Isla Pickering is the CFO of Law Debenture, a FTSE 250 investment trust with a professional services business at its core. She stepped into the role at the start of 2025, taking on her first CFO position after more than 20 years in finance.
She is focused on supporting a profitable and growing business while helping shape how the finance function adapts to new technology and increasing regulatory demands.
Her experience in professional services continues to influence how she approaches leadership, with a strong emphasis on clarity and control while building teams that can support long-term growth.
How did you become a CFO?
I did a management sciences degree, which was very much a general business degree. Towards the end of that, I was looking at graduate roles and was drawn to accountancy firms. I was interested in the numbers side of business and liked the idea of doing my accountancy qualification to give me a strong grounding.
I joined KPMG after university and qualified as an accountant. I worked with a variety of clients across general markets and financial services. I really enjoyed it, but I decided I was never going to be a partner.
I moved into industry and took a commercial finance role at Hilton Hotels, then moved to Linklaters, where I spent nearly 15 years in a range of finance roles. I worked my way up to Group Financial Controller and also spent time leading internal audit, which gave me strong experience on the control side.
After that, I joined LEK Consulting as Group Financial Controller. I was really enjoying that role when I was approached for the CFO position at Law Debenture. I had not been actively looking to become a CFO, but it is naturally the next step in a finance career.
What attracted me to the role was the structure of the business, combining an investment trust with a professional services firm, and the opportunity to bring together my experience and step into that leadership role.
What skills or traits does a good CFO need?
For me, one of the most important skills is the ability to translate numbers. You need to take complex financial information and explain it clearly to different stakeholders, including people who are not from a finance background.
You also need a strong understanding of the business and how it connects to the numbers.
Attention to detail is really important as well. You need to be able to spot when something does not look right.
Another key trait is the ability to bring teams together. You cannot have every skill yourself, so you need to identify what is required and build a team that covers those areas. I think of it a bit like leading an orchestra, bringing different parts together for a common purpose.
What excites you most about your current sector?
One of the things that excites me most is that we are a profitable business that is continuing to grow.
That gives us the ability to invest, both in the business itself and in new opportunities. There is a real focus on growth, both organically and through investment.
I am also very interested in how we can use technology. There’s a lot of potential to improve how we operate and how we support clients, as well as creating efficiencies within the finance function.
What is the best bit of business advice you’ve ever received?
If you do not know, do not guess; ask questions.
That is something I learned early in my career. When I was more junior, it meant asking colleagues and learning from others.
As you become more senior, it evolves into bringing in the right experts when needed, whether that’s within your team or external advisors.
It’s something that has stayed with me throughout my career.
For me, it is the regulatory and audit burden.
Over the years, the regulatory environment has become more demanding, which is understandable, but it does take up a significant amount of time.
Simplifying compliance processes, without reducing the necessary oversight, would free up time to focus more on growth and efficiency.
What do you do outside of work to protect yourself from burnout?
Spending time with my family is really important to me. I have two young children, and that time helps me switch off.
I also enjoy being outdoors. I have a dog, so I spend time walking, and I also have a horse, which is another way I relax and disconnect.
Those things together help me step away from work and recharge.
What’s the biggest challenge facing your sector at the moment?
Technology is both exciting and challenging at the same time.
Internally, it is about how we adopt new tools and make sure we have the right controls and processes in place. Externally, it is about how professional services firms use technology and AI to improve efficiency and client service.
There is a lot of opportunity, but also a need to make sure it is implemented in the right way.
Who has been the biggest inspiration or driver of your professional development?
There have been a few people throughout my career.
Early on, there was a senior colleague who taught me the importance of presenting yourself well and maintaining high standards. That is also where the advice about asking questions came from.
During my time at Linklaters, I worked closely with a CFO and a Group Financial Controller who both believed in me and supported my development. They gave me opportunities that I might not have put myself forward for.
That support was especially important during key moments in my career, including returning to work after having children. Having people who believe in you and support you through those periods makes a big difference.
What’s been your proudest achievement in your current role?
I have been in the role a little over a year now, and I am really pleased to have successfully navigated that first year as a CFO.
It has been a big step up, and I am proud of the relationships I have built with the executive team and the board during that time.
That has been a key part of settling into the role.
If you weren’t a CFO, what would you like to do?
I would probably be working with horses.
I would be very happy getting up in the morning, going to the yard, and spending my time taking care of them.
What is currently inspiring you today and why?
My children inspire me every day.
When I need motivation, music is something that really helps. It gives me energy and helps me get going.
It is something simple, but it works.
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Isla Pickering is the CFO of Law Debenture, a FTSE 250 investment trust with a professional services business at its core. She stepped into the role at the start of 2025, taking on her first CFO position after more than 20 years in finance.
She is focused on supporting a profitable and growing business while helping shape how the finance function adapts to new technology and increasing regulatory demands.
Her experience in professional services continues to influence how she approaches leadership, with a strong emphasis on clarity and control while building teams that can support long-term growth.
