Last week I had the privilege to serve as a panelist at a Northwestern Pritzker School of Law event entitled “Symposium 2020: AI, the New Law Firm Attorney: Artificial Intelligence Entering the Legal Profession.”

The event’s keynote speaker Seyfarth Shaw Chair Emeritus Stephen Poor and our panel explored the growing impact of Artificial Intelligence (AI) tools in the legal industry to help lawyers achieve more by getting out of the repetitive, routine and mundane tasks that lawyers have performed in the past so they can “practice at the top of their license” as Mr. Poor stated.

I love the phrase “practice at the top of their license” as all lawyers will need to do more of this – especially as we see the rise of tech intensity as technology plays a bigger role in our professional and personal lives and leading technology like AI is increasingly used by lawyers, law firms and other legal organizations to deliver legal services to their clients.

As AI tools seek to automate and perform certain tasks that have been traditionally performed by lawyers, I believe that the Emotional Intelligence or Emotional Quotient (EQ) skills that lawyers use everyday to deliver legal services to their clients will be more important than ever before as stronger EQ skills will help enable lawyers to truly “practice at the top of their license.” Since AI, algorithms, machines and technology do not embrace EQ, the proverbial “soft skills” that are often associated with EQ can help lawyers provide even more high-impact/high-value legal counsel to their clients and differentiate their legal services from others.

As we use AI and other technology tools to better serve our clients, here are some EQ-centric skills that all lawyers and law students should develop, hone and embrace as “21st Century Lawyers”:

Be An Active Listener: Many lawyers can probably learn to listen more and speak less. Take the time to sharpen your listening skills and avoid being distracted when listening to others so you can better understand your clients, your team and your opposing counsel.

Embrace Empathy: In order to better serve our clients we need to create more proximity to them, learn more about them and put ourselves in “their shoes” so that we can clearly understand their needs and interests in order to help solve their problems.  The same holds true for having greater empathy for the lawyers and allied professionals that we need to work with on a regular basis to deliver legal services to our clients. We can all learn from the empathetic leadership of social justice activist Bryan Stevenson on how to put “empathy into action.”

Strong Collaborator: The ability to partner well with others, share knowledge, build upon the work of others and make others better are critical skills for all lawyers. Having a team-first and collaboration-first temperament is vital.

Relationship Builder: Invest the time to earn the trust of both your clients and those that can enable you to best serve your clients. While terrific technology like LinkedIn exists to help develop those relationships, please remember that there is still no substitute for the in-person relationships and connections that we develop with people.

Advocate & Influence: Lawyers are “sellers” as we are constantly persuading and advocating on behalf of our clients.  In my role as a lawyer at Microsoft I find myself always “selling” and trying to influence nearly everyone that I work with – whether it be my management, my peers, my team, my clients and our great customers and partners.

Great Communicator: When I was growing up in the 1980s, Ronald Reagan served as our President and his reputation as a “great communicator” was instrumental to his being elected twice as President. As lawyers we also need to be “great communicators” who are skilled in the art of communicating in a clear, concise, impactful and easy to understand manner.

Excellent Judgment: In my opinion a lawyer’s “special sauce” is her/his judgment when advising their clients on matters. Such judgment and intuition is honed over a period of time based on the culmination of a lawyer’s experiences so she/he can enable their clients to engage in smart risk-taking.

Break Down Barriers: Lawyers who can skillfully navigate through blockers, have a bias for action to drive matters forward towards resolution and have a reputation for getting things done on behalf their clients will always be in high demand. As a wise person once told me, “being done is better than being perfect.”

Feedback Seeker + Implementer: Some have said that feedback is a “gift” – especially constructive feedback. One of the ways that we can improve and serve as more impactful legal advisors is to actively seek such feedback from our clients and others who we work with – and to take action to convert such feedback towards self-improvement.

Always Ethical: While technology advances and solutions like AI become more prevalent in the legal profession, lawyers will need to demonstrate greater leadership in upholding high standards for ethics and integrity. Embracing strong integrity and ethics are non-negotiables for all lawyers and are the foundational elements for earning trust.

