In conversation with: Simon Hardcastle, Endless LLP

The journey from private practice to an in-house role is not always linear. In this interview we explore some of the potential motivations and challenges that shape such a move, and find out why the role is, at its heart, about helping everyone in the business do their role more efficiently and effectively.

Simon took what he describes as a traditional route into the law, starting his career in the Corporate team at Walker Morris. After 5 years (and a short career break), he joined power generation business Drax on secondment, and began to think that in-house might not be such a bad idea after all. Following another secondment, this time at Endless LLP, Simon took the plunge and became their first (and only) lawyer in 2012. 

Simon Hardcastle, GC, from Endless LLP in conversation with Debbie Jackson, Partner, Walker Morris
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Debbie Jackson in black and white
Simon Hardcastle head shot in black and white

Hi Simon, it’s great to see you again. We’d like to understand more about your journey from Walker Morris to your current in-house role. Can you tell us what the key differences are between the 2 roles, in terms of daily responsibilities and expectations? And were there any surprises or adjustments that you’ve had to make?

My move to Endless was actually a fairly easy transition, because they had been clients while I was at Walker Morris and then I’d been on secondment with them as well. So, it did feel like one of the easier moves I’ve made. Before my secondment to Endless, I also did a secondment with Drax (at a power station near York) which was a valuable steppingstone; it meant I needed to learn about an industry I’d never worked in before and really start to understand the business on a whole new level to enable me to put my legal advice in context. I was better prepared for my next secondment, and it gave me a taste of life outside a law firm. In my view, one of the key differences between in house and private practice is the extent to which you’re doing the ‘job’, and by that I mean dealing with the practical application of the law and legal issues for your internal clients. I realised that I had a choice to make – either continue in a law firm and follow the partner track which would mean more time spent managing a business team and developing client relationships, versus an in-house role where the pressures would be different, but I would be more involved in the decision-making processes and activities of the organisation.

In house is a different approach and absolutely something that takes some adjustment. First of all, I think you have to shake off the concept that you’re an advisor, because actually you’re part of the decision-making process. You need to be really solutions focused and have the confidence to give practical recommendations which effectively manage legal risk. Adapting to that mindset early on is very important. I would also say that in house, you need to think holistically about the legal risk within the business, including establishing systems and processes to help manage that risk rather than just reacting to what’s being asked of you in the moment. This is particularly important where you’re the sole lawyer in businesses and can be stretched thinly. When you’re part of a growing organisation, the demands on you and your time are always increasing and you’ve got to become adept at identifying where you can have most impact and having processes in place to manage lower risk areas.

Can you tell us a bit more about how your role has evolved? What has changed in the legal landscape that has had an impact on what you do?

The Private Equity landscape has evolved significantly over the past decade. It’s matured as a sector, and with increasingly more sophisticated processes and counterparties that increase the complexity of raising funds and making investments, we are subject to more prescriptive regulations and need to consider wider non-financial criteria (such as ESG factors) which all impact how we run our business and select underlying investments. There’s also far more focus on operational resilience at the firm and its ability to cope with macroeconomic events. It’s often the GC’s role to help manage these areas and supplement their teams where needed. At first, regulatory and compliance were an expected part of the role of GC, but now we’ve separated the roles, because it’s so important to manage that risk effectively. We hired an expert to do that around 5 years ago. I’d say that a lot of GCs, in this industry in particular, spend as much time on risk, operational and governance issues within their business as they do dealing with purely legal matters.

What advice would you give to lawyers who have recently transitioned from law firms to in-house positions in terms of adapting to their new environment and responsibilities? What are the key challenges lawyers face when moving in-house, and how can they navigate these challenges effectively?

I touched on this a little in my previous answer, and I think the key is to spend time getting to know the business so you can put your legal advice in a practical context. During my time with Drax, I had to immerse myself in an industry that initially I knew very little about. So, when I had to navigate for example a freight contract, I needed to understand the journey the product was taking from port to site to be able to put specific legal issues into a practical context that would work on the ground. I think it’s important to show people that you’re interested in them and their role and to understand what they would like from you to be enable them to perform their role effectively. A solutions focused mentality is crucial, but you also have to accept that you won’t have the answer to everything immediately – and having the confidence to say to colleagues that you need time to find an answer to their question is not a failure, but a strength.

