“Contract drafting is more than just following the rules” — Loio’s interview with Laura Frederick

This interview is part of Loio’s series of interviews with legal enthusiasts about the ins and outs of the legal industry.

The following is the interview with Laura Frederick, ex-Tesla and ex-Big Law technology transactions attorney with 25+ years of experience working on commercial contracts and operations, the founder of the How to Contract practical training platform, managing attorney at Laura Frederick Law, and author.

Let’s dive in!

Laura, your professional path is truly extraordinary.  You’ve achieved so much success as a lawyer at companies like Tesla and Morrison & Foerster and now with your new contract training platform called How to Contract. Wow! Could you please tell me about deciding to become a lawyer and about your education and career path? Did you always want to be a lawyer?

Not at all. I never met a lawyer growing up. I only knew what I saw on TV. They always were brilliant and eloquent. I didn’t think I was smart enough to do what I thought lawyers did. That changed my freshman year in college when I met a lot of other students who planned to go to law school. I thought, well, I’m at least as smart as they are. I could do that. But I still wasn’t sure. I considered getting an MBA or Masters in Economics but was scared off by all the math. I loved writing and words, so I decided that law school was a better fit.  

I didn’t like law school that much. I didn’t have that much interest in a lot of the subjects and found the format hard to digest. I did well, but it wasn’t something I enjoyed.

After law school, I did a Fulbright grant where I studied international commercial arbitration. I picked that subject because I thought it would be helpful for my career. Then I spent my first three years working in the area of franchise law. It was ok, but still not something I loved.

It wasn’t until I started doing technology transactions as a third-year lawyer that I fell in love. I loved the speed of the deals, the creativity, the complexity, and pretty much everything about it. So, I’ve been fortunate that I’ve loved what I’ve been doing since I was a third-year lawyer. 

I spent the first ten years working in law firms. I decided on a change when I was a 9th-year associate. I was working massive Big Law hours with a 3-year-old, a 1-year-old, and was pregnant again. So, I finally said enough is enough. 

Having off on the evenings and weekends to spend with my family became my biggest priority. I found an in-house job at an energy company in a smaller town in Pennsylvania. I worked there for about five years. I had one more child there, giving me four kids, all under the age of 5 when the last one was born. It was a crazy time.

Then I moved to California for family reasons and worked in a series of solar energy companies. I worked at SolarCity, which was acquired by Tesla, where I worked for another two years. 

The Tesla job was the ultimate career peak. I loved the people, the work, and the company. I really loved everything about it. However, even though I couldn’t have designed a better job, there was still something missing. I realized it was the flexibility and freedom in my life. 

So in January 2019, I quit Tesla to open my law firm. By this point, I was a single mom with 100% custody of my four kids with no family nearby to help. I also was the only income without a second income to fall back on. That was a really tricky part, especially because I had no clients and no real plan or experience. I’d never worked for myself in 24 years. 

But I took the plunge. I am a hard worker and had been successful in what I’d done before. So I thought, “Well, why wouldn’t I do well with this? I could do this!” I had eight months of living expenses in the bank. I figured I’d find a job if it didn’t pan out.

The first year was tough with my law firm. I had to get used to a billing life again, figure out all the administrative stuff, find clients, and figure out my niche. But after about a year, I hit my stride. It’s been fantastic and the best decision I ever made.

You’ve got quite a following on LinkedIn (over 16,000 followers) and a team of groupies 🙂 How did you do it? Why did you turn to LinkedIn? What are your tips for those who are starting out?

I’m having so much fun on LinkedIn. I think part of what comes through in my posts and why people gravitate toward them is my complete and absolute love of contracts. I love these practical parts of contract law and negotiating and helping clients. It’s been so fun to meet others on LinkedIn who also are passionate about it.  

I decided to jump into LinkedIn in August 2020. I had done a marketing plan to expand my law firm. I loved vendor contracts more than any other kind of work I’d done. So I decided to refocus my law firm just on vendor contracts for sophisticated businesses.

I knew that to attract my ideal clients I needed to demonstrate my contract expertise. Before that point, I had never done much on LinkedIn: I posted my job moves, went on once in a while, and just surfed, but I rarely posted. 

Around that time, I saw a post by someone who had taken a challenge to post every day for 30 days. I thought: “I could do that.”  I figured I had about ten ideas for posts. I wasn’t sure I’d come up with any more ideas for posts, but why not try. 

I immediately found there was a massive hunger for practical contract information. A lot of the writing is academic about the case law and not sharing the practitioner’s perspective. I also saw that a lot dealt with how to write clearly but not the reality of our job, with all the compromises and frustrations we have as practicing attorneys. 

The other reason I think people gravitated to my posts was that I shared everything I know. I mean everything. I never held back. 

I think a lot of lawyers don’t open up their best information or keep it too vague to be helpful. You know, “be careful with indemnities.” This is great to say, but it doesn’t help people. 

My focus was to give, then give again, then give some more. I wanted to share as much as I could about what I’d learned over my lifetime. 

