Working With Lawyers – Tech Adoption

You can’t talk about legal technology without talking about, and to, lawyers. Also vodka. Kidding.

Anyone who has spent more than an hour trying to get lawyers to use pretty much anything other than Word and Outlook will know that adoption is a Sisyphean task. Lawyers have a general negative reaction to anything you show them. They expect perfection and ease of use, and hate any disruption to their normal (though admittedly imperfect) workflow.

I don’t pretend I’m a change expert (except on my resume, obviously), but I have had some success in (1) convincing lawyers to just try the new shiny thing, and (2) actually incorporate it into practice.

This post is the first of two on working with lawyers in technology rollouts. These posts will focus on the interpersonal interactions we all encounter, rather than the planning required for a rollout (communications plans, sponsorship, etc.). Here, I’ll talk about some common objections that come up, and how to handle them. Next time out, I’ll talk about lawyer personas and how to work with different ones.

Preliminary Notes

I already mentioned that lawyers have a “general negative reaction” to new technology. Interestingly, I have found that there are a limited number of specific reasons lawyers will present as to why what you’re showing them can never work. However, this range is specific to the particular technology. In other words, you’ll get one set of reasons for Product A and another for Product B.

  • Know your technology! Know the ins and outs, and be prepared to acknowledge what’s missing. If you’re showing content, know what’s there and what isn’t. Lawyers are absolutely excellent at pointing out flaws and omissions (it’s their job), and will find the chink in the armour.
  • Do a soft rollout to understand what the specific objections will be. Showing your new tool to a small, carefully selected group will give you a sneak peek of the range of objections – and you can prepare even more fully.
  • Know what success will be. Develop aspirational metrics (number of initial logins, for example) to keep driving towards.

Common Objections, or, How I Stopped Worrying and Learned to Love the Rollout

“This Isn’t Something I’d Use”

During your rollout, someone will say this. Here’s your response:

To an associate: “This is an important investment the firm is making around innovation/efficiency. It’s important you learn it and give it a try.”

Why This Works: Associates do not want to be the odd ones out when it comes to firm investments. You can usually be a little more directive with associates.

To a partner: “Sure! This is an big investment the firm is making, and it’s really important that you, as a leader, have an understanding and encourage the associates to use it.”

Why This Works: You’re asking them to be leaders – this appeals to everyone’s ego. You’re not asking them to click here and then there.


“This Doesn’t Have X and I Won’t Use It Until It Does”

Sigh. The missing X could be anything – lack of API into another firm system, an underlying precedent library, the wrong font.

You: “Yes, we’ve heard that and we’re working with the vendor on improvements. The vendor is very open to changes – tell me more.”

Why This Works: You’re painting the vendor in a positive light and deflecting the negative from you personally. More subtle, though, is the first sentence. Lawyers are autonomous and highly skeptical of others; they won’t like hearing they’re not the first to find this supposed failing. Once the lawyer has finished telling you how something should work (which can be genuinely useful), you just steer them right back to the next item. They appreciate being heard.


“I’ve Seen Things Like This Before. It’ll never work.”

This will come from a senior partner, and, frankly, they have indeed seen many a technology fail before. Be direct.

You: “I understand! Nonetheless, this is a big investment, and I want you to just suspend your disbelief for a few minutes.”

Why This Works: There’s the investment piece again. More importantly, you’re acknowledging their skepticism and bluntly asking for a few moments of cooperation. It’s hard to say no, especially if you can deliver this in a lighthearted way.


  1. I’ve heard of lawyers who still, in this day and age, don’t use email and have their assistants type up all of their correspondence for them. At what point does avoidance of technology become professional negligence?

  2. Reading this post, I’m getting the impression that perhaps it’s not necessarily the attitudes or the personalities that require change but the technology itself that requires new thought or change in design. For instance, new technology that requires “adoption” comes across as an intrusion. Technology should be an enhancement to a profession or to an already existing skill set not something that can be perceived as a nuisance. Perhaps the focus should be on how the technology can demonstratively assist, or even better, inspire the user to “do” better or “be” better at what they’re already doing.