Embrace Change: As technology continues to advance at a rapid pace, the only constant during our current era known as the Fourth Industrial Revolution is change. We need to be open to proactively adapting and evolving as legal advisors or else we run the risk of becoming extinct and irrelevant.

Lawyers should not fear AI or the so-called “robots.” Instead, let’s both embrace AI as a tool to serve our clients and “double-down” to improve our EQ and soft skills so we can deliver the high-impact legal services that all of our clients deserve.


Near the end of my first year of law school I unfortunately witnessed one of my classmates having what appeared to be a nervous breakdown during a class after a confrontation with a professor.  Although that incident occurred over twenty years ago, I remember it like it was yesterday and it was my first exposure to the significant challenges associated with wellness in the legal profession.

Last year the American Bar Association (ABA) issued its first ABA Profile of the Legal Profession report and it contained this quote in its “Lawyer Well-Being” chapter: “In September 2018, the American Bar Association launched a campaign to address the troubling rates of alcohol use, substance use and mental health issues among lawyers. Recent studies show that lawyers struggle with these problems at levels substantially higher than the general population and other highly educated professionals.” These unfortunate facts were also backed up by a wealth of supporting data that was referenced in the report.

Several years ago when my son was just a few months old we took our first flight with him to visit our family in New York for Thanksgiving – and please see a picture below of my son and I waiting for our flight at O’Hare Airport in Chicago. Right before takeoff the flight attendant specifically reminded my wife and I that in the unlikely event the cabin losses air pressure and the oxygen masks drop that we should be sure to put the oxygen masks on ourselves first before doing the same with our son. While of course I have heard this similar announcement countless times prior to takeoff on planes, listening to this advice as a new dad was a bit unnerving. However, I think this episode serves as a great lesson for all of us. After all, you can’t be any good to yourself, your family, your friends, your employer and your clients/customers unless you first take great care of yourself. 

Like all of you I have experienced challenges both in my personal life and during my legal career. Here are a compilation of my own wellness best practices that may be helpful to you both during your own wellness journey and as you promote stronger wellness practices as leaders for your legal organizations.

Mental Wellness

  • Embracing Mindfulness: Mindfulness and meditation are becoming hot topics in Corporate America as employers seek to provide employees with more tools to better manage stress in the workplace. One of my favorite mindfulness “gurus” is Dr. Michael Gervais – who serves as the sports pyschologist for the Seattle Seahawks professional football team and I have had the good fortune to participate in his mindfulness trainings a few years ago. Dr. Gervais often talks about the importance of embracing mindfulness so that we can do a better job at “being present” in life. While I will confess that I don’t fully use mindfulness techniques in my life, I do embrace what I call “mini mindfulness” as I use mindfulness practices such as deep breathing exercises with my eyes closed for a few minutes immediately before work situations that may cause stress for me – such as when I lead an important conferences call, prior to delivering presentations, etc…
  • Get Proper Sleep: A lot has been written about how our society is getting less sleep – which of course negatively impacts our productivity and wellness. Over the years I have struggled with getting a good night’s sleep and here’s a few of my lessons learned with smart sleep hygiene:
    • Be Device Free: Don’t check out any of your devices for a few hours prior to going to bed to avoid stimulating your mind and eyes.
    • Avoid Fluids Before Bed: In my view the less we need to wake up during the night to go to the bathroom, the better.
    • Be Careful with Sleep Medications: Nowadays there are plenty of over-the-counter and prescription sleep medications available to those who have difficulty sleeping. While of course you should consult with your doctor regarding such medications, please be careful of their potential negative side effects.
    • Take a Bath/Shower Before Bed: Anything you can do to calm yourself down and relax prior to bedtime is a good thing.
    • Avoid Intense Conversations Prior to Sleep: I also try to avoid any serious or challenging discussions with my family or others as I want to peacefully ease into my sleep.
    • Go To Bed Earlier Versus Later: I used to be a night owl but nowadays I have been going to bed earlier and waking up earlier.
  • Balance Your Digital and Real Worlds: As technology is playing a bigger role in all of our lives with something known as “tech intensity,” I feel like we live in two worlds nowadays – the so-called “real” world and the “digital” world – where I spend way too much time on my devices and on social media. In my view as technology advances, it’s becoming more important for us to spend more 1:1 and in-person time with each other and to make sure that we put the appropriate boundaries in using technology in our lives – and especially as it relates to investing in more high-quality personal interactions with family, friends and co-workers.
  • Delete Work Email from Phones: About two years ago I made the decision to delete my work email from my phone. Like many of us I spend way too much time on my phone and I could not resist the temptation to constantly check my work emails outside of core work hours. As a result, work and work emails would constantly be at the forefront of my mind and since I had difficulty resisting checking my work emails on my phone at nights and on the weekends, I simply deleted the Outlook app on my phone. While I no longer have work emails on my phone, I still continue to be very responsive to my team and clients in answering email via my outstanding Surface Laptop and my teammates and business clients also know they can always reach me on my proverbial “Bat Phone” via text or calling my cell phone as needed.

