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.). Heâs 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. Itâs 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. âThey would learn the âhow-toâ of that field while working with more experienced attorneys,â Winneg explained, âand clients would pay those fees.â But no longer. âToday, law firms are under pressure to change that approach,â he said. âSome law schools, such as BU, teach law students the basics of transactional practice, including drafting a contract.â
The atmosphere of academe benefits Winneg, too. âWhen I prepare for class, I need to think about things I normally do by rote,â he said. âI must anticipate questions about matters I havenât thought about in years and have ready answers.â
The experience also has sharpened his communication skills. âI sometimes try to express complex concepts in one swoop,â Winneg said, âand thatâs not always the best approach. Now when presenting, I concentrate on speaking in a simpler, straightforward way.â
Embracing Healthy Risk
Leaving the legal field for education seems like a risky propositionâitâs not exactly a linear progression, after allâbut Winneg is accustomed to stretching his limits. For example, he walked away from a well-established private practice with no subsequent job.
Per Winneg: âAs 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 couldnât find time to come up with a next move, let alone implement it. It was now or never, so I left.â
Winneg considered moving into venture capitalism, then turned his sights toward in-house work. A fortuitous phone call from Skaddenâs 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 workâunlike 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. âSome attorneys love the intellectual side of law,â Winneg said, âand attaining the right answer for its own sake. I prefer to get the answer and apply it practically to a business situation. And thereâs more opportunity for that as an in-house attorney.â
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.
âMany of my added responsibilities came from administrative and internal governance issues,â Winneg said, âthings you donât see in private practice.â
Leading By Doing
As GC, Winneg didnât manage in the classic sense. âYou have to perform certain âmanagementâ functions to ensure the company reaches its goals,â he said, âbut youâre working with professionals whoâve had a lot of training. If they need to be micromanaged, youâve hired the wrong people.â
Instead, he prefers to set a clear mission, and then lead by doing. âAs GC, I look at the Legal Department as a service organization. Itâs there to satisfy its customers, the internal clients,â he said. âThe key metric for me is responsiveness. Clients wonât recall whether you drafted a perfect contract, but they will remember that you got back to them quickly, or that you didnât.â
To that end, heâll 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.
Peer Mentoring
Although Winneg had no formal mentorsâleaping from law firm associate to corporate GC in a single boundâhe was instrumental in forming a sort of support group with other GCs.
âDuring 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 situationsâpicking new transfer agents, finding out-of-state representation, developing a contract management functionâand find solutions,â 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.
âItâs much better than dealing with theories,â Winneg said. âWeâve found that the best advice comes from GCs who have actually dealt with those situations.â
Poet Robert Frost wrote: âTwo roads diverged in a wood, and I/I took the one less traveled by/And that has made all the difference.â These lines summarize Winnegâs approach to a successful career.
âTake risks and seek opportunities that are outside of your comfort zone,â he said. âBeing thrown into the fire and having to succeed is the only way to grow.â
Frederick Jerant is a freelance writer based in Allentown, Pennsylvania.
Neal's Key Partners:
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