This is what it takes to be a Boston Red Sox lawyer.

Ending up as a lawyer for the Boston Red Sox wasn’t a career David S. Friedman envisioned.

I’ve known Dave since 1993 when we started as classmates at Harvard Law School, and if someone had told him back then he’d be working at Fenway Park, he would have laughed and said no way.

David S. Friedman, Esq., at 2015 TEDxBeaconStreet. Photo by John Werner Photography.

How did Dave Friedman end up at the Red Sox? “It was an accident,” he says. “A lot of it was being in the right place at the right time.”

Like Dave himself, that answer is modest. (Seriously, Dave is one of the nicest guys you could possibly meet.) It doesn’t, however, tell you about the combination of brilliance, hard work, dedication, training, good luck, mentoring, and circuitous path that put him in the right place at the right time. So here’s the full story. [This article is adapted from "How to Become an SVP and In-House Lawyer for the Boston Red Sox" at www.brycelegal.com]

The Red Sox Gain a Purple Squirrel

So how does a government lawyer end up at the Red Sox?

In 2009, Dave’s former boss, former Massachusetts Senate President Robert E. Travaglini —although not a lawyer himself—heard of the corporate legal department’s opening and put Dave in touch with the Red Sox. Alan Dershowitz, who had been Dave’s and my first-year criminal law professor at HLS and who personally knew some of the Red Sox’s owners, served as a reference in the hiring process.

As it turned out, there was a strong correlation between what Dave was working on at the AG’s Office and what the Red Sox needed—both had a strong policy element. Dave’s ability to toggle between advocacy and policy, and between corporate interests and government law, was critical.

Jared Redick, founder and principal of The Redick Group in San Francisco, says, “The most interesting roles can emerge out of a seemingly disparate mastery of skills. When blended, those skills can create the needle-in-a-haystack candidate that so many companies seek.” [Get Jared Redick’s Job Description Analysis, a tool that helps people identify the intersection between where they’ve been and where they want to go.]

The most interesting roles can emerge out of a seemingly disparate mastery of skills. When blended, those skills can create the needle-in-a-haystack candidate that so many companies seek.

Melba Hughes, a co-managing partner in In-House Practice Group in the Atlanta office of preeminent legal and executive search firm Major, Lindsey & Africa, adds: “Law firm practice develops technical legal skills. Judicial clerkships lead to a greater understanding of how laws are applied and interpreted. They strengthen legal reasoning and legal writing skills. But companies aren’t in the business of practicing law. In-house lawyers need to be able to think and work strategically with business people.” In Dave’s case, Melba notes his experience working in different environments and with different types of people was an asset.

Dave is what legal and executive recruiters call a “purple squirrel,” says Dina F. Cappuccio, Esq., founder and principal of the legal recruiting firm Advocate Consulting, as well as a long-time friend and colleague of mine from my days on a law firm hiring committee. “In addition to his obviously stellar academic credentials and achievements, Dave had a unique background that combined experience in distinct and very relevant areas.” Each position prepared him, in its own way, for the opportunity with the Red Sox. Dina explains: “As a litigator at a prestigious firm and later with the government, Dave honed his advocacy skills in multiple contexts. In his very different role as a policy advisor for the Massachusetts State Senate President, he had the opportunity to work on major policy issues and see first-hand the inner-workings of state government. At the Massachusetts AG’s office, he’d held real leadership and managerial roles.” In other words, he was that almost theoretical perfect candidate standing out in a marketplace of many solid lawyers: a purple squirrel.

Clearly the Red Sox agreed.

Glamour and Misconceptions about Sports Law

There are a lot of misconceptions about attorneys in the sports industry. For example, people usually assume Dave has a lot of personal contact with big name players. “They imagine me at the negotiating table with David Ortiz and his agent.”

They imagine me at the negotiating table with David Ortiz and his agent.

Sports law has always been considered a dream job, says Deborah Ben-Canaan, a partner based in the Washington, DC office of Major, Lindsey & Africa and the leader of its DC In-House Practice Group. “Whenever we recruit for a team general counsel, we are inundated with hundreds of résumés from lawyers who fell in love with the sports team as a kid, or who envision the role involves a lot of player interaction and glamour.” Dave’s experience at the Red Sox, says Deb, is more typical of lawyers in the sports industry, even at the GC level: “Many of the legal issues that surround being the general counsel of a sports team are no different than those that other GCs may face.”

