Unlocking ‘Value in Failure’ in Legal Tech Spaces

By Siddharth de Souza, Shreya Vajpei, Nimrat Kaur Dhillon, and Rachit Sharma

Introduction

Walk into any legal tech conference and you'll hear the same soundtrack on repeat: funding announcements, product launches, client wins, accelerator acceptances. The ecosystem has become a carefully choreographed performance where everyone speaks in the language of triumph, each story polished to gleaming perfection for maximum impact.

But behind every "overnight success" in legal tech lies a graveyard of pivots, false starts, and hard-won lessons that rarely see daylight. The AI contract tool that took eighteen months to build but nobody wanted to use. The blockchain solution that judges ignored in favor of paper files. The "strategic partnership" that consumed a startup's resources while delivering nothing but customization headaches.

These stories exist in whispered hallway conversations but they're systematically edited out of the official narrative. 

At Justice Adda and the Indian LegalTech Network, we want to reframe the conversation. What if, instead of hiding our failures, we celebrated them? What if the very setbacks we’ve been trained to bury could become the foundation for deeper learning, stronger connections, and better solutions?   This led us to create India’s first LegalTech Fail Camp - a space to map setbacks using the “Value in Failure Canvas” at the Agami’s Justicemakers Mela in Bhopal, India.

We were inspired by the emergence of the CV of Failures, which Melanie Stefan reflects on, in her piece in Nature arguing that: 

‘As scientists, we construct a narrative of success that renders our setbacks invisible both to ourselves and to others. Often, other scientists' careers seem to be a constant, streamlined series of triumphs. Therefore, whenever we experience an individual failure, we feel alone and dejected.’

We strongly believe that when failure stories disappear from legal tech conversations, we lose our roadmap for innovation—founders repeat the same costly mistakes, investors shy away from necessary risks, and breakthrough solutions get buried under the fear of admitting what didn't work.

What does it mean in the Indian legal tech ecosystem?

India's legal tech ecosystem has developed a strange habit: it systematically throws away its most valuable asset—hard-won knowledge about what doesn't work. The numbers tell the story. Of 938 legal tech companies that got started, only 85 managed to raise funding, 16 reached the next major round, 8 made it further, and just 7 reached final stages. But here's the key insight: these aren't 931 "failed" companies—they're 931 separate teams who independently figured out the same painful truths. Multiple founders discovered that law firms change slower than startups need them to. Countless entrepreneurs found that what lawyers want differs from what they'll pay for.

Source : Legal Tech in India Overview - Tracxn

Without a sharing of failures, each startup is essentially expensive research into whether technology can solve old legal problems. When these findings disappear with every company closure, we force new entrepreneurs to learn the same expensive lessons from scratch.

When failure becomes shameful, everyone focuses on looking successful instead of being successful. Startups tout impressive-sounding metrics  (speed) instead of what matters (actual usage). Entrepreneurs play it safe with small improvements instead of big breakthroughs, because taking risks feels too dangerous. When failure knowledge gets locked away, the whole system stops learning.

Those 931 companies weren't failing in completely different ways—they hit the same walls, and made similar mistakes. If their insights had been shared, the next wave could have avoided obvious traps and solved genuinely new problems instead of rediscovering old ones.

What do we want people to get out of this?

1. Turn setbacks into shared assets 

We want entrepreneurs, technologists, and investors to recognize that setbacks—missed deadlines, unrealized features, rejected pilots— are not shameful endpoints but critical data points for learning. When entrepreneurs start logging and sharing these experiences, we transform individual setbacks into community wisdom. The goal isn't to celebrate failure for its own sake, but to provide the insights that make future successes more likely. 

2. Build a supportive, transparent community

Creating channels (workshops, forums, ‘failure fairs’) for candid storytelling will reduce isolation and stigma. When law firms, startups, and academic institutions openly discuss what went wrong, they collectively accelerate problem‑solving, identify systemic barriers, and refine best practices.

3. Encourage iterative experimentation

With failure normalized, stakeholders will feel safer to pilot cutting‑edge solutions—whether AI‑driven contract analytics or blockchain‑based dispute resolution—learning quickly from mis-steps and iterating towards robust models. 

4. Build an ecosystem that is resilient  

Ultimately, the goal is a healthier legal tech ecosystem: one that expects setbacks, learns from them, and integrates those lessons into more sophisticated, user‑aligned solutions. By reframing failure as progress, we hope to empower more founders to take calculated risks, more investors to back transformative ideas, and the community as a whole to drive meaningful change in how legal services are delivered across India.

