Greg Garnett is Darwin’s Technology Director and has held multiple senior technology positions within UK top 50 law firms. 

In this article, he reflects on how legal technology decisions have changed, and why firms now need clearer evidence before committing to major technology choices.

When I started my legal technology career in 2016, my biggest fear was a server going down just before home time.

At the time, that felt like the job. Keep systems available. Keep email running. Keep the firm working.

Today, as I spend my days at Darwin working with legal technology leaders on strategy and major technology decisions, the landscape looks very different. Over the best part of a decade, I have seen a significant amount of change in how legal organisations operate, compete and adapt to technology.

But one of the biggest changes is not just the technology itself. It is what the decision now needs to prove.

When stability was the main priority

When I started in a large international law firm, the focus was largely on uptime.

We were running traditional three-tier infrastructure, standard MPLS connectivity and legacy applications. Stability was everything. Keeping the lights on was what kept me awake at night.

I will always remember working a 24-hour shift after an Exchange database availability group corrupted at the end of the day. The next 12 hours were a blur of trying to make sure the firm had email by morning.

Back then, email was the centre of business operations. A single day of downtime would have carried a serious cost, both commercially and reputationally.

So the priority was clear: protect availability, protect continuity and keep the firm moving.

The turning point

For me, the shift began around 2016.

Hyperconvergence started to gain traction. Traditional networks began moving towards software-defined models. SaaS and cloud became serious strategic conversations, not just technical options.

At the same time, cyber risk became much more visible.

Global security incidents increased. The market filled with new security products. Firms wanted to simplify their estates, but in many cases ended up with more tooling, more complexity and more decisions to make.

Cyber security moved firmly onto the board agenda. It became a core part of the role: protecting client data, managing risk and still enabling the business to grow and adapt.

That balance is still one of the hardest parts of legal technology.

Technology has to move the firm forward. But it also has to protect what the firm cannot afford to lose.

Why legal technology decisions feel different now

Many firms are rightly thinking about how they stay competitive.

AI, automation, cloud platforms, client portals, data analytics and new billing models are all part of the conversation. But the question is rarely as simple as “should we do this?”

The better question is: is this the right move for this firm, at this time, in this environment?

That answer will be different for every organisation.

Law firms may compete fiercely, but legal IT leaders often operate in a closely connected community. They share experience, speak openly and learn from each other. That is valuable. But what another firm is doing today might not be what your firm needs to do tomorrow.

The risk is either moving too slowly because the decision feels complex, or moving too quickly because the market makes something feel inevitable.

Neither is ideal.

Doing nothing can leave a firm behind. But moving

What a demo cannot prove

A supplier demo can be useful. It can show capability. It can create interest. It can help people understand what might be possible.

But it cannot prove everything the firm needs to know.

It cannot prove whether the technology fits the firm’s real environment. It cannot prove whether the integration will be straightforward. It cannot prove whether the data model, permissions and governance are right.

It also cannot prove whether fee-earners will use the technology in the way the business case assumes, or whether the firm is ready to support it properly after go-live.

That is where legal technology decisions have changed.

The product still matters. But the decision now has to stand up across infrastructure, cyber security, governance, adoption, operational fit and commercial value.

Cloud is a good example

Cloud is a good example of why context matters.

Moving to the cloud is not automatically the right answer in every situation.

If a firm has recently refreshed its infrastructure, signed a three-year colocation agreement, moved core applications to SaaS and is only planning to “lift and shift” workloads without using cloud-native capabilities, then the case may not be strong enough yet.

That does not mean cloud is wrong. It means the decision needs to be tested properly.

What is the firm trying to achieve?

Greater resilience? Better scalability? Lower operational overhead? Stronger security? Reduced long-term cost? More flexibility?

If those outcomes are not clear, the project can quickly become a technical migration rather than a business decision.

The same applies to AI, automation, client portals and data platforms. The question is not just whether the technology is impressive. It is whether the firm has enough evidence to support the decision.

The areas legal IT leaders are now being asked to prove

From the conversations I am having with law firms, the focus is increasingly on a few key areas.

AI and automation are moving from experimental conversations into operational ones. The focus is no longer just whether firms should adopt AI, but how they use it responsibly, securely and in a way that supports real legal work.

Cyber security and data governance remain central. Law firms hold sensitive client data, and any technology decision has to consider access, control, compliance, resilience and auditability.

Cloud-native platforms and connected systems are also becoming more important. Firms are trying to move away from fragmented legacy environments and towards systems that work better together across case management, document management, finance, communication and client service.

Client-facing digital experiences are another area of focus. Clients increasingly expect secure portals, easier document sharing, electronic signatures and clearer visibility of progress.

Data is also becoming more important commercially. Firms want better management information, stronger insight into profitability and clearer ways to understand how work is moving through the business.

All of these areas can create real value. But they also increase the standard of proof behind the decision.

It is no longer enough to say the technology looks strong. Legal IT leaders need to show why it is the right option, how it fits the firm and what risks still need to be managed.

Preference has to become proof

In my experience, technology decisions become harder when the supplier conversation moves faster than the internal case.

A product looks strong. The demo goes well. The direction feels sensible.

Then the questions start.

Why this option? Why now? What risks remain? What evidence supports the choice? Can we support this properly? Will it deliver the value being promised?

That is the point where preference has to become proof.

A strong shortlist can help. A good demo can help. But neither replaces a clear brief, tested evidence and a recommendation the firm can stand behind.

What stronger decisions tend to have in common

The strongest technology decisions usually have a clearer view of five areas.

They have a clear view of fit: whether the technology solves the right problem for the firm, not just in theory but in the way people actually work.

They have a clear view of control: whether the firm can explain the risks around data, access, security, governance, cost and supplier dependency.

They have a clear view of adoption: whether partners, fee-earners and operational teams will use the technology in the way the business case assumes.

They have a clear view of value: what success looks like, how it will be measured and whether the benefits are realistic.

And they have a clear view of resilience: whether the firm can support, secure and maintain the solution properly once it is live.

These areas matter because legal IT leaders are rarely just choosing a product. They are building a recommendation that needs to make sense to partners, risk teams, finance, leadership and the people expected to use the technology every day.

A practical question before the firm commits

Legal technology will continue to move quickly. AI, automation, cloud, security, data and client experience will all keep reshaping how firms operate.

But the strongest decisions will not come from chasing every new idea.

They will come from taking a measured approach.

Assess. Test. Measure. Deliver. Reassess.

Before committing to a major technology decision, one question is worth asking:

Have we tested whether this option works for our firm’s real environment, or have we only seen what it can do in the supplier’s?

That is where confidence is built.