‘As a result of my commercial background, my practice at the Bar will be filled with high-value, complex commercial cases which will magically appear from almost day one of practice because of my understanding of companies, markets and directors.’

This is a slightly exaggerated version of my answer at pupillage interview to the question: What will your background bring to your practice at the Bar? I had spent 14 years working in the investment banking industry, mostly in European equities. In my mid-thirties I resigned, went to law school to become that odd creature in the eyes of some, a mature student, before starting to look for commercial pupillages.

My words were said as much in hope as expectation and, despite my response, Chambers was kind enough to offer me pupillage and tenancy. What transpired, though, made my answer partly true, even if the magical appearance of cases from day one didn’t quite happen. Through a combination of good fortune, supportive solicitors and a genuine interest in the subject matter, I built a commercial practice involving a significant amount of company/shareholder/director dispute work.

How to survive the AI onslaught?

When asked to consider what it is that might allow barristers to retain an edge in the age of AI, I was reminded of my answer to that interview question. Like many barristers, I suspect, I am very far from being an expert in AI. I use LLMs (large language models) suspiciously and find myself relieved when I spot errors. I recognise that the AI embedded in our legal database is useful for starting the process of research, but that is about the extent of my usage.

I recently attended a mediation where my client, a wealthy businessman, said he asked ChatGPT what he should do every time he needed to make a decision. The answers he shared were riddled with cliché and were either wrong or unlikely to get him the settlement he wanted. We, the solicitor and I, gently suggested that we did not take the tack suggested by AI.

With all this in mind, what I offer below might be more optimism bias than anything else. I do think that having a feel for businesses and what directors/shareholders want from litigation is a significant part of being a commercial barrister and might allow us to survive the AI onslaught. The question is how a barrister achieves that. I hope that a few pointers might assist.

Getting familiar

Firstly, the numbers matter. When I started out, I had the ability to read a report and accounts, decipher a balance sheet and question directors about their businesses in a reasonably informed way. For those who have done a law or arts degree and have not encountered many balance sheets, I would recommend taking a course in accounts/financial analysis. This might sound dull, but the more you can familiarise yourself with accounts, the more at ease you are going to be with directors discussing their businesses and the thing that drives all business – the numbers.

This familiarisation process has an added benefit. The valuation of companies and certain other assets often involves the creation of a notional P&L and cash flow statements from which can be derived either sustainable EBITDA to be used in a multiple based valuation or a discounted cashflow valuation. A course on financial analysis and the confidence that will bring is likely to allow a better feel for these types of valuations.

Connecting in conference

Secondly, being able to question directors or business owners about their business, what they want from them and what they want from litigation is key. I do find that directors open up, perhaps even trust me more because I can question them or talk about their businesses with some understanding.

Thirdly, many commercial disputes particularly those involving shareholder/directors are far more personal than a cold analysis of the numbers would suggest. Questioning lay director/shareholder clients in conference should certainly be about the business and the technical aspects of the dispute, but it should also be about the personalities of the clients themselves and the opposition. Unfair prejudice petitions are with good reason sometimes called business divorce. If you can get to the bottom of the reason for the falling out by careful questioning, then it might assist in settlement or even at trial when cross-examining.

This is not a suggestion that barristers in conference with clients start with a question along the lines of ‘so tell me about yourself’. It is more that careful, sensitive questioning about business approach and style, the management or shareholder dynamic and ethos of an organisation can allow a better understanding of a dispute and the motivation of the parties.

Having said that, simple, direct questioning may not always be appropriate, I do find that something akin to ‘what do you want out of this’ at the end of a conference is a useful question. It might even be ‘the’ question. It is possible that one can labour under misapprehension in the absence of having asked outright what a client wants. I tend to find that clients are relieved to have been asked and (mostly) are prepared to offer a frank response.

Improving your cross

Fourthly, I struggle to see how AI is going to replace a barrister with a good head for business and the business in question at trial. There are all sorts of reasons for this, but one might be cross-examination. It is likely that your cross-examination prep is going to be better informed if you know and understand the business and the numbers that underpin it. If you are cross-examining an expert on their valuation/analysis of a business, your performance once you get to the cross itself is likely to be better if you know the business and the accounts.

An anecdote to support this: in a case a few years ago in front of a challenging judge who will remain nameless, I had struggled to quieten unnecessary judicial intervention by a judge who seemed to have made up his mind at an early stage in proceedings (not in my client’s favour). I started cross-examining the expert and realised that he was not as familiar with the numbers as he should have been. I knew this because I was very familiar with them. It was at this point that the judge seemed to be rather more interested in my case.

What to take from all of this?

I am starting to see ways in which AI complements what we do but I struggle to see how oral advocacy can be replaced. In particular, engaging with clients and understanding what truly motivates them through careful questioning feels beyond AI – or at least suggests a future where barristers work alongside it. There may be hope for us yet.