GC-turned-law professor Neal S. Winneg condenses and compartmentalizes complex concepts for a future generation of lawyers
Neal S. Winneg has compiled an impressive resume over the past 18 years, acting as Chief Legal Officer for Jumptap Inc., The Princeton Review Inc., Upromise Inc. and The Learning Co. Inc. (formerly known as SoftKey Intl.). He’s also been affiliated with Skadden Arps, a multibillion-dollar law firm, Dimensional Foods Corp. and the Massachusetts Interactive Media Council.
Currently, Winneg is teaching a transactional law class at Boston University (BU), where he earned his juris doctor degree, while he contemplates his next challenge. It’s a refreshing break from the nonstop duties of a corporate general counsel (GC), and enables him to better equip the next generation of lawyers.
Traditionally, transactional law was an on-the-job learning experience for first-year associates. “They would learn the ‘how-to’ of that field while working with more experienced attorneys,” Winneg explained, “and clients would pay those fees.” But no longer. “Today, law firms are under pressure to change that approach,” he said. “Some law schools, such as BU, teach law students the basics of transactional practice, including drafting a contract.”
The atmosphere of academe benefits Winneg, too. “When I prepare for class, I need to think about things I normally do by rote,” he said. “I must anticipate questions about matters I haven’t thought about in years and have ready answers.”
The experience also has sharpened his communication skills. “I sometimes try to express complex concepts in one swoop,” Winneg said, “and that’s not always the best approach. Now when presenting, I concentrate on speaking in a simpler, straightforward way.”
Embracing Healthy Risk
Leaving the legal field for education seems like a risky proposition—it’s not exactly a linear progression, after all—but Winneg is accustomed to stretching his limits. For example, he walked away from a well-established private practice with no subsequent job.
Per Winneg: “As an Associate with Skadden Arps, I worked hard in M&A [mergers and acquisitions]. It was an all-consuming job. When I was ready for a change, I couldn’t find time to come up with a next move, let alone implement it. It was now or never, so I left.”
Winneg considered moving into venture capitalism, then turned his sights toward in-house work. A fortuitous phone call from Skadden’s Boston office steered him toward Canadian company SoftKey Intl. (later The Learning Co.), which had moved to Boston as the result of a three-way merger and sought a GC as a new U.S. public company.
Winneg interviewed with SoftKey and joined the corporate world. The move helped him reach a personal goal of having a real stake in the work—unlike that which he had been encountering in the private-practice world, where attorneys are essentially hired guns.
He also sees law as a building block, not an end in itself. “Some attorneys love the intellectual side of law,” Winneg said, “and attaining the right answer for its own sake. I prefer to get the answer and apply it practically to a business situation. And there’s more opportunity for that as an in-house attorney.”
He adds that corporate private practice focus is narrow, whereas a GC deals with litigation, contracts, intellectual property and other matters that help the company attain its objectives while complying with legal requirements.
“Many of my added responsibilities came from administrative and internal governance issues,” Winneg said, “things you don’t see in private practice.”
As GC, Winneg didn’t manage in the classic sense. “You have to perform certain ‘management’ functions to ensure the company reaches its goals,” he said, “but you’re working with professionals who’ve had a lot of training. If they need to be micromanaged, you’ve hired the wrong people.”
Instead, he prefers to set a clear mission, and then lead by doing. “As GC, I look at the Legal Department as a service organization. It’s there to satisfy its customers, the internal clients,” he said. “The key metric for me is responsiveness. Clients won’t recall whether you drafted a perfect contract, but they will remember that you got back to them quickly, or that you didn’t.”
To that end, he’ll even push some of his own matters aside when needed by a member of his legal team. His input might be the key to keeping a project moving ahead, and a lackadaisical approach would create frustration for his team.
Although Winneg had no formal mentors—leaping from law firm associate to corporate GC in a single bound—he was instrumental in forming a sort of support group with other GCs.
“During my first year with The Learning Co., I talked with the GCs of two other companies. We agreed it would be great to have a network of executives to discuss common situations—picking new transfer agents, finding out-of-state representation, developing a contract management function—and find solutions,” Winneg said.
That lunchtime skull session led to the creation of the Boston Area General Counsel Group, an online community of local GCs who submit questions and share answers based on their own experiences.
“It’s much better than dealing with theories,” Winneg said. “We’ve found that the best advice comes from GCs who have actually dealt with those situations.”
Poet Robert Frost wrote: “Two roads diverged in a wood, and I/I took the one less traveled by/And that has made all the difference.” These lines summarize Winneg’s approach to a successful career.
“Take risks and seek opportunities that are outside of your comfort zone,” he said. “Being thrown into the fire and having to succeed is the only way to grow.”
Frederick Jerant is a freelance writer based in Allentown, Pennsylvania.
Neal's Key Partners:Goodwin Procter LLP (Corporate Law) | Outside GC LLC (On-Demand General Counsel)
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