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Jack Shepherd

Principal Business Consultant, iManage

Quotation Marks
“Lawyers naturally think of themselves as “problem-solvers”. But as noted above, lawyers really need to be “problem-finders” before they are “problem-solvers.”

How lawyers can successfully drive change in the legal world

How lawyers can successfully drive change in the legal world


Jack Shepherd proposes ways in which legal professionals can maximize their chances of success in technology and innovation roles.

I started my career as a solicitor. I studied law at university and went to law school. Law was my life, and I had the classic personality type for a solicitor. I was risk averse; a control freak with a preference for doing things my way. I was scared of admitting any knowledge gaps – everybody had to know I had the answers, and I naturally thought my way was best.

There was one chink in the armour: my interest in technology. I had always been a keen coder, but had never had the opportunity to use any of these skills in practice. One day, an opportunity arose for me to do something a little bit different: I took a secondment to the innovation team of my law firm.

My mission was to build a transaction management tool for the firm that could simplify transactions and reduce the number of emails on a complex deal. The tool would replace Microsoft Word, and provide complete certainty on where all documents and workstreams stood.

In this role, I worked as 'the voice of the lawyers' with a team of developers to ensure that the product was built in a way that would actually work for the intended users.

My plan was to run this project in the same way I had my legal work. I began to get frustrated, and it quickly dawned upon me that the skills that had served me well as a lawyer might not be the same set of skills that I would need for success around technology, change and innovation.

Lawyer vs tech

I had always thought of my aversion to risk and confidence in my own processes as assets to my work. But while all those things might serve you well in a traditional legal setting, they can get you into trouble when working outside of a legal project.

For example, I thought that the way that I worked and approached certain tasks was the way that all lawyers worked. As a result, I didn't speak to lawyers much when I was building the product. Why would I need to? I was a lawyer myself; I knew how they worked.

During the course of the project, it became apparent that we had created a product that worked very well for me. But I wasn’t the one using the product – hundreds of other lawyers were. And as it turned out, they had different ways of approaching things. These differences were subtle but important. Get them wrong, and the entire product could break down.

For example, the product I was building had a feature that helps process comments received on a document from another law firm. My personal practice always reviewed those comments, decide which I would accept, and type them into my draft. The product was designed around that workflow.

I received feedback that this did not cater to lawyers who work differently to me. It turned out that when processing comments received from another law firm, other lawyers would use that draft and remove comments they rejected, rather than typing them into their own draft. The product simply did not work for those people.

Furthermore, the product had completely missed guiding users through the means by which a revised document is sent back to the law firm. Of course, this was obvious to me – but I was the one developing the product.

I realized that a legal background can be a double-edged sword for any lawyer moving into technology, change and innovation. It is not enough to think that you can sleepwalk your way into a successful skillset just because you are a practicing lawyer yourself. I now believe that lawyers have to learn three key skills in order to be successful in this field.

Understand your users’ needs, not your own

As noted above, it is important to appreciate the nuances in how people work. These may be different to your own personal preferences. The first thing lawyers should do when working in a technology project is to remove their own biases. The best way is speaking to the people affected by the change initiative or project being undertaken.

This itself is an art – closed questions should be avoided, no questions asked should have just a “yes or no” answer. For example, “would this be helpful” is a bad question because you get a binary response. It would be far better to pose a question such as, “talk me through how you give your client confidence you are on track to close this deal”. This question will establish an open narrative.

Eventually, the person you are speaking to will very openly talk to you about all the problems and pains they have in their work. Understanding those problems and pains will give you the hooks you need to deploy a successful change initiative.

Focus on the desired outcome, not on features

Lawyers naturally think of themselves as 'problem-solvers'. But as noted above, lawyers really need to be 'problem-finders' before they are problem-solvers. Otherwise, you are solving problems that people don’t care about.

An example of this is the 'feature checklist'. When law firms are looking at a new technology tool, it’s common to make a feature checklist and then compare different products based on what features they've got.

Counterintuitively, the most successful approach is to not look at the features first, but to focus on the desired business outcome. From your discussions with other lawyers and people affected by the change you are trying to instill, what are the problems you’re trying to solve?

What are the business outcomes that you want to achieve – e.g., profitability, better employee satisfaction and engagement, better client experience?

Once you figure the desired outcome, you can work backwards through the problems you must solve to get there, and only then to the solution.

For instance, it might be that a law firm is looking for a product than can help with due diligence, and they find a product that can carry out clause extraction to help people review thousands of contracts. But what if users don’t really care about this process, and the thing clients are really frustrated about is how due diligence reports are presented?

Looking at the due diligence process through the lens of a product means you risk missing the problems that really matter to people. Putting the problem first helps establish the value of addressing the right areas – helping ensure better overall success with the technology.

Embrace one-to-many, not one-to-one

Many legal professionals pride themselves on creating bespoke work product. It is not uncommon to hear people say that their work cannot be standardised at all. Such people operate on a 'one-to-one' service delivery model: build once, deliver once.

As pressure on legal fees increases, this model becomes increasingly unsustainable. It also leads to a lack of information sharing, because learnings are not shared from one product to the next. Many law firms are starting to look at a model that scales, where work product is built once, delivered many times. This is the “one-to-many” model. Work quality tends to be cheaper and more resilient.

These different approaches come to the fore in technology and innovation projects. When working on these projects, lawyers must adopt the 'one-to-many' approach. There is no point in building a tool just for one person; it needs to work for multiple people. This makes the focus on outcomes and user needs incredibly important.

It also means that every facet of these projects needs to be thought out carefully. A simple request such as “move this button to the left” might be acceptable in the one-to-one approach, because only one person is affected. But when working in a change project, hundreds of people might be affected by this change, and you should consider the impact.

Increasing the odds of success

For companies that work in tech, many of these principles will be familiar. But for lawyers, these things do not come naturally, because they are often opposed to the very qualities that have created great lawyers.

Lawyers who embrace these principles will therefore enhance their odds of success when moving into technology and innovation roles. In a rapidly changing legal industry, those lawyers who can effectively harness technology and help the firm navigate a path forward will find themselves increasingly in demand, with their role only growing in importance.

Jack Shepherd is legal practice lead at iManage RAVN He was formerly an associate solicitor at Freshfields Bruckhaus Deringer