16-17 June 2027 – London, InterContinental O2 | Magazine

LegalTech Diaries Volume 16

Matthew Stringer

Co-Founder and CEO
Stridon

LegalTech Diaries Volume 16

Matthew Stringer​

Co-Founder and CEO
Stridon

You’ve been building Stridon for close to two decades, long before “legal technology” became a category that attracted venture capital and conference stages. How has the conversation with law firm leaders changed over that period, and what do firms still consistently underestimate about the relationship between their technology infrastructure and their business strategy?

When we first engaged with law firm leaders, the conversation was largely about keeping the lights on. Reliable systems, periodic refresh cycles, and managing risk. That’s no longer where the discussion sits. Today, it’s firmly about operating model and competitive positioning: how firms drive productivity, respond to talent constraints, meet client expectations, strengthen cyber resilience, and, increasingly, how they approach AI as a catalyst that demands action. 

But the consistent underestimation is this: technology infrastructure isn’t simply a back office utility, it’s the delivery system for the firm’s strategy. When firms buy tools in isolation, they often end up with a patchwork that doesn’t integrate well, isn’t adopted, and quietly increases friction.

The other blind spot is that modern technology is now a continuous delivery model, not a one off or cyclical project. That requires intentional separation of strategic planning and operational delivery, with clear governance, risk management, and feedback loops.

And with AI specifically, a frequent underestimation is the amount of investment – in time, effort and money – to effectuate a meaningful behavioural and culture shift that has a positive and lasting impact.

What does a genuinely people-led transformation look like in practice at a law firm, and where do you see the change management process most commonly break down?

A genuinely people-led transformation starts from a simple recognition: technology doesn’t transform organisations, people do. The firm’s job is to build confidence, form habits, and shift behaviour, not a force rollout dressed up with uninspiring training.

That means visible and positive leadership: sponsors who use the tools themselves and talk honestly about what they’ve learned. A vision connected to what people actually care about, better client outcomes, less drudgery, time back for the thinking that drew them to the profession. And a champion network that’s a genuine community of colleagues who help to shape the programme, surface friction early, and translate value into their team’s language.

The best programmes treat change as continuous and collaborative. Encouraging peer discussion, and open and transparent feedback that is acted on so people know their voice matters.

Where it breaks down is rarely technical. Leaders delegate to IT and the programme reduces to a “traditional” deployment. Sponsors go silent, reinforcement is skipped, champions lose momentum, and early adopters feel stranded. Adoption plateaus, cynicism sets in, and trust in the next initiative becomes harder to earn.

Generative AI is creating a new category of cyber risk for law firms, from data leakage through to more sophisticated phishing attacks. At the same time, firms are under pressure to adopt AI tools to stay competitive. How should a firm’s technology strategy balance the opportunity of AI against the security exposure it introduces, and are you seeing firms get that balance right?

The right balance starts with an honest premise: AI expands the threat landscape and exposes existing governance gaps. For law firms, client confidentiality, matter level data handling, and SRA obligations now sit under the same lens as identity and access controls.

The strategy shouldn’t simply be a binary “deploy or block” approach. It should be to adopt within a well governed environment where safe, ethical use is the default with the right support structures to aid people through the change. In legal, governance has a particular shape: clear policies on what may be processed by which tool, alignment with engagement letters and outside counsel guidelines and full observability over AI use across the organisation. Recent UK court rulings on AI-generated citations are a reminder that supervision is a professional duty, not a technical preference.

Cyber sits alongside this. Firms need data classification, risk-based access, audit logging and identity controls as a foundation. Without them, AI governance becomes paperwork.

Are firms getting it right? It’s mixed. The ones moving successfully start with a small, well-governed footprint, measure value, then scale. The ones struggling either rush to tools without a strategy, or stall until shadow AI fills the vacuum – and with it, uncontrolled exposure of client data and risk.

AI breaks that equation structurally. The cost of processing a million documents with AI is a fraction of the cost of having associates do it manually and it is a fraction that does not scale with document volume the way human labour does. The concern about AI widening the gap, that only the largest firms will access the best tools, misunderstands how legal technology is priced. Enterprise legal AI is sold as a subscription, often with a usage-based component.

A more pragmatic path is to scale AI capability through existing, proven vendors rather than trying to build that strategic vision top-down before they’ve earned the confidence to do so. This is faster, lower-risk, and lets the evidence accumulate in a way that can actually inform bigger decisions later.

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