Rebecca Holding-Lisser

Interviewed by Maryam Irfan

There is no single blueprint for building a successful legal career, and Rebecca Holding-Lisser’s journey is a brilliant example of why.

From a route into law that wasn’t always straightforward to building a career in commercial real estate across Bruntwood, Royal Mail and now leading Asda’s Property Legal team, Rebecca has experienced first-hand how much of a legal career is built beyond qualifications alone.

We caught up with Rebecca to talk about building trust, thinking commercially, adapting your expertise across different businesses, stepping into leadership, and what the next generation of in-house lawyers should start developing now.

We hope you enjoy Rebecca’s insights as much as we did!

Q: You’ve spoken openly about living independently from 16 and not getting the A level results you had hoped for because of your personal circumstances. Looking back, what helped you keep moving forward and build the legal career you wanted?

I only ever wanted to be a solicitor so there wasn’t a Plan B so what kept me moving forward was sheer stubbornness and dogged determination. I’ve also always wanted to prove people wrong. When I was struggling during my A levels because of trying to balance my personal life with my studies a teacher told me I’d never be a solicitor if things carried on the way they were. That was like a red rag to a bull, and I knew that would just act as fuel. I’m a big believer in everything happens for a reason and I think my circumstances at 16 have taught me strength and resilience which any lawyer will need at times.

Q: Commercial real estate has been the thread through your career, but you’ve applied that expertise in very different businesses, from Bruntwood to Royal Mail and now Asda. When you move between sectors, what stays transferable and what do you have to learn again about the business?

First and foremost, I am a property solicitor, that’s my foundation; property law is property law and that doesn’t change because of the business you’re working for. Once you have the foundation, you can then build on that in whatever business you’re in. I think the most important thing you must learn about the new business very quickly is the business’s appetite for risk – I’ve always said my job as a property lawyer is a risk manager. When you’re in private practice you highlight the risks and let the client choose. When you’re in house, in particular you highlight the risks but your advice will also help the business navigate them and move forward in a way that supports the commercial outcome while appropriately managing legal exposure.

Q: Aspiring legal professionals are often told to be “commercially aware”, but that can feel quite abstract. From your experience in-house, what does being genuinely commercial look like in the day-to-day decisions a lawyer makes?

This I think is the ‘why’ question. Businesses are rarely looking for legal advice in isolation; they are usually trying to achieve a commercial objective and need to understand the legal risks and options that sit around that objective. Day to day, that means understanding the commercial impact of legal advice, weighing risk against opportunity, and tailoring recommendations to help the business meet its strategic goals.

Q: Working in-house means advising colleagues whose priorities may be commercial rather than legal. What have you learned about earning the trust of non-legal stakeholders, particularly when the legal answer isn’t necessarily the answer they want to hear?

My dad runs his own business and one piece of advice he always gave me was that people buy from people they like. That has stayed with me throughout my career. Building trust starts with being approachable, understanding the pressures your stakeholders are under, and developing strong relationships. Once that relationship is established, trust is built by consistently delivering high-quality, pragmatic and timely advice. Colleagues need to know that when they come to Legal, they will get clear guidance that helps them achieve their objectives rather than simply being told what they cannot do.

One of the biggest lessons I've learned is that stakeholders can usually accept being told "no" if you take the time to explain the risk and, more importantly, offer an alternative solution. In my experience, there is almost always a compromise or a different route to achieve the underlying commercial objective.

Particularly in-house, earning trust is about being seen as a problem solver rather than a blocker.

Q: You now lead Asda’s Property Legal team. What has surprised you most about the shift from being responsible for your own legal work to leading others, and how has it changed the way you approach your role?

I am by nature a people pleaser and a do-er and I really enjoy being a property lawyer, doing the work and solving the problems. When you move into a leadership role, your success is no longer measured purely by your own output. Instead, it's about enabling others to succeed and creating an environment where the team can perform at their best. I've had to work hard to become comfortable delegating work rather than instinctively doing everything myself.

That has changed the way I approach my role. Rather than focusing solely on delivering legal advice, I spend more time supporting development, removing obstacles and helping the team prioritise their workload. I've learned that sometimes the best thing I can do is step back and allow someone else to take ownership, even if I could do the task myself.

Q: For a trainee or junior lawyer hoping to build a career in-house, what experiences or skills would you encourage them to seek out early in their career, beyond developing their technical legal knowledge?

I don't think this advice is limited to those pursuing an in-house career. One of the most valuable skills any lawyer can develop is the ability to communicate confidently with all types of people. In fact, I would actively encourage aspiring lawyers to gain experience in retail or hospitality. Those environments teach a huge number of transferable skills, including negotiation, staying calm under pressure, managing competing priorities and balancing the expectations of different stakeholders. All of these are critical skills for a successful lawyer.

My other top tip is to cut the jargon. Clients rarely want a lengthy legal explanation; they want a clear answer and an understanding of the practical implications. If you can't explain a legal issue in simple terms to a non-lawyer, you probably don't understand it well enough yourself. The lawyers who add the most value are often those who can distil complex legal issues into clear, practical advice that enables the business to make informed decisions.

Thank you so much to Rebecca for letting us interview her! You can find her on LinkedIn here.