Meet the lawyers of LawY: Holly Hickman

Hi Holly, tell us a bit about yourself and your career in law.

I worked in family law for just under seven years, and whilst my path into that specific area wasn't entirely straightforward, it’s given me a comprehensive understanding of what makes a fulfilling legal career.

I studied English as an undergraduate and initially planned to go into commercial law, likely inspired by many seasons of Suits. I completed work experience at a commercial law firm in Germany, which allowed me to flex my language skills, and work towards dual qualification. However, I found the technical aspects of German law quite demanding because it is not a common law jurisdiction, and the work itself didn't engage me as I had hoped.

After a brief period in property law at a small commercial firm, I considered moving to criminal law as a barrister, drawn by a vision of providing access to justice. However, a conversation with an experienced family barrister made me think more strategically about my career direction, and they suggested family law might be a better fit.

That conversation proved pivotal. At that time I was working in a family firm and  discovered that I had a real aptitude for the work, particularly – at that time - care proceedings. I was fortunate to be mentored by an exceptional solicitor who invested heavily in developing my skills and knowledge, and I found the work itself especially compelling because I was able to see how the law could genuinely protect vulnerable families and children gave me a strong sense of purpose.

My experience spans both private practice and work with various local authorities in London, so I have an insight into how family law operates from multiple perspectives. I also had the opportunity to work at the Court of Appeal assisting a Lord Justice and Lady Justice. I have therefore followed cases from the pre-proceeding PLO process through to appeal and have a grasp of the importance of stringent case management and an insight into the judicial approach to proceedings.

My varied experience across different aspects of family law has given me deep insights into the challenges practitioners face daily, which is why I'm passionate about being part of the LawY team and helping other lawyers work more effectively and efficiently because – aside from anything else – I know the value of time, and how in practice it often feels like there is such a lack of it.

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What excited you about joining the legal tech industry?

To be honest, it wasn't a path I had initially envisioned for myself, but I had reached a challenging point in my traditional legal career where I was experiencing burnout and feeling somewhat disillusioned with the profession. It's a crossroads many lawyers face; exploring the question of where you want to take your career and whether you are still getting that fulfilling sense of purpose that I think is necessary.

My entry into legal tech was quite serendipitous. A friend who works in recruitment had seen a maternity cover position at LEAP and suggested I might be well-suited for the role. While that particular opportunity didn't eventuate, it led to my current position at LawY. I'll admit I initially felt quite out of my depth. I had never considered myself particularly tech-savvy, so the transition felt daunting.

However, conversations with my godfather, who works in IT, helped shift my perspective. He'd always spoken passionately about the rewarding nature of technology and its potential for meaningful impact, particularly in the modern age. I was also greatly assisted by the LawY team who provided, and continue to provide, so much valuable knowledge and support.

What genuinely excites me about this industry is the opportunity to address real challenges that legal practitioners face daily. Rather than feeling constrained by traditional practice limitations, I'm energised by developing solutions that enhance how lawyers work; helping them work more efficiently and practise with greater confidence and a modern skill-set, which is invaluable in the twenty-first century.

There's also something quite compelling about the conversations this work generates. People are consistently intrigued when they learn I work in AI, and it opens up discussions about innovation and the future of legal practice in ways my previous  work didn’t.

What I find most rewarding is being part of a team where half our members are lawyers and the other half are technophiles. This means we're shaping solutions from a genuine understanding of the profession's unique pressures and requirements, whilst producing a technologically brilliant service. So, we're not just creating technology; we're crafting legitimate tools that truly serve the legal community's needs.

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What were some of the biggest challenges you faced in legal practice?

Looking back, there are several challenges which I believe many lawyers would find familiar.

I found time recording was particularly onerous and, ironically, I struggled to find the time to record my time. The constant need to capture every six-minute increment, recall activities from hours earlier, and maintain awareness of billable time felt like it detracted from the substantive work of practising law.

The time-intensive nature of document preparation was another significant hurdle. Drafting lengthy documents and correspondence often meant starting from scratch for each matter, consuming substantial portions of the working day with tasks that, while essential, weren't necessarily the most strategically valuable aspects of legal practice.

However, the most substantial challenge I faced was legal research, particularly when I transitioned to working at the Court of Appeal. With my background in family law, I found myself handling appeals across diverse practice areas, effectively starting from the foundation with each new area of law.

The research process was remarkably time-consuming and  often involved extensive library work, reviewing numerous online resources, and consulting with colleagues across different specialisations. It wasn't uncommon to invest several days researching a single appeal, whilst simultaneously managing multiple other matters.

Even within family law, each case presented unique elements so I was always conducting research to either keep abreast of legal developments, or re-acquaint myself with sub-sects that I hadn’t dealt with recently. Returning to specific applications – such as for a Secure Accommodation Order – after a period often required significant time to refresh knowledge of current requirements and recent legal developments.