On-the-Job Mentoring

Mentors have played a major role in Dave’s legal career at the Red Sox.

Those on-the-job mentors include General Counsel and EVP Ed Weiss. Weiss left Time Warner after some 13 years to join the Red Sox as General Counsel in September 2009, arriving shortly before Dave was interviewed to join the legal team.

Another of Dave’s mentors at the Red Sox is (now retired) President and CEO Emeritus Larry Lucchino, who has a long history in sports law and sports team management and who is committed to mentoring. Also a lawyer, Lucchino graduated from Princeton University and Yale Law School, where he was a classmate of Hillary Clinton and a year ahead of Bill Clinton. After law school, Lucchino was a litigator at leading Washington, DC law firm Williams & Connolly, where he worked on matters for Baltimore’s baseball team and Washington’s football team, before stints as President / CEO of the Baltimore Orioles and the San Diego Padres.

Too many people try to develop relationships only after they’ve started actively thinking about a new role when in fact, they should have started years earlier.

“Hearing and messaging the stories of executives and c-suite members every day,” says Jared Redick of The Redick Group, “I’m still surprised by how many cite their networks as a big part of their success. It’s hard to overstate the essential place that genuine connections and relationships play in career development. Unfortunately, too many people try to develop relationships only after they’ve started actively thinking about a new role when in fact, they should have started years earlier.”

[Watch a lively 2014 conversation with Lucchino and Dave in the Harvard Law School series “The Boss & Counsel,” hosted by HLS Dean Martha Minow.]

The Role of In-House Counsel

Law firms often push lawyers into tightly focused niches, while in-house departments are often the opposite. Whether a particular in-house position is general or niched depends a lot upon the size of the legal department relative to the complexity of the company it serves. A lawyer in a multinational pharmaceutical company with 400 in-house attorneys may have a super-specialized job, “but if you’re one of four or five attorneys for a baseball organization, your work is going to be much more general,” Dave explains.

Even more important is the different perspective between outside counsel and internal corporate legal departments. The law firm experience, especially for associates, is sometimes compartmentalized. As Dave describes it, “Someone comes to you with an issue, you write a memo, you give them an answer, and you’re done, end of story.”

In contrast, in-house counsel of all levels must have a strong sense of overall corporate objectives, and be mindful of those objectives at all times. “To be a really good in-house lawyer, you have to really understand your company and the overall operation. That involves asking the questions, but also listening and being curious.” As in-house counsel, Dave says, “You’re not trying to solve discrete legal problems in a vacuum. You have to really understand the company and how the issues fit into the overall corporate strategy and operations. What may seem like an isolated issue may have long-term, Big Picture consequences. Maybe you take a position in negotiation or litigation on one matter that makes the company vulnerable on other fronts or creates exposure that an outside lawyer wouldn’t think about—it’s not her job to think of that because she can’t know as much as about the business as we do. It’s the job of in-house counsel to worry about that.”

In-house lawyers also need to have flexibility. “The right philosophy for in-house lawyers is not to be the obstacle—the person who says no—but to be the person who problem solves to get to yes. That doesn’t mean that you can always get there. There are times when, unfortunately, the answer from legal is ‘no, you can’t do that’ or ‘no, you shouldn’t do that.’ But you’re going to be much more effective if your internal clients know you’re there to help them solve their problems.”

The right philosophy for in-house lawyers is not to be the obstacle—the person who says no—but to be the person who problem solves to get to yes.

Deborah Ben-Canaan of global legal and executive recruiting firm Major, Lindsey & Africa agrees that this mindset is critical no matter what industry the lawyer serves. “A successful in-house lawyer, especially a successful general counsel, must be a business advisor and a consigliore to the executive team,” she says. “Taking an organization’s business goals into account is of utmost importance. The more internal clients feel the general counsel and entire corporate legal department is aligned with their needs, the more they willingly go to the legal team for advice before making decisions, both big and small.” 

A successful in-house lawyer, especially a successful general counsel, must be a business advisor and a consigliore to the executive team.

Because then-Red Sox President and CEO Lucchino is a lawyer himself, he looks to hire lawyers who can contribute across the entirety of the organization. “I have a respect for the versatility of lawyers,” Lucchino says in “The Boss & Counsel.” “It is true that there is an opportunity for lawyers to do more. And if your CEO is a lawyer, then he recognizes that. I throw Dave into other [non-legal] problems as much as I can.” As part of that conversation, Dave added that to get beyond being a narrow lawyer, “Above all, lawyers need to get comfortable taking risk. I think lawyers—a lot of us are risk-adverse. That’s why we go to law school. But lawyers need to be comfortable taking smart, calculated risks at the right time.”