One other aspect that’s key to navigating the challenges you may face, particularly where you are first in the role, is understanding the business context of the legal risks you encounter. This is important because budgets are not unlimited, so whilst you need to have an awareness of the complete picture, you need to prioritise those things with the biggest potential impact and the greatest chance of happening. If you try and tackle everything at once, you’re setting yourself up to fail.

How do you manage the relationship between the legal department and other business units? What have you found effective in fostering collaboration?

I sit in on the weekly investment team meetings so that I can hear what everyone is up to, and I think it’s important to show an interest in what they are doing, even where there is no direct ask of the legal team. I also schedule time into my day to speak to people, whether that’s over Teams or sitting down with a coffee or a sandwich over lunch. Those conversations help you build the bigger picture of what’s going on in the organisation and where your input might be needed. I put a lot of thought into the tools I might be able to provide that will make life easier for other parts of the business and that will enable me to manage legal risk without being directly involved all the time. That might look like standard documents, a playbook to help navigate particular situations, or some training to cover off an issue that comes across my desk on a regular basis. All these things are, at their heart, about enabling everyone to do their job efficiently and effectively, while also managing risk within the organisation. Linked to this, I also always take time to explain why I would like something to be done in a certain way, so that the different parts of the business understand their role in managing risk and can feel reassured that it’s a valid thing to be spending time on. Asking for feedback is really helpful in shaping manageable solutions to problems and I will always ask the team for feedback after each project to see where we can improve things next time round.

What role does continuous learning and professional development play in your career? Can you recommend any resources or practices for lawyers looking to stay current in their field?

There’s no doubt this is important, and I try and keep an eye out for what’s on offer in terms of conferences and seminars on technical matters, as well as information from our industry body (BVCA). I try and dip into the areas that are most relevant to current business needs. But actually, as I’ve got more senior, it’s the softer skills that I want (and need) to develop, because it’s these that will allow me to deliver the technical side of things in the best way for the organisation. I’m a firm believer that how you give your advice is just as important as the advice itself!

Because I’m the only person in the legal team, I appreciate that it can be hard to be objective about my performance and the areas I need to develop, so I make a point of taking part in 360-degree appraisals. I’d also add that it’s worth leaning on your panel firms, because working in-house can sometimes be a lonely place, so developing a network of people you can bounce ideas off and provide training that deals with the CPD side of things, really is important. I would also recommend networking with peers in your industry as they are often dealing with similar challenges in their businesses. PE is quite London centric, so we’ve set up a local group of legal, finance and compliance professionals which meets informally to discuss issues and challenges.

Considering your experiences, what are the most rewarding aspects of working in an in-house setting? Are there any specific achievements or milestone in your in-house career that you are particularly proud of?

Honestly, being recognised by colleagues for the role you play on a project is incredibly rewarding; being name checked by colleagues on our internal comms tool for the help you’ve given is something I’m always happy to see and witnessing change in the business as a result of my initiatives is also something I feel very proud about. Arming colleagues with the tools to do their jobs well and watching them progress to effectively dealing with issues without your input is immensely gratifying and shows that you’re helping your business move in the right direction. From a business perspective, the most valuable things I do save us time and enable my colleagues to focus on the areas where they can have the most impact on our business. It’s the simplifying of complex ideas or processes that is right at the heart of what successful in-house lawyers do.

Can you share any personal anecdotes or examples of challenges you encountered and how you overcame them?

The one skill that everyone should master is the ability to summarise – your Board will thank you for it! As Albert Einstein once said, “If you can’t explain it simply, you don’t understand it well enough”.

“Arming colleagues with the tools to do their jobs well and watching them progress to effectively dealing with issues without your input is immensely gratifying and shows that you’re helping your business move in the right direction.”

Simon Hardcastle, GC, Endless LLP
Simon Hardcastle, GC, from Endless LLP in conversation with Debbie Jackson , Partner, Walker Morris