Pinsent Masons legal director Penny Simmons explains why the field is more dynamic and commercial than many students assume, and shares advice for aspiring lawyers
Tax sits at the heart of almost every major business decision, and for Pinsent Masons legal director Penny Simmons, that central role was what first drew her in.
“I wanted to be a lawyer from about the age of 10,” Simmons recalls, citing childhood favourites like L.A. Law. Even then she was drawn as much to logic as to drama: “I always liked maths and science,” she notes. At university, she combined the two by studying law and accounting.
During her training contract, she sampled litigation (and even flirted with employment law), but it was the tax modules that captured her imagination. “I really loved the tax modules,” she says, and by the time she reached her private equity seat, the penny dropped: “The whole reason why funds were structured the way they were was tax,” she explains. That realisation “massively informed” her decision. “I was like, ‘Right, I definitely want to do a tax seat,’” she recalls. Tax’s foundational role across the legal landscape ultimately persuaded Simmons to qualify and build her career in the area.
In her field, they call it “the beauty of tax” because unlike many areas of law, it never stands still. “Tax is always changing,” she says. Budgets come and go, governments rewrite rules and “whatever you thought the position was last year… the position isn’t that the year after.” Politics, business and tax are deeply entwined, and the headlines ahead of each UK Budget show just how closely the public pays attention. The area is constantly shaped by global events, macro and micro-politics, and shifting government priorities. That churn, far from wearing her down, energises her. “That makes for a really interesting job. It means you are constantly using your brain and clients actually like to speak to you because you have something interesting to say.”
The complexity of UK tax is legendary. Successive laws rarely simplify matters — instead each Budget adds “layers upon layers” of intricacy. “It’s like an onion,” she adds. When she qualified, there were three yellow books and one orange containing all the tax legislation in force. Today, there are five yellows and two oranges, covering direct and indirect taxes respectively. Too often, she argues, government acts hastily, layering new rules over old ones and then carving out exemptions when unintended groups are caught. More consultation and reflection, she believes, would prevent much of the unnecessary complexity this approach produces. In practice, her work is more strategic and commercial than many assume. “I don’t do transactional tax work,” she explains — she isn’t the one drafting tax clauses on big deals.
Instead, she advises businesses when making commercial tax decisions and on strategies to manage tax risks. Much of her focus is on employment taxes, helping companies decide how to engage people when providing services, particularly whether to engage people as employees or via agencies and other intermediaries, a decision with very different tax outcomes. A current example is the scrutiny on umbrella companies, with new rules soon making clients jointly and severally liable for unpaid employment tax debts. It’s “very strategic as well as being commercial,” she explains, because companies need staff to operate and they need to ensure they have flexible and resilient labour supply chains and she helps them decide “how they’re going to engage people.”
Through it all, Simmons is very clear that her role is never about “avoiding or paying less tax”. The suggestion that tax lawyers simply “help businesses pay less tax” makes her laugh. “No, I don’t do anything like that,” she clarifies. Her focus is on educating clients about their obligations and ensuring they comply and manage the risks of inadvertently failing to comply to avoid future headaches. As she puts it, she’s “helping them make commercial business decisions to ensure that they comply with all their taxes in the way that the UK’s HM Revenue & Customs expects them to.” In short, she helps businesses do the right thing on tax so the authorities never need to drag them into a dispute.
So what make a good tax lawyer? Analytical rigour and attention to detail are essential, she tells us. “Tax is an area for those who actually want to look at the law and want to pay attention to the legislation.” But one myth needs debunking: “Being a tax lawyer is not about maths. We don’t do maths, that’s for accountants to handle,” she laughs. No one is going to ask you to calculate income tax. What matters is the ability to problem-solve — to “read the law, analyse the law and apply it to a commercial situation.” Patience and curiosity, she insists, matter more than a calculator.
On career journeys, her advice is refreshingly down-to-earth. Paths rarely run straight — guidance she would have welcomed herself as a student. “Your journey is probably going to be like curves and bends in the road,” she observes, so focus on where you want to end up. Above all, never be afraid to admit what you don’t know. “Always ask questions and always ask for help,” she insists. It’s far better to pause than to bluff — especially in an interview. After all, even at the top of the profession, the UK tax system is far too vast for anyone to know everything.
Her final message to aspiring tax lawyers? It’s a field for curious, commercially minded problem-solvers. “It means you are constantly using your brain. It’s interesting and exciting,” she says. For students who relish detail and puzzles in business, tax law may prove far more thrilling than they ever imagined.
Penny Simmons will be speaking at ‘Why tax is interesting — with Pinsent Masons’, a virtual student event taking place on 9 October. Apply now to attend.
