How to buy legal technology: don’t be fooled into thinking it’s easy

Jack Shepherd
7 min readSep 2, 2022

Throughout my legal technology career, I have seen a number of different approaches when it comes to buying legal technology. The ideal approach to buying technology prioritises the business value technology delivers ahead of everything else.

Unfortunately, it is all too easy to be distracted by the promise and excitement of new technology. This leads to the two most popular buying approaches being “buying what sounds cool” and “the feature checklist”. The former is driven by hype, the latter is driven by an obsession with features. Both start with the technology, not the value it delivers.

In this article, I explain why it doesn’t make sense to start with technology. Instead, law firms and legal teams should adopt a structured and analytical approach around identifying tangible business problems to solve.

Here are the three main approaches to buying technology…

#1 Buying what sounds cool

It’s no secret that technology in law is full of hype right now. Whether it’s contract lifecycle management, artificial intelligence or document automation — it’s hard for anybody interested in legal technology to ignore these things.

So when a social media legal ops influencer that has 10,000+ followers pops up on your screen lauding the successes of their project involving one or more of these soundbites, you pay attention. You think, “oh wow, we are way behind the curve”. The risk of being left behind becomes too much, and you immediately contact a few tech providers to arrange some demos.

The problem with this approach is that it does not acknowledge that technology is just a means to an end, and rarely the end in itself. You quickly find yourself tangled in a web of pushy salespeople convincing you that their solution is the best, and will fix all your problems.

You become fixated on the technology itself, rather than the problems it solves and the things it delivers for your organisation. You forget that technology is just a means to an end. Focusing on the means rather than the end is never a good idea.

Buying what sounds cool” might deliver a good press release, a half-true LinkedIn post or an impressive one-liner about innovation in a client pitch that is never revisited. But if your focus is on actually delivering change and improvement in the lives of lawyers and their clients, it is a lazy approach.

Here are some key indicators of the “buying what sounds cool” approach:

  • Buying decisions are primarily guided by how a particular type of technology (e.g. blockchain, artificial intelligence etc.) could be deployed
  • Once tools are deployed, not measuring how often they are used and not taking any steps to improve that number
  • Placing undue emphasis on the “look and feel” of a piece of technology, at the expense of the fundamental tasks and jobs it helps people do
  • Not having a detailed understanding of the exact type of person, work type or geography for whom a particular product can deliver value

The vast majority of practising lawyers and clients do not care about snazzy technology. They are busy people, often juggling a whole host of work commitments not only against each other, but against commitments in their personal lives. They might well spend a few minutes hearing you speak about new technology, but most of all, they care about how it is relevant to them and how it helps them overcome the issues they have in their everyday lives. If you are guilty of the “buying what sounds cool” approach, it might make sense to start by understanding those things instead.

One final note on this approach. Many in technology and innovation leadership positions might be thinking something like, “it’s our job to be the visionaries — we need to show people the art of the possible”.

I agree with this statement. It’s just that showing the people the art of the possible is never the starting point. The art of the possible always needs to be anchored in what problem it fixes that people have right now. Unless you understand that, any vision or art of the possible you illustrate to people will struggle to resonate.

#2 The feature checklist

The second buying approach involves drawing up detailed requirements for a particular kind of solution. For example, a business looking for a knowledge management solution might require it to have personalised dashboards, “Google-like” search and intuitive filtering functionality. The end product is a feature checklist, which is a usually a spreadsheet or table running several pages long.

The feature checklist is often adopted at a point when a company decides it knows what it wants. Members of the technology or innovation team gather in a room and decide what features their dream product would have.The exercise is predominantly directed at the individual features of a product.

This is a very popular buying approach for law firms and legal teams, particularly among those who have legal experience themselves. However, it has two key problems.

First, it suffers from similar woes to the “buying what sounds cool” approach insofar as it approaches things through the lens of technology. People become so fixated on a particular line item in their feature checklist, that they lose sight of why that row is in there in the first place. Indeed, maybe that question was never asked in the first place.

As a tech supplier, I often find myself looking through feature checklists and asking, “so what?” and “why?”. To take an example from above, why does your knowledge management system need personalised dashboards? What will people use this for? What working issues do people have now that personalised dashboards will fix?

Second, the lack of analysis on “so what” and “why” leads to biases towards particular features contained in the feature checklist. For example, if we discover that the requirement for personalised dashboards is intended to solve the problem of lawyers not seeing new knowledge content, why is this the best solution to that problem? What about search suggestions or notifications? Why do the dashboards need to be personalised?

A pre-emptive focus on a particular solution ignores the fact that there might be multiple ways of meeting a given need. This can lead to mistakes in the buying process. A firm fixated on personalised dashboards might disregard a technology product that fixes the same underlying problem, albeit in a different (and better) way.

These first two approaches to buying are undoubtedly the most popular. Their shared shortcoming is that they prioritise technology and features above everything else, without considering the underlying things they need to solve.

I have also seen buying approaches that combine these two approaches — a cocktail consisting not only of a feature request, but a request that the feature is implemented in a way that sounds snazzy and cutting-edge. For example, “it needs to have personalised dashboards…that use artificial intelligence”.

#3 Outcomes and jobs

If you are reading this and thinking “how else can we buy technology”, I don’t blame you. The buying approach I prefer seems counter-intuitive at first. But it delivers the most success in the long run.

The third approach is the outcomes and jobs approach. Here, buying does not start with technology at all. It starts with a firm understanding of what outcomes you would like to drive.

A high-level outcome might be something like “increase profitability”, or “stop people leaving”. You will generally end up with multiple outcomes to focus on. For example, “stop people leaving” by “improving quality of work” by “reducing manual work” by “optimising the way we do signings and closings”.

I call this the “outcome stack”. In an ideal world, you start at the top (e.g. “stop people leaving”) and work out how to achieve that outcome at lower levels of granularity (“e.g. optimising signings and closings”).

The outcome stack provides the vital anchor in your buying processes that ensures you are focusing on the right things. It requires you to do research, and helps you discover problems you might not know about. For example, why are people leaving? Why is our team not profitable? It prioritises value above the means you take to get there.

Once you have a rough idea of your outcomes, it’s time to talk about jobs. The question here is, “what underlying jobs do people need to do?”. For example, if the lowest level in your outcome stack is “optimising the way we do signings and closings”, you now need to ask “what jobs are people doing in a signing and closing?”.

This involves identifying the people involved in the process in question, and asking what they do now and how they work. From here, you can end up with a list of jobs (e.g. “getting documents executed”, “finalising negotiations” etc.).

You can then go on to document how people do those jobs. This helps you understand the problems people are facing. And because you have started with your outcome stack, you have a high level of confidence that solving those problems will contribute to the high level outcomes you identified.

You end up with a detailed and specific business analysis of your problem area that you can share with potential vendors, who can help you work through what the best solutions are to your problems and to meet your desired outcomes. Most of all, you are focusing on the most important thing, which is the end rather than the means.

Adopting the outcomes and jobs method of buying technology requires practice. Identifying the right outcomes and related jobs requires a diverse skillset, which requires bringing together multiple people within an organisation.

Full adoption of this approach is a journey, not a simple switch. You can make improvements to your buying process by always having regard to the outcomes you want to deliver, rather than leading with the technology. This helps you answer questions lawyers will inevitably have, such as “what’s the point”, and “why is this relevant to me”.

This article was originally published in the Modern Lawyer



Jack Shepherd

Ex biglaw insolvency lawyer and innovation. Now legal practice lead at iManage. Interested in human side of legal tech and actually getting things used.