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No one wants to work with a textbook

Reginald Matthews was excited about a career in law, but over time he got ground down by the pressures of trying to fit the mold of a stereotypical lawyer. Reassessing what sort of lawyer he wanted to be has helped him reignite his passion for the law.

While there’s an element of the philosophical when Reginald Matthews says no one wants to work with a book, the statement also says a lot about his experiences – good and bad – in law, and what, to him, are the traits of those who make good lawyers.

Humanity and effective communication skills are qualities he values, and he’s inspired by those he regards as his legal icons, people who don’t set out to win but rather come to an agreement, and those who genuinely want to help others. “Good people make good lawyers. They pour their heart and soul into the community, not into the prestige of their career,” he says.

He mentions his mother, Mary J Fair Matthews, Esq, Professor Curtis L Mack, the 2020 recipient of the Distinguished Alumni Award of the University of Michigan and Partner (now retired) at McGuireWoods LLP, and Mike Binns, Associate General Counsel, Head of Patent Portfolio Strategy at Meta, and Justin Bouchard, Associate General Counsel at Calendly, as positive influences, people who have helped him to shape himself and his career.

His journey from law school to his current role as Contracts Administrator at US technology start-up Calendly, has been challenging, the road to success proving a somewhat bumpy ride. Trying to fit into the stereotypical lawyer mold nearly broke him, and he became disenfranchised with his line of work. But it was also a learning curve, an opportunity to adopt a fresh approach, one that sat more comfortably with him.

When Matthews’ looks back at his time in law school, he views it as all-encompassing. “You can lose your sense of humility and personality in achieving your goal. Because legal training is so focused on students acquiring and comprehending legal knowledge, it's easy for them to lose sight of themselves in the process. Which results in bookish lawyers."

The step from bookish lawyer to socially awkward lawyer, one who regurgitates legal information without thinking about how they communicate it, isn’t a big one. And while there is nothing wrong with being bookish or even a little socially awkward, communication is key when trying to explain information effectively to clients. Coming across as human, approachable and easy to understand helps foster the lawyer-client relationship.

But the hamster-wheel high-stakes, fast-paced legal world, all the while trying to fit into the lawyer stereotype, led to Matthews’ burning out. The setback made him take stock. "People sacrifice a lot to fit the lawyer box, and in doing so lose traits that could help them be better lawyers. Some people become lawyers for the money and prestige, some because they want to help others. What I want to do is to interpret the law to problem solve and help others, be that the business or an acquaintance."

Since working in the legal department of Calendly, Matthews' eyes have been opened to a different way of practicing; he has become part of a more informal and vibrant culture. "Being in tech, I realized that I can be a legal counsel who is smart and effective but still make friends in my company and want to turn up to work every day."

He also believes in applying a healthy dose of humanity to his work. "Clients want to have conversations with human beings, not a textbook on civil procedure, torts or data privacy."

Matthews is often surprised yet amused when people find out he works in law. He enjoys telling them, "you can make jokes about lawyers, I'm not going to sue you! I'm a human being, we can have a normal conversation, my job does not dictate how I treat you."  

And while Matthews strives not to be a bookish lawyer, he describes the realities of practicing law as "having a book of knowledge", and he strongly believes that knowing how to wield that knowledge is what makes a great lawyer.

We've all seen fictional stereotypical ruthless lawyers, characters such as Harvey Specter from TV series Suits or Martin Vail in the movie Primal Fear, lawyers hellbent on winning no matter the cost. Real-life lawyering is different. Matthews makes the points that aggressive litigation makes up only a small percentage of the law; most lawyers and in-house counsel focus on negotiating an agreement or providing clients with comprehensive legal advice. Which isn’t an easy task as legal documents, be they ten pages or 60 pages, can be daunting to people.

Mathews says lawyers tend to be very direct and literal with their interpretation of the law and it’s easy for them to forget that their clients do not share their comprehension. He believes it's important to communicate necessary legal information to clients in as few paragraphs as possible, or in a tailored document. It’s about utilizing the "book of knowledge", lawyers interpreting the law and communicating it to others in a way they can understand.

The way in which information is imparted shapes how clients interact with their lawyers. Effective communication is particularly pertinent when working in-house where lawyers want a relationship with the business where they have a reputation as a trusted advisor. “If you can communicate legal advice to your business in a way that is easy to understand, it's likely people will be more willing to call on you more often,” says Matthews.

Essentially, in-house lawyers want to help rather than be a handbrake, an asset to the business they work for.

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