How to Run Legal Tech Trials That Drive Results

Breaking into the legal market isn't easy—especially if you're selling technology to law firms. The unique challenges of this market require a strategic approach that goes beyond standard B2B sales tactics. Law firms operate with distinct pressures and cultural norms that significantly influence how they adopt new tools.

At the heart of successful legal tech sales lies a critical strategy: leveraging evaluation phases like Pilots, Proofs of Concept (POCs), and Trials. These are essential trust-building mechanisms that can make or break your success in selling to law firms.

If you are already getting wins from pilots but are more focused on converting large deals or firm-wide agreements, we recommend looking at Part 2.

Understanding the Law Firm Landscape

Law firms present a unique confluence of characteristics that make them particularly cautious about adopting new technology:

• Deep-Seated Risk Aversion: The legal profession is inherently risk-averse. Lawyers face strict ethical duties of confidentiality and competence, with potential malpractice liability if errors occur. This translates into natural skepticism toward unproven technologies.

• Complex Partnership Structures: Unlike typical corporate hierarchies, most law firms operate under partnership models where decision-making requires building consensus among multiple influential stakeholders. This consensus-driven process can be slow and complex.

• The Tyranny of the Billable Hour: The dominant economic model for law firms intrinsically ties revenue to time spent, creating a complex relationship with technologies that promise efficiency. Technology that reduces billable time can be perceived as threatening revenue.

• Stringent Security Requirements: Law firms are custodians of highly sensitive client information. Attorney-client privilege and ethical duties demand robust data protection, with severe consequences for breaches.

These factors create a uniquely high barrier to entry for legal tech vendors. A successful approach must address them holistically, which is why evaluation phases are so crucial.

POCs, Pilots and Trials

As you explore how to demonstrate value with prospects, you will likely come across several terms which seem like they are used interchangeably. While it doesn’t matter what you call this stage of the sales cycle, it’s important that you and your client are on the same page as to what the scope is.

When you choose a POC vs Trial vs Pilot?

Here is how we would define each:

Proof of Concept (POC)

• Definition: A focused, short-term exercise (often lasting weeks) designed primarily to validate technical feasibility and core functionality within the firm's specific technology stack.

• When to Use: Early in the sales discussion, particularly when IT expresses concerns about technical viability, security, or integration challenges.

• Typical Scope: Limited to specific technical questions, often using sample or anonymized data.

• Key Stakeholders: Primarily IT, security teams, and technical champions.

Pilot

• Definition: A small-scale, real-world implementation within a specific segment of the firm (typically a practice group or team) over a defined period (one to six months). It answers: "Does this technology deliver value and will our lawyers use it?"

• When to Use: After technical feasibility has been established, when seeking buy-in from practice group leaders by demonstrating tangible benefits.

• Typical Scope: Focused on defined use cases relevant to the participating group, often using live client data (with appropriate security measures).

• Key Stakeholders: Practice group leaders, end-users, IT support, and potentially finance for ROI tracking.

Trial

• Definition: Temporary, often time-limited access (14-30 days) to the software, allowing individual lawyers to explore independently.

• When to Use: Best for user-friendly, standalone solutions where the value proposition is easily understood without significant setup or training.

• Typical Scope: Self-directed exploration of standard features, typically with sample data.

• Key Stakeholders: Individual users and potentially innovation teams promoting internal adoption.

This table summarizes the key differences:

Feature	Proof of Concept (POC)	Pilot	Trial
Primary Goal	Validate Technical Feasibility & Security	Validate Workflow Value, User Adoption & ROI	Allow Independent User Exploration & Generate Interest
Typical Scope	Limited features, specific technical hurdle/integration	Defined use cases within a specific practice group/team (5-40 users)	Subset of features, self-directed exploration by individuals/small teams
Typical Duration	Short (Weeks)	Medium (1-6+ Months)	Short, Fixed (Days/Weeks)
Data Handling	Sample, Anonymized, or Limited Test Data	Live Client/Matter Data (Requires stringent security & protocols)	Sample or User's Non-Sensitive Test Data
Key Stakeholders	IT (Security, Infrastructure), KM, Technical Champion	Partners, Practice Leaders, End-Users (Lawyers/Staff), IT, KM, Finance	Individual Users (Lawyers/Staff), IT (Security Approval), KM/Innovation
When to Use	Early Stage: Address IT/Security/Integration concerns	Mid Stage: Prove value/ROI to Partners/Users after tech validation	Early Stage: User-friendly tools, generate broad interest, empower champion

Timing Your Evaluation Proposal

Timing is critical when proposing an evaluation to a law firm. Understanding their decision-making processes helps you align your proposal with their priorities:

• Align with Budget Cycles: Law firms typically plan budgets annually or in line with the end of their financial year end. Timing a pilot so its successful conclusion occurs before major budget decisions allows the results to directly inform investment planning. (We assume that this is a unbudgeted project.) Connect to Strategic Initiatives: Technology adoption is more likely to gain traction if it directly supports one of the firm's declared strategic priorities. Frame your pilot proposal as advancing a specific firm goal.

