5 tips from Steve Jobs to convince skeptical lawyers to use technology

Photo by AB on Unsplash

Ever heard of the Pebble watch?

Five years before the release of the Apple Watch, Pebble was the most-funded Kickstarter product of all time, raising over $10 million in 2012. Pebble contained many of the features that we see in today’s smartwatches, but the technology never took hold. Pebble ultimately sold its assets to Fitbit in 2016, a few months before Apple released their Watch, which went on to be wildly successful.

So what makes some technology successful? How can lawyers ensure that when they finally choose great legal technology, it actually makes an impact?

Brand new legal technology comes full of promises, presenting the opportunity to free your team to focus on exciting, important legal work and be relieved of the boring, repetitive work that old systems and processes require.

But many legal technology projects fail, not least because lawyer’s aren’t taught about how to drive adoption.

In this article, I’m going to share 5 tips to help you ensure that your hard fought technology project actually pays off. Ultimately, you need to become a technology hero within your team and your company, rather than the person responsible for that clunky piece of techno junk that no-one knows how to use.

Tip 1: Choose the right technology

The first step to ensuring that people love your technology is to identify a user-friendly and impactful solution that solves meaningful problems within your business.

If your goal is a high adoption rate, you’re going to need an intuitive, approachable system, something that Steve Jobs understood well. Jobs obsessed over the user-friendliness of his products. Most people don’t need to be trained on how to use an iPhone, and as a result, adoption and use rates are extremely high.

Photo by Przemyslaw Marczynski on Unsplash

Busy lawyers are unlikely to adopt technology that is clunky and difficult to master. If your chosen technology requires training programs and comes with a dense user manual, it’s much more likely your team and the business is going to lump your new technology into the ‘too hard’ basket and move on.

Enslist beta testers

To ensure you’re choosing the right technology, get your team members involved early. When you’re deep in the technology search and have spoken with multiple vendors and witnessed multiple demos, it’s easy to forget what it’s like to access legal technology for the first time.

Bring a range of team members with you to demos and share screen grabs/videos with them as much as possible to ensure you’re receiving a wide range of opinions about the usability and accessibility of your chosen platform.

Tip 2: Be a visionary

You need a compelling vision of a better future powered by your legal technology if you are to overcome the natural tendency of lawyers to resist change. Without an understanding of the scope and impact of the benefits your technology will deliver, lawyers are unlikely to become evangelists for your chosen software.

One of Steve Job’s greatest assets was his ability to rally people behind an unrealised (and sometimes barely possible) vision of the future. Through his impassioned keynote speeches and in fiery internal meetings, Jobs articulated the potential for great technology to transform the way we work and think. These visions were so compelling that they brought the future forward into reality.

Share the benefits

Creating and propagating a compelling vision for your legal technology requires understanding and then communicating all the benefits your team will experience. These include:

  • Economic benefits (how it will save your organisation money and create a financial competitive advantage in the long run);
  • Productivity benefits (how much time lawyers and business users will save by using the technology) and;
  • Individual benefits (how the technology will help lawyers progress their careers and focus on their work; or help the sales team close more deals and spend less time filling out order forms)

Once you have an understanding of the core benefits of the technology, you can tie that to a bigger vision for your legal function that aligns with your company’s broader mission. Communicate the benefits, vision and mission loud and clear for even the most curmudgeonly lawyers on your team to hear.

Creating a compelling vision for technology is about helping people understand what’s in it for them. If you can clearly demonstrate how it makes people’s lives better, you stand a much better chance of running a successful legal technology project.

Tip 3: Create fans

Once you’ve crafted your vision, build a team of adoption champions who can evangelise your project and coach others on the benefits you’ve identified.

Your vision will likely resonate with a few other technology-inclined team members, but you’ll want to expand your scope to assemble a group of advocates that represent your company. Look beyond the traditional early adopters to include a range of people — especially those people who are great communicators and networkers.

Build a community around your system

Photo by Gianandrea Villa on Unsplash

Steve Jobs was excellent at enlisting enthusiastic fans for his products. Jobs created an identity around Apple products so that buying an iPod or an iMac became a statement about your personality, and thus something you were likely to share with others. Apple users are “the crazy ones, the misfits…the ones who see things differently” and ultimately, the people who changed the world.

While you don’t need to create an army of fanboys who will line up outside your office the night before you launch your technology, you can draw inspiration from Jobs’ ability to bring others onside. Seek out other team members from across the organisation who will identify with your vision and become fans of your project.

Tip 4: Highlight quick wins

After you’ve launched your technology, you’ll need to shift your focus to driving adoption and highlight the benefits for your organisation. Spotlighting the positive impacts provides evidence that your vision is true, encouraging more people to get onboard.

When Apple rolls out a new iPhone operating system, the marketing is centered around easy-to-access features that will make a quick impact. Apple boasts about the beautiful new home screen or the upgraded high-resolution camera — both of which are obvious, accessible tools.

Loud and proud

Photo by Jason Dent on Unsplash

Identify the quick wins your technology delivers and celebrate them. If your new Matter Intake/Request Legal Support App is making it much easier for business clients to access the legal team, grab a testimonial from one of your clients and share it with a couple of other relevant business units via email. Case studies provide evidence that you were right about the technology making a positive impact on how people work.

Sharing the success of your technology is a bit like marketing. The more frequently and clearly you can communicate the message that your technology is easy to use and creates benefits for the business, the more likely you will achieve success. In fact, it’s not a bad idea to involve your marketing team to help you spread the word!

Tip 5: Make it a routine

All the hype and marketing in the world won’t make a difference if you cannot institutionalise technology within your organisation. You’ll want to bake the use of your chosen technology into the routines of relevant people and set up systems that ensure those routines don’t slip.

Steve Jobs understood this principle well. Jobs always aimed to build hardware for his products that seamlessly integrated into people’s lives, emphasising sleek design and accessibility. Similarly, Apple software creates routines for its users through notifications and reports. In addition, the Apple stores make it easier than ever to integrate technology by providing free training at the Genius Bar help-desk to ensure people are able to to make maximum use of their Apple products.

Make it a thing

To embed your new technology into the routine of your business, you might:

  • Regularly survey users about their experience with the technology and report the results;
  • If your system generates reports and analytics, share weekly updates on the numbers (or even better, ask one of your ‘fans’ to take ownership over this process);
  • Create training manuals and record demonstration videos detailing how to use the technology, and then integrate these training tools into the onboarding phase for new employees.

Your goal is to enmesh your chosen software in the fabric of your organisation. By evaluating all the existing systems and procedures within your company, you can identify ways to weave your technology into the routines of employees and thus maximise the value and impact of the software.


Lawyers aren’t trained to take on the role of technology evangelists, but they often find themselves responsible for driving the adoption of their chosen software, or risk being in charge of an expensive piece of technology that no-one uses.

To drive adoption and create success from your chosen technology, you need to choose a technology that aligns with your organisation’s mission, create a compelling vision to inspire employees, communicate quick wins and institutionalise the technology in the day-to-day of your company

— — —

Sam Burrett is an Associate Commercial Director at Plexus, where he consults with General Counsels and Legal Leaders to create efficient legal functions, implement technology and reduce external spend.

Sam also hosts The Leading Lawyer Project, a weekly interview podcast exploring why some lawyers stand out from the rest, and regularly posts about the habits, traits and personalities of successful lawyers on Medium.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store