Planes, Trains & Automobiles: Three Advantages of a Litigation Background in Contract Negotiations

I have been a litigator for six years. And now, I want to move in-house to engage in the most satisfying part of being an attorney—collaborating with my clients from day one to be a constructive part of building their business. The biggest hurdle standing between me and my dream job is the notion that litigators don’t have adequate contracting skills.

But many litigators devote their lives to contracts just as ardently as transactional attorneys. Over the course of several job interviews, I waffled about how to explain this. After ample time spent condensing my observations into a cohesive narrative, I fell back on my love of cinema for an appropriate analogy.

So, with due respect and reverence to John Hughes, let’s talk about Planes, Trains, and Automobiles to demonstrate three ways that litigators can add value to an in-house legal team.

Litigators as Air Traffic Controllers

Legal departments are airports. Contracts come in and out constantly, varying in size, complexity and nature. In-house counsel must be adept at multitasking and prioritizing. They must not only understand the project in front of them, but where that project fits into the company’s current operational footing and its short- and long-term goals.

Air traffic controllers do the same thing. Though admittedly, seeing planes land and take off is probably far more exciting than watching emails sail in and out of your inbox.

Litigators use these skills daily. For example, I managed five to fifteen matters, involving up to twenty-five individual clients, daily. That work included ensuring I was on top of necessary deadlines and that I understood my client and the environment in which we were operating. Tracking rulings and opinions in other cases, keeping an eye on upcoming legislation, and being aware of my client’s personal, professional or institutional challenges was critical to achieving an optimal result for them.

The same is true for attorneys within an organization. In my conversations with them, many general counsel cannot sufficiently emphasize the significance of being able to keep on top of various, demanding workflows and keep up when a flurry of activity disrupts that flow. Litigators live this experience, often exclusively working on situations others would call a crisis.

The air traffic controllers in the tower keep the airport functioning at optimal efficiency through even the most significant challenges. If your team needs someone who can handle surprises, crises, or just a big pile of work with grace and efficiency, you want a litigator.

Litigators as Train Inspectors

Contracts are fundamentally trains conveying goods, services, licenses, and promises of all kinds down the track. When all goes well, they speed up, slow down, and get to their destination without incident. But, unfortunately, trains derail. A derailing can lead to quick negotiation, arbitration or litigation.

When litigation arises, the litigator steps in as a train inspector. They didn’t load the train. They didn’t lay the tracks. They neither built nor conducted the locomotive. Their job is determining who and what made the train derail.

That is a unique, valuable insight in contract development. In-house counsel work to minimize risk, but litigators build their careers on seeing the wreckage first-hand. That experience gives them a keen eye for dangerous provisions and how to avoid their pitfalls, which they can offer in hindsight.

But we can turn that hindsight into foresight.

Put the derailed train back on the track, and trace it all the way back to the drawing board. Wouldn’t it make sense to have someone involved in the design who can tell you how to keep a train from derailing, based on years of experience studying how they do?

If your answer is “yes,” you want a litigator on your team.

Litigators as Taxi Drivers

Finally, each project that comes across an in-house counsel’s desk is a passenger in a taxi. There’s a goal, a destination, and parameters. It’s your job to help them get there.

Taxi drivers have an innate sense of the cities in which they function. They know the main thoroughfares and side streets and keep on top of how construction or major events may alter their routes. They also want the same thing the passenger wants: to get to their destination quickly and safely. Where they provide unique value is in risk tolerance and a willingness to push themselves to see just how efficient they can become.

For simplicity, let’s make the passenger sales: they want their deals done for the best price as quickly as possible and want as many of them as they can get. If they like your work, they’ll be back in your cab time and again.

It’s true that litigators’ jobs tend to focus on eliminating risk, and it can be hard to shake that mindset when they transition in-house, where risk is a natural part of life. However, litigators also work with their clients to develop, and fearlessly execute, risk-laden strategies when their cases can benefit from it.

Litigators thrive in those moments. They neither embrace them recklessly nor seek them out in every situation, keeping their passenger safe from unseen dangers. But once they learn your organization, litigators have the capacity to see the narrow shortcuts where they can hit 75 – and leverage their understanding of your risk tolerance to propel your teams to their goals faster.

Litigators Make Excellent Contract Negotiators

Litigators have unique insights and value to add to any contract development process. They are trained to multitask and triage, foresee pitfalls, and instinctively driven to know when a risk is needed and valued by their teams. They are a potent, and oft-overlooked, addition to any in-house department.

To paraphrase the inimitable John Candy from the movie Planes, Trains, and Automobiles:

I like them. They like them. Their clients like them. Their teams like them. Because they’re the real article. What you see is what you get.

If you haven’t thought about how a litigator may round out your in-house legal team, now is the time to start.

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  1. Xander, your article is brilliant also hits exactly the mark of my experience. The dynamics, the scope, the final result of a judicial or arbitration dispute placed in relation to the elements (especially the contract and the evidence) present at the beginning of the story, make the litigators potentially capable of discussing a contract and constructing it effectively with respect to the risk of litigation.

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