• Understand Their Timeline: Law firm decisions are rarely swift. Expect timelines measured in months, with multiple stakeholders needing to weigh in. Plan your sales cycle accordingly.

Defining Success Metrics That Matter to Law Firms

Measuring Legal Tech Success During Evals

A successful evaluation requires clear, agreed-upon success criteria that resonate with law firms—this is often an overlooked stage. Without explicitly defining what success looks like, how will the firm know whether the evaluation achieved its goals?

Quantitative Metrics

• Efficiency Gains/Time Savings: Measure decreases in time required for specific legal tasks and link these to billable impact.

• Cost Reduction/ROI: Demonstrate financial benefits through direct cost savings or calculated return on investment.

• Risk Reduction/Quality Improvement: Track error rate reduction, enhanced compliance, or improved security posture.

• Adoption Metrics: Monitor active users, usage depth, and user retention throughout the evaluation.

Qualitative Metrics

• Lawyer and Staff Feedback: Gather direct input on perceived ease of use and value.

• Partner Endorsement: Secure positive feedback and vocal support from influential partners.

• Perceived Client Impact: Collect feedback suggesting improved client service or outcomes.

• Integration Success: Confirm smooth integration with essential firm systems.

Best Practices for Successful Evaluations

Executing a successful evaluation requires a strategic approach. It needs to combine rigorous planning with agile execution while remaining sensitive to the unique culture of the specific law firm.

• Deep Understanding of Firm Culture: Invest time in researching the specific firm's culture, practice areas, technology stack, and established workflows.

• Secure Executive Sponsorship: Identify and cultivate champions at multiple levels, particularly influential partners who can navigate internal politics.

• Involve IT from the Outset: Engage IT early and collaboratively, addressing their security and integration concerns proactively.

• Focus on Specific Practice Areas: Target your evaluation on high-impact use cases within a clearly defined practice group where your value proposition is most compelling.

• Provide Dedicated Support: Offer responsive, tailored support that respects lawyers' time constraints and demonstrates your understanding of their workflows.

• Set Clear Expectations: Maintain open communication and establish realistic expectations regarding objectives, timeline, and potential outcomes.

Common Pitfalls to Avoid

Even with careful planning, things won’t always go according to plan. There are certain challenges which we’ve seen arise over hundreds of evals:

• Partner Disengagement: When the initial champion becomes too busy with client work, the initiative can stall. Secure multiple champions and maintain regular, value-focused communication.

• IT Roadblocks: Security concerns or integration complexities can derail progress. Engage IT deeply from the beginning and provide comprehensive documentation.

• Unclear Value Demonstration: Without clear metrics, the benefits may remain abstract. Establish measurable success criteria upfront and track them diligently.

• Firm Politics Missteps: Failing to understand internal dynamics can lead to alignment with the wrong stakeholders. Map key influencers and rely on internal champions for guidance.

To Charge or Not to Charge?

Should you charge for evals?

One of the questions you will certainly be asked is whether you charge for evaluations. First, it’s important to understand the scope of the project (is it a POC, trial or pilot?), and then consider the pro/con of charging:

Arguments for Charging:

• Signals value and increases commitment

• Covers vendor costs for implementation and support

• Sets a pricing precedent for the full solution.

Arguments Against Charging:

• Facilitates market entry and reference acquisition

• Lowers barriers for novel technology adoption

• Positions the evaluation as a collaborative value exchange

Consider your company's stage, the solution's maturity, and the strategic value of the specific firm when making this decision.

Additionally, you will also come across firms which on principle refuse to pay for any pilots. Often, these are the larger firms you will be trying to win. In these instances, we suggest pivoting towards a shorter trial which can be a helpful compromise.

Building Long-Term Partnerships

A successful evaluation transforms the vendor-firm relationship from transactional to strategic. By demonstrating deep understanding of the firm's challenges, delivering measurable results, and navigating the complexities with professionalism, you position yourself as a trusted advisor capable of helping the firm leverage technology to achieve broader objectives.

For legal tech founders and sales teams committed to winning in this market, mastering the evaluation process is essential. Success requires more than the best technology; you have to prove that it solves a specific problem and align with your customers’ strategic objectives.

When executed correctly, an evaluation becomes the key that unlocks sustainable growth and lasting partnerships in the legal technology market.