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!

A few weeks ago, on the way back home from a great family vacation in Italy, I traveled on a long 10 hour flight from Rome to Chicago.

Since I have a hard time sleeping on planes, I watched several movies on the “friendly skies” of my United Arlines flight.

I was in for a big treat as I watched “Top Gun” and “Top Gun Maverick” back-to-back. I’m a big fanboy of Captain Pete Mitchell AKA “Maverick” and sometimes I consider myself the “Maverick” of in-house lawyers. 😉

One of my favorite scenes in Top Gun Maverick is a dialogue early in the movie between Rear Admiral Chaster “Hammer” Cain (played by Ed Harris) and Maverick (which of course is played by my man Tom Cruise) where Admiral Cain strongly expresses to Maverick that the human element should be eliminated from the Navy’s aviation arsenal and pilots should be replaced by drones. Here is that exchange between Admiral Cain and Maverick below:

Admiral Cain: “The end is inevitable, Maverick. Your kind is headed for extinction.”

Maverick: “Maybe so, sir. But not today.”

The scene is somewhat akin to the conversation happening today regarding the potential impact of AI on certain jobs and professions.

In my opinion, lawyers should use AI as a tool to serve their clients. Or, to use a more suitable Top Gun or Top Gun Maverick analogy, lawyers have great opportunities to use AI technologies as their “Wingman” when serving clients.

Here’s some important skillsets that I believe lawyers will need to continue to develop and grow as AI tools become more pervasive across the legal profession:

✅️ Communicating with Clarity & Persuasion

✅️ Earning Trust with Clients, Colleagues and Adversaries

✅️ Collaborating More Effectively with Others

✅️ Engaging in Smart Risk Taking

✅️ Having Emotional Intelligence

✅️ Relentless Prioritization of Work

✅️ Embracing Empathy

✅️ Demonstrating Persistence and Resilience

✅️ The Ability to Adapt with Speed and Agility

✅️ Being Comfortable with Using Leading Technologies like AI

What other skillsets would you add and what do you think will be AI’s impact on the legal industry moving forward?

While the new “Barbie” movie has become a box office phenomenon, I’m incredibly impressed with the longevity and ever-growing popularity of the world’s most famous doll.

Of course, Barbie is a fashion doll manufactured by the toy company Mattel, Barbie was launched in 1959 and it was created by American businesswoman Ruth Handler.

Incredibly, Barbie has been around for six decades – and it continues to be at the forefront of our culture.

In fact, Barbie is like fine wine which keeps getting better with age. I have difficulty identifying other similar iconic brands that have continued to be highly relevant for so long and have also flourished over time.

Regardless of your views about Barbie, there’s a lot that legal and business professionals can learn from Barbie and Mattel about how to sustain and grow your brand over a very long horizon.

So, here’s some lessons learned from Barbie:

🎀 Constantly Reinvent Yourself: Barbie is no longer just a doll with clothes and accessories. Barbie has adapted over time to include a wide range of branded goods such as books, apparel, cosmetics, video games and audiovisual content – and there are many other areas where we see Barbie.

🎀 Constantly Market Yourself: The Barbie “Marketing Machine” is currently on full display with the rollout of the new Barbie movie. “Barbiecore” and “Barbiemania” are unavoidable nowadays!

🎀 Be Relevant to Everyone: There seems to be a Barbie doll that almost every kid and adult can appreciate and identify with. For instance, there’s even a New York Yankees Barbie (picture above) that I adore as a lifelong Yankees and baseball fan.

🎀 Grow Your Total Addressable Market (TAM): Whether it’s my 6 year old niece or my 103 year old Grandma who both love Barbie, there’s no doubt that Barbie’s TAM of customers, partners and vendors have grown across generations and geographies across the globe.

🎀 Stay Strong & Resilient: Like lots of brands, Barbie has had her ups and downs over the years. She has been involved in lawsuits, parodies, tough competition, years of slow sales, etc…However, Barbie remains persistent and keeps driving forward with strength and resiliency.

🎀 Remain True to Yourself: While there’s no doubt that Barbie has transformed over a long period of time, at Barbie’s core she is very much the same doll from her early days – manufactured to approximately 1/6 scale and 11.5 inches tall.

What else can we learn from Barbie which is relevant in Corporate America?

Sharing this interesting article from this week’s The Economist about the power of being concise and redundant in our communications which I believe is instructive for in-house counsel.

Here’s my favorite quote from the article which is a great best practice for in-house lawyers when they communicate with clients: “The advice to keep it trim is still good counsel. Blaise Pascal, a French author of the 17th century, once apologised for a long letter by saying: “I have not had time to make it shorter.” Keeping things tight can be hard work for the writer, but it saves time for the reader, at least up to a point. Make your prose as lean as necessary to keep your reader reading—but not more.”

In my experience as a corporate counsel, I have learned that it’s super important to communicate in a succinct, clear and impactful fashion with my clients. Here’s a few things I do:

☑️ Keep your email communications to your clients no longer than the size of your laptop screen.

☑️ If you have created a 5 page memo for your clients, make it no more than a 2 pager.

☑️ If you are asked to deliver a presentation, deliver it it under 15 minutes. I know of few business clients who want to hear a lengthy presentation from a lawyer (I know that I don’t)😀.

If we communicate with too much complexity and legalese, we will simply lose the attention of our clients and they will tune us out.

However, when we do communicate with our clients, legal teammates and others, it is also important to overcommunicate and be redundant when needed to stress our key points – especially as we live in a digital first world where people are constantly multitasking and we are competing for the attention of our work colleagues.

When I have important points to stress to my clients and legal colleagues like “compliance is a non-negotiable” or “get the legal team involved early and often,” I may sound like a broken record. However, I’m also hoping that my repetition in communications in these key areas will be remembered, learned and embraced over time.

What are your best practices as an in-house counsel when you communicate with your clients?

Nowadays, there’s so many legal technology providers to choose from for legal departments and law firms. Trying to select the right legal technology provider for the needs of your organization is not an easy task.

March 2023 seems to be #LegalTech month for the legal industry with the American Bar Association (ABA) TechShow in Chicago and LegalWeek in New York City.

In recognition of these two important legal industry events, I recently wore my vintage 1980s era Chicago White Sox uniform (since the ABA TechShow was in the Windy City) and produced my #3Strikes video ⚾️ which lawyers can use as a “mini” checklist on these 3 top areas for lawyers to carefully consider as they evaluate legal technology solutions for their legal departments and law firms:

✅️ Earn Trust: Trust cannot be claimed. Instead, trust must be earned. Take the time to clearly understand what a technology solution is all about (and what it is not about). Make sure that a provider offers you suitable customer case studies and references. Gain clarity on how a provider properly secures your vitally important data. Bottom line, make sure that your technology provider is constantly earning your trust!

✅️ Drive Business Outcomes: How does a legal tech provider enable you to achieve real business outcomes? For instance, will a provider’s solution help you achieve cost savings? How does a provider’s solution enable you better serve your clients? Will a provider’s solution help you share information more freely and break down organizational silos?

✅️ Technology Ease of Use: Historically, lawyers have been slow at adopting technology. Lawyers will be more willing to use technology that is simple and easy to use. Lawyers will be less willing to use technology that is complex and difficult to use. People and organizations will only derive benefits from technology if it actually used and consumed.

Best of luck in evaluating and selecting a legal technology provider!

One of my favorite things to do in my spare time is to read books about athletes as they provide great lessons for our personal and professional lives.

I recently finished the book entitled “The Last Folk Hero: The Life and Myth of Bo Jackson” by Jeff Pearlman.

It’s an excellent book as it takes us through the life and times of the greatest two sport athlete who excelled at professional football and professional baseball. Of course, I was a fanboy of Bo Jackson back in the day as evidenced by his autographs from my sports memorabilia collection in the pictures below.

The book details Bo Jackson’s journey from Bessemer, Alabama to Auburn University to Minor League Baseball to Major League Baseball with the Kansas City Royals to the National Football League with the Los Angeles Raiders (currently the Las Vegas Raiders) to his devasting football injury to his comeback in Major League Baseball with the Chicago White Sox.

While Bo Jackson was an incredibly gifted and a once in a lifetime athlete who was also at the center of Nike’s highly successful “Bo Knows” marketing campaigns, I think his greatest triumph and lesson for us was his incredible resiliency.

Against all odds, Bo Jackson was able to overcome a speech impediment and was able to return to the baseball diamond after he sustained a debilitating injury which required a hip replacement.

IMO, Bo Jackson’s greatest gift to his legions of fans and the public wasn’t his iconic touchdown runs or his mammoth home runs or his world-class speed or his incredibly strong arm that threw out daring baserunners – all of which can still be watched nowadays on YouTube.

No, his greatest gift to us was to underscore the importance of #grit#perseverance and #resiliency. Thank you Bo Jackson for being a great role model! 

As many legal organizations are increasingly focused on appropriate resource allocation and relentless prioritization of work, it’s important for senior leaders in legal departments to thoughtfully delegate work.

Presidents Day was earlier this week and I think we would all agree that being a President of the United States is a highly challenging job!

Of course, a critical responsibility for any President is for he/she to effectively delegate important work to his/her team. Likewise, senior legal department or law firm leaders who have the privilege to manage people also need to effectively delegate work to their teammates.

Please check out my latest 3Strikes video as I provide these 3 tips when delegating work to members of your team:

👍Just Do It: As we look for opportunities to work smarter, demonstrate trust in your teammates by delegating work and opportunities to them.

✋️ Provide a Great “Hand-Off”: Set your teammates up for success when delegating work by providing them with important background information and coaching.

✈️ Offer “Air Cover”: We provide legal guidance on complex matters and our advice may be challenged by others. Always be sure to have your legal teammate’s “back” when you trust them to counsel your clients.

