Law Firm Innovation: In 2022, Be A Better Salesperson

By Harris Tilevitz, Chief Technology Officer at Skadden Arps Slate Meagher & Flom.

Much has been written about the changes in legal technology in 2021: the plethora of new products, and the acquisitions and consolidations facilitated by the huge amount of cash in the private equity and venture capital worlds. But more should be written about the inability of law firms to actually take advantage of the technology they have acquired.

Innovation takes not only the ability to sort through the new product offerings, but also, the wherewithal to understand user demands and influence the culture to adopt new methods and technology. Our goal in 2022 should be to become the consummate salespeople, to fully understand our firms’ needs, and convince users to start integrating the products we have acquired into their practices.

I have been at Skadden for almost 34 years. I was hired, initially, to develop an in-house litigation support capability. I interviewed with the (now retired) executive director, the Firm’s first managing partner and a litigation partner I had met during my tenure in Lexis’ now-defunct Litigation Support Group. Each asked two similar questions:

• What was my perception of the Firm’s position in the marketplace vis-à-vis automated litigation support (‘ALS’)?

• What in my experience would help me bring the Firm into the 20th Century, technology- wise?

In today’s parlance, perhaps, the questions would be:

• Is Skadden considered by the marketplace to be an innovator in the area of ALS?

• What can you bring to Skadden to help the Firm adopt these new tools?

Like similarly situated large firms in the late ’80s, Skadden had some internal ability to provide ALS services to its attorneys. All of it was delivered on the mainframe, none of it was user-friendly and it was expensive to set up and maintain. The personal computer, which would eventually replace mainframe systems, had been introduced in 1981, and when I joined in 1987, PCs were only beginning to be distributed to attorneys.

At Skadden in 1987, there was a long runway to introduce technology innovation and a willingness to spend wisely, whatever was needed, but a general reticence on the part of users to change how they worked or spend time to learn the advantages new technology offered More difficult was understanding the lawyers’ needs, ‘getting in the door’ to educate attorneys about what technology could do, showing people what the firm was looking at buying, and convincing them that the tools could make their jobs easier and their clients happier.

In retrospect, I should have spent considerably more time with the attorneys. The skills I had learned when Lexis sent me to Xerox’s Professional Selling Skills course as a newly minted law school graduate could have been easily applied to my new role at Skadden. A 2019 LA Biz Journal article put them into three categories:

• Overcoming Objections

• Closing Skills

• Probing

This excerpt below from the same article explains what the course taught in sales terminology, but it is pretty easy to extrapolate how a new law firm CTO might approach creating an innovative environment in a law firm, engaging more with lawyers, understanding what tools are needed, and convincing lawyers to use those tools:

Overcoming objections is discovering what’s really on the mind of the prospect [emphasis, added]… Closing skills are the ability to take the [lawyer] on a mutual journey of understanding, where both sides share information and next-step decisions are agreed to. Professional closing starts at first contact and doesn’t stop until a sale is made – or not…

The last component, probing, is the foundation of the other two. There are two kinds of probes: directive and non-directive. Directive probes elicit only yes or no responses: ‘Would that benefit you?’ ‘Is that date good?‘. Non-directive probes require more illuminating words: ‘How would that benefit you?’ ‘What date would be best for you?’ Notice a non-directive probe begins with one of the interrogatives: who, what, when, where or how. Professional salespeople know when to use the right kind of probe at the right time along the journey of understanding.’

My role, then, was not only to be a technologist charged with making sure the Firm had the tools it needed to practice law in the then-nascent high tech era, but also to be an internal sales agent: selling change and benefits, teaching skills, fostering trust, and always probing.

A recent post by Lex Fusion’s three founders on Bill Henderson’s Legal Evolution site alludes to the need for better selling skills to advance the use of legal technology. It discusses the ‘misery of missing tools’: firms investing in tools to make the job of the attorney ( mainly the in-the-trenches associates) easier, but lawyers never learning these resources are available to them (the ‘missing feature fallacy’) and the reluctance to promote or adopt a new way, product, or process because of alleged product gaps or imperfections:

‘It is sadder still – and shockingly common – when no one even need buy a new tool because the organization has owned it, or a worthy analog, for years… Yet the lawyers themselves have no clue the tool is at the ready. How is this anything but a problem of cultural adaption?

