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.

There’s no doubt that artificial intelligence (AI) is one of the hot topics that we have been talking about so far during the first month of 2023. In fact, perhaps 2023 will be the year of AI – especially as technology continues to rapidly advance and we discover more real-world use applications for AI that can help fuel a new wave of digital transformation for organizations.

This interesting article in The New York Times last month does a great job in framing the rise of #GenerativeAI that has been led by ChatGPT.

As #inhouselegal departments continue to optimize their resources and engage in relentless work prioritization, there are interesting opportunities for legal teams to deploy generative AI like #chatbots to serve their clients.

Chatbots may be used by clients of #corporatecounsel as a form of “self-service” to help address the multitude of repetitive and lower legal risk questions that are asked of #inhousecounsel.

Using such #AI resources as a digital legal concierge for clients can help free up time for in-house attorneys to perform higher-impact work for their organizations.

Here are some possible subject matter areas which could be “chatbot ready” for corporate counsel to use with their clients:

🤖 How to Engage with the Legal Department and Legal Department Primary Contacts

🤖 Standard Form Company Agreements

🤖 Company Contract Signing Authority & Appovers

🤖 Basics of Confidential Information Protection

🤖 Basics of Intellectual Property Protection

🤖 Company Internal Policies

🤖 Smart Social Media Usage

🤖 Basic Legal Considerations for Marketing/Advertising

🤖 Basic Legal Considerations for Developing Customer/Partner Proposals or Responding to a Customer’s/Partner’s Request for Proposal (RFP) or Request for Information (RFI)

I’m super excited to see how advancements in AI will help lawyers better serve their clients!

Relentless prioritization of work is increasingly an important skill for in-house counsel and business leaders.

Here’s my checklist of steps that corporate counsel can take to ruthlessly prioritize their work and be even more productive:

☑️ Alignment on Work > Maximum Impact: Gain clarity from your legal management team and senior business clients on specific work areas you should be focused on that drives high business and legal outcomes.

☑️ Analyze Your Work: Capture and document the various types of legal work you perform.

☑️ Classify Your Work: Group your legal work into two primary categories: (1) work that drives high business + high legal impact; and (2) lower impact work.

☑️ Focus on High Impact Work: Spend most of your time and energy on high impact work as that work provides the greatest value to your organization.

☑️ Spend Less Time on Lower Impact Work: Limit your time spent on less impactful work. When needed, redirect such work to paralegal/program manager resources, trusted third party legal providers who provide services at commercially reasonable fees, technology automation solutions or business clients who embrace self-help resources that you previously created. Also, consider simply “stop doing” low-risk aspects of that work.

☑️ Delegate More: If you have the privilege to lead a team, trust your teammates and delegate more work to them.

☑️ Embrace Better Time Management: Spend less time on conference/video calls so you can free up time to get more real work done. Consider convening calls that are shorter in length, only participate on calls where you provide value, learn or build key relationships, block your calendar for call-free times to focus on doing real work, record calls that can be viewed on-demand when needed, avoid calls where issues can be solved via emails/instant messages, etc….

☑️ Done is Better Than Perfect: Lawyers don’t need to be perfect in rendering legal counsel. Our time seeking perfection often puts us into the zone of diminishing marginal returns.

☑️ Embrace Change. Our business environment is very fluid. The high impact areas that you are working on now are probably different than those areas you worked on last year. Be sure to update and refresh the high impact areas that requires deep legal support so you can continue to deliver maximum legal value to your organization moving forward.

Best of luck on your journey to relentless prioritization!

Many experts are predicting that we will see growing business uncertainty during 2023 in the US and that perhaps a recession may even be on the horizon.

If that is the case, a challenging economic climate provides opportunities for in-house counsel to really “show-up” for their clients and to deliver higher-impact legal services. For instance, during this period of economic “headwinds,” our clients will need corporate counsel to help (1) unblock new revenue opportunities with customers/partners, (2) lower their costs of doing business; and (3) make sure they are still acting with integrity and compliance.

Back in 2017, I wrote an article for Bloomberg Law entitled “10 Things Lawyers Should Consider When Taking Risk” where I put together a methodology which I have used in my career to help my clients engage in smart risk-taking.