  • Take “Real” Vacations: Several years ago a very senior Microsoft lawyer reminded me that it is important to take “real” vacations since they are necessary to “vacate” your mind and come back to the workplace refreshed – and she was absolutely right. However, as we know, many of us in Corporate America still take “fake” vacations – including myself.  In this LinkedIn article from a few years ago I provided some best practices to help enable you to take a “real” vacation. While I have slipped in not taking some “real” vacations over the past few years due to the demands of my job, I’m starting to do a better job practicing what I preach and I also recognize that if my team sees me taking “fake” vacations and answering emails/taking conference calls during my vacations, they may feel compelled to do the same.
  • Know When to Say No: As lawyers and legal professionals, most of us are very busy and there seems to be a never ending amount of work to do. However, we also do not want to be overwhelmed with our work and jobs so that we can bring our best every day to the workplace and feel good. Leaders should create a safe environment with their teams to let them know that it’s OK for them to say they are at capacity with their workload so that work can be redistributed to other teammates as needed.
  • Avoid Negativity: As I have become older and more experienced I have learned to do a better job trying to stay away from negative thoughts and/or negative people as they are roadblocks to moving forward and being hopeful. While I also tend to be a realist, filling my brain with more positivity and filtering out the negative “noise” out there continues to serve me well.
  • Listen to Music: One of my favorite pastimes nowadays is listening to music. I listen to music whenever I’m “in motion” in my car, jogging, walking, in an Uber, on the train, on a plane, in Starbucks, etc…While my playlist is largely filled with my favorite songs that I grew up to during the 1970s and 1980s – and my family, my friends, my co-workers and the public would probably make fun of my playlist – I find that listening to music is a great escape from the everyday stress in my life. One of my favorite bands is ABBA and there’s nothing like listening to “Dancing Queen,” Voulez Vous” or “Lay All Your Love On Me” to put me in a great mood – regardless of how my day is going.

  • Promote Remote Work: In my opinion, the current and future of the workplace is remote work powered by leading cloud computing technology tools like Microsoft Office 365.  While some legal organizations may frown on a remote work environment, I do believe that such arrangements helps to improve work life balance/integration for lawyers and legal professionals – including their levels of wellness.
  • Keep Perspective: Many years ago when I was frustrated at work my dad reminded me to keep my job in perspective. He told me that as a “deal lawyer” my employer pays me a lot of money for basically putting words on a piece of paper. The point being was that I needed to stay well-grounded in reality and while of course my job is very important to me – my vocation does not involve saving lives like a fireman or a doctor. While our jobs are important, as lawyers we can probably do a better job at keeping our jobs in perspective.
  • Take it Easy: As a lifelong Eagles fan – NOT the Philadelphia Eagles football team but the music group Eagles – one of my favorite songs is “Take It Easy.” Those three words are a simple reminder for all of to relax more, be less stressed out and to not take ourselves too seriously.

