From Litigator to Deal Lawyer: Q&A with Eric Hutchins of Oracle

Eric HutchinsIn my seminars, I’ve encountered people who started out as litigators, then shifted to working with contracts. That caused me to wonder what that transition involves. Eric Hutchins, corporate counsel with the Cloud Legal Team at Oracle, is one such seminar participant. He was kind enough to have this exchange with me about his transition. If you’ve made such a transition yourself, I invite you to tell us about it in the comments.


Ken: Please tell my readers a bit about yourself.

Eric: I graduated from law school in 2006. I joined the litigation group of a law firm that year, where I worked primarily on patent litigation. It was a wonderful experience. I had the privilege of working with some extremely talented lawyers and generous mentors. The caliber of lawyering on both sides of those cases honed my litigation skills, perhaps most important among them my persuasive writing.

I stayed with the firm through a merger in 2010, but I started to consider leaving two years later. A mentor once told me what has become something of a truism—that making partner is like winning a pie-eating contest in which the prize is more pie. In the fall of 2012, I was in the same place that I think a lot of law firm associates find themselves in: Did I want more pie or did I want to try something else? As luck would have it, an opportunity arose for me to join the legal department at Oracle. I had worked for Oracle as outside counsel for many years and I liked the lawyers I knew there. So I joined the Litigation Group within Oracle Legal that year.

Ken: How did you come to shift from litigation to contracts?

Eric: Almost immediately upon starting at Oracle, I reached out to groups outside of Litigation. I was eager to take on my new role as “the client” in my litigation matters, where I could gain more substantial strategy-setting and case-management expertise compared to my role as a law-firm associate. But I was equally excited to gain experience in areas of practice that were completely new to me.

Given my intellectual-property background, I was able to find opportunities in patent licensing, M&A due diligence, and other non-litigation work. In January 2014, I saw an open position in the nascent Cloud Legal Team. I had some previous experience doing patent licensing and similar transactional work, but this was an opportunity to dive into a new and exciting field. I talked to my manager, the associate general counsel in Litigation, and she was very supportive. I interviewed and was fortunate enough to get the job.

Ken: What are your responsibilities now?

Eric: I think that my number one responsibility—no different than most other commercial counsel, I suspect—is to help the salespeople close deals while respecting Oracle’s particular risk tolerances. When customers consider purchasing Oracle’s cloud services, we have our form agreements, but I and others on my team are frequently called in to negotiate with the customers and draft changes. We also prepare guides to our forms, for the salespeople and contracts managers. And, less frequently but no less importantly, we are tasked with drafting changes to our forms—perhaps someday we’ll make them MSCD-compliant!

In such a quickly evolving industry, contract norms are a moving target, so there’s always a lot of discussion about how best to approach any given issue. The Cloud Legal Team is composed of lawyers with disparate legal backgrounds and a broad range of skills. Some of us were litigators, others were commercial lawyers, and still others were M&A or venture capital lawyers. Many came from big firms; others came from in-house roles elsewhere. It’s a very talented group and I’ve learned a lot from them in a very short period of time.

Ken: How would you compare your litigation work and your contracts work?

Eric: I see a lot of common ground between the two disciplines. Both litigators and deal lawyers are concerned with risk. Dyed-in-the-wool deal lawyers have an advantage due to the sheer quantity of contracts they’ve worked on. They’ve seen every permutation of a given provision, and that wealth of experience is a real benefit when it comes time to draft changes. Litigators, meanwhile, have a clear sense of how contract language might be used in court—we’ve tried cases for misrepresentation and breach, and we’ve been on the receiving end of indemnification, exclusive-jurisdiction, and arbitration provisions. That often gives us insight into the actual risk (as opposed to the contract risk) involved in a deal. Being able to advise management how a change in the contract is likely to play out if a real-world dispute ever were to occur can sometimes help move a deal forward.

Legal briefs are persuasive writing—when done well—whereas contracts state rules. Although the goals differ, both briefs and contracts benefit from clear, concise language. Litigation is superb training for both forms of writing. Briefs, unlike contracts, are constantly subjected to the crucible of the judicial process where, ultimately, judges grade your homework. Poor writing is, sadly, still prevalent in litigation, but contract drafting is even more problematic because it lacks an adversarial process that fosters iterative improvement. When I joined my new team here at Oracle to work on cloud services deals, I had already developed a proper distaste for adverbs, misuse of the word “shall,” misplaced punctuation, and surplus verbiage. I do not, of course, mean to say that litigation offers the only or best experience to train good legal writers, but I think it is an experience that can only help make one a better overall practitioner.

Ken: I’ve been known to say that litigation work and transactional work require such different temperaments that it should be easy enough to figure out whether one is a litigation person or a contracts person. Obviously, things weren’t that clear-cut for you. How do you think this played out in your case?

Eric: Good question. I have had the good fortune, both at law firms and now at a large corporate legal department, to work with an array of talented lawyers. And it occurs to me that not all successful litigators share the same temperament, just as I am confident that not all successful deal lawyers share the same temperament.

But one characteristic that all of these successful lawyers share is good judgment. By that, for example, I mean knowing when meticulous attention to detail matters versus not losing sight of the forest for the trees. Or recognizing which disputes in a given negotiation are high value or high risk and must be prioritized. Knowing when you need to tell your client (and the other party) that a given course of action isn’t appropriate, and knowing how to explain your reasoning in ways that ideally promote everyone’s interests. Everything else can be learned, with sufficient time and effort, but sound judgment is impossible to cultivate if the seed isn’t already there. If a lawyer has good judgment, then he or she can learn the rest and be a successful litigator, or transactional lawyer, or estate-planning lawyer, et cetera.

Ken: What would you say to any litigator contemplating a career-change to contracts work?

Eric: Don’t underestimate the value of the skills you already have acquired. Contract drafting and negotiating a deal (as opposed to negotiating a litigation settlement) are very different from what you have been doing, but your experience as a litigator has tremendous value. Seek out good mentors who do the type of contracts work you’re contemplating. Take CLE courses relevant to your anticipated area of practice. Then, just go for it.

Categories Q&A

About the author

Ken Adams is the leading authority on how to say clearly whatever you want to say in a contract. He’s author of A Manual of Style for Contract Drafting, and he offers online and in-person training around the world. He’s also chief content officer of LegalSifter, Inc., a company that combines artificial intelligence and expertise to assist with review of contracts.

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