Lawyers need to get comfortable taking risk.

What In-House Counsel Looks for in Outside Counsel

In selecting and hiring outside counsel, Dave tells me FSG is usually looking for specific legal expertise. “We have a relatively large in-house department for a sports organization, so we handle a lot in-house. When we go outside, it’s for a reason—really good judgment and expertise in the type of matter we’re looking to handle. We understand there’s a cost for someone who is really, really good.”

Legal recruiter Dina F. Cappuccio explains how the market for outside counsel has changed in recent years. “When the economy tightened, companies looked to save on legal spend. Competition for business among law firms is fiercer than ever, as many companies are doing what the Red Sox are doing—handling more and more matters in-house, and sending less work to outside counsel.”

So how do you stand out as an outside counsel trying to generate business? Dina says, “Networking and relationship building are key. People need to know who you are, and you need to build trust.” Melba also recommends outside counsel develop relationships with in-house counsel, but to really demonstrate their value-add (which as Dave says, in-house counsel are willing to pay for) they have to understand the business model. They also need to understand the economic, regulatory, and competitive landscape the company is working within. (Notice that theme! It’s something I talk to clients about regularly, but it’s important they hear it not just from a legal career coach, but from in-house clients and legal search consultants as well.)

Industry expertise and subject matter expertise are value-adds corporate clients seek when retaining outside counsel.

“Industry expertise and subject matter expertise are value-adds corporate clients seek when retaining outside counsel,” Melba says. “If you have expertise, then you can help business people and in-house counsel make strong, intelligent decisions.” Dina agrees. “After years of aggressive law firm merger activity, many firms have become multinational and can handle very specialized, sophisticated work. Developing an area of expertise—or attaching to a firm with the right platform—can be very helpful in going after specialized work valued by top sports organizations.”

Advice for Lawyers on Career Development and Breaking into the Sports Industry

Dave was one of the more than 150 attorneys I interviewed for the 2011 classic edition of “How to Get a Legal Job: A Guide for New Attorneys and Law School Students” and in Spring 2016, he’ll teach “Management and Leadership Skills for Lawyers” as a lecturer at Harvard Law School. But regardless of whether you’re a law student, junior lawyer, mid-level lawyer, or senior-level lawyer, Dave’s recommendation for attorneys wanting to get into the sports industry is the same: “There’s no magic piece of advice other than to just really develop your skills. Writing skills are always a premium, as are analytical, negotiating, and listening skills.”

Given the sheer volume of attorneys interested, employers are very selective. Legal and executive recruiter Deborah Ben-Canaan says those who are considering a move should be prepared to take a sizeable pay cut—compensation for lawyers in the sports industry is often lower than other industries, such as financial services or life sciences. Additionally, lawyers should have a variety of experiences covering union and traditional labor law, including disputes and litigation. Beyond technical legal skills, managerial and leadership skills are critical. “Top communication skills, emotional intelligence, political savvy, and gravitas are key to leading the legal teams of these prestigious organizations,” Deb says.

Top communication skills, emotional intelligence, political savvy, and gravitas are key to leading the legal teams of these prestigious organizations.

Start building your expertise, Dina Cappuccio says. “Join relevant associations and take any and all opportunities to network with them. Writing articles can be good marketing tools, and publishing can be as simple as posting on LinkedIn.”

And get started now, or your chances to land a top position in an elite sports institution, or land the team as a client, may start dwindling fast. Dina explains, “Outside counsel need to start planting the seeds very early in their careers—or even sooner, beginning in college and law school—since it takes much time and effort to start to build and nurture a network.”

Top Three Career Development Takeaways

I’m fortunate to spend a great deal of time talking about best strategies for career development, professional development, and career transitions with executive coach and former executive recruiter Jared Redick, also quoted above. Jared is an expert career consultant for c-level executives and rising stars in Fortune 100 companies, including some of the world’s most desirable brands. We see a lot of overlap between what it takes to be a sought-after corporate leader and what it takes to be a sought-after attorney—particularly in-house counsel, since in the best organizations in-house lawyers are incorporated within the overall leadership structure.