Introducing the Value in Failure Canvas

In order to think from the standpoint of failure, we looked at metrics of what constitutes success, and then examined how we could think about similar issues from the point of view of things that did not work out. We explored frameworks such as the Business Model Canvas, as a tool for brainstorming, as well as a visual tool, and reflected on how we could build a similar canvas that would think about failure.

The "Value in Failure” Canvas was created using a re-purposed Business Model Canvas, a simple visual tool for outlining key components of a business model. We adapted the canvas to highlight common challenges and failures that many startups face. The elements were arranged in a grid, with each section providing enough space for participants to record their thoughts. We started by organising the headings into a grid representing eight key failure areas. Once the grid was in place, we complemented each block with simple, relevant iconography that immediately conveyed the essence of that section. 

Further as part of the design, we chose a simple and minimalist style throughout the design. Clean lines, a limited colour palette, and clear typography were chosen to keep the message in focus and the grid uncluttered. Here's a breakdown-

Misunderstanding customer needs:

Struggling to understand a problem, particularly focussing on the gap between assumptions and actual customer requirements.

Challenges in communicating value:

A breakdown in communication, reflecting the difficulty in effectively conveying an idea or product’s unique value.

Solutions that didn’t solve the problem:

An attempted idea / solution that failed to work in practice.

Identifying unsuccessful partnerships:

Searching for issues, including the process of uncovering misalignments and challenges in collaborations.

Targeting the wrong audience:

A misplaced target, and the consequences of mis-directed marketing or outreach efforts.

Difficulties in teams:

A lack of cohesion, alignment, or compatibility within a team.

Teams are often lauded when they work in tandem, but what happens when things come unstuck, and how can one overcome it? Oftentimes teams can struggle due to disciplinary differences, or growing too fast. 

Clashes in values:

Ideological or strategic conflicts that create tensions within an organization.

Values are a key consideration in building the sustenance of a team. 

Impossible funding and funders:

Funding is the moment that determines the long term sustainability of enterprises, and yet when one hears about unsuccessful funding, it is very rarely discussed as something that could be built from.

How to use the Canvas?

The Canvas is designed as a worksheet; it can be used by individuals as well as groups. We encourage participants to think through each of the boxes, and work on them one at a time.

The Canvas can be used for self introspection, but it can also be used to facilitate conversations and a workshop. At the Justicemakers Mela, we had participants from the legal tech field and from other fields, each of whom shared different experiences of failure through the canvas. These ranged from difficult clients, to a hostile work environment, to unsuccessful deals. What was revealing from the workshop was that despite being in a room where people did not know each other, the framework of thinking in terms of failures, as something that could be shared, and discussed without shame, or judgment, lead to authentic, and real conversations, that not only encouraged listening but also several moments of support and solidarity.

Future iterations of the Canvas

The ‘Value in Failure’ Canvas was first designed with Legal Tech builders in mind—to help them reflect on mis-steps and learnings in their product journey. But we found that the same tool can be valuable across the ecosystem. Future iterations could include customized versions for legal teams trying to adopt new technologies, where internal blockers or failed pilots often go unspoken. The Canvas helps surface these issues constructively. It’s also useful for students exploring non-traditional legal careers, giving them a way to map uncertainty without fear. We’re also considering versions for organisations navigating digital change, where setbacks often signal deeper structural challenges. These directions are still evolving, but we see the Canvas as an honest way to spark better conversations across different corners of the legal world. It’s about making space for reflection—wherever change is happening.

If you would like to sign up for a workshop with us, please write to us at contact@justiceadda.com and contact@indianlegaltech.net

(Siddharth de Souza is the founder of Justice Adda and an Assistant Professor at the University of Warwick.

Shreya Vajpei stands at the intersection of law, technology, and business, drawing on her background as a practicing lawyer to shape a more dynamic legal ecosystem. Named among the O Shaped List 2025, Top 30 Legal Tech Innovators in APAC and the Top 30 Women Legal Innovators in Asia, her journey shows how balanced optimism and purposeful change can influence every aspect of the profession. She is the founder of the Indian LegalTech Network.

Nimrat Kaur Dhillon is an independent LegalTech and Innovation Consultant, and the CSO at the Indian LegalTech Network. She's curious about everything from computational law and legal informatics to how we can build better legal communities and think differently about the law itself. 

Rachit Sharma is currently working as Associate (Legal Research and Design) at Justice Adda, India. He has done his undergraduate from National Law University and Judicial Academy, Assam. His interests lie in legal research and designing projects centered around access to justice.)