Interview | Caryn Sandler (Gilbert + Tobin) | A conversation about leading 'real' innovation

Caryn Sandler Image.jpeg

Cristabel Gekas from TLF Vic recently had the opportunity to interview Caryn Sandler, Partner and Chief Knowledge and Innovation Officer at Gilbert and Tobin. G+T has firmly established itself as a leader within the legal innovation landscape both within Australia and internationally, having most recently won ‘Most Innovative Law Firm in Asia Pacific’ at the 2019 Financial Times Innovative Lawyers Awards. In this interview, Caryn talks candidly about the challenges and rewards of driving real innovation with G+T’s clients, within the firm and throughout the legal profession more broadly. Caryn also shares her insights about how the G+T has pursued a multi-disciplinary approach to innovation and her biggest lessons in leading effective change within the legal profession.

1. A bit about Caryn…

What’s your favourite place in the world? (Credit to Andrea Perry-Peterson and the amazing ‘Reimagining Justice’ podcast for letting us recycle this question).

I would have to say Europe. I lived and worked in London for some time and did a lot of travel. I particularly love Italy. I love the culture and the history there. 

What’s something in your life that you’re excited about right now? 

I’m going to be really boring and say I’m very excited that I’ve just completed a renovation and new pool, which has been a long and difficult process.

What did you want to be when you grew up? 

From my recollection, I wanted to be a physiotherapist, or a psychologist. As you can see, I’ve completely gone the opposite way! 

2. Changes in the legal innovation landscape  

In your current role, you work with the firm’s clients to transform and  streamline the delivery of legal services. What is the biggest challenge in-house counsel continue to face in streamlining or automating low value work?

From my perspective, there is a lot of appetite internally within a lot of in house teams to transform the way in which they are working, and to streamline or automate low value tasks. 

The challenge I see on a regular basis is the legal team doesn’t necessarily have the broader organisational mandate to change. The result is that they don’t often have the resources, and they don’t have access to technology to help them along the way. 

When I reflect on my role, I live and breathe this stuff. Legal technology is evolving so quickly, you do need to have a strong handle on the changes and landscape. That requires extra effort in and above their days, which are already very long and full. 

There are some organisations which have a broader organisational mandate for change. But often legal is last to get access to those resources to enable change. 

You’ve previously mentioned that client confidentiality and privacy concerns make it difficult to harness the critical mass of data required for legal AI to take off. In your opinion, what will be the best solution to this tension?

Technology-based responses 

I have thought about this for a long period of time, and it is a really tricky issue to solve. The whole concept of artificial intelligence is that it requires data to enable you to get the best output from it. There is a real tension here. Because of confidentiality concerns, firms are only able to use the data they have access to, to train their own instances of AI. 

I think over time AI will become sophisticated enough that it won’t require so much data to train it. I’m certain that the technology will evolve in that way over time. 

Another thing we have tried is to redact the sensitive information from legal documentation. The problem with this approach is because you are redacting some of the information, the AI is not good at identifying and extracting clauses when it doesn’t have sufficient context.

One could also jumble the content of the documentation so that it becomes indecipherable. The idea here is that the document would look so different to a traditional document that it would no longer breach confidentiality – but again, there are difficulties with this approach. 

Legal responses 

I’m hoping overtime that the technology will solve the current issue we have with the technology – in that it becomes so sophisticated it doesn’t require large data sets. But, some important conversations need to take place at the moment. This might include back-to-back confidentiality agreements. It’s important that this happens, because it is certainly in the interests of the legal profession for AI to take off in the way that we need it to. 

There are also jurisdictional issues to be considered. For example, in the U.S, there are publically available repositories of documents that can be tapped into to develop AI. So we would be at a competitive disadvantage in Australia, considering the greater access to legal documentation in the U.S.  

You have previously predicted that AI technology will be a major disruptive force to the legal profession in the next five to ten years. What are the new and emerging applications of AI within the legal industry? 

