidently they can find reliable, practical answers. General internet searches provide background, but they rarely deliver guidance that is ready to use. While there are a lot of helpful materials online, there is also a lot of nonsense. Sorting through it takes time. Traditional research tools, however, focus on case law, statutes, and secondary sources — resources in-house lawyers seldom need. Modern research and know-how tools for in-house legal departments focus on practical application rather than academic analysis.

What these tools do well:

• Deliver curated analysis written for in-house lawyers
• Provide checklists, templates, and practical guidance
• Track jurisdiction-specific legal developments
• Reduce reliance on outside counsel for routine questions and templates

Here is what this looks like in practice. With the right legal research tool, a commercial lawyer supporting multiple regions can get up to speed quickly on unfamiliar warranty requirements of different countries. An employment lawyer can confirm best practices in multiple jurisdictions before advising the Human Resources department. A litigation attorney can get a checklist of how to properly run an internal investigation. The team spends less time reinventing the wheel and more time applying their judgment.

Key evaluation criteria:

• Coverage aligned with your industry and geographic locations
• Practical resources rather than pure case law and statutes
• Search functionality that delivers relevant results quickly
• Frequency and reliability of updates
• Ability to support generalists working outside their specialties
• Smart use of artificial intelligence

Drafting and document automation tools

When it comes to drafting and document automation tools, a common error of in-house lawyers is over-automating. Forcing complex deals into rigid templates creates frustration and the need for multiple workarounds, which eat away at the efficiency such tools are designed to provide. Instead, start with high-volume, low-complexity documents.

While drafting contracts is the lifeblood of most in-house legal departments, not all drafting adds equal value. Many agreements follow repeatable patterns, yet lawyers constantly start from scratch. Drafting and automation tools standardize templates while preserving flexibility and increasing turnaround time dramatically.

 What these tools do well:

• Centralize and govern templates and clauses
• Automate first drafts using structured inputs and department contract playbooks
• Reduce negotiation cycles through consistency
• Lower the risk of outdated language
• Use AI smartly

Putting this into practice with the right tools allows business teams to generate first drafts of routine agreements using approved templates and clauses. Lawyers can then focus on exceptions and risk analysis rather than the low-value grunt work of formatting and repetition. Deals move faster, and money comes in the door quicker, which wins the hearts and minds of the business.

Key evaluation criteria:

• Ease of creating and maintaining templates
• Flexibility for non-standard deals
• Integration with document and signature systems
• Easy adoption by lawyers
• Self-service for business users
• Artificial intelligence as a key component

The role of the AI assistant

Any useful legal tech today will include artificial intelligence as a key component. It also has a role as a standalone assistant — think of a super smart, eager intern. But the most common error in the use of artificial intelligence tools today is treating AI as a replacement for judgment. While AI accelerates work, it has little to zero comprehension of context, nuance, or risk tolerance. Something in-house lawyers typically excel at. Any use of AI — on its own or as part of a tool — requires that lawyers or other users recognize that they remain 100% accountable for the work product. Just like you would never send the first draft of a document from an intern to the CEO without review and revision, the same is true for AI output.

That said, AI assistants have moved quickly from novelty to necessity. When used thoughtfully, they augment legal teams by increasing efficiency, reducing friction in drafting, and speeding up routine work. No in-house legal department can function properly without some type of AI assistant tool.

Practical use cases today:

• Summarizing long documents or correspondence
• Assisting with legal research and issue spotting
• Drafting or revising language under supervision
• Answering routine internal legal questions
• Surfacing internal know-how and prior work
• Brainstorming

For example, with the right AI assistant a lawyer preparing for a call can quickly summarize a lengthy agreement or prepare an issues checklist to guide the conversation. A junior lawyer can generate a first-pass issues list that a senior lawyer reviews and refines. In short, the department moves significantly faster without adding bodies and without cutting corners, if they use the tool properly.

Key evaluation criteria:

• Reliable and trustworthy vendor
• Strong data security and confidentiality protections
• Transparency around sources and limitations
• Clear boundaries for appropriate use
• Seamless integration into existing workflows

As has been said by many, you need to work collaboratively with AI, not just hand work to AI.

A structured process for selecting and implementing legal technology

Every failed legal tech implementation shares the same root cause — the legal department bought software before it fully understood its own processes. This means that the key to selecting and implementing legal technology is spending time understanding the legal function’s processes and actual needs, such as the problem that you are trying to solve.

Here is your checklist to do just that:

• Identify needs and align with business priorities
  • Start with the business. Legal technology investments should support organizational goals such as growth, efficiency, risk reduction, or cost control. Alignment makes approvals easier and outcomes more meaningful.
• Stack-rank needs to determine sequencing
  • You cannot do everything at once. Prioritize initiatives based on impact, urgency, and readiness. Foundational tools often enable more advanced capabilities later.
• Develop a defensible business case
  • Avoid overselling savings. Conservative, credible numbers build trust and make success easier to demonstrate.
  • Translate legal pain points into business terms, including costs, risks, and efficiency gains. Show your math and the expected ROI on the investment.
• Create a clear requirements document
  • A short, focused requirements document keeps evaluations grounded and prevents scope creep. Clarity beats comprehensiveness every time.
• Market research and evaluation
  • Use demos, trials, and references. Test real scenarios. Include actual users in evaluations.
• Vendor due diligence and purchase
  • Confirm total cost of ownership, implementation support, data rights, and exit terms. Buy what works today, and not what is “coming soon” on the vendor road map.
• Implementation, training, and user acceptance
  • Adoption beats features. No legal department fails because software lacks features. Many fail because lawyers quietly stop using it.
  • Implementation determines success. Focus on communication, training, "super-users," and user feedback. Get your team to engage in the process so they have input every step of the way.
• A realistic 90-day, 6-month, and 12-month roadmap
  • The first 90 days: Foundation. Focus on clarity, ownership, and communication. Avoid early over-customization.
  • The first six months: Adoption. Configure, train, pilot, and fix issues quickly. Invest early in data quality.
  • The first 12 months: Optimization. Measure outcomes, expand usage, and share wins. Make the technology part of daily operations.

Technology is a strategic investment

Legal technology is not just a collection of tools. It is a strategic investment in how the legal department operates and delivers value. When chosen thoughtfully and implemented with discipline, technology increases efficiency, reduces costs, and allows lawyers to focus on what matters most.

There is no finish line. The goal is to build a strong foundation that supports the business today and adapts to what comes next. Technology serves people, not the other way around, and the best outcomes come when smart tools are paired with sound judgment and strong relationships with all the stakeholders.

To learn more about the best suite of AI-driven legal tech available to legal departments, explore CoCounsel Legal from Thomson Reuters.

Sterling Miller, COO and General Counsel – HILGERS PLLC

Sterling Miller is a four-time general counsel who spent almost 25 years in-house. He has published seven books, among his newest is “The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done” and writes the award-winning legal blog, Ten Things You Need to Know as In-House Counsel. Miller is a frequent contributor to Thomson Reuters as well as a sought-after speaker. He regularly consults with legal departments and coaches in-house lawyers. He received his J.D. from Washington University in St. Louis and an undergraduate degree from Nebraska Wesleyan University.