Physical Wellness: While you need to take great care of your mind, you also need to take great care of your body. Here are my learnings:

  • Eating Right: It’s taken me a long time to realize that physically you pretty much are what you eat. For years I have always had great discipline in working out, going to the gym, etc….but I really never had the same discipline with my diet. Being smart about what I eat and managing my weight continues to be a daily struggle for me. Here are some of the eating habits that I try to embrace:
    • Drink Lots of Water: When you are hungry try to fill yourself up with water.
    • No Sodas: I used to be the king of drinking diet sodas but nowadays I avoid them.
    • Avoid Alcohol: Basically I don’t need the extra calories of alcohol or to waste any money on it.
    • No Late Night Eating: For years I would wake up in the middle of the night, go to the kitchen, eat another meal and then go back to bed. Nowadays I’ve been embracing a modified version of intermittent fasting where I stop eating by 8pm at night and don’t eat anything again until at least 8am the following day. Fasting for 12 hours is something that I can do while a typical intermittent fasting practice of 16 hours is a big stretch for me.
    • Eat More When Your Burn More: On the days that I go jogging and burn more calories I’m OK with increasing my calorie intake and “cheating” on foods that I really want to eat. On the days I don’t go running I stay away from foods like breads, pasta, anything fried and sugar.
    • Use Your Calories Wisely: Don’t waste the limited number of calories that should eat per day on something that you don’t like.
  • Jogging: Over the last several years I have taken up jogging as a way to try to stay fit and to do a better job with managing my weight. When I moved to Chicago in 1996 I was an avid jogger, then stopped for a while and I started up again in 2012 after I lost my aunt to breast cancer. At that time I was also a new dad and I realized that I needed to be in better physical shape so that I could be around for as long as possible for my family. My regimen is that I go jogging three days a week – on Wednesday (5-6 miles), Friday (5-6 miles) and Sunday (8-9 miles).  While I run like a clydesdale, I try to run faster during my Friday runs. The beauty about jogging is that you can do it virtually anywhere and I also make sure to go jogging when traveling for work, on vacation, etc….I also find jogging to put my mind at ease and it enables me to think very clearly.

  • Walking: While jogging is not for everyone and some folks may not be able to physically jog, a great alternative is to take long walks. On the days I don’t go jogging I still try to get outside and walk as much as I can.
  • Do Some Aerobic Activity: Even if jogging/walking does not appeal to you there are so many other physical activity options that you can choose from to improve your physical well-being. Just try something.
  • Do Some Resistance Training: When I was younger I used to go to the gym a lot of and did a fair amount of resistance training with free weights. While I don’t belong to the gym anymore, I try to get my main form of resistance training via doing elevated pushups everyday – which you can pretty much do anywhere and at anytime.
  • Just Keep Moving: My Grandma will be turning 100 years old in May and she seems like she has not changed that much since I was a young boy. One of her keys to such longevity is that she is always moving and she seems to be in constant motion. She inspires be to not be a “couch potato.”
  • The Earlier the Better: Whatever exercise workout/routine you decide to pursue try to get it done earlier in the day versus later in the day – even if it means waking up earlier in the day.  We all lead busy lives and putting off any physical activity until later in the day increases the likelihood that you’ll find excuses not to do it. The runs that I go on in the early mornings always makes the rest of my day much better.
  • Be Smart: Also be careful not to over-extend yourself during any physical activity and be sure to hydrate and take breaks as needed. For the past several years people have suggested that I should train and run for a marathon. While that sounds great, I’m not interested in subjecting my body to the intense training associated with a marathon and I’ve been fortunate to be largely injury-free as an adult.
  • Periodic Medical Check-ups: Be sure to have an annual medical physical with your primary care physician and complete required tests/procedures that are recommended by your physician due to your age, family history or otherwise. A sixty-something year old friend of mine – who happens to be a leading lawyer – never had a colonoscopy performed and his physician recently discovered a cancerous growth in his colon. While it was successfully removed and his medical prognosis is very positive, he should have had a colonoscopy performed when he was 50 years old.
  • If You See Something, Say Something and See your Doctor. No one else knows our bodies as well as we do. If you see/feel something wrong with your body or any unusual pain be sure to see your physician immediately – and don’t let work, work travel, meetings, conference calls, etc….get in the way of scheduling and showing up at those medical appointments. Also if a spouse, partner, family member or friend shares something about their body that does not seem right, please insist that she/he see their physician immediately.

