What Is the Future of the Legal Profession? Flexible Talent, AI in the Courts, and Why the Profession Needs to Redesign Itself
Beyond The Fine Print, Episode 17
The legal profession, as Rory O'Keeffe opens this episode, has always had a slight Truman Show quality. The billing targets are met. The Latin is impeccable. The weather is permanently partly cloudy with a reasonable chance of partnership. Nobody asks why the tide only comes in on billable hours. Until someone taps the glass.
Dana Denis-Smith OBE tapped the glass 15 years ago, then went away and built a door. Founder of Obelisk Support, architect of the First 100 Years and Next 100 Years initiatives, and the Law Society of England & Wales's incoming president for 2027 - the eighth woman to hold that role - Dana has spent two decades creating the flexible legal talent market before flexible work was fashionable, and quietly compiling the data to prove why the profession keeps getting it wrong for women.
This is not a comfortable episode. It was not designed to be. If you work in-house, lead a legal team, or run a scaling business that uses external legal resource, the questions Dana answers here have a direct bearing on the quality and diversity of the legal talent available to you.
Listen on Spotify, Apple Podcasts, AmazonMusic or YouTube. Episode runtime: approximately 52 minutes.
What does the legal profession look like from the outside looking in?
Dana came to law through Romania, journalism, and The Economist before joining Linklaters. That route is unusual enough that Rory uses it as a deliberate starting point:
“what does someone who arrived with an outside eye actually see about a profession that those inside it are too close to notice?”
Her answer is nuanced. What drew her in was not the public persona of the combative lawyer, but what sits behind it: intellectually curious, genuinely humane people who do not always get the credit they deserve. The alienating exterior, she suggests, is partly structural. Legal training conditions lawyers to detach - to be objective for their client - and that detachment can become a habit that extends to the practice itself. You stop questioning how you deliver the work, not just the work itself.
The second observation is harder to dismiss. The legal profession has spent decades articulating the value of law in terms of its own lofty ideals - rule of law, underpinning of democracy, the framework of predictability - and those ideals are real and important. But if the person on the street cannot connect them to their own life, or feel that the legal system is functioning for them, the profession is talking to itself. The credibility of legal institutions is not self-sustaining. It has to be earned repeatedly. And the profession, on the whole, has not been doing that work.
Has flexible working actually changed how the legal profession values talent?
Obelisk Support was founded in 2010, when the argument that a lawyer should be able to work around a child - rather than treat parenting as a disqualifying event - was still genuinely uphill. Dana describes the early conversations: firms that could not see underutilised talent because the talent was not presenting itself in the approved format.
Fifteen years on, and the landscape has shifted. There is now a meaningful distinction between firms that understand flexibility as a genuine business asset and firms that are simply better at talking about it. That distinction, Dana notes, is actually useful: it gives lawyers and clients a clearer signal about organisational values, rather than a uniform surface of vague commitments.
But the more disruptive shift is not remote working or flexible hours. It is AI.
The question has moved from why does a lawyer need to work the way they have always worked to why do we need a lawyer at all, and what specifically is the value they provide. The profession has not yet landed its answer to that question. The pieces, as Dana puts it, have not fully settled into a puzzle. The train is moving fast past the station, and not everybody is on it.
What is actually happening with AI and hallucinations in UK courts?
This is where the episode shifts into territory that anyone using AI tools in a legal or commercial context should pay attention to.
Rory references recent research from Matthew Lee of Doughty Street Chambers tracking reported AI hallucinations in UK court proceedings - fabricated case citations submitted to courts as if they were real. The number at the time of recording: 58 reported cases. That figure covers what lawyers have volunteered to disclose. It is not drawn from published judgments. The real number is almost certainly higher.
The judiciary's response has been clear. Litigants are being held personally responsible for every fabricated citation their AI tool invents. This is not an unreasonable standard. A professional is expected to check their work before submission. That has always been the baseline.
What makes this a genuine access to justice problem, rather than simply a professional standards failure, is the context in which many of these tools are being used. Legal proceedings are expensive to navigate. Court backlogs in England and Wales are substantial - proposals are currently in circulation for judge-only trials in certain case categories as one attempt to clear the queue. People who cannot afford legal representation are turning to AI tools not out of laziness, but because they have limited alternatives. And those tools are producing citations that do not exist, to courts that apply full professional standards to the result.
The technology is not the problem. As Dana puts it: if you want the technology to be your barrister, that is a question about your own professional standards, not just the tool's limitations. But the access point at which people are using these tools, without the professional training to verify output, is a genuine systemic risk.
Is the future of the legal profession female?
Dana’s view is unambiguous: yes, demographically, it already is. The overwhelming majority of law graduates are women. The majority of those admitted to the profession are women. The question is not whether women are entering the legal profession. The question is why they are still not reaching the top of it in proportion to their numbers.
Her analysis of the partnership assessment framework is precise and worth sitting with.
The criteria by which lawyers are assessed for partnership have not been substantially updated. They were largely written by the group that was originally being assessed: men, many of whom came through routes that included military service, where leadership was understood to mean something specific and visible. The framework measures the behaviour and presentation of that original group. Women are then assessed against a standard that was not designed for them, and unsurprisingly many are found short of it - not because they are less capable or less commercially effective, but because the measurement tool is miscalibrated.
The practical consequence is that women who are doing excellent work, meeting commercial targets, and building strong client relationships are being passed over for partnership at the point where subjective assessment kicks in. The problem is not exclusively about caring responsibilities, although those remain unevenly distributed. It is about how we define what a successful legal entrepreneur looks like, and whether we have updated that definition to reflect the actual population being assessed.
What does the access to justice crisis mean for business leaders?
The access to justice crisis can feel like a civic concern - important, but at one remove from the day-to-day of running a company or managing a legal team. It is not. It is a talent pipeline problem: the lawyers best placed to bridge the gap between the legal system and the public are often the ones who burn out earliest, because Legal Aid funding does not pay the bills, and criminal and family law practitioners absorb enormous workload for limited financial return. The profession loses a specific kind of practitioner - the one with real coalface experience of how law functions for individuals - and that loss shapes the quality of advice available further up the chain.
It is also a regulatory risk problem. As the legal system becomes more complex, more digital, and more expensive to navigate, the risk of individuals and small businesses making uninformed decisions increases. Those decisions create claims, disputes, and regulatory exposure that eventually land on someone's desk.
And it is a procurement problem. If you use external legal resource, the depth and breadth of talent available to you is shaped by how well the profession retains and develops the people coming through it.
How do you redesign a legal system that has stopped working?
Dana’s approach to this question is structural and future-first. Her argument is that we consistently iterate on what we have rather than imagining what a better system would look like and working backwards from it.
She gives two anchor points for a redesign that is grounded rather than utopian.
The first is demographic reality. The future of the legal profession is female. That is not a value statement. It is a data point. If you start from that demographic and ask what changes would need to be made to allow that population to progress and thrive, you can identify three or four concrete things immediately. That is a more tractable design problem than a complete reimagining.
The second is financial reality. There is no treasure chest of public funding waiting to transform the court system. The technology to improve access, reduce friction, and create more clarity for non-expert users already exists and is relatively affordable. COVID moved the profession further in eighteen months than it had moved in the previous decade, because it had to. That acceleration can be maintained intentionally, rather than waiting for the next emergency.
The resistance to bold redesign is understandable. People do not buy a destination they cannot visualise. Incremental change is politically easier than systemic change. But incremental change on a system that is demonstrably not working will not produce a different outcome. The profession knows the problems. Victims wait too long. Judges and lawyers are leaving under the strain. Attrition figures at senior level are not improving. Continuing along this trajectory and expecting a different result is, to use the classic formulation, the definition of something we should probably avoid.
Key takeaways from this episode
The legal profession's credibility is not self-sustaining. The gap between institutional ideals and public experience has widened, and that has practical consequences for how law functions as a framework.
The shift from flexible working to AI as the primary disruption to the legal workforce is significant. The question is no longer about where and when lawyers work. It is about what a lawyer is for, and how that value gets communicated.
AI hallucinations in UK courts are a documented and growing problem. 58 reported cases is a floor, not a ceiling. Litigants are being held personally accountable. Professional standards have not moved. The gap between what tools can do and what users understand about their limitations is a genuine access to justice risk.
Partnership assessment frameworks in law firms were built by and for a specific demographic, and have not been updated. Women are being assessed against criteria that do not reflect their actual strengths, and the profession is losing talent as a result.
The access to justice crisis is not just a social problem. It is a talent pipeline problem, a regulatory risk problem, and - for businesses using external legal resource - a procurement problem.
Redesigning a legal system requires starting from where the future is already pointing: a more digital system, a more female profession, and a public that needs to understand its rights rather than just know that lawyers exist to protect them.
Technology aligned to legal work - word-led, accessible, and capable of handling nuance - is the most realistic lever for expanding access. The profession's job is to deploy it with integrity, not to resist it until forced.
About this episode's guest
Dana Denis-Smith OBE is the founder and CEO of Obelisk Support, the flexible legal talent platform she built from the ground up in 2010. She is the architect of the First 100 Years and Next 100 Years initiatives, which document and celebrate the history of women in the legal profession. In 2027, she will become President of the Law Society of England and Wales - the eighth woman to hold that role. Dana is one of the most consistent and data-grounded voices on flexible working, access to justice, and gender progression in law.
About the host
Rory O'Keeffe is a solicitor regulated by the Solicitors Regulation Authority, former Partner at Matheson and former Director of Legal Services at Accenture. He is the founder of RMOK Legal, an SCL-accredited Leading IT Lawyer, a member of the Society for Computers and Law's AI Committee, and the author of AI Advantage: Thriving Within Civilisation's Next Big Disruption (2025). Beyond The Fine Print is the tech law podcast for in-house counsel and business leaders, covering AI regulation, digital law and commercial legal strategy. Available on Spotify, Apple Podcasts and YouTube.
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