Effective delegation of legal tasks and activities enables your team to deliver higher impact legal services and provides opportunities for your teammates to grow!

I was saddened to learn about the passing of legendary baseball broadcaster and player Tim McCarver yesterday.

When I was a kid, I wrote a letter to McCarver asking for his autograph on my 1973 and 1976 baseball cards in the pictures above and below. McCarver generously obliged – which is an example of how he tirelessly served baseball fans as a player, leading broadcaster and game ambassador.

In memory of the great Tim McCarver, here’s some lessons for us to learn from him and which we can apply to the workplace:

⚾️ Reinvent Yourself: Early in his baseball career, McCarver helped lead his St. Louis Cardinals teams to two World Championships. As his career progressed, he transitioned from being a starting catcher to a back-up catcher. When his career ended, McCarver embarked on an outstanding broadcasting career which resulted in his induction into the Sports Broadcasting Hall of Fame. McCarver’s ability to embrace change throughout his career is exemplary for us in Corporate America.

⚾️ Relationships Matter: During his player career as a catcher, McCarver built deep relationships with two outstanding and highly influential baseball pitchers: Bob Gibson and Steve Carlton as he was their “personal” catcher. These close relationships with “Gibby” and “Lefty” certainly helped prolong McCarver’s career on the playing field. Whether you are on the baseball diamond or in Corporate America, relationships with the right people matter in your career.

⚾️ Transparency: As a broadcaster, McCarver was not shy in offering his open and honest opinions about a game to his audience. In fact, some baseball players refused to shake McCarver’s hand because they didn’t like him voicing his opinions. McCarver’s authenticity as a broadcaster is something that we need to see more from leaders in Corporate America.

⚾️ Providing Insights & Clarity: One of McCarver’s strengths as a broadcaster was his unique real baseball world insight that he constantly shared with his audience. He also delivered that insight with great clarity so that non-baseball fans could easily understand what was happening during a game. The ability for corporate leaders to drive clarity with their teams and to share thoughtful perspectives to help their teammates be successful is critical.

⚾️ Be a Storyteller: When you listened to McCarver during a game telling story after story after story, you felt that you were hanging out with your close uncle. Storytelling is an increasingly important skill for success in Corporate America and McCarver was a supreme storyteller.

⚾️ Excellence > Longevity: McCarver played baseball in four decades from 1959 to 1980. After his playing career he called a then-record 23 World Series and 20 All-Star games. He was an outstanding ambassador for our National Pastime for generations of baseball fans. McCarver exemplified excellence and constantly delivered high value to the fans – which is also a recipe for sustained success in Corporate America.

Rest in peace Tim McCarver.

The funny lawyer-centric cartoon in the picture above was recently posted to the “The New Yorker Cartoons” Instagram account.

This cartoon reminds me of lawyers who overengineer and overcomplicate #contracts for their clients.

Since establishing thoughtful contracts are fundamental to the success of most businesses, creating and negotiating meaningful contracts are a critical skill for many lawyers – especially #inhousecounsel.

Here are some of my best practices when forming contracts with third parties:

📃 Clear is Kind: Driving clarity in contractual wording is of utmost importance so that you and your contracting partner clearly understand your respective obligations. I try to draft contractual wording in a manner that would be easily understood by my 11-year old son.

📃 Use Umbrellas: Avoid having too many standalone contracts with its own complete set of terms and conditions. Instead, look for opportunities to combine arrangements under a master or “umbrella” set of common base contractual terms that applies across individual arrangements.

📃 Bigger is Not Better: Look for opportunities to shorten your contractual arrangements to include only the “must-have” contractual provisions. Embrace contract simplicity and don’t turn your contract into a legal treatise.

📃 Fairness: Develop standard contractual provisions that are mutual, balanced and fair. Avoid “one-sided” contracts that imposes most/all of the risk upon your contracting partner.

📃 Consistency: If your organization uses multiple and different contracts, be sure there is symmetry and consistency between the same contractual provisions that reside across those contracts.

📃 Benchmark & Differentiate: Study the publicly available standard contracts of your competitors to help ensure that your own base contracts are “market” or “industry-standard.” In addition, try to differentiate your organization by including contractual provisions that are more appealing than those offered by your competition.

📃 Contract Annotations & Fallbacks: Develop a bill of materials for your standard contracts to include an internal set of contract annotations to help your team explain/negotiate your contracts and to have alternative contract provisions at your ready when needed. Consider automating such tools in a #ChatGPT type of format for easy internal use within your organization.

📃 Obtain Feedback: Proactively obtain input from your contracting parties (and their legal counsel) about their contract formation experience with your organization. Use such feedback to improve and periodical update your standard contracts and how your organization negotiates with others.

📃 Earn Trust: Be sure to always act professionally and to earn the trust of your contracting partners. In my experience, the best contracts are the ones that we put into a drawer and never have to look at again. They are built upon the foundation of mutual trust and respect of the contracting partners.