Tl;dr

• Deploying legal tech can be time-consuming and failure-prone
• My advice: Just like when you’re dating, try to figure out quickly whether there are any dealbreakers
• To do that efficiently, start with a small project
• Also: assign an internal owner, get your vendor to help with the implementation, and try to estimate the ROI

Hey friend,

I hear you’re evaluating some new legal tech to your team.

That can be daunting and fraught—e.g., at Grammarly, we tried to deploy a contract diligence tool for six months before we eventually gave up. Brutal.

From that experience and others, I wanted to share some suggestions.

My primary suggestion is to fail fast. There are a ton of reasons why a particular product won’t work—it doesn’t do what it says it will, it’s not user-friendly, it takes too much effort to set up, etc. Just like dating, the quicker you can figure out if there are any dealbreakers, the better off you’ll be.

With the above in mind, here are some tactical suggestions:

• Scope down the project to the smallest possible use case. E.g., if you’re trying a new CLM tool, use it for DPAs or NDAs. That way, you can minimize the setup time while also determining usability, functionality, and set-up effort.
• Assign one person on your team to “own” the tool. Again, this saves you time and resources if the tool doesn’t turn out to be useful or worth investing in. Also, it’s likely that there’s someone on your team that will be psyched to try new tech.
• Implement some good project-management practices: Regular check-ins (two weeks?) that document progress, a calendar of key dates, and a project plan (that is, a single doc that specifies who is doing what, where you are, what’s happened so far, what’s happening next, etc.) are all good ideas. Like any project, it’s going to be more complex than it seems and good documentation and process can go a long way to making it easier.
• Make your vendor work for you. Configuration and set-up can be 90% of the work for any new product. Given that the vendor is the world-class expert in their tool, have them do as much as the setup as you can get them to. A good vendor should make sure that you’re delighted with their product.
• Try to figure out if the tool is worth it. This is tough, and will be largely subjective but, to the extent possible, try to figure out a metric that justifies the price. One good tool is to estimate the time saved. Telling your CFO that the tool will save you 200 hours of boring diligence work, for example, will be compelling.

I hope that helps! Let me know if anything is unclear or if you have any feedback or thoughts.