I was asked a while back about my expectations for the return on investment for my LinkedIn time. I had no plan when I started. I just started, and it took off. And I’m my own boss, so I have the freedom to spend time doing what I want. I enjoyed it and kept going. I think I’m up to about 278 days straight posting. I have my long list of about another 50 items, and I’m sure there will be lots after that. I think if I sat down, I could easily come up with 100 more things to discuss. I don’t see myself running out of ideas.

After successfully launching the “How to Contract” practical training platform, you wrote a post starting with these heartbreaking words “I had a party about seven years ago and not a single person came” and finished it with the awesome news with your numbers. You ended up with 230 people who signed up for your How to Contract membership, compared to the 50 that you targeted. Congratulations on achieving such success! How did you come up with the idea to start the “How to Contract” training program? What is your “why”? 

I love the practice of law but not the academic study of it. I don’t want to be a law school professor or write law review articles. 

But what I do love is helping people learn how to do work with contracts. I want to help them learn all the nuances, techniques, and tactics that we need to know to work for clients on commercial contracts. That’s my why and the essence of How to Contract.  

It started with me posting daily contract tips, which essentially offered a 1,300-character training tidbit every day. After about a month or so, I started getting a lot of requests to put all of the tips together in a separate handout that I could give to people. That led me to decide to publish a collection of tips in a book. 

I’m all about just-dive-in-you-will-figure-it-out. That’s why I thought I’d just self-publish something on Amazon. I put together the tips I had — 91 contract tips and six life tips — in a Word document, hired somebody to format it for me in the Kindle format and uploaded it to Amazon. It became a big hit. I’ve now sold about 1,600 copies. I hear from people how much they enjoy my daily tips and the book and how they impact their careers and lives. 

Seeing the success of the tips in the book made me want to do something more. I dove into building the platform myself. I prefer to create things myself so that it reflects me and my vision. 

I launched in March and it has been my dream come true ever since. It’s a place for me to create and share content. I plan to add courses later this year, but for now, my focus is on creating tons of valuable training for lawyers and contract professionals. 

The thing most of my members love is access to all my 278 contract tips. My members can scroll through them by topic or do a keyword search to find the exact one they need. I also do monthly training and share a new job aid each week, like checklists, negotiation scripts, and guides. We cover one subject each month.  We started with confidentiality, then damages, and limits of liability, and now we are doing indemnification.  

The membership is only open to new members three times each year.  This lets us focus on supporting our members rather than always selling and onboarding. The good news is that we are about to open the doors to new members very soon.  We’re going to open to new members on June 1st.

What is your favorite thing about this initiative? 

It is the people.

I’ve met so many incredible people and feel so connected to this community of contract enthusiasts. We have everything from new lawyers and new contract professionals to more senior and more experienced professionals. We have paralegals from small law firms to partners in Big Law. My members share that they are learning every day for me, whether it is a new perspective or refreshing what they kind of already knew. 

All of us come together to talk through contracting. Because contracts is such a diverse and complex subject. It’s not just something you learn in law school and are done. You can never learn everything about contracts, which is why I love it so much. You can never master contracts. You can only try to get better and better at it and spend a lifetime doing it. That’s what I’m doing too.

I’m learning every day. And it’s another thing I love most about this project. Because I’m refreshing my knowledge and spending time just really thinking about some of these subjects that are so interesting to me. And I get to help people gain more confidence and grow in their skills and careers. It is incredible that I get to be part of people’s life journey.

What are your plans for the future?

I hope to continue doing what I’m doing now, nurturing the community of the How to Contract Network, building out the training platform, offering more courses, and keeping the membership going. I enjoy the membership dynamic of having a community where we’re collectively working on something together. 

I’m going to be publishing an update in my book this fall. I’m exploring how I can use technology to make my tips more accessible and helpful when and where people need them.  I also have another big related project that I’ll be announcing in the next week or two. 

I’d love to continue to spend as much time as I can on content and training. 

What is your favorite thing about contract drafting? 

There are many different things I adore. Mostly I love the creativity of drafting commercial contracts. Contracts are the ultimate puzzle. No two are ever alike. They are constantly changing and there’s so much that we have to think about when we draft. 

It’s true that we draft within a set of rules that the law requires. We follow some conventions to make sure the contract is clear, written in an active voice, and covers legal requirements. But the fun of contracts is learning the nuances, editing, and revising each contract to make it into the best version we can. We learn nuances to drafting that people who aren’t as familiar with it don’t know. 

And our learning is not just for the sake of learning, as we see in some academic settings. For us practicing lawyers, learning enables us to do a better job helping our clients. There’s so much creativity in how we draft, what we put and don’t put in there, how we negotiate the terms. The vendor or the customer will change something and you’ll have to decide whether to accept it or change something about what they’re proposing to what they might accept that’s still good for you. 

Contract drafting is more than just following the rules. Despite what some people suggest, there is no one best approach to contract drafting. It’s always customized to the business dynamics, the client priorities, the bargaining power. There are so many different dynamics to consider when we review and revise. 

I love the freedom to create something great. It’s essentially like a complex word puzzle to me.

What are the biggest challenges when it comes to contract drafting and reviewing? 

For most professionals, the biggest challenge is the time available. If we had more time, we all could draft better, clearer contracts.  But most lawyer and contract professionals operate with minimal time to work on each one. As an in-house lawyer, you have maybe five, ten, or more contracts to do by the end of the workday. We don’t have time to improve them all as the academics suggest. Each one probably would need three hours, but that’s not doable. So, you may just be able to squeeze in 30 minutes on each one. 

So when we have that kind of limitation on time to work on our contracts, it becomes so critical to learn what matters.  We see things all the time that we could fix, but we evaluate and decide to let it be because we don’t have time to fix it. 

Do you think that contracting is the area that can benefit from the use of legal tech? Why or why not? Is it important to optimize contract drafting? Why or why not?

Yes, for sure. I’m excited to see how legal tech can help us with our contracts. 

Right now, there are so many different contract vendors out there doing such a great job of automating and regulating how companies do contracts. I think it’s fantastic. The world can benefit from it. 

But even with more tech, there will always be a role for lawyers and contract professionals there. At the end of the day, we have two parties who have to agree on the terms of their relationship. Just as no two people are the same, no two deals are either. There are always nuances and variations. Plus, as the contract value increases, our attention to all of the details with a contract does, too. 

I see legal tech helping us all manage the regular deal flow and the post-signature processing and management. I think that’s the niche that legal technology can really support lawyers and contract professionals. 

What has changed in contracting and the routine in general over the past 25 years that you’ve been working in this field? 

You don’t have to worry about the Y2K clause anymore. 🙂 

I started in tech transactions in late 1997 and Y2K was everything. We spent a lot of time talking about it when drafting provisions. That was a highlight of my early career. 

For those who don’t know this, Y2K stands for the year 2000. Back in those early days of computers, it was costly to have memory. To save on memory, many computer programs used two digits for the year and 00 for the shutdown. So, all those programs had to be rewritten as the two-digit year 00 approaches. There was a lot of risk and fear in the marketplace about signing up with the vendor and them not being able to perform. We spent a lot of time talking about what fixes they were going to do for Y2K and how they were going to promise us that none of their software would have a problem on that date. 

Another thing is emailing. I remember the first time I used email for work. It was 1995. The vendor charged us by the minute to type and read emails, so we charged clients. It was ridiculously expensive, so we’d write an email in a word processing program and then copy it over to send by email. Thankfully, that’s changed. 

What other changes do you think will happen in the future?

I think we are going to see a lot more systematic contracts for smaller things. Vendors and customers will come to platforms or agree on templates that systematize a lot of the risk shared. I think there’s a lot of potential for that and companies will pursue that. 

I believe that will be the biggest change as we move towards a more systematic approach to smaller contract deals. 

How will contract drafting change in the future?

It’s a good question. I know there are programs out there that can run a quick review of your contracts and identify gaps between your versions and the ideal contract provision. That’s certainly helpful, but there will always be the human element of that. 

Computers and AI are a long way off from knowing our clients and understanding the nuances of our business as we do.  

At the end of the day, contracting is about knowing the client, their business, their bargaining power, and their priorities. 

But for simpler, more run-of-the-mill kind of contracting, I can see us all moving to industry-standard templates.

Being a lawyer, how many contracts have you reviewed throughout your career? 

I thought about this before. There’s no way to know, so I guessed that I reviewed about 50 contracts a month. Measured over my 25 years of practice, that’s 15,000 contracts.

What is your favorite part about being a lawyer? 

It’s getting to help my clients. I enjoy the part of being part of a team working with my clients to achieve their goals. My job is a step for them to improve something — either to sign a vendor or make money. I get to help them do that and show them the path and protect them along the way. I think that part of it is the most magical for me.

How do you envision the lawyer of the 21st century? What skills should they have? 

The number one skill I see lawyers need is writing. When I think about a lawyer that I want to hire, it’s not based on where they went to school or what kind of grades they have had. It’s about their ability to write concisely, precisely, and clearly. It is such an essential skill for lawyers and anybody working with contracts. 

The second one is having business judgment and understanding the risks that their clients face. It’s about keeping that open mind and being able to see the big picture. That this one little provision is not really about this little provision. It’s really about the bigger picture of risk allocation at mitigation between the parties. 

Do you think that legal tech skills will be essential? 

Definitely. It’s already important. It’s how we can become more efficient and gain more time in our schedules by using the technology efficiently. I think that will continue to be critical for all new lawyers. 

If you could have lunch with any prominent legal industry figure, who would that be? Why? 

Not a single figure, but instead, I would love to have lunch with the people I have been talking to on LinkedIn since I started posting last August. There are people I talk to almost every day or at least a couple of times a week in the comments on my post. They live all over the world. A lot of them are in my membership of the How to Contract Network. I would love to meet them all in person. I’m trying to figure out how I can make that happen someday. 

Thank you very much, Laura Frederick!

The interview was conducted by Jane Kuhuk, PR Manager at Loio.

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