What struck me most was the substantial time investment required simply to establish a solid foundation for research. While you might know relevant authorities existed, locating them and understanding their application to specific circumstances was exceptionally time-intensive, particularly in a faced paced area of law, such as family law, which can change rapidly.

This experience has shaped my appreciation for what we're achieving at LawY. When legal professionals can be immediately directed to relevant authorities and provided with a solid research foundation, it represents a significant advancement in efficiency. This doesn't diminish the importance of independent analysis or consulting additional resources; those remain fundamental to good legal practice. However, having that initial framework substantially enhances productivity, particularly when it is delivered in a neat form in one place.

Ultimately, it's about enabling lawyers to concentrate on the high-value aspects of their practice, such as strategic analysis, client advocacy, and the complex problem-solving that defines quality legal work.

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How does being a lawyer influence the way you think about product design or user experience at LawY?

I think that fundamentally, my practical experience influences how I approach product design and user experience at LawY. It provides me with essential first-hand insight into our users' needs, workflows, and pain points and means I can easily empathise with the toils of practice, which we aim to alleviate.

My legal background allows me to anticipate how practitioners will interact with our platform in real-world scenarios. I understand the mindset of a lawyer logging in on a Monday morning – the competing priorities, time pressures, and the need for reliable, actionable information – because I've walked in their shoes for years. This perspective helps me identify potential friction points in the user journey that might not be apparent to those without legal practice experience.

Having personally used practice management systems, including LEAP and SOS, I can draw on direct experience of what works well and what creates frustration for legal professionals. This insight proves invaluable when we're designing features or refining existing functionality; I can quickly identify whether a proposed solution aligns with how lawyers actually work.

During our product development discussions, having the input of Jae, Jess, Christine, Kyle and me, who understand the realities of legal practice, ensures we as a company maintain focus on genuine user needs rather than theoretical preferences. We can collectively advocate for design decisions that reflect the realities of legal practice; whether that's the precision required in our AI-generated responses, the importance of comprehensive citations, or the need for intuitive navigation when working under tight deadlines.

This legal expertise helps us strike the right balance between sophisticated functionality and practical usability. We understand that lawyers need un-complicated tools that enhance their expertise rather than complicate their workflow, and that perspective directly informs every product decision we make at LawY.

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Have you received any feedback from lawyers that really stuck with you?

Absolutely. Several pieces of feedback have genuinely shaped my perspective on what we're achieving at LawY.

A particularly memorable moment occurred during a seminar we conducted in Manchester with local firms. A criminal law practitioner volunteered – entirely unprompted – that she'd completed a document in one-third of the usual time using LawY. What struck me wasn't merely the efficiency gain, but her genuine conviction about the platform's impact on her practice.

We're consistently hearing from lawyers who report saving approximately 200 hours annually, and considering LawY has only been available in the UK for twelve months, I believe we're seeing just the initial benefits. However, the feedback extends beyond mere time savings. It's about what that reclaimed time enables. Some practitioners are investing more deeply in client relationships, others are expanding their caseloads, and many are achieving better work-life balance.

What's particularly noteworthy is the enhanced professional confidence we're observing. Lawyers frequently tell us they're using LawY to cross-reference and validate their legal analysis, which reinforces their expertise and decision-making. There's a genuine sense of professional advancement in staying at the forefront of legal technology.

I've also been impressed by conversations with prospective users who develop interest in LEAP subscriptions specifically due to LawY's integration. While there's often initial hesitation about AI adoption, we consistently see that shift once practitioners experience the platform's practical application.

This feedback reinforces a fundamental principle I hold: AI won't replace lawyers, but lawyers who effectively leverage AI will possess a significant competitive advantage or, as my colleague Peter likes to say, “AI won’t replace you, but a lawyer using AI will”. Ultimately, our work contributes to improved access to justice and enhanced quality of legal decision-making, and this feedback confirms we're progressing in the right direction.

To quote the Master of the Rolls at a recent Generative AI event:

“…to summarise, there are three excellent reasons why all lawyers and judges should embrace AI: those we serve are using it. It will make what we do available to more people, more cheaply, and allow us to do necessary things more quickly, and it will be at the centre of the future work of lawyers…”

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What's one thing you wish more lawyers knew about using AI-powered tools like LawY?

What I wish more lawyers understood is that AI tools like LawY are designed to enhance legal practice, not replace the fundamental role of the lawyer.

There's often hesitancy around adopting AI technology, with concerns that it might somehow diminish professional expertise or the essential human elements of legal practice. However, the reality is that clients continue to need the strategic thinking, professional judgement, and nuanced understanding that only experienced lawyers can provide. AI cannot replicate these core competencies.

