Challenging the Traditional Law Model: How Work Flexibility Brings More Happiness

We got in touch with Ben due to his goal of creating a more flexible work arrangement for corporate lawyers. Below, we talk about why he left his job at Kirkland & Ellis and how InCloudCounsel presents an opportunity for lawyers who want to still practice law, without being tied down to long hours at a law firm.

Can you share your journey as a lawyer and what motivated you to leave the legal sphere?

I went to law school in order to keep my options open. I never really had dreams of becoming a partner at a law firm, but I went to law school and went to Kirkland & Ellis. I became a corporate lawyer and ultimately had a really good experience.

As a lawyer, I enjoyed the people I worked with and learned a lot. I saw what it meant to work hard and take pride in that work, while still maintaining quality when quickly completing unfamiliar tasks. It provided me with good experience and training, but after a few years, I looked around and realised that success at Kirkland – or any law firm – wouldn’t have been ‘success’ for me. So, that made the work harder for me, because there wasn’t a goal ahead of me that I wanted to achieve. I was jealous of the people who knew what their goal at the firm was and what they wanted to achieve because it was a great career, but none of that stuff resonated with me.

So when I moved out to San Francisco with my wife, I set out to solve some of the problems that I had seen – both in terms of adding efficiency to some parts of legal practice – and also offering an opportunity for corporate lawyers who maybe wanted another way to practice, in a way that the practice would revolve around their lives and not their lives revolving around their work.

Can you just share a bit about InCloudCounsel and what motivated you to start it up?

At the same time, we wanted to address some of the inefficiencies that my co-founder was seeing on the business side and that I was also certainly seeing on the legal side.

InCloudCounsel offers a solution to negotiate and manage routine legal work to help companies streamline processes; it is a platform for doing high volume legal work for large companies. This means we use a distributed network of attorneys, so, essentially, we do the work that the companies of a certain scale see in really high numbers. These things may include NDAs and vendor contract service agreements (etc.).

We do this by using a group of specialist attorneys in the US and around the world. These are lawyers who used to work in big law practices and for whatever reason, decided that it didn’t make sense for them anymore. In essence, the lawyers we use have really good training but wanted to work in a different way.

I was motivated to create a different method for attorneys to practice that could allow them to be successful in their own way. If someone wanted to be a stay at home parent or an entrepreneur, found a non-profit company or be a children’s book author, they could achieve that dream on their own terms. We wanted to help them.

At the same time, we wanted to address some of the inefficiencies that my co-founder was seeing on the business side and that I was also certainly seeing on the legal side. Large law firms are great for big matters, but for the smaller tasks, you are still often paying a generalist junior associate a very large bill to do something that does not require large law firm rates.

Therefore, we set out to solve those dual problems: providing lawyers with a different option in their careers to work more flexibly and remotely, while addressing the issues that large companies were facing every day tied to handling their high volume legal work and all the data that is in those documents.

You can always pick up where you left off, so if you want to try something a little different, try it, especially if you are not happy.

What do you think should be the first steps for a lawyer if they wish to create a better work-life balance?

First, define what success is for you because I think that success is different for everyone. People ought to have an understanding of what they are actually trying to achieve, what would actually make them happy. That’s the threshold question in order to take an honest view as to what they think will make them happy and make them successful. From there, it is easier for them to prioritize everything else. You have to be willing to sacrifice a little, but hopefully not too much.

For lawyers, maybe seek other options that will create a better balance. Maybe it’s working with a company like InCloudCounsel or with another similar company. The hardest thing is taking the initial steps.

When I first left Kirkland, for a couple of years after I would constantly be asked: “how do you leave?” The answer is: you just leave. It is hard when you’re accustomed to your lifestyle and so the first step is a really difficult one. The risk on the other side also is not that huge. You can always pick up where you left off, so if you want to try something a little different, try it, especially if you are not happy.

Flexibility is the key here. It makes lawyers and employees, in general, a lot happier. I do think this model will work well for the legal industry.

Do you think InCloudCounsel challenges the traditional practice of law firms?

Yes and no. I do think the legal practice and traditional legal practice is going to have to change; it’s going to have to adapt to new working conditions and new technology.

It may even be the case in the future that law firms are not the best place to do every type of legal-based job and it may progress to be more of a siloed process to what types of work certain law firms handle. This may lead to law firms and their lawyers being able to focus on the really high-value work for their clients and not have to do the minutia tasks between midnight and 3:00 a.m.

Is this a threat for law firms? I don’t think so. I think we’re all part of an ecosystem that is going to hopefully make the practice of law more efficient, more humane and ultimately, better for everyone involved. Flexibility is the key here. It makes lawyers and employees, in general, a lot happier. I do think this model will work well for the legal industry.

There will also be challenges when there’s not a name brand associated with the attorney that you’re working with, which makes it harder to know the quality level of their work.

What do you think the benefits and even the negatives are, for this type of work model?

A good benefit is that you won’t be paying massive overhead for a big law firm to do a simple job. For lawyers, they can work on their own terms and create their job around their lifestyle. But there are challenges which face this model.

What large companies don’t want to happen is having a random attorney pick up their document in a morass of other documents. They still need to really pay attention to quality and consistency and so this isn’t like other gig economy services, like Uber, where you say “I need a service agreement done and whichever driver shows up will be able to do it for me.” There’s a limit to what the gig economy can and should handle. With InCloudCounsel, the attorneys on our platform become dedicated, semi-permanent extended teams of our clients.

There will also be challenges when there’s not a name brand associated with the attorney that you’re working with, which makes it harder to know the quality level of their work. That’s why our attorney network has a rigorous vetting process that admits less than 5% of all applicants.

Nonetheless, I do think the positives certainly outweigh the negatives, in terms of sort of happiness and quality, for both attorneys and for customers.

Ben Levi is co-founder and COO of InCloudCounsel, a legal technology company that automates and enhances high-volume legal processes for large companies. Prior to InCloudCounsel, Ben practised corporate law at Kirkland & Ellis.