Why Selling Tech Into Legal Is Hard

Sandro Tuzzo
5 min readJan 16, 2020



The legal field is behind in adoption of technology and there are a number of reasons for this. Not only are lawyers difficult to sell new technologies to, but we are often viewed as a problematic group of people in general. The presumption is that we’re always looking for a fight, we are greedy, cheap, afraid to try new things, and never able to be reasonable. In fact, this disdain for lawyers tracks back for centuries, as Shakespeare once wrote “let’s kill all the lawyers,” to quote a more extreme example of this sentiment.

As a lawyer myself, I can certainly attest to the fact that we can be a difficult group- but that only scratches the surface. The truth is, as always, much more complicated than that. I practiced law for nearly twenty years and then, realizing how desperately behind our profession was in using technology, I spent several years building and selling software to lawyers- with the aim of making legal practices more efficient and, in turn, less frustrating.

Suffice it to say that this was, and continues to be, a challenging endeavor. As such, I am starting a series of essays where I hope to share with you what I’ve learned thus far- so that those selling into this space can be more prepared. For this essay, I’ll delve more into what I see as some of the lesser known, but more defining, characteristics of attorneys- at least as it applies to trying to sell something new to them. The following essays in this series will expand upon these characteristics and propose best practices. While my experience relates primarily to selling to litigators, I think many of my observations apply to the profession in general.While my experience relates primarily to selling to litigators, I think many of my observations apply to the profession in general.

We’re usually too busy, and we like it that way

For starters, most of our profession bills by the hour and we are pretty much preoccupied by this concept all the time. The problem is that not all of our work is billable, we bill a high hourly rate when we do, and we face a client population that is gradually becoming more comfortable scrutinizing our bills and finding ways to cut down on legal fees. Because of this, we’re always looking to maximize our time spent billing for our work and squeezing activities that are not billable into the moments in between.

As a result, no matter how busy we are, there’s always an underlying fear that new business will dry up even if it never actually does. Although it would certainly seem ideal to have a balanced amount of work that is steady and consistent, practicing law is filled with fluctuations and is really a “feast or famine” game.

I mean this not only with regards to making money, but more specifically, about the way we allocate our time in general. We either have nothing going on or way too much, there is rarely anything in between. Reasons for this vary- cases are unpredictable, client emergencies are commonplace, courts can be demanding and inflexible- but what’s more relevant for our discussion here is that lawyers are preoccupied by being too busy. In fact, we’ve sort of internalized this preoccupation as it being something that we thrive upon…..or so we think.

Lawyers like to put out fires

If you’ll allow the comparison, most firefighters will tell you that putting out a forest fire is much more appealing than clearing brush to prevent one from starting in the first place, and I would argue that the motivation of lawyers is largely no different. Legal disputes are, after all, filled with the same chaos, complexity, and unpredictability as a forest fire and both firefighters and lawyers share a common urgency and appeal to resolve the chaos.

Don’t get me wrong, firefighters and lawyers are different in many ways- but, at the end of the day, we are both drawn to messy and out of control situations. We thrust ourselves into the middle of these situations, rather than at the beginning or end, and we prefer to use our skills to control and stabilize active problems, rather than ones that are either predicted or have concluded already.

This appeal to urgency gives lawyers satisfaction and a sense of purpose which is, in many ways, essential for us to have in order to perform well in our roles as problem solvers. In fact, if you ask most lawyers what they wrote about in their law school admissions essay, you will frequently hear something about them being drawn to resolving conflict and not so much by preventing it. After all, at its essence, the law is about applying a system of rules and regulations to an existing conflict.

As clients, we look for this quality as well. Let’s face it, most people, when hiring a lawyer, will feel more assured when the lawyer handling their matter has actively dealt with the most extreme version of their particular situation- since it provides reassurance that the lawyer is experienced at what he/she does. This is why most experienced lawyers tout their many years of experience bringing disputes to a resolution rather than those disputes that they have helped to actually prevent from occurring.

An ounce of prevention….is just not our thing

Now, there is a good part of legal practice that focuses on preventing, rather than responding to, conflict. However, it’s easier to prevent problems from occurring when you are familiar with the specifics of what the problems are in the first place- which is why law schools teach aspiring lawyers the rule of law by primarily studying case law- which is nothing other than the study of legal problems that blew up, went to court and were ruled upon (and confirmed by Courts of Appeal) as the law of the land.

So you see, we don’t really like to do things like apply the scientific method or use other popular methodologies employed in other professions that act in a preventative capacity. It doesn’t line up with our “professional impulses” and, frankly, we can’t bill as many hours for it. Instead, we prefer to jump in to an existing or imminent conflict and fix it.

In my next essay- why lawyers pinch pennies……and more.



Sandro Tuzzo

I’m a recovering attorney, current entrepreneur and consultant to startups and early stage teams. www.sandrotuzzo.com