The gaps in AI

There will be some interesting applications of AI going forward, but it’s very hard to predict. At the moment, AI is very good at extraction, but it’s not great at drawing conclusions from the data. What I mean by that is AI might be able to tell me a certain piece of information is a ‘change of control’ clause or a ‘parties’ clause or a ‘date.’ But the AI isn’t able to tell me the ‘change of control’ is triggered in the context of the transaction. 

That is probably good thing for the legal industry at the moment. Lawyers want to do high value work. So we have a long way to go in this field, and it’s very difficult to predict how far the AI will go. 

Knowledge management 

Also keep in mind the legal profession is a profession of knowledge. AI has some enormous potential within the context of identifying and retaining knowledge within an organisation. For example, I’m looking at AI at the moment to see if we can surface up knowledge to our lawyers in a more streamlined way. Normally, lawyers would have to trawl through documents to try to find example clauses. I’m trying to see if AI can pick up granular detail in clauses for our lawyers, rather than having to trawl through that information. 

Document management

The other area where we are starting to see the emergence of new applications of AI are in document management systems. Netdocuments, Kira, RAVN and iManage. You can certainly see where that is going. The IP and knowledge of the law firm is all contained in their document management system. If you can successfully get the AI to pour over those documents, you will most certainly uncover interesting information and trends. This will be enormously helpful in pricing matters, etc. 

So, from a knowledge management perspective, AI has the potential to enable us to gain a deeper knowledge of how to manage our matters, without having to engage in time consuming manual work. Asking staff to complete surveys at the end of matters I think will be extremely powerful in advancing this technology in the future. 

The legal industry has traditionally looked inwards when thinking about change and disruption. What lessons can we glean from other professional service industries when driving innovation? How can we foster greater collaboration in this area?

I think it’s absolutely critical to think about other industries. It is well understood that law firms and legal organisations need to change the way they are operating. But, if you think about the banking industry, among others, this type of change happened a long time ago. So, I particularly like the quote by William Gibson: “the future is already here, it’s just not evenly distributed.” I think the legal profession can really take heed of a comment like that. 

Medical industry 

I think the legal industry can leverage some of the developments happening in medicine right now. There is no doubt that much of the work in medicine is incredibly complex, requires extensive university and practical training. But we are starting to see that certain tasks are now being automated or done by robotics. 

I think this is interesting for the legal industry, because whilst there are some tasks that require real human intellect, there are certainly some tasks that are far more routine and often voluminous in nature. We need to challenge the assumption that some of our work can’t be systematised or streamlined in a similar way. 


There is also a lot to be learned from other professional service industries from a pricing perspective. I don’t think anyone would argue that the billable hour is inconsistent with innovation. It’s certainty something that G+T tries very hard not to engage with. If something can be done cheaper and faster, we will pass on those benefits to our clients. But the reality is that we work within an industry where we still have the billable hour, and  this is inconsistent with the pursuit of efficiency.  

For many years, investment banks have priced on the basis of value creation. We can learn a lot from this. The more collaboration we can have with other organisations that have navigated disruption to some degree already, the better off the legal industry will fare. 

The need for a multi disciplinary approach 

A lot of other profession services industries offer services in a multi-disciplinary manner, and I think this is something we also need to consider. Traditionally legal has been quite poor in this area.  

3. IntraprAneurship within G+T 

How has Gilbert and Tobin avoided containing its innovation strategy within siloes? How has the firm encouraged practising lawyers to actively drive innovation within the firm in a manner that is complementary to the practise of law?

Firm leadership 

In my opinion, the overarching reason for our success this far at G+T is that we have incredibly strong leadership promoting innovation and ‘doing things differently.’ G+T really signalled to the market last year that we are committed to being a future-fit law firm, ready and willing to do things differently. 

