As is the case in most industries, sales in legal tech are driven largely by relationships, but keeping the love alive—or even getting it started—in the land of lawyers is easier said than done. In fact, those bonds may already be fragile to begin with.

Michael Boland, director of e-discovery services at Clark Hill, thinks the relationships between law firms and their vendor representatives may be stronger than they once were. However, he also called legal a "completely thankless industry."

"That stickiness factor is a very difficult thing to attain because lawyers just want to throw you under the bus when something goes wrong. And it could be something that they did, it could be something that's totally their fault, but it doesn't matter—the vendor did it. That's the easy person to blame," Boland said.

Even planting the seeds for a relationship in the first place is something of a crapshoot. For example, Boland said that whether or not he responds to a sales cold call or introductory email can sometimes depend on what kind of a mood he's in and how busy he happens to be on any given day.

Still, Boland does tend to at least read each sales email that drops into his inbox and even responded to one earlier this week, curious about the presence of a new company in a sphere in which he is already well-versed.

"But I can tell you right now that I'm not going to buy anything from him," Boland said.

Legal tech vendors can't always count on the presence of a curiosity gap, though.

Meredith Coleman, an attorney at Kissel Hirsch & Wilmer, thinks the best way for tech vendors to reach lawyers with marketing is by providing an update on something that's changed in the legal industry or in the law itself.

"Feed me something new that I can then digest and learn and pass back to my clients, that this is how things are changing and this why this is the new tech that we're using and this is how it's going to be helping us and this is how it's going to improve efficiencies," Coleman said.

It's not an approach that she has personally noticed a lot of legal tech companies taking. One reason may be that lawyers such as Boland feel they can get that information elsewhere, such as conferences and panels.

He favors a more direct and to the point approach—but one thing that can derail the whole process before it starts are vendors who neglect to research his firm in order to find the appropriate point of contact.

A sales person who sends out a mass, firm-wide email usually results in Boland fielding calls from multiple attorneys attempting to bring something he already knows about to his attention.

"It just creates 10 times more work for everybody," Boland said.

Complicating the issue for legal tech vendors somewhat is that firms of various sizes may have different structures in place for the onboarding of new tech solutions.

Coleman said it's important for tech vendors to get to the right people, but at every firm the right people are different—meaning that many wrong people may get dialed.

"For us, we're a mid-sized firm. Our administrative people are really the people you want to get to. If you call up one of our equity partners, they are busy doing other things," Coleman said.

However, cold calls and emails aren't the only channels of marketing in the world. In an email, Camden Hillas, associate general counsel at the process management and workflow automation company Nintex, said it's becoming more common for vendors to have partnerships with a bar association or a professional group like the Association of Corporate Counsel.

What she's looking for from a marketing campaign is succinct, but possibly difficult to achieve in a crowded marketplace.

"Basically, in a time where there are a huge number of potential tech solutions, I want some demonstration that either your solution is unique in being formulated to solve a specific pain point, or that other similarly situated companies or legal departments have already implemented the solution successfully," Hillas said.