Achieving mental and physical wellness is a lifelong journey. Of course there’s no one roadmap and there’s plenty of roadblocks along the way. Don’t be discouraged by obstacles, keep driving forward and don’t be shy in seeking help when needed.

One of my favorite topics is how lawyers and the legal profession can embrace leading technology to achieve more and better serve their clients. As we being a new decade, technology is becoming a bigger part in all of our lives, we are seeing a growth in tech intensity and there are great opportunities for lawyers put technology to work to help their clients.

Over the past few months I have delivered presentations on this important topic at the #MakeLawBetter Conference at Chicago-Kent College of Law and at the ALAS Firms Administrators Conference in Chicago. I have also had the opportunity to speak to various Microsoft customers regarding opportunities for their legal teams to accelerate their respective digital transformations.  In this post, I share my thoughts regarding various steps that all legal organizations can take to embrace tech intensity so they can be more productive, more collaborative and better serve their clients.

Lawyers Must Be Innovators 

I have begun my talks by sharing an important quote from Microsoft CEO Satya Nadella. When Satya become CEO in February 2014, the very first thing he did was to send this email to all Microsoft employees introducing himself and providing his vision for Microsoft on a go-forward basis. That email contained this very insightful quote: “Our industry does not respect tradition — it only respects innovation.” While of course Satya was referring to the information technology industry where Microsoft has been a leader for over 40 years, I think his quote is equally applicable to our legal profession. In order to best serve our clients, lawyers need to constantly innovate. If not, lawyers will be “disrupted” and our clients will go elsewhere for legal support – or if you are an in-house counsel they may not reach out to you for your advice at all (which is never good).  In my opinion, technology is a lawyer’s best friend and it can help us accelerate our innovation on behalf of our clients so that we can deliver high-impact and high-value legal services.


Modern Legal Tech Intensity 

There are plenty of areas for legal organizations to leverage technology to better serve their clients and help solve problems.  However, I try to keep it simple with these four primary areas to modernize the delivery of legal services:

  • Empower Legal Professionals: How can technology be leveraged to help enable legal professionals to engage in greater collaboration and deliver their legal services faster and in a more comprehensive fashion?
  • Engage Clients: How can you use technology to better understand your clients, be more empathetic to them and be more responsive to them?
  • Enhance Risk Management: In an increasingly regulated environment where earning trust is always paramount, how can legal organizations use technology to enable compliance, be more cybersecure and engage in smart risk-taking?
  • Optimize Operations: How can legal organizations use technology to drive more efficiency, productivity, enhanced decision-making and “stop-doing” certain low impact and low value work?

Culture is King 

A foundational element in embracing tech intensity is to help ensure that your legal organization has the right culture in place to fully use and consume technology. The management “guru” Peter Drucker has made the following quote famous in the corporate arena: “Culture eats strategy for breakfast.”

While leading technology has great potential to help your legal organization, if your legal organization has not established the appropriate culture to take advantage of such technology, the return on your technology investments will be limited. My own employer, Microsoft, has been on a journey in transforming its culture over the last several years. While there is no magic formula per se in developing the right type of culture to help ignite greater digital transformation, here are some key areas to consider as your evolve the culture of your own legal organization:

  • Embrace Change: In our fast-paced world, the only constant is change and as we all know being open to change and actually changing – both in our professional and personal lives – are very difficult things to do. Our customers, partners and competitors are all adapting and legal organizations also need to be able to change quickly to better serve their clients. Such change also involves being willing to evolve to use new and different types of technologies to better serve your clients. Here is one of my favorite quotes from Winston Churchill:

  • Promote the Growth Mindset: Ideally your organization will strive to create a culture where your employees are constantly learning and growing.  Stanford professor Carol Dweck wrote a leading book several years ago called Mindset where she stresses the importance of embracing a growth mindset mentality versus a fixed mindset mentality. Having this growth mindset mentality positions your legal organization to digitally transform faster and better serve your clients.
  • Feedback is Fabulous: Be open to providing practical and actionable feedback to your team and actively seeking feedback from your teammates and your clients/customers. Of course, when you obtain such feedback be sure to do something with it in order to improve yourself and your legal organization.
  • Be Bold: As many of us know, the legal profession is known to be a highly conservative one. However, legal organizations should be unafraid in taking smart risks when it comes to managing its teams, delivering legal services, making decisions about using appropriate technology and driving its organizations in a positive manner so they can better serve their clients. Think about appropriate and smart risk management to propel your legal organization forward versus having zero appetite for risk. Here are my 10 Ps of Smart Risk-Taking.

