An Interview With Chad Silverstein
Assuming the only important part of the contract to read is the financial terms. Business people assume the legalese doesn’t matter or incorrectly assume it’s complicated and don’t read it. This couldn’t be further from the truth. Legalese is still English, and I would never expect a business person to know the full effect of a provision or understand how to change it if needed. However, if we work together, we can create a better outcome for the company. Plus, when disputes arise, key terms such as termination, renewal, indemnity, and quality assurance provisions can affect whether you politely part ways or end up in court.
In today’s fast-paced business world, the complexity of legal matters can often be overlooked, leading to significant repercussions for businesses of all sizes. From startup ventures to established corporations, the absence of legal guidance can result in critical errors that affect growth, operations, and sustainability. These mistakes range from issues with contracts and intellectual property to compliance and employment law, each carrying the potential for financial loss and reputational damage. I had the pleasure of interviewing Lynn Gefen.
Lynn Gefen currently serves as Chief People Officer, Chief Legal Officer and Corporate Secretary at TerrAscend, a leading North American cannabis company. Prior to her roles at TerrAscend, Ms. Gefen served as Deputy General Counsel, Chief Risk and Compliance Officer, and Assistant Secretary at HomeServe, a publicly traded, independent provider of home repair service solutions. In addition to her roles at HomeServe, Ms. Gefen has worked for Diageo North America, a global leader in beverage alcohol, focusing on regulatory matters, privacy, and compliance, and for Citrix Systems, a multinational cloud computing and virtualization technology company, where she led a team with global responsibility for corporate and compliance matters including securities, commercial transactions, litigation, governance, and employment. Ms. Gefen began her legal career as an associate at Thacher Proffitt & Wood and Holland & Knight. Ms. Gefen received a J.D. from American University and a Bachelor of Arts from the University of Florida.
Thank you for joining us. To start, could you share your “origin story” with our readers? How did you begin your career? What challenges did you face in the early days? How did you overcome them?
I began my legal profession on the traditional “Big Law” path, which created a good foundation for my future career in-house. What was most memorable about those early days was developing a keen eye for detail, learning my way around the large closing room, and, frankly, embracing the opportunity to lean into those ahead of me to continue to grow. One of the challenges I faced was simply the number of expected hours at my job. Back then, working around the clock until very late in the morning, running changes, or waiting for the courier was common. Being a lawyer was simply more time-consuming due to the lack of technology. Do you remember when faxing was the norm, and we didn’t have the internet or email to close on a scanned copy of a signature or use Docusign? I didn’t really think about the sheer volume or hours; it was simply a rite of passage. Reflecting on it now, though, it taught me grit and determination, skills that helped me as I progressed in my career.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
I’ve always been a fan of historical fiction, thanks to my general intellectual curiosity and keen desire to solve a problem. One of my favorite historical fiction books was The Other Boleyn Girl. I found that period of time fascinating and began going deeper to learn more about the monarch of that time. What captivated me so much was the general notion of duty. Duty is something that I take very seriously in my everyday work. I feel a profound sense of duty as an in-house lawyer, a duty to the Board, a duty to our shareholders, and a duty to do the best job I can to mitigate risk so my company can grow and achieve its goals.
Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
I tell this story a lot. My favorite quote and motto I continue to live by is “Listen to understand rather than listen to reply.” Growing up in a household with three sisters, we simply had to speak loudly, constantly fighting for attention and interrupting each other to be heard. This habit continued when I began my legal career, and I quickly discovered I would be more effective if I listened completely rather than being quick to react. I learned that if I fully understood the point made by my colleague, we’d achieve more simply by understanding each other. Being patient and listening has helped me build teams that value each other and our diversity. Together, we can be more successful.
How have you used your success to make the world a better place?
I’m excited to do more in this area moving forward. I strive to make the world a better place through mentoring, whether it be guiding my daughters or coaching members of my professional team. Mentoring is one of my favorite things about being in leadership. I have shared career lessons and experiences about juggling being a mother and a successful professional. As I look to a life beyond my career, I am committed to using my success to do more for the underserved in my community.
Ok, let’s now turn to the central part of our interview. What is the most common legal mistake you see businesses make due to the lack of proper legal counsel, and what are its potential consequences?
This is an easy one. The most common mistake I’ve seen when lawyers aren’t brought in is not sufficiently anticipating what could happen when parties reach a disagreement. I’ve seen business teams fall victim to this over and over again. Everyone is happy on the way in, but it’s my job to anticipate what may go wrong — because something always does — and to make sure the company has options to avail itself of in that circumstance.
Can you share an example where early legal intervention could have significantly altered the outcome of a business dispute or challenge?
I’ll give you a simple example that everyone can relate to. My company’s finance team signed a consulting contract with a vendor. They failed to have legal review the contract, thinking it was a simple, straightforward transaction — and it was — however, there was a provision in the boilerplate legal terms — a non-solicit clause — that said if you hire anyone that currently works, or has been employed at the vendor company, you have to pay a liquidated damages fee. No problem, right? Nothing could go wrong. Of course, a vendor employee applied for a job at my company. We hired that person, and then the vendor wanted their fee. If someone from my team had been involved, we would have built a carve-out for general solicitation so that the provision would not have been triggered (since we didn’t directly recruit the individual). Legal review can help ensure these events are thought through upfront to ensure the business deal is clear.
