I Spent 4 Weeks Uncovering Lawyers’ Top Objections To Tech. Here’s What I Found.

When I started my company, I knew the problem I wanted to solve: getting more lawyers to adopt Legal Tech. I had encountered this problem in my own experience as a lawyer, but there were two key questions I still needed to answer:

  1. What stops lawyers from trying new technology?
  2. What can Legal Tech companies do to remove those barriers?

In order to answer these questions, I spent four weeks interviewing lawyers from all over the world to uncover their biggest doubts when it comes to new technology. In this article, I’ll share lawyers’ top 3 objections when buying Legal Tech, and what Legal Tech companies can do to overcome those objections and close the deal.

Bad Sales Experiences 

The Objection

Most salespeople think of objections as hesitations they’ll need to rebut at the end of a demo or sales presentation. But in Legal Tech, the first objection you need to get ahead of is lawyers’ resistance to the sales demo itself. Even if a lawyer is interested in your product and actively looking for solutions, they fear getting sucked into a demo that will ultimately be a waste of time. As one lawyer aptly put it:

So many startups are stuck talking about their own features and product details. I need to know how they can improve our work lives. And I need the nutshell version—I don't have time for a long thing.

The Solution

From your very first interaction with a lawyer, you have to definitively prove three things:

  1. You can communicate your product’s value clearly and concisely.
  2. You can demonstrate that value in the context of their specific needs.
  3. You are not going to waste their time.

How do you accomplish that? By making every interaction as productive and personalized as possible. Start by showing that you’re not just delivering a generic pitch—be sure to do your due diligence and customize your communication accordingly. (And I can’t miss my opportunity for some shameless self-promotion: if you really want to knock it out of the park, use a personalized interactive demo from Jade!)


The Objection

One of the sales objections I found most interesting was lawyers’ concerns about how a new technology will integrate with their existing software and processes. Lawyers often expressed frustration that new technologies aren’t always set up to send and receive information from existing software. When that happens, they have to input the same information in multiple places, duplicating admin work and slowing down their processes.

The Solution

Be proactive in talking about how your product can work with a lawyer’s existing software and systems. If your product has built-in integrations that connect it to other technologies, talk them up! They’re more important to the buying decision than you may realize.

It’s not a deal-breaker if you don’t have built-in integrations—it just means you have to get creative. Familiarize yourself with platforms that help connect apps to each other—like Zapier and IFTTT—and brainstorm ways to create workarounds. (For example, my CRM and to-do list app don’t connect directly to each other, but because they both connect with Gmail, I can still automatically send information from one to the other.)

The bottom line? Always ask your prospects what tools they currently use, and spend some time getting to know the products that come up most frequently. If you can present a plan that fits your product into existing workflows, you’ll be ready to tackle the integration objection.

Privacy And Security

The Objection

When you make a living by identifying all the risks in a given situation, the risk-spotting mindset never turns off. In talking to lawyers about the risks they worry about with new software, one concern came up over and over again: privacy and security. Lawyers have an obligation to evaluate each piece of technology they use and ensure they feel comfortable that it can appropriately handle any confidential or privileged information. Particularly with technology that's newer to the market, they worry about whether that technology meets all of their regulatory requirements.

The Solution

Be sure you’re prepared to talk in detail about all things privacy and security—both in terms of your product’s features and your company’s internal processes and policies. Don’t forget to do the same for the other products you use in your business day-to-day—lawyers will want to know about every touchpoint their information is going to hit. It’s useful to have an overview of all of this privacy and security information on hand to share with prospects. 

No matter how great your product is, at the end of the day, privacy and security concerns can make or break a sale. When talking to lawyers about privacy and security, you’re really talking about trust—and trust is something that Legal Tech companies have to firmly establish and continuously build upon.


There are a number of objections that come up in the Legal Tech sales process over and over again. In the weeks that I spent talking to lawyers about their top objections, the most common concerns were: (1) bad sales experiences, (2) integrating new products with current software and systems, and (3) privacy and security compliance. But if you go into each new sale prepared to proactively address these concerns, you’ll spend less time overcoming objections and more time wow-ing lawyers with your product.


What other tips do you have for overcoming objections in Legal Tech sales? Send me an email or message me on LinkedIn for a chance to be featured in an upcoming article!