  • Diversity & Inclusion (D&I): One of my favorite quotes about D&I is from D&I leader Verna Myers where she says “Diversity is being invited to the party; inclusion is being asked to dance.” Having a culture that embraces D&I and the different and important perspectives that more diverse employees provide also can help legal organizations be ready and more prepared for digital transformation.
  • Set the Tone at the Top: Of course, senior leaders in a legal organization need to set the right tone about their cultures both by their words – but much more importantly – by their actions.

Leading Digital Solutions – The Big 3

While there are lots of great technologies in the marketplace nowadays, I believe that legal organizations should focus their digital transformation efforts on these “Big 3” of the digital world: Cloud Computing, Data and Artificial Intelligence.

Cloud Computing

I remember negotiating my very first cloud computing contract with a major financial services customer at the end of the last decade during June 2009.  Since that time the cloud computing marketplace had grown exponentially, it has become highly mature, robust and reliable and the cloud has provided the foundation for the generation of the massive amounts of data that we have access to nowadays and the growing prevalence of artificial intelligence.

While the cloud can benefit legal organizations in a number of different ways, in my opinion some of the key benefits of deploying cloud solutions involve the “3 Cs” of cost, cybersecurity and collaboration.

  • Cost: By using cloud solutions you can save money and take costs out of your legal operations. By not having tangible technology like servers “on-premises” in your organization, you can lower your costs since you no longer need to acquire/lease such technology,  you don’t need the space to store and run such technology, you don’t need to spend money powering such technology and you don’t need to have professionals responsible for maintaining/fixing such technology. Instead, you can in essence outsource your computing needs by partnering with a third party hyperscale and reliable cloud provider that can deliver cloud solutions to you on a remote basis via their data centers and the internet. In addition, leveraging high-powered cloud workplace collaboration tools can enable members of your legal organization to work on a remote-basis and your organization can reduce those costs associated with having a traditional physical office environment. For instance, large law firms may have an opportunity to reduce their operating costs by downsizing the footprint of their offices and enabling their workforce to serve their clients on a remote basis powered by cloud solutions – and such remote work may also help improve the quality of work life for their lawyers and legal professionals.


  • Cybersecurity: As we know many legal organizations have access to highly sensitive data regarding their clients – and as we also know the cybercriminals are growing more sophisticated, bolder and are increasingly using technology as a weapon to target and obtain access to your data.  Instead of protecting that highly sensitive data on your own, consider getting some help and storing and protecting such data in the state-of-the-art and highly secure data centers of hyperscale cloud providers who are in the business of using leading technical and operational measures to protect data and comply with a wide range of important data security standards and laws. For example, as a major cloud services provider Microsoft invests over $1 Billion annually on cybersecurity and offers a wide range of data privacy, security and compliance features that are part of its cloud solutions.  It is virtually impossible for any legal organization to replicate the breadth and depth of security and compliance measures taken by hyperscale cloud providers in an increasingly regulated environment and by improving your legal organization’s cybersecurity position you can continue to earn the trust of your valuable clients.

  • Collaboration: A constant challenge for many legal organizations is the ability to constantly collaborate and share knowledge in a manner that allows them to deliver more high-impact legal services to their clients. As lawyers and legal professionals it is very easy for us to remain “stuck” in our proverbial silos. Using leading and easy-to-use cloud-based workplace collaboration tools enables lawyers and legal professionals to break down those silos and collaborate in a more meangingful fashion. As an example, the Microsoft legal department uses the powerful and highly secure persistent chat tools that are part of Microsoft Teams to ignite richer collaboration with our legal teammates and business clients.  In an article entitled “Digitally Transform with Microsoft Teams,” I outlined various use cases for Microsoft Teams in legal organizations.

Data, Data, and More Data

I believe that data is a highly underutilized asset by legal organizations.  Being a huge fan of our country’s national pastime of Major League Baseball (MLB), I continue to be amazed at how MLB teams extensively use data and analytics to evaluate baseball talent and to make important decisions. As we begin the new decade, I believe that we will increasingly see legal organizations adopt this so-called Moneyball approach to data-driven decision-making and here are a few ways that your legal organizations can use data to better serve your clients:

  • Data in Contracts: Chances are your legal organizations are involved in shaping and negotiating a wide range of agreements for your clients. If so, consider mining those contracts and its associated contractual provisions to spot trends, common issues, “fallback” provisions, etc…that can make you and your clients smarter when establishing such contractual arrangements with third parties.
  • Data on Social Media: During this decade we have seen the continued growth and use of social media.  There are terrific opportunities to learn from the vast amounts of data that can be found on LinkedIn, Twitter and Facebook. I use the data on social media as a way to learn more about Microsoft, my clients, our customers, our partners, our competitors, and recent developments at the intersection of law, business and technology so that I can deliver more high-impact legal services to my clients.
  • Organizational Analytics: One of my favorite Microsoft Office 365 tools is Workplace Analytics where I have access to data on my daily ways of working to help me be more productive in the workplace and to help balance the integration of my work and personal lives. By having richer insight into my workplace habits like how much focus, collaboration and quiet times that are part of my daily schedule I look for opportunities to work smarter and gain more productivity.
  • Data and D&I: As many of us know advancing D&I continues to be a challenge in the legal profession. However, legal organizations can improve D&I so they can better serve their clients by using data to closely measure their legal organization’s D&I progress, being transparent about such D&I metrics reporting to identify the opportunities and challenges for improvement and then taking actual action to move their D&I focus forward. After all, as Peter Drucker also once said, “What’s measured improves.”
  • Data and Outside Counsel: The relationship between in-house legal teams and their outside counsel law firms are extremely important to their mutual success. In-house legal departments need greater value from their law firm providers while law firms are seeking greater business opportunities from their in-house legal clients in an increasingly competitive legal services marketplace. In-house legal teams and law firms can analyze the data associated with both the scope of services rendered by law firm providers and the time spent in delivering such services to spot trends, identify potential efficiencies and to help create alternative fee arrangements that can be mutually beneficial to in-house counsel and their law firm providers.
  • Make Your Data “Pop”: As your legal organization uses data to drive better decision-making, please consider how that data is presented to your senior leaders and clients for maximum impact. By using tools such as Power BI, your legal organization can tell its own data story by creating stunning reports with interactive data visualizations.

Finally, while it is always great to have access to interesting data and analytics, they mean absolutely nothing unless your legal organization puts such data and analytics to work to drive improved business and legal outcomes for your organizations and your clients.

Artificial Intelligence 

Although Artificial Intelligence (AI) is still in its infancy, AI solutions – and its impact upon society – are increasingly capturing the attention of the legal profession. In my opinion as AI tools continue to advance and become more sophisticated, there will be more opportunities for legal organizations to use AI as a tool to deliver legal services to clients. As an in-house lawyer I am excited about the prospects of using AI solutions to handle the routine, repetitive and mundane tasks that lawyers have traditionally performed and engage in more “stop doing” and “de-lawyering” so that it can free up time for my team and I to perform more higher value work for my business clients.

There are a variety of use applications for AI solutions in the legal industry and the recent 2019 Legal Tech Buyer’s Guide and graphic below by LawGeex does an excellent job depicting those range of areas  that may be ripe for AI in the provision of legal services.

In addition to the AI use applications above, there are also opportunities for legal organizations to use more “entry-level” AI solutions in the form of chatbots and/or digital assistants that may be able to perform various operational related talks for lawyers (e.g., scheduling meetings, timekeeping, booking travel) or interacting with clients to help answer certain common questions.

As lawyers increasingly use AI solutions I believe it is important to recognize that these solutions should be viewed as a tool by lawyers to supplement their legal services and not as a wholesale replacement for lawyers. While AI solutions can be highly valuable for lawyers, AI solutions also have several limitations and in my view should not be viewed as a substitute for a lawyer’s judgment, intuition, emotional intelligence and other key customer obsession-type skills used by lawyers in providing legal services. In addition, lawyers also need to understand the important intersection between AI and ethics and my company has taken a leadership role regarding responsible AI.

Tech Intensity Tips 

Finally, here is a compilation of “Top Ten” best practices to keep in mind as your legal organization embraces greater tech intensity.

  • Solve Problems: As your legal organization deploys technology, always remain well-grounded on the specific issues/problems that you are seeking to resolve for your legal organization and your clients.
  • Start Small Projects: Seek to develop some “quick wins” when using technology.
  • Perfection is Not Required: Lawyers have a tendency to seek perfection, but remember that “good enough” is often sufficient when lawyers leverage technology to better serve their clients.
  • Use What You Have: Always remember to first fully utilize and exhaust your existing investments in technologies to help realize an appropriate return on your investments – and especially since acquiring new technologies costs time and money.
  • Get Help: Legal organizations should not be shy in seeking the help of technology professionals as needed as they “skill-up” in the ever-changing world of technology. Also keep in mind that in the US currently 38 states now require lawyers to embrace the duty of technology competence.
  • Lawyers Define Requirements: Although it will make sense for legal organizations to seek the guidance of technology professionals as applicable, lawyers should still define the specific needs for technology solutions as they know their clients and legal organizations the best.
  • Evaluate and Select Technology Vendors You Trust: Be sure to conduct the necessary due diligence to select technology providers that you can truly trust since they will have access to highly sensitive data regarding your legal organization and client.
  • Adopt User Friendly Technology: If technology is not relatively easy to use legal organizations will face challenges in getting their lawyers to embrace it.
  • Establish Appropriate Training:  When using new technology be sure to set your team up for success by initially delivering practical and hands-on training and designating lawyers on your team to be technology-specific “champs” so they can serve as a constant resource for their teammates.
  • User Adoption is Key – Including Leaders: Even if you acquire the greatest technology in the world, it will have little to no positive impact unless you actually use it – and team leaders should set the right “tone at the top” through their own usage of technology.

As we begin a new decade it is an opportune time to carefully consider how your legal organization can drive more tech intensity to better serve your clients. Best of luck in your journey!



I have always been a big believer that embracing diversity and inclusion can enhance both our professional and personal lives. Throughout my life I have been positively influenced by important people who come from diverse backgrounds and experiences. While these individuals have helped me become a better lawyer and leader, they have also made me a better person. Here are some of their stories and how they have impacted me.

My Father

My father grew up in the South Bronx after my grandparents migrated to New York City from Puerto Rico. Being Hispanic, my father was subject to discrimination because of his ethnicity – especially at school where he was treated differently by his classmates, teachers and administrators. He then served in the US Army during the height of the Vietnam War. Although he rarely talked about his service in Vietnam, my father was a highly decorated veteran.

Like many Vietnam veterans who fought for their country during a divisive war, my father also faced discrimination when he returned home. When my father passed away last year I delivered his eulogy and celebrated his larger than life personality as he was highly confident, bold and willing to agitate when needed – which helped him survive both the South Bronx and Vietnam and overcome discrimination. I have tried to model these attributes as part of my team’s ways of working to deliver trusted advisor legal support to our business clients who are helping our customers digitally transform. We need to exude self-confidence when serving our business clients, be fearless and creative in taking smart risks as we shape and close important customer deals, and be willing to break down barriers and navigate through complexity to get things done.

My First Legal Job

Like most law students I needed extra money during law school. So, at the beginning of my second year at Columbia Law School I applied for a part-time job opportunity at its Office of Career Services to assist an in-house employment lawyer at IBM named Michael Faillace – who happened to be blind. After interviewing with Michael at IBM’s headquarters in Armonk, New York he offered me the job.

Serving as a reader and assistant to Michael during law school was an incredible experience. