I remember being in Junior High School when President Reagan nominated Sandra Day O’Connor to be the first female US Supreme Court justice back in 1981.

At that time it was very, very long overdue to have a woman sit on our country’s highest court.

I have always admired Justice O’Connor. Not just because she was a trailblazer by being the first woman to serve on the Supreme Court – but also because Justice O’Connor was a fierce defender of the rule of law.

In my view, Justice O’Connor was also highly ethical, balanced and level-headed as a Supreme Court Justice. These are important traits that we don’t always see from members of our judiciary in the United States nowadays.

One of my favorite stories about Justice O’Connor involved her interaction with Pro Football Hall of Fame running back John Riggins at a Washington DC event back in the mid-1980s which captured plenty of media attention. Mr. Riggins provides some perspective about what happened via his X account.

Fast forward 40+ years later and we still need more women to be in more senior leadership positions across the legal profession as judges, attorney generals, district attorneys, public defenders, law firm partners and general counsels.

Here’s my favorite quote from Justice O’Connor: “Do the best you can in every task, no matter how unimportant it may seem at the time. No one learns more about a problem than the person at the bottom.”

Rest in peace Justice O’Connor.

Over the past few months, I’ve had the privilege to talk about artificial intelligence at events with Microsoft, Thomson Reuters, the Ohio State Bar Association, the Intellectual Property Law Association of Chicago and the Association of Corporate Counsel-Chicago.

Here’s 5 AI takeaways that I have landed with audiences at these events:

☑️ Be AI Ready: It’s “AI all the time” as we continue to see new AI related announcements on a daily basis. Stay well informed about AI, learn from others and consider designating lawyers on your team who can serve as AI legal subject matter specialists.

☑️ Take Action: Don’t wait for AI-centric laws to be enacted as AI is here to stay and the pace of AI innovation will continue to accelerate. Be proactive in delivering necessary AI legal advice to your clients – and especially when it comes to shaping your organization’s AI policies/practices and conducting appropriate due diligence on AI providers.

☑️ AI is a “Team Sport”: The AI legal landscape is broad and involves a range of surface areas from ethics to IP to data privacy to cybersecurity to employment law to contract negotiations to regulatory law. Take a multi-disciplinary approach to AI legal matters.

☑️ Be Smart with AI Usage: Understand how your organization is using AI tools – and especially as your legal organization embraces AI to better serve your clients. While IMO lawyers don’t need to be AI technology “experts,” most US. legal ethics rules require lawyers to understand the risks and benefits of using technology and some states (e.g., California, Florida) are already issuing AI legal ethics opinions for lawyers.

☑️ Learn from the Past: We have all embraced other leading technology advancements that have impacted how we work like the rise of the PC, the internet, smartphones, social media and cloud computing. Take the legal lessons learned from navigating with those developments in the past and apply them to your AI journey.

I’ve attended some legal industry conferences and events this month where in-house counsel have asked me questions about internal company policies regarding AI.

Some of these questions have ranged from should my organization have an AI policy to what should such a AI policy say to can you please provide me with a sample AI policy and other similar questions.

I think we will be seeing more questions in this area from in-house lawyers as AI solutions become more prevalent.

While I’m not in a position to provide legal advice to others given my role as a corporate counsel, here’s my guiding principles regarding the development of AI policies for an organization:

☑️ Policy or No Policy?: Senior company leaders in conjunction with advice from their legal counsel are in the best decision to determine whether an AI company policy is required or not.

☑️ Learn from the Cloud: Many organizations nowadays have a policy about cloud computing since cloud usage is so widespread. If your organization has a cloud policy, apply the learnings from that experience in creating a suitable AI policy.

☑️ Don’t Cut & Paste: There’s no “one size fits all” AI policy as you need to tailor one for the specific needs of your organization.

☑️ Clarity & Simplicity: Don’t overengineer your AI policies. Make them super clear and straightforward.

☑️ Policy Updates: Make periodic updates to your AI policy as needed. If you have a legacy AI policy, consider updating that policy given the developments in the generative AI space over the past year.

☑️ Policy Implementation: If you establish an AI policy, be sure that your organization follows through on its requirements and that you provide AI policy awareness and training to your teammates.

☑️ Get Help: If needed, seek outside counsel assistance in developing your AI policy. Exhange AI policy development ideas and best practices with other in-house counsel. Of course, if you want some initial internal AI policy ideas, perhaps ChatGPT can help you get started 😉.

As the group’s lead guitarist, the iconic musician George Harrison was the primary singer only on a few Beatles songs.

One of those songs (which was also written by Harrison) was called “Taxman.”

Based on this recent NY Times article, it seems like AI is the new “Taxman” as the US Internal Revenue Services (“IRS”) will be using AI as a tool to investigate potential tax evasion.