A multi-faceted approach to innovation

One of the biggest successes we have is the way we have structured the Legal Services Innovation (LSI) team. The LSI team is made up of knowledge management, transformation, LPM and Legal Informatics. By bringing those skillsets together on client matters, we tap into diverse expertise, which gives us a competitive edge. We also have a separate innovation unit, g+t<i>, which is primarily made up of lawyers and partners interested in innovation. This unit gives us a lot of reach within the firm. 

Internal education and support 

We understand that the work of our practising lawyers is absolutely crucial to our innovation strategy. We are trying to cultivate an understanding that innovation is just as important as client work. 

We recently launched an internal innovation called ‘Project Invigorate.’ The Board and Partners approved a $1 million investment into this initiative. This is a commitment from G+T that time spent on particular work, either approved by myself or core to the innovation strategy, is actually counted as billable for the purpose of lawyer’s performance reviews or any career advancements. 

Education and support

We constantly educate our lawyers in this space, so it is front of mind for our lawyers on a daily basis. I’m very much a proponent for bringing more and more technology into the organisation, because that is going to be the way of the world moving forward. This is part of the change management piece we deliver internally. 

The beauty of my team and having me as partner is that people know who to go to. Lawyers might be brilliant at their legal work, but they might not have a good understanding of legal tech, AI, data analytics or LPM. 

We are trying to embed those capabilities, as well as support legal services innovation with our client facing work. 

4. Lessons on leadership 

What have been your most important lessons as a leader in the legal innovation space, both in Australia and internationally? 

For me, there are two key takeaways: 

1. Never be complacent. 

The trend now is that legal organisations are well and truly aware of the need to innovate. At G+T we are constantly trying to push boundaries and we always think about what is next – we have a focus on continuous improvement. We might win a Financial Times award for the Most Innovative Law Firm, but we need to ensure we keep the momentum up – that’s the hard part, staying ahead.   

2. Innovation needs to be real 

It’s very important to me that we practise what we preach in the market. Innovation by press release does not resonate with me at all. It’s got to be real, and that’s what makes me most proud of being at G+T. It’s all about what being transparent about what we are really doing. 

5. Education for law students 

How can law students position themselves during their early career to take up a role in knowledge management or legal operations in the future? From my perspective, I think there needs to be a greater focus on shifting mindsets, and building an understanding that legal innovation is everyone’s problem, rather than a marketing device or something for ‘creative’ or ‘tech minded’ people. 


Yes, I would absolutely agree that it’s all about mindsets. Number one, you must be curious. It’s absolutely critical that students understand that the market is shifting, and that they turn their minds to what else is out there. 

Pursue opportunities 

I now rotate summer clerks and graduates in my LSI team. Whether they want to settle or not into my team is a different story. If students have a real interest in this technology and innovation area, I would encourage them to actually conduct research to establish which firms and organisations can offer them this type of training. It will be invaluable going forward. 

Be critical, and think about continuous improvement 

I also think it’s important that law students bring a mindset of continuous improvement and process to their work. I think there are very few organisations that don’t have some form of innovation agenda happening inside the firm. It’s all about engaging in those initiatives. Early career professionals should feel empowered to critically challenge what they are doing on a day-to-day basis. They bring a new and fresh perspective to the delivery of legal services. Law students should to shift away from the mindset that this is ‘someone else’s problem’ and start thinking ‘this my problem, and I need to fix this, and I’m going to find ways to assist the organisation in doing this.’ 

I’m also not of the mindset that law students need to have coding skills to successfully work in legal firms. I can’t code. But I do understand what technology is capable of and really have a ‘process-orientated’ mind. With these ingredients, I think law students can go really far.

Author’s note: For those of you interested in learning more about how we can equip law students for the future practise of law, I highly recommend reading “Legal Innovation: Education in Australian Law Schools”, by Andrea Perry-Petersen and Michael Lacey. You can read the article by following this link: You can also check out Andrea’s new podcast ‘Reimagining Justice’ here

Aaron Patel