Stop Following The Rules And Start Coloring Outside Of The Lines

It is true that there are many hard and fast rules that must be followed. It is also equally true, however, that 'rules' are not really rules, but a matter of perspective or interpretation.

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Pablo Picasso once said: “Learn the rules like a pro, so you can break them like an artist.” As a junior lawyer in private practice, I was most comfortable when I could say firmly and with confidence, “This is the law, these are the facts, and, therefore, this is how I recommend that we proceed.” As a senior in-house lawyer, I learned very quickly that I did not have that luxury. I learned that I had to be flexible in my mindset.

It is true that there are many hard and fast rules that must be followed. It is also equally true, however, that “rules” are not really rules, but a matter of perspective or interpretation. It is important to know the difference. To be a successful in-house lawyer, I knew I had to be a problem solver and I had to be open to doing law differently.

To delve into this topic more, I sat down with Flo Nicolas, one of the most creative lawyers I know. Dubbed the #nonboringlawyer and Contract Tech Queen, Flo Nicolas is revolutionizing the old-school legal tech industry. Flo currently serves as the chief growth and community officer for the How to Contract Network and as host of a new steaming series called Contract Tech Showcase. Flo and I talked about how in-house lawyers could approach the contract process creatively using technology. I have included highlights of our conversation below.

Lisa Lang: Is creativity a necessary quality for an in-house counsel to have?

Flo Nicolas: To answer this question, you need to know what it means for a lawyer to be creative. Being creative for a lawyer means bringing a different mindset to the table. It is not just about the law. It is about thinking differently — “thinking outside the box” and presenting creative solutions to complex problems. Business teams don’t want an in-house lawyer saying, “you can’t do this, and you can’t do that.” If in-house lawyers want to be  successful, they must reimagine their role. They cannot be just legal advisors. They need to be strategic business partners.

LL: How can an in-house lawyer use their creativity to be more successful in their work?

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FN: In-house lawyers can leverage their creativity and be more successful by being proactive rather than reactive. In-house lawyers should not be seen only as problem solvers who are consulted after problems arise. In-house lawyers need to be seen as collaborators, willing to be part of the creative process before a project launches. In-house lawyers need to show that they are valuable assets. The role of the in-house lawyer does not have to be limited to drafting and reviewing contracts toward the end of a process. They can and should have a seat at the business table during the entire process.

If you are an in-house lawyer working with product teams and engineers, ask to attend product and development meetings. Be present, be engaged, ask questions, and provide input to the teams that would benefit from the legal and business perspectives.

LL: Can creativity be taught?

FN: Creativity can be taught to any in-house lawyer willing to be flexible and adaptable. Lawyers are already tasked with keeping up with the ever-changing laws, rules, and regulations in the legal industry. So, it’s critical for in-house lawyers to tap into their creative side to find new ways to adjust to all these changes. During the pandemic, in-house lawyers were instrumental in helping companies quickly adapt their processes in a remote environment while still achieving company objectives by adapting and embracing technology in an effort to serve their client’s needs in a remote environment. They began learning how to use various automated software tools to help all phases of the contract management life cycle. Studies have shown that in-house lawyers are beginning to successfully adopt and leverage technology and will that they will continue to do so in the foreseeable future.

LL: Is there a difference between being creative and being innovative?

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FN: You cannot have innovation without creativity. Ideas are conceived and result in innovation. Creativity is the catalyst that is needed to spark innovation.

LL: Do you consider yourself a creative lawyer?

FN: I 100% know that I am a creative lawyer, and I always look at things analytically. I thrive when I can look at problems from different perspectives. I have never had the mentality of “this can’t get done.” I have always looked at alternate ways to achieve an objective while minimizing the risk to the extent possible.

LL: In what ways do you express your creativity through your work?

FN: I refuse to be characterized as a dull, cold-hearted, and robot-like lawyer. Instead, I use humor and emojis in the pieces that I write. I also create entertaining and educational gifs. I am committed to changing the lawyer stereotype. I sprinkle what I do with a flare of theatrics! This is why I am called the #NonBoringLawyer.

I have leveraged the power of LinkedIn to grow my legal technology following and advocate for the utilization of legal and contract technology to create more robust legal teams. I educate others about legal technology through creative means such as creating videos and humorous gifs.

LL: Are there other ways you have seen others express their creative side?

FN: The best example of lawyers expressing their creative side is TikTok sensations Alex Su, head of community development at Ironclad, and Catherine “Cat” Casey, chief growth officer at Reveal Brainspace. Alex and Catherine have paved the way for lawyers like myself to feel more comfortable using social media and creating humorous video content. Both Alex and Catherine have huge followings on social media and what they are doing is clear evidence that there is a platform for lawyers who are leveraging their creative side.

Business and tech-savvy in-house lawyers are the hottest trend around right now. In-house lawyers who are not afraid to roll up their sleeves, get involved, and provide creative input will most certainly become the most sought after lawyers.


Lisa Lang is an in-house lawyer and thought leader who is passionate about all things in-house.  She has recently launched a website and blog Why This, Not That™ (www.lawyerlisalang ) to serve as a resource for in-house lawyers.  You can e-mail her at lisa@lawyerlisalang.com , connect with her on LinkedIn  (https://www.linkedin.com/in/lawyerlisalang/) or follow her on Twitter (@lang_lawyer).

Dubbed the #nonboringlawyer and Contract Tech Queen!!, Flo Nicolas is revolutionizing the old-school legal tech industry. She is the author of the LinkedIn article Legal Playbook – The Plan of Action You Must Have and ContractNerd.com guest writer for the article called How to create and use a signature authority chart. Flo is currently the Chief Growth and Community Officer of How to Contract Network and Host of a new steaming series called Contract Tech Showcase. She is also a Cable and Utilities Committee and Library Trustee Board Member. Flo is experienced with corporate technology operations and knowledgeable at leveraging data analytics and legal technology to optimize contract life-cycles, increase contract workflow efficiency and productivity.