3 Lessons I’ve Learned About Leadership in Legal Tech

By Etia Rottman Frand, VP Litigation Partnerships, Darrow.

The most important litigation decisions are often made long before a case is filed. This is particularly true for firms that operate on a contingency fee basis, where case outcomes dictate their ability to continue to advocate for future cases. For the past four and a half years, I’ve led a team that works directly with plaintiff attorneys at this moment of decision. Our job is to understand how they operate, which cases are right for their practice, and present them with suitable potential matters, identified through Darrow’s legal intelligence. Our work sits at the intersection of law and business, and requires making constant judgment calls.

This vantage point has shaped how I think about team building and leadership.

Every conversation my team has with a firm involves tradeoffs. The responsibility is to present information clearly enough for a partner to make an informed choice. Overstating confidence or glossing over uncertainty may move a conversation forward in the short term, but it can erode trust and weaken the partnership over time.

This means prioritizing judgment over process adherence. I look for team members who can read a room, understand the needs of our partners, and make decisions without needing explicit instructions.

Legal technology should serve the same goal. The strongest platforms help professionals evaluate and connect signals that indicate legal violations, weigh risk, and make informed calls when certainty is unavailable. Human judgment remains central to the practice of law. Technology’s role is to support it, not replace it.

1.      Hire for Judgment

Darrow operates in a fast moving environment and requires individuals who can keep up. That reality lends itself to how I think about the hiring process on my team. I look for people who can deeply understand processes, but that can also assess a situation and decide whether to follow them or recalculate.

One of the ways we assess this is to give candidates a real situation with minimal background information, as they would have in their everyday work. We create a simulation where we act as potential clients, and the candidate is a member of our team, and we engage in a conversation about a potential matter we believe the client could successfully litigate. Candidates are given almost complete freedom to structure this conversation as they see fit.

Being put in a situation like this gives us a unique window into someone’s decision making processes and independent judgment. Since every candidate structures the conversation differently, we, as interviewers, are also inevitably unscripted, which creates opportunities for both sides to assess and react to the situation without having a structured path for every scenario.

I pay close attention to how candidates handle uncertainty. Do they know how to open a conversation with an attorney who has no context of Darrow? Do they explain who we are in a way that reflects the firm? When the discussion shifts unexpectedly, do they adapt?

This is important because the role sits at a critical junction in the lifecycle of a potential partnership with a firm. Strong judgment ensures that case opportunities are presented with a clear understanding of risk and reward. It allows my team members to engage partners in a way that respects both their time and investment decisions.

2.      Design for Dissent

In high stakes environments, dissent doesn’t emerge organically. It has to be deliberately designed into the organization, and communicated as something that’s not only permitted, but expected, regardless of role or seniority.

In most intelligence organizations, analysts identify important early warning signals, and despite usually not having decision making authority, they are often present in the decision making room. Not as a symbolic gesture, but because they are encouraged to opine and confirm or dissent from conclusions and recommendations as they take shape. 

This design serves a second, equally important function: it counters hubris. Authority, speed, and confidence can often create a chilling effect and discourage others from signaling that something may not fit the prevailing narrative. When dissent is treated as friction rather than signal, organizations lose their ability to self correct. Over time, certainty replaces curiosity, and risk accumulates unnoticed.

Legal and technology-driven organizations face the same dynamic. Early litigation decisions depend on recognizing weak signals before they become obvious. Designing for dissent ensures that alternative interpretations, edge cases, and uncomfortable data points are surfaced early, when they can still shape outcomes.

3.      Technology Supports Human Judgment

Technology plays a critical role in early litigation decisions, but only when its purpose is clearly defined. Its value lies in making information legible, connecting signals, and reducing friction preventing evaluation. It does not decide what should be done.

I first learned about The Emergence and Transformation of Disputes: Naming, Blaming, Claiming by Felstiner, Abel, and Sarat during law school. The article offers a useful lens for understanding how disputes come into being. Before a case exists, an experience or an accumulation of facts must first arise to a pattern, which must  be recognized as an injury (naming). Only then, can it be attributed to a responsible party (blaming), and only then can it be asserted as a claim (claiming). Most potential disputes never reach the final stage because the earlier transformations fail to occur.

This is a reminder that harm must first become intelligible before it can be addressed. When signals remain fragmented, meaningful evaluation is impossible.

Legal tech can reduce the friction that prevents action by surfacing patterns and placing information in context. The decision what to do with that information is still ours.

At Darrow, technology is used to connect scattered public data and organize disparate signals into a coherent picture that can be evaluated and ultimately, developed into litigation.

Leadership is about decision quality when certainty is unavailable. And technology should support judgment the way flight instruments support pilots, who are trained for moments of spatial disorientation, when the body’s instincts can signal ascent while the aircraft is actually descending. In those moments, instruments don’t replace the pilot – they restore orientation when intuition becomes unreliable. Data and tech play the same role in complex decision making: not telling leaders what to do, but helping them stay aligned with reality.

Explore how legal intelligence is reshaping early litigation decision making at Darrow.

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[ This is a sponsored thought leadership article by Darrow for Artificial Lawyer. ]