How do changes in digital technology and online business practices complicate legal issues for businesses without dedicated legal advice?
The ease of communication today is both a blessing and a curse. Email and chat make it easy to reach people, but people do not realize that these mediums are just as controlling regarding the party’s intentions as any other written communication. So, be careful not to say something you wouldn’t say orally in an email. I always counsel my clients and friends alike, save tough topics for old-fashioned conversations. Electronic communication lacks tone, can be misinterpreted, and will be used against you.
In your experience, how does the absence of legal counsel impact a business’s approach to contracts and negotiations, and what advice would you give to mitigate these risks?
Without legal counsel, the business typically focuses on the financial terms and leaves the “legal fine print” alone. This is a fatal mistake. Legal terms are part of the business deal. Things like termination provisions, indemnification, warranties, quality control, and renewal provisions are just a few common areas where, without the appropriate language, you could end up with a problem.
What legal pitfalls do new businesses often overlook during their initial setup and growth phases, and how can they proactively address these issues?
Companies must focus on compliance and building a good legal foundation as early as possible. Failure to establish a good foundation can prevent the company from being able to scale when growth opportunities arrive. The goal is to grow smart, stay out of court, and, in my experience, building a good foundation minimizes this risk.
Here is our main question. Could you list and briefly explain “Top 5 Mistakes Businesses Make Without Legal Counsel” based on your experiences and insights? If you can, please share a story or example for each.
1 . Assuming the only important part of the contract to read is the financial terms.
Business people assume the legalese doesn’t matter or incorrectly assume it’s complicated and don’t read it. This couldn’t be further from the truth. Legalese is still English, and I would never expect a business person to know the full effect of a provision or understand how to change it if needed. However, if we work together, we can create a better outcome for the company. Plus, when disputes arise, key terms such as termination, renewal, indemnity, and quality assurance provisions can affect whether you politely part ways or end up in court.
2 . Handshake or “napkin” deals.
The temptation to cut corners on contracts and save money on legal fees can be particularly strong. However, this can expose the business to significant legal vulnerabilities. These include the risk of disputes over ambiguities and the enforceability of agreements that don’t accurately reflect the parties’ intentions. Once, I had a case where an agreement was sketched on a napkin. This is not a joke. In this case, an independent consultant was hired to find properties and was meant to receive shares of stock in the company for each property. So, on a napkin were simply names of properties and share amounts. Unfortunately, there were no specified terms, such as a time period or other conditions, so we were forced to rely on people’s recollections and emails to piece together the parties’ intentions. This means you are in for a long haul and certainly will end up in court, which was the case here.
3 . Over-relying on email or other digital communications.
Emails live forever. Let’s be honest: most companies don’t regularly delete emails (although they should!). The casual nature of email leads some to say things they may not be proud of in hindsight. I’ve seen this repeatedly throughout my career: an email passes my desk that makes me cringe, or you find that “gotcha” email from your CEO when you are evaluating who said what when you are in a dispute. I advise avoiding email for important conversations and using it solely for conversational purposes. If you must use email, draft it carefully and encourage your company to delete email regularly.
4 . Not properly factoring in new and evolving regulations.
Whether it’s data protection laws or changes in employment law, the ground under us is perpetually moving. The consequences of not keeping pace are real and range from financial penalties to reputational damage that can scare away customers. If you do nothing else as you build your company, ensure it has a good foundation of employee practices, know the core rules for the space you operate in, and comply with them. Follow the law as you construct your business, follow the law in your hiring practices, foster a good workplace culture, and you will avoid significant headaches.
5 . Failing to exercise good recordkeeping.
Proper recordkeeping is vital for all areas of a company. You must retain the relevant information, whether it be tax or basic employee records. Aside from financial information, you also need to keep clear records of your contracts and employment practices/issues. Creating a contract won’t help if you can’t find it or if you are missing an amendment. If employment issues arise, you’ll need to be able to pull up records to show what actions you took, when you took them, and what the outcome was.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I’m from a family who overcame significant obstacles to provide me with a good education, a safe home, and who taught me the value of hard work. I’d like to think I can help others similarly from modest homes where both parents worked to put food on the table to reach for the moon. I have wanted to be a lawyer since I was eight. I had no role model to follow, so I built my career path with sheer will and determination. There are many people out there who I’d love to inspire to chase their dreams no matter the obstacles.
As we wrap up, how can our readers follow your work?
I don’t have much time beyond my work and family, but I do post things important to me on Linkedin. https://www.linkedin.com/in/lynngefen/
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program.
To learn more and connect with Chad visit: chadsilverstein.io
Lynn Gefen Of TerrAscend On The Top 5 Mistakes Businesses Make Without Legal Counsel was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.