Start planting the seeds very early in their careers—or even sooner, beginning in college and law school.

Jared and I discussed our top three takeaways from Dave’s journey to the Red Sox.

1. There is No Substitute for Excellence.

Yes, Dave is smart and well educated. Those are clearly advantages that have helped doors open for him. “But being smart and well educated isn’t enough to rise to the top when everyone around you is also smart and well educated,” Jared points out. Dave’s also great at what he does—as a hands-on lawyer, as a legal strategist, as a business partner, as a leader, and as a team player. That excellence across the board, which in turn led to an exceptionally strong professional network built over decades, enabled him to succeed at every level.

2. Come Out of Your Failures Stronger than You Went In.

Even Dave hasn’t been immune to disappointment. His law firm collapsed, throwing him and everyone else suddenly out of work. He lost his state election. Dave turned those “failures” into additional career opportunities. Note that it’s far easier to do that when you’ve built a reputation for excellence and have a strong professional network before the professional crisis occurs. People bounce back quickly from adversity because they’ve laid the foundation in advance. “In other words,” Jared says, “there is a direct correlation between your ability to bounce back from adversity and the amount of work that you’ve put into developing your professional expertise and your network.”

3. Being in the Right Place at the Right Time Is Not an Accident.

As I said earlier, Dave is modest. Being in the right place at the right time when your dream job opens up is not merely good luck. It’s the culmination of years of building a widespread reputation for excellence and developing influential professional relationships. It’s about being the type of lawyer (and person) who others want to stake their own reputations on and whose success others want to be a part of. “That’s why he has a such a powerful network that brings him opportunities and is willing to stake their own reputations on him,” Jared says.

There is a direct correlation between your ability to bounce back from adversity and the amount of work that you’ve put into developing your professional expertise and your network.

And it’s about building a profession presence so that employers and recruiters can find you, particularly for the needle-in-a-haystack positions mentioned earlier. Jared says, “LinkedIn has become a great place for passive candidates who are ‘happy where they are’ but open to those needle-in-a-haystack opportunities to carefully make their stories visible to search firms. It’s a bit of an art, but it’s a great new development in career development.”

Bonus: No One Succeeds Alone.

Underlying this entire article, and particularly these career development tips, is the concept of networking. Many attorneys dislike the concept of networking. They see it as opportunistic or salesy. But that’s not what networking is, and that’s not why professional and personal networking matters.

Networking isn’t about cynically cultivating relationships that can open doors. Networking is about genuine connection with people who share your values and recognize each other’s worth, and who are willing to work together to help each other succeed.

Networking isn’t about waiting until you need a job, and then frantically contacting every person you used to know to ask for help. Networking is about building of trust relationships over time, and cultivating those relationships so that you are looking out for opportunities for each other.

No matter how smart, well educated, and determined you are, you cannot advance far alone. All attorneys need friends and mentors to reach their own legal dream jobs.

Conclusion

Let’s be honest. There are only a handful of jobs like Dave Friedman’s. And we can’t all be president of Harvard Law Review, U.S. Supreme Court law clerks, and in-house counsel at the Red Sox. We can’t all be purple squirrels.

However, a big part of what makes Dave’s job a legal dream job is that he loves it. Ultimately your task isn’t to get Dave’s dream job. Your task is to find your own dream job—a job you can love, a job that’s best for you. Fortunately, law jobs, JD-preferred jobs, and law-related jobs come in so many different varieties and environments, and require different skill sets.

Remember: “There’s no one path to finding a job you love,” legal search consultant Melba Hughes says. “What’s important is that you understand yourself, that you know what you love, what excites you, and what you’re willing to do to get there. Then develop your skill set to accomplish it.”

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Read "How to Become an SVP and In-House Lawyer for the Boston Red Sox" in full at www.brycelegal.com

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Shauna C. Bryce is a graduate of Harvard Law School with 20 years in law and legal careers. She is a career strategist for lawyers at all levels — from law students to executive-level attorneys in Global 100 law firms and Fortune 500 businesses in the U.S., Europe, and Asia. As a lawyer, she worked in the Manhattan flagship office of a Global 100 law firm and served on the hiring committee of an Am Law 200 law firm. Her advice column, Ask the Hiring Attorney?, is published by Bloomberg Law. She’s the author of several books and the Bryce Legal? Career Advice for Lawyers blog. www.BryceLegal.com