The culture is not conducive to innovation and the result is far too many legal tech orphans – forever waiting to be adopted. Often, the orphans themselves are blamed… When illusory perfection is the standard for adoption, the status quo will reign even when it is universally acknowledged as suboptimal. The status quo is not subject to scrutiny. In fact, the status quo is rarely even subject to comparison. Rather, the continuation of the status quo is dependent on the level of scrutiny applied to its would-be successors – with the bar to entry almost always being orders of magnitude more onerous than [achieving] ‘better than the status quo‘.’

Sales organizations, even in the smallest startups, understand the criticality of a skilled, specially trained team of people dedicated to the promotion and adoption of new product, pre-and post-sale. There is a reason the Product Development Department, which arguably has the greatest familiarity with product nuances, inherent limitations, and granularities, isn’t charged with creating champions, closing deals and product adoption. The same skill set that makes someone an exemplary lawyer, an outstanding KM professional, a visionary IT leader, does not make them a de facto expert on product evaluation and adoption, perhaps the opposite.

The best salespeople also foster ‘repeat business’. They do this by minimizing the friction of adoption, taking an often-difficult task within a firm and making it as invisible as possible and reducing the pain common during change. By doing so, they gain trust and make sure they get called again the next time there is an opportunity.

I looked back at the ‘Challenger’ or ‘Insight’ selling models from my Xerox class and was reminded that the most successful salespeople–and let’s get comfortable with that word because lawyers and law firms do it all day, every day, whether they call it that or not–tell a story. They first ask broad questions and listen openly. They then offer the ‘prospect’, in this case, a client, a compelling new perspective. They connect it with the client’s current reality, leading them to how it can be realized, both before and after the investment is made.

So, in 2022, I suggest first, that everyone in technology and knowledge management needs to learn and be comfortable with, basic consultative sales skills. This might be an unnerving departure for the former lawyers in many of these roles, inculcated in the practices of not asking a question to which they do not already know the answer, avoiding risk at all costs and leading with caveats.

Second, we need to have open-ended conversations with lawyers on all levels. Surveys are great for specific, directed questions. But, like searching meta data, the survey results may get you exactly what you want from your interviewee, but they will also likely miss the nuance and important information around the edges.

Open-ended engagement, however, like fulltext searching, provides a much broader answer, allowing you to filter out what may be temporarily less useful, but leaving you with a great deal of actionable information. The result is improved engagement on an ongoing basis. The message will circulate within your firm that while we may be the experts on organizing information or reviewing technology, ultimately, we rely on the attorney to tell us what they need to practice law better and to better serve their clients.

In summary, my goal for 2022, and what I think should be the goal for all of us in the Law Firm KM and Practice Technology world, is to help build a culture where our lawyers feel listened to. Where they have been given an opportunity to freely talk about what tools and processes might help them reduce the amount of time they spend on the mundane tasks.

Where lawyers can fully understand the technology we have already acquired and how it can best be used. Where IT and KM staff can spend enough time engaging with lawyers to help them overcome their objections to using the technology, and probing to best understand what tools might be needed in the future.

The technology is there. The money is there, too, to buy the technology. What is and has been missing in most of Big Law, has been the selling and closing skills. Here’s to a successful 2022 – hope you all meet your quotas!

Note: The opinions stated herein are those of the author and do not necessarily represent those of the Firm or any one or more of its clients.

About the author:

Harris Tilevitz is the Chief Technology Officer at Skadden, Arps, Slate, Meagher & Flom, LLP. He has been innovating in legal technology since 1981.

1 Comment

  1. “So, in 2022, I suggest first, that everyone in technology and knowledge management needs to learn and be comfortable with, basic consultative sales skills.”

    [in a sarcastic tone] My goodness, how vulgar!

    A lot of tech founders feel uncomfortable selling. But if your product is any good, if it really is beneficial for customers to use it, then you are doing them a favour by letting them know about it and by helping them clarify in their own minds how they are going to get their organisations to buy it – and to use it.

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