Selling Legal Tech To Lawyers Is Tough. Here’s Why.

Successful customer acquisition strategies are all about understanding your buyer persona—who they are, what they do, and what problems they face on a daily basis. But when it comes to selling Legal Tech to lawyers, typical buyer personas don’t capture two things that are vital to success: (1) lawyers’ unique personalities, and (2) the legal system’s unique operations. In this article, we’ll take a deep dive into lawyer psychology, the systematic factors that influence lawyers’ buying decisions, and how Legal Tech companies can use this information to drive growth.

How I Discovered Legal Tech’s Unique Challenges

Let me provide some context on how I started building an expertise in—and a product that helps solve—the problems Legal Tech companies face trying to sell to lawyers.

I've been an advocate for Legal Tech my entire career. I started at a traditional law firm, moved in-house, and ultimately spent most of my career leading the legal and business development teams at a Legal Tech company. But even as my job environment became more tech-forward, it never got easier to implement new technology, and I never understood why.

The epiphany hit me when my boss hung up in the middle of a software demo. She was grilling the sales guy about regulatory compliance, and as soon as she heard an answer she didn’t like, she left the call. At that moment, my gut told me two things: 

  1. Lawyers aren’t the same as other tech users.
  2. Legal tech companies aren’t adapting their strategies accordingly.

Lawyers Have Unique Personalities

As it turns out, my gut was right. Twenty years of research have found it to be true: lawyers’ personalities are different from the general population. In Herding Cats: The Lawyer Personality Revealed, Dr. Larry Richard identifies three personality traits that are higher amongst lawyers, to a statistical significance: skepticism, urgency, and autonomy. He also identifies two traits that are significantly lower amongst lawyers: sociability and resilience.

Applying Dr. Richard’s research, my experience with my boss made perfect sense. Grilling the sales guy on compliance shows high skepticism—questioning others’ assertions and scrutinizing their answers. Deciding the demo wasn’t worth her time is high autonomy at play—favoring internal priorities and systems over external. And hanging up in the middle of the call epitomizes high urgency—the need to get things done immediately.

The significantly low traits—sociability and resilience—aren’t as readily apparent in this story, but they’re important to its greater meaning. As Dr. Richard explains, people with low sociability are uncomfortable with new relationships, making them more likely to rely on existing relationships over forming new ones. As for low resilience, this usually indicates defensiveness, resistance to feedback, and hypersensitivity to criticism.

So, if a lawyer is using an older technology, they’re increasingly likely to stick with that vendor, making it even harder for new entrants. And once a lawyer writes off a new technology, they’re increasingly likely to defend their decision—making it extremely difficult to change their mind.

The Legal Industry Operates In Unique Ways

The difficulties facing Legal Tech companies don’t just stem from the personalities within the legal profession though. Factors like billable hours, law firm structures, industry regulations, and even the nature of legal work itself all affect the acquisition and adoption of Legal Technology. 

Billable Hours

When discussing the legal industry’s notorious “tech resistance,” first place people like to point fingers is the billable hour, claiming lawyers don’t actually want technology that helps them do their work faster. But not every moment of a lawyer’s day can be billed to a client, and lawyers certainly want to expedite any low-value—not to mention boring—admin work on their plates.

In reality, the effect of billable hours is more nuanced than a black or white desire to improve efficiency. To lawyers, billable hours aren’t just about making a profit—they’re about keeping your job. How you stack up to your peers. Your career trajectory, your pride, your sense of achievement. It’s not about how billable hours affect the desire for efficiency—it’s about how billable hours affect lawyers’ priorities, and where new technology falls on the priority list as a result.

Law Firm Structures

Law firms traditionally operate on a partnership model. At its simplest, this means multiple lawyers jointly own and operate the firm. This structure generally favors committee-based decision-making, rather than delegating certain decisions to individuals. (In my product research, I’ve found that this is still true in firms with a managing partner overseeing day-to-day business operations.)

The more people required to make a decision, the more complicated the decision becomes—from difficulties in logistics to difficulties in reaching a consensus. Legal tech companies have more stakeholders to sway, and longer to wait before those stakeholders make a decision—making their sales cycles inherently long.

We’re beginning to see some progress on this front, with certain states approving alternative corporate structures and some law firms beginning to adopt new leadership models. But these firms are still in the minority, so the effects of traditional structures are still worth noting.

The Gravity Of Legal Work

People hire lawyers for some pretty important stuff—accusations of crime, custody of children—the list goes on. The nature of legal work is so impactful on clients’ lives that lawyers take an oath to put their clients’ interests before their own. If we’re willing to entertain the possibility that meeting a billable hour quota is a higher priority than new Legal Technology, then completing client work and upholding this ethical duty has to be a higher priority too.

Even if you’re someone who thinks lawyers are deserving of all the negative adjectives you hear in lawyer jokes, the threat of getting disbarred for ethical violations means these rules are important to lawyers across the spectrum of good and evil. And the reach of these ethical rules extends further than you might expect. 

Rules And Regulations—And Ambiguous Guidance

The rules and regulations surrounding confidentiality and attorney-client privilege affect every detail of how a lawyer practices—including the technology they use. Unfortunately, exactly how technology is supposed to comply with said rules and regulations remains unclear.

Lawyers know they need to seriously evaluate the security of their software, but the rules and ethical opinions about how to do so are disappointingly vague. Most of the guidance out there says to weigh a myriad of factors on a case-by-case basis before each and every technology decision. There’s no clear yes-or-no answer to even the most pervasive technologies. (I’m not exaggerating—no guidance has definitively said whether lawyers can or can’t use Gmail.)

With the methodology left open for interpretation, there’s no standardized way for lawyers to evaluate—or for Legal Tech companies to prove—that a technology meets requirements. As a result, due diligence varies significantly from firm to firm—an industry-wide inefficiency that drags out the decision to use new technology even further.

How To Make This Work For You, Not Against You

In combination, lawyers’ personalities and the nature of the industry create a perfect storm that works against Legal Tech companies. Combining billable hours, client work, and an urgency to get everything done immediately, it’s hard to get lawyers to make time for you. Combining multiple stakeholders with autonomy, it’s hard to get all the decision-makers in the same room. Combining emerging technology with a preference for existing relationships, it’s hard to convince lawyers to change the tools they’re using. Combining regulations with skepticism, it’s hard to get through due diligence. And combining this entire difficult process with defensiveness, your first impression might be the only chance you get.

But with the right tools, you can turn these weaknesses into your greatest advantages. Using interactive demos, you can let lawyers lead the conversation and cut to their most pressing issues. Make those demos easily accessible outside of sales calls, and every stakeholder can view them on their own time. Using personalization, you can expedite due diligence and answer the questions most relevant to a given practice area and jurisdiction. With a faster, easier sales process, you can lower switching costs. Combining all of this, you’ll cater to a lawyer’s needs—creating a great first impression that’s sure to last.