How To Sell To Lawyers
Some insights from my five years successfully carrying a sales quota on behalf of legal tech startups
This is a picture of some of the awards I won as a legal tech sales rep and my business cards showing my career progression during my first three years
Over the weekend, I wrote a post that was pretty popular on Twitter:
In this article I’ll explain how the concepts I described in the thread work, and share a few stories that illustrate how I came up with these ideas.1
Be up front about your weaknesses.
When I was clerking at the federal courthouse in Chicago, I’d sometimes go up to the 27th floor to watch the country’s best appellate lawyers argue before the Seventh Circuit. One of the most impressive skills they had was the ability to make concessions. Like, the judge would ask a question, and it was clear the lawyer didn’t have a great answer. But they would concede the point and explain why it didn’t matter.
Not all lawyers had this ability.2 It required a solid grasp of the facts of the case, an encyclopedic understanding of the law, and a deep understanding of what mattered in the big picture. I always admired this skill and wanted to develop it for myself. I never had the chance—I left law way before I had the chance to argue at the appellate level—but I got to do it in the most unlikely of places: tech sales.3
When I arrived at my first startup, after I left the practice of law, I watched how the sales reps talked to their prospects. They would never acknowledge any weaknesses in our product, even though we had many. I thought back to my experience watching the appellate lawyers make concessions and wondered if it wouldn’t be more effective to concede that yes, our product wasn’t perfect—but then explain why the “feature gap” didn’t matter.4
Eventually I was became senior enough to run my own deals and I frequently acknowledged weaknesses during sales conversations. It was such a strong move. Not only did I gain a lot of credibility—after all, who expects a sales guy to openly discuss the product’s flaws—I was surprised by the response. Many lawyers went into the call expecting to argue and debate, so when I pointed out a weakness, the lawyer would reflexively disagree with my point.5
The best part was that this had long term advantages in my sales career. I began to be known as the sales rep who would shoot straight, and some buyers who decided not to buy at first (because the product didn’t fit their needs at the time) would boomerang back.6 When skeptics find out that you can be trusted, they will go out of their way to help you—even if it takes years before that ends up happening.
The little things matter. A lot.
I’ve written before about why details matter, especially in the legal industry. Like it or not, it’s just a fact. Lawyers, especially large firm lawyers, care about details to the point where it’s unproductive. But if that’s who you’re selling to, you’ve got to embrace that thinking.7 Which means you absolutely must pay attention to the details during your sales process.
Many outsiders don’t realize how much law firm lawyer performance depends on hours billed. That means that for every minute that the seller spends with the lawyer, that lawyer has to spend a minute staying late at work, billing hours. I remember sales veterans from other industries thinking that all attorneys were arrogant. “No,” I remember explaining. “Just very busy.”
And yet during those first few years of sales, I remember getting a lot of feedback from senior people saying that I needed to do more small talk. “If I teach them something, or provide business insights—that’s even more valuable than small talk” I recall saying, perhaps less eloquently.8 I think a lot of sellers come from industries where drawn out pleasantries are expected, and buyers *want* to be pitched.
Clock management is super important too. This is true when pitching lawyers but also true for any busy exec. It’s interesting how senior executives work styles are so similar to lawyers. I think it’s because time is such a valuable commodity, and they just want you to get to the point. Providing checkpoints (“we’ve got 5 minutes left and I want to leave time for questions”) shows that you respect the value of their time.
On the flip side, if you use a phrase or term incorrectly, you lose credibility a lot faster than you would with “normal” people. It’s just a culture thing for lawyers.9 We are trained to avoid typos and grammatical errors in everything (again, to the point where it’s a problem) so we will judge you for doing the same. Unfortunately sales selects for a different set of skills. So if you can communicate clearly, in both written and spoken mediums, you will have a huge advantage.
Your track record will be scrutinized more than you think.
I’ve also written about legal’s obsession with credentials before, although in the careers context. If a lawyer is looking to buy from you, they know that it’s going to be too hard to process all of the relevant information available. So instead they look at proxies for quality. They will look to your past. Incidentally that’s why they look for typos in your email—it’s a sign of your attention to detail.
But it extends beyond that. Lawyers will size you up based on your resume. It’s natural for them to do—after all, they do that to each other when going up against each other. When I practiced law, I would immediately look up opposing counsel to see what school they went to and what firm(s) they practiced at. I confess that I still do that today generally, even though I realize it’s kind of silly.10
What that means is, you must be prepared to supplement what you’re saying with references and testimonials. This is why social media like LinkedIn is so powerful in this space by the way. It provides you a way to show social proof, whether it’s identifying successful firms and companies you’ve worked with in the past, or even showing how well-liked you are by your professional peers.
And what’s true for individuals is even more true for organizations. I remember at one of my past early stage startups, we didn’t have any credibility because we didn’t raise money from a brand name investor, and we didn’t have very many customers. So we decided to frame our offering as associated with a prestigious institution—Harvard Law. Our pitch was “We’re technology founded out of Harvard Law.”11
Other ways you can leverage “the past” include:
Publicly sharing well known customers (e.g. Fortune 500) for marketing. Basically saying that your product is used by the largest companies.
Referencing your investors for recruiting. Basically saying that investment firms with strong track records are betting on your startup.
Announcing executive hires who come from well-known employers in your industry. Suggesting to investors & recruits that your startup is well run.
All of these credentials and signals are valuable. They do often signal quality. But they are often imperfect too. My point is that lawyers give these factors a lot of weight—perhaps more than they deserve. So you should be aware of that.
Look, sales is hard. It’s hard for everyone. But if you’re looking to sell to lawyers, you have to understand how they think. Play the field as it is, not as you wished it was. This is true for legal tech, but also beyond that—whether you’re interviewing for a job or selling recruiting / staffing services.12
Thanks for reading my article. If you sell to lawyers, and would like more specific advice on how to do it more effectively, consider signing up for a paid subscription. I share a deep dives on sales & marketing based on my operational experience in legal tech startups.
The ideas in this post are more tactical in nature. For a more abstract, conceptual framework about sales process, check out my earlier article, appropriately titled Selling To Legal: An Introduction
I want to acknowledge I know decisions aren’t made only based on what happens during oral argument. But it’s so public and visible so I thought it would be a good way to illustrate my point. In fact, you often have to make concessions in your briefs if you want to maintain credibility for your argument. Weaker advocates will provide blanket statements to support their arguments. Which were far less persuasive than the nuanced positions others would take.
That entry level sales job served as the foundation for my content creation career. For more on that, check out How My Entry Level Sales Job Helped Me Find A Huge Opportunity Years Later
Overselling is a big problem in tech. But the fact that software is now sold on a subscription basis (as opposed to a one-time sale) means that you can’t get away with lying to sales prospects. If you oversell, the customer will just cancel their contract at the end of the term. In a way, this change in economic model has generally led to better behavior by salespeople and tech companies.
One time I spent 20 minutes listening to a sales prospect argue with me about why my product was a good fit for his firm. I’d tried to “disqualify” him early on, because it sounded like he didn’t get enough case volume to warrant an investment in e-discovery technology. But he did. His desire to “beat me” in our conversation led him to revealing his true case volume which was larger than he’d suggested earlier on. And since I was trying to make the sale, I let him win. It was one of the most surreal experiences I’ve had in tech sales.
Incidentally this is always why you want to play “long term games with long term people.” Many tech sales reps are mercenaries who stay in a particular company or industry for just a few years, and then move on. Since they won’t stay for long, they won’t get in trouble when the customer eventually finds out what they’ve done, so they have more of an incentive to lie to earn more commission. I knew I’d stay in the legal community for longer, so out of self interest, I’d be more honest. Today, my former sales prospects continue to reach out to me to see if they can buy whatever it is I’m selling. Over time, having this kind of credibility and trust is pretty powerful.
This did not come to me naturally. But because I worked at a large firm where they obsessed about the most trivial of details, I developed a lot of systems and habits to avoid careless mistakes. I’m still not perfect, but compared to most sales reps, I’m pretty good.
Interestingly, many of the people who gave me this advice were not sellers—they were managers and executives. I think for those folks, they are used to interacting with other people within the company—where small talk and pleasantries do matter—and generalized that experience to sales on the front lines where things couldn’t be different. Any sales professional can tell you, for many of these calls you are earning every second you have with them. The prospect has no obligation to talk to you—they can just hang up on you at any moment. This is 1000x true when the prospect is a busy law firm lawyer.
Sales enablement probably matters more when selling to legal than other places. Especially since many sales reps try to build rapport by making legal references, which are often done poorly. If you’re going to use jargon or legal concepts, make sure you know what you’re talking about.
Of course there is a grain of truth behind looking at someone’s background. For example when I look at salespeople, in b2b SaaS, I like to see 2-3 year long tenures. If you’re a sales rep who can’t seem to stay at a sales job for longer than one year at a time (unless you’re an entry level sales rep who moved because of advancement, that’s a different situation) that’s a strong sign that you’re weak at sales. One or two short stints might just be bad luck but 3 or more is a pattern.
This actually was something I validated in an A/B test based on thousands of live cold calls. The association with Harvard Law produced much higher conversion rates, as opposed to a classic pitch about what customers we worked with.
If you’re in a leadership role in an early stage company, check out How to create repeatable sales for your legal startup.