LegalTech Trainwreck #2

LegalTech Trainwrecks #2 (Online Negotiations)

Over the past two years, I’ve prototyped and discarded about a dozen potential legaltech products. It’s a soul-destroying process in many ways, but a journey that I think is necessary to discover not only what the market wants but also what’s the right problem and product for me to work on.

I’m sharing the stories from these failures so you can learn from them, salvage from them, or just be entertained because who doesn’t like a good trainwreck?

Harnessing tech for live negotiations

Remember pre-pandemic, piling into a colleague’s office, punching 20 digits into a speaker phone, and counting the beeps as each participant joined?

COVID-19 killed the dial-in conference call. But the shift to online video calls brought about more than just letting people see each other on screen. It also opened up a world of possibilities by allowing for the first time the ability to infuse those meetings with innovative technologies. This might not matter for your Monday morning team catch-up. But what about high-stakes, high-powered negotiations? Despite being one of the most important and valuable services lawyers provide to their clients, it’s an area that’s been starved of innovation for years. Who wouldn’t want an edge in those situations? 

I dutifully interviewed around 30 lawyers about their experiences negotiating via Zoom/Teams. Two big pain points emerged:

  • It’s difficult to communicate privately or coordinate with your own side when people are joining remotely. 
  • It’s hard to judge non-verbal cues over video.

Could we solve these problems by building either a Zoom/Teams plug-in or even a brand new video conferencing product specifically optimised for commercial negotiations?

You bet.

The prototype

With a mocked-up design in hand, I began seeking feedback from potential users. People thought it was cool. Brilliant even. They could definitely see how it would be useful.

I asked how people currently managed private communications with their team during online negotiations. Emails, instant messages and text messages were the usual responses. Everyone agreed these were easily missed, often misinterpreted and generally unreliable. ‘Great,’ I thought. ‘This platform will solve these problems.’

I asked what issues arose for people as a result of these difficulties coordinating with their team. Again, the responses were enthusiastic. People were anxious about saying something their team didn’t agree with, it was hard to get team members to speak up when they needed to, and because nobody could be completely sure what their own side was thinking, almost every substantive point would need to be ‘taken away’ to be discussed offline, resulting in lost momentum and extended timelines. ‘Fantastic,’ I thought. ‘This product is going to provide some great benefits.’

The only concern raised was that the product needed to be easy to use. ‘Of course,’ I thought. ‘What tech product doesn’t need to be easy to use?’ But something about the way people expressed this concern made me think there might be something else at play. I had to dig deeper.

It seems obvious, but people in the middle of a live negotiation have a lot going on, listening carefully to the discussion, thinking about what they are going to say, and anticipating how others will react to that. It’s not a situation that’s very conducive to multitasking. And although none of my interviewees ever said it explicitly, the real concern was that people were already struggling with cognitive overload, barely able to stay on top of everything happening during these meetings. Would additional tech tools really help them?

What I had thought was a design challenge was actually a dead-end. It didn’t matter how slick and easy to use my product could be. In the thick of negotiations, people simply don’t have the brain space. 

Lessons learned

In hindsight, this was a particularly dangerous project, not just because I had put the solution before the problem but because I had fooled myself into believing I hadn’t put the solution before the problem.

Ostensibly, the problem I was solving was that it’s hard to privately communicate with your own side during live negotiations, and that it’s hard to read what the other side is thinking through a webcam. The reality though was that I had started with the premise that people are now doing all their live negotiations online, so let’s build a solution that leverages that fact.

This led to my discussions with potential users suffering from confirmation bias. People agreed live online negotiations are challenging. Of course they are. Anyone can fire off ten things that make them difficult. But why would technological bells and whistles be the best solution to that problem?

In the end, I abandoned the product before writing any code. This is not to say others can’t make something in this area work. There are several legal industry-specific video conferencing platforms on the market, although mostly focussed on dispute resolution, whereas I had focussed on commercial negotiations. And there are a number of start-ups building Zoom/Teams plug-ins that can perform various impressive tasks in real-time such as automated note-taking, speech and sentiment analysis, and even checking whether you’ve covered your key speaking points. On top of this, we’re all waiting to see what exactly Microsoft’s generative AI-powered Copilot will do when released into Teams.

It’s definitely an exciting field, but for me, it was time to cut my losses, take the learnings, and move on to the next project. 

If you’re interested in reading about more legaltech trainwrecks, please follow me on LinkedIn!

Follow the link and enjoy reading the LegalTech Trainwrecks #1 (No Confetti) article too.

 Daniel Yim
Daniel Yim writes and teaches on legal technology and transformation. He is the founder of technology start-ups Sideline and Bumpd, and previously worked worked at Gilbert + Tobin and Axiom.

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