What AI can offer is significant support with research-intensive tasks, document drafting, and comprehensive legal authority searches. It functions as an advanced research tool that can process vast amounts of information efficiently, allowing lawyers to focus their time on higher-value activities like case strategy, client counselling, and complex legal analysis.

From a professional responsibility perspective, I believe there's an argument that practitioners have an ethical obligation to their clients to explore tools that can improve efficiency and help manage costs. When we have access to technology that can streamline certain processes whilst maintaining quality, lawyers should consider whether avoiding such tools aligns with their duty to serve clients effectively and cost-consciously.

The lawyers I've observed who derive the most benefit from AI tools approach them as sophisticated assistants that support their decision-making rather than replace it. They maintain full control over their legal work whilst leveraging AI to enhance their research capabilities and operational efficiency.

Ultimately, AI tools like LawY are about empowering lawyers to deliver better outcomes for their clients, not about replacing the irreplaceable human elements of legal practice.

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What advice would you give to lawyers still not sure about leveraging AI in their firm?

As someone who's witnessed firsthand how transformative AI can be for legal practice, I understand the hesitation many lawyers feel. It's completely natural – we're a profession built on precedent and careful consideration, so approaching new technology with caution makes perfect sense.

But here's what I'd say: the landscape is shifting rapidly, and the Master of the Rolls has made it clear that embracing AI cautiously and responsibly isn't just encouraged – it's becoming essential. We're genuinely in a moment of radical change, and those who adapt thoughtfully will thrive.

The reality is that efficiency has become a cornerstone of modern legal practice. Courts are increasingly scrutinising costs, and clients expect value. If you're spending hours on research or drafting that AI could help you complete in minutes, you're not just being inefficient – you're potentially pricing yourself out of the market or facing criticism for unnecessary costs.

I'd encourage lawyers to start small. You don't need to revolutionise your entire practice overnight. Begin with something like legal research – use AI to accelerate your initial research phase, but still apply your legal expertise to analyse and verify the results. This way, you're leveraging technology whilst maintaining the rigorous standards our profession demands.

The key is finding AI tools that are purpose-built for lawyers, with proper safeguards and verification processes. At LawY, for instance, we've built in 'lawyer-in-the-loop' features precisely because we understand that legal work requires human oversight and expertise.

Remember, AI isn't about replacing lawyers – it's about freeing us from time-consuming tasks so we can focus on higher-value work like strategy, advocacy, and client relationships. Those are the areas where our expertise truly shines and where clients see the most value.

The Master of the Rolls is right – we need to be open to change. But we can embrace it responsibly, on our own terms. Sir Geoffrey Vos delivered an excellent keynote speech at the Lawtech UK Generative AI event earlier this year and within it made clear that “there is no real choice about whether lawyers and judges embrace AI – they will have to – and there are very good reasons why they should do so – albeit cautiously and responsibly”.

Ultimately, where technology goes, the world will follow, and in a profession where we have 160,000 practising solicitors in England and Wales alone, practitioners cannot afford to be left behind.

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What are you most excited about for the future of LawY?

Honestly, I'm just so excited to see where this journey takes us! The growth we've experienced has been absolutely incredible – we've got over 43,000 users globally now and we've just hit over a million questions. The expansion since last summer, particularly with our USA launch, has been mind-blowing.

From a development standpoint, I'm constantly amazed by what our tech team comes up with. I'll admit, when they first pitch ideas to me, I don't always immediately get it – but then watching those concepts come to life is genuinely awe-inspiring. Take Rapid & Deep Research, for example. I was curious to see how users would respond to these new features, and now I'm really seeing their strengths shine through with the brilliant feedback we're getting.

We're already setting our sights on 2 million questions, which feels both ambitious and totally achievable given our momentum. But beyond the numbers, I'm really excited about how we can keep evolving to serve our users even better.

What I find particularly fascinating is wondering whether law firms will start winning clients by actually promoting their AI capabilities. It's such an interesting market shift. Though there's a flip side to this – I heard about a lawyer who was sacked by their client because the client kept running the lawyer's work through ChatGPT and finding it more comprehensive. That's a real wake-up call for our profession.

The truth is, everyone has access to AI now – including our clients. We need to acknowledge that reality. I think there's genuine risk in losing client trust if you're completely resistant to AI and efficiency-enhancing technologies, particularly when the client is paying for a rounded service

It's an exciting time to be part of this transformation in legal practice, and I can't wait to see what we build next.

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In conclusion

This conversation with Holly perfectly captures why we're so passionate about what we're building at LawY. As the legal landscape continues to evolve rapidly, we're committed to staying ahead by keeping practising and former lawyers at the heart of everything we do. Because when you're built by lawyers for lawyers, you don't just understand the challenges – you're actively working to solve them, one feature at a time.