8 Tricks To Seamlessly Become Both A Business And Legal Professional

Tips for anyone seeking to bridge the industry divide -- both lawyers seeking to break into business, and business professionals seeking to break into law.

happy-diverse-team-lawyers-partner-with-associates-300x205When John Orta, currently the General Counsel and Corporate Secretary at Metromile, the industry-shifting pay-per-mile insurance startup, was a young litigation associate, he saw the value add of a business degree and headed off to business school. Rather than a full career pivot, Orta combined his legal and business experience and has continuously chosen a career path where he actively uses both skill sets. Over the course of Orta’s successful career as a business/law chameleon, he has gathered the following tips for anyone seeking to bridge the industry divide — both lawyers seeking to break into business, and business professionals seeking to break into law:

  1. Roll Up Your Sleeves: As a startup veteran, Orta believes “Startups are a perfect place to break into a business role, though keep in mind it is not as easy and as glamorous as it sounds.” “If something needs to get done, just roll up your sleeves, show your commitment and value, and then learn a lot of business skills in the process. Even manning the front desk — which is something I do regularly — will teach you a lot.”
  2. Leave Your Ego at the Door: You will likely work with colleagues who have less education, though possibly more experience, than you do. You need to be open minded to all ideas. “For example, on more than one occasion I’ve discovered what provisions in our contracts might be unnecessarily confusing by listening to feedback from the sales and customer support teams. Easy fixes like that make everyone’s life easier.”
  3. Have Confidence in Your Business Skills: “Just because someone has a J.D. or is a member of the bar association doesn’t mean they’ve checked their business sense at the door.” In fact, Orta strongly believes in evaluating lawyers on multiple dimensions, just like we do with all other business professionals. For example, Orta is a skilled attorney, but also has HR skills. “I love being responsible for HR. It gives me immense pleasure to figure out how to discover, hire, and retain talent. And talent is a big part of success in Silicon Valley, where daily competition for talent is fierce,” he says.
  4. Become Good at Math: Orta doesn’t laugh at the old adage that lawyers go to law school because they’re bad at math. Any lawyer hoping to transition into the business world needs to have some skill with numbers. “It is hard to build a company on a purely qualitative value proposition,” he explains. “That is a sure road to a business failure.” Lawyers who are “bad at math” can learn these skills in business school or take classes on essential math skills, such as financial statement analysis, while earning their J.D. However you attain it, a grasp on numbers is a must, according to Orta. “Numbers move markets. Numbers build business. Numbers explain partnerships. If you can’t follow the money, your value at the table is highly limited if it exists at all,” he says. “At the end of the day lower costs, higher revenue, more customers, and other similar quantifying metrics dramatically increase the odds of success.” A business with no numbers is like a bird without wings — it just won’t fly.
  5. Actively Know the Business: When Orta hires attorneys for his team, business savvy is an absolute must. “I screen for attorneys who are curious and ask questions. As lawyers, we are almost always the only people in the company who read the fine print,” he explains. “So, we need to understand the company’s business, why we do certain things, and what implications they may have for the future.”
  6. Go Beyond Redlines: According to Orta, a key behind adding actual value is thinking past standard redlines. “People assume the lawyers will deal with warranty or indemnification provisions, but those are often the least important aspects of deal. The real value-add happens when in-house counsel understand the business objectives so that they can accurately describe — and often question — the structure of the arrangement.”
  7. Listen Before Talking: Unlike the adversarial nature in much of the legal world, the business world is a team sport. “You can’t be a good team player unless you listen first, and then show a genuine interest in the ideas of others by asking relevant and meaningful questions,” says Orta. “There is an art in asking a question,” Orta explains. “You must listen with intent toward identifying and truly understanding the issues, the impact of those issues on the company, clients, and employees, and the importance of a timely solution.”
  8. Build Lasting Relationships: “At every job since business school, I’ve worked with someone who knew my work. For example, I found my current opportunity at Metromile through the Head of Product who I worked with at OpenTable.” Similaly, Orta says, “I found my opportunity at OpenTable through the CFO, with whom I worked at E-Loan.” Orta emphasizes that the business world is small, and the startup world is even smaller. “Ultimately people, and business people specifically, like to work with people with whom they’ve worked well in the past.” It is wise to build deep and wide relationships at work if you are at all interested in transitioning to a business role.

Becoming a business/law/industry chameleon has given Orta a more satisfying, multi-dimensional career, where he can pursue this interest. Likewise, making an industry transition could be the right choice for many other lawyers and business professionals. Ready for a change? Orta’s tips can guide you through a seamless transition into the intersection of law and business.


Olga V. Mack and Katia Bloom are startup enthusiasts who embrace the current disruption to the legal profession. Long gone are the days when in-house legal departments simply manage outside counsel or provide services. Today’s legal department is a sophisticated business unit that co-manages the company’s bottom line, embraces technology, and analyzes risks constructively. Mack and Bloom love this change and are dedicated to improving and shaping the future of the legal profession. Together they passionately collect and share inspiring stories of legal leaders who are thriving through the ongoing tectonic shift. Mack and Bloom are convinced that the legal profession will emerge from this revolution even stronger, more resilient, and inclusive than before. They are currently co-authoring a manual of the skills and traits lawyers need to succeed in — and even enjoy — today’s rapidly evolving in-house legal departments. You can reach them at [email protected] and [email protected] or @olgavmack and @bloomkatia on Twitter.

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