I believe these principles – which I call the 10 Ps of Smart Risk-Taking – are still applicable for in-house counsel and their clients. I’m sharing excerpts of that article below for lawyers to leverage to help their clients during these uncertain times:

While there’s no singular definition or way to engage in smart risk-taking, a good starting point involves embracing these two fundamental concepts: (1) never, ever assume any integrity risks; and (2) never put your customers, partners and employees at risk.

Since embracing compliance and respecting your customers, partners and employees should be straightforward foundational pillars to guide your clients in making risk-based decisions, let’s consider some specific smart risk-taking practices that you may want to consider employing when advising your clients. Over the years I’ve developed a methodology that I call the “10Ps” of smart risk-taking. While I originally created these “10Ps” to help advise my clients in taking smart risks during complex contract negotiations, I believe this framework can also be applied more broadly.

Let’s review these “10Ps” one by one:


Consider whether you are focusing on theoretical risk or on the actual and tangible effect in assuming a specific risk regarding the matter where your advice is sought. It is much easier to thoughtfully assess a potential risk if you break it down to understand its real, quantifiable and practical impact to your clients versus viewing it in an abstract fashion.


Simply put it is not a smart risk to undertake any obligation that your organization cannot perform and fulfill. Doing so may lead to confusion, unhappy customers and partners and potential disputes.


Be mindful of the future expectations and precedent that you may set by taking on more risk. When you decide to assume additional risk in a certain situation, make sure that you take a long-term view of that risk, as it may not be contained to just one isolated matter.


Depending on the level of risk that you are asked to assume, it is critical to first obtain any applicable approval from specific stakeholders(s) that may be required as part of your organization’s internal processes. Respecting and following through on an organization’s internal controls and procedures is an important element of smart risk-taking.


It is always instructive to understand what your organization has done in the past to address a specific risk. Any prior approval, denial, lessons learned or alternative solutions for such risk (and their associated analysis) will help shape your risk-taking determination.


Try to ascertain whether the key players in your industry – your competitors and other marketplace leaders – are also agreeing to the same types of additional risk that your organization may be considering. While it may be challenging to obtain such information since it may be confidential, any publicly available marketplace intelligence may be helpful in determining whether the additional risk that your organization is considering is indeed commercially reasonable and industry standard for your marketplace – and thus more easily rationalized as a smart risk or not.


As we all know in our social media driven environment, news and other information travels extremely fast. Actively consider how your smart risk-taking guidance may be perceived outside of your organization in the event it becomes public.


When analyzing and balancing risk your organization should stay true to its fundamental core values and principles. Such values and principles should always serve as your organization’s “north star” that guides its smart risk-taking decision making process.


Even though we live in a fast-paced and technology-driven world, please make sure that you are deliberate and patient regarding your smart risk-taking decision-making. Take the necessary time to gather the appropriate facts, slow down a bit so that you and your clients can think clearly, and do not be pressured into making a quick and less than ideal smart risk-taking decision.


Remember that your clients are busy professionals who probably do not have a legal background. Be sure to clearly communicate your smart risk-taking recommendations in a format that is succinct and easily understood by a regular person.

Helping your clients engage in smart risk-taking during these uncertain times provides all lawyers with a great opportunity to demonstrate their skills as trusted legal advisors.

During this time of increased business uncertainty, it’s important for legal departments to adopt a Moneyball approach in running their legal teams. In case you did not know, Moneyball is a terrific book written several years ago by Michael Lewis and it became a popular movie starring Brad Pitt.

Moneyball is essentially a philosophy for running a professional baseball organization that was originated by the Oakland A’s baseball team where the A’s embrace cost efficacy and data analytics as part of how they run their baseball organization. Over the years, the A’s have had very good baseball success with its Moneyball approach.

In my latest 3 Strikes video which I recently posted on LinkedIn, I wore my “vintage” Oakland A’s baseball jersey and outlined this Moneyball mindset for in-house legal departments based on these 3 key areas:

⚾️ Cost Optimization: Look for opportunities to gain greater value from your third-party expenditures and seek to reduce your costs where possible.

⚾️ Data, Data, Data: Really understand what types of work and activities that you and your teams perform every day for your clients. Group such activities into two areas: (1) high-impact work; and (2) low-impact work.

⚾️ Operational Excellence & Relentless Prioritization: Once you have the specific data regarding the types of work that you do, spend more time delivering high-value work to your clients and less time delivering low-value work to your clients. Be sure to ruthlessly prioritize your work based upon its importance to your clients and to avoid potential legal/compliance risk.

Best of luck with this Moneyball mindset!