Here’s a key passage from the article: “Mr. Werfel explained that artificial intelligence is helping the I.R.S. identify patterns and trends, giving the agency greater confidence that it can find where larger partnerships are shielding income. That is leading to the kinds of major audits that the I.R.S. might not have previously tackled.”

This use case for AI is very interesting for the following reasons:

☑️ It’s an example of the public sector embracing Digital Transformation in the form of AI to help solve problems.

☑️ It demonstrates how a traditional and regulated profession, tax and accounting services, can use AI as a tool to perform its work.

☑️ It reminds us that organizations have a growing opportunity to use AI as a tool to drive a culture of compliance.

Of course, another important takeaway is don’t cheat on your taxes!

One of my favorite songs is a classic rock song by a band called The Who entitled “Won’t Get Fooled Again.”

The song was written by Pete Townshend of The Who and it has a highly recognizable keyboard/organ rhythm and sound to it.

The song ends with these iconic lyrics: “Meet the New Boss, Same as the Old Boss.”

While the ending lyrics to this song are very catchy, in my experience in Corporate America, the reality is that every boss is different.

Throughout my career, I have had many, many bosses. In fact, I have had 3 different managers over the past 20 months.

During your career, you need to be highly adaptable as you will wind up reporting to and learning from different leaders.

When you find yourself reporting to a new boss, try not to get worried and stressed out.

Instead, embrace my set of guiding principles ⏬️ for engaging with a new boss:

🎸 Get Off to a Fast Start: Making positive first impressions with your boss is crucial. Be positive and highly enthusiastic!

🎸 Communications Clarity: Gain clarity with your boss on her/his preferred method and frequency in communicating with you.

🎸 No Surprises: Bosses don’t like to be blindsided so make sure that you keep your boss very well-informed of your work and key matters.

🎸 Don’t Complain: Most bosses don’t have high tolerance for constant workplace complainers.

🎸 Propose Solutions: When you bring an issue or problem to your boss’s attention, act as a problem solver and propose a thoughtful solution.

🎸 Respect Time: Your boss is very busy. Don’t waste her/his valuable time.

🎸 Ask for Feedback: Feedback is a “gift” and periodically seek feedback from your boss.

🎸 Earn Trust: It takes time to earn the trust and confidence of our bosses. Do your best in earning that trust and confidence every single day.

As one of my highly respected mentors told me a long time ago, one of our key roles in Corporate America is to make our bosses look great!

If you have a new boss, remember that she/he is different from the old boss so be ready to embrace change!

What else would you add to the list above?

I’m a very long suffering New York Knicks basketball fan. Even though the Knicks have not won a National Basketball Association (NBA) championship in over 50 years, I still bought a “vintage” Knicks jersey of my man #33 Patrick Ewing, who is one of my favorite former Knicks players, last month (and I still need to buy a jersey of my other favorite Knicks player, Bernard King #30).

As both a hardcore Knicks fan and as a lawyer, I just read about a recent filing of a lawsuit by the Knicks against another NBA team called the Toronto Raptors.

The Knicks sued the Raptors claiming that a former team employee who joined the Raptors stole proprietary information from the Knicks and shared it with the Raptors.

In my view, the lawsuit serves as a reminder that although we are quickly moving into a new technological area that is led by AI, there continues to be a “war” for great talent and employees are still highly important assets for any organizations.

As in-house counsel, here’s some good reminders for us at the intersection of employment law and information security:

🏀 Employment/Confidentiality Agreement: It’s always a best practice for company employees to sign a standard, thoughtful and suitable employment/confidentiality agreement on their first day of work.

🏀 Employee Leaving for a New Role: When an employee leaves for a new opportunity, I think it’s always a good idea to conduct an exit interview with that person, provide a copy of his/her signed employment/confidentiality agreement to that person and to remind that person of his/her ongoing obligations under that agreement. Also, consider eliminating an employee’s access to company confidential information when he/she tenders his/her resignation.

🏀 Due Diligence with New Hire: Before you hire a new employee, if possible, it’s important to understand the nature of any existing employment/confidentiality agreements or other unique contractual arrangements that such new employee may already have in place.

🏀 New Employee’s Role with New Employer: I believe that a new employer should avoid putting any new employee into a role which may potentially serve to cause that new employee to violate existing obligations with a previous employer.

🏀 Teammates of New Employee: The teammates of that new employee should avoid asking certain questions or seeking information from that new employee that can be viewed as “digging” for confidential information that the new employee had access to at his/her previous employer.

While my Knicks still need to make some more offseason moves to be a viable contender for a potential NBA championship, I’m looking forward to the upcoming basketball season and Let’s Go Knicks!

I love this article in last week’s The New York Times about the growing use of AI tools across the construction industry 🚧.

Interestingly, AI and the construction industry share lots of similarities to AI and the legal industry ⚖️.

Of course, AI can’t physically assembly a new building – just like AI can’t represent a client in-person in a courtroom proceeding or be physically present at the negotiation table like lawyers.

Also, as this quote from the article explains, the construction industry (just like the legal industry 😉) does not have the strongest track record for embracing technology: “The construction industry is the largest in the world, in terms of dollars spent, yet we are the least productive in terms of technological adoption and productivity gains.”

However, as the article expains, AI tools are increasingly deployed for construction projects and are speeding up the construction process: “Drones, cameras, mobile apps and even some robots are increasingly mapping real-time progress on sprawling job sites, giving builders and contractors the ability to track and improve a project’s performance.”

Sarah Liu, a partner at Fifth Wall, a venture capital firm focused on real estate investments, provides this terrific summation about AI: “The best companies aren’t touting themselves as AI companies. They’re touting themselves as problem-solving companies.”

As lawyers, let’s learn from the growing construction industry on how we can use AI tools to be outstanding problem solvers for our clients and move with greater speed and agility!

It’s been said that “data is the new oil”🪔- and that is certainly the case with the growing prevalence of AI solutions.

The need for incredibly large sized datasets – and high-quality data – is vitally important to help train AI algorithms and to properly fuel AI.

In fact, data and AI are a dynamic duo. They are like a modern-day Laurel & Hardy, Batman & Robin, John Lennon & Paul McCartney, Bert & Ernie, and Laverne & Shirley – they need each other to be highly successful.

In this recent highly informative article from The Economist entitled, “AI is Setting Off a Great Scramble for Data,” it states that “A data land grab is under way…Demand for data is growing so fast that the stock of high-quality text available for training may be exhausted by 2026, reckons Epoch ai, a research outfit.”

Some of the other key 🔑 points from this article are as follows:

©️ As the demand for data rises, potential copyright infringement claims will also rise.

📈 There is a significant increase in the number of deals to help secure viable sources of data.

ℹ️ Don’t forget about your company’s own vast internal sources of information like unstructured datasets.

As you develop an AI strategy, make sure that you also focus on data, data and more data – especially since every organization is a data organization.

Picture courtesy of Thomson Reuters.

A few days ago, I attended a terrific Association of Corporate Counsel -Chicago luncheon that was sponsored by Thomson Reuters on the topic of “Managing Legal Departments’ Priorities: Insights & Tools for Success.”

Hillary McNally from Thomson Reuters delivered a great presentation on the increasing opportunities for in-house counsel to leverage leading technology like artificial intelligence (“AI”) and large language models (“LLMs”) to drive better scale and legal services to their clients.

My favorite slide from the presentation AKA “the money slide” 💸 is above which outlines these 5 legal subject matter areas where AI and LLMs can be used as a tool for corporate counsel to work more efficiently:

📃 Contract Analysis

⚖️ Regulatory Compliance

📄 Document Drafting

📚 Legal Research

💡IP Management

As AI and LLM tools become more mature and prevalent, we will see even more subject matter areas where these tools will enhance the delivery of legal services by lawyers and legal professionals.

My tips when using AI in the legal profession are to start with small projects, work with AI providers who you can trust and learn from others in the profession who are already using AI technology to deliver legal services to their clients.

It’s important for us to have hobbies – especially as many of us in the legal and technology professions spend a great deal of time being laser-focused on our careers.

As a I get older (and more mature 😎), I’ve increasingly realized the importance of having a wide range of interests that are outside of the workplace and your family.

As an example, during the pandemic, I rediscovered collecting sports memorabilia.

When I was a kid, I collected a wide range of sports memorabilia like baseball cards and autographs. I used to pester my Dad and Mom to take me to baseball card shows in the NYC area where I grew up and I would spend my allowance and my small savings account on baseball cards at these shows.

Fast forward many years later, I attended my first National Sports Collectors Convention AKA “the National” in the Chicago area last weekend.

Sporting my Dave Parker 🐍 Baseball Card shirt that I bought at a Pittsburgh Pirates game in PNC Park last Summer (and the “Cobra” deserves to be inducted into the Baseball Hall of Fame), I was like a kid in a candy store checking out an incredible range of sports memorabilia under one roof at the Donald E. Stephens Convention Center near O’Hare Airport.

It was fun to pick up some items from the National for my collection like a few vintage Roberto Clemente cards and a classic Patrick Ewing New York Knicks jersey – that I already wore last night at a local outdoor festival.

It was also cool to view a highly graded PSA “9” of a 1952 Topps Baseball Card of the legendary Mickey Mantle that has an estimated value of $6M!

While a lot have things have changed in the sports memorabilia arena since I was a kid, the National was very well-attended and it was terrific to experience the positive energy in a very fun hobby.

So, my message to you is have hobbies that are of interest to you so that you can improve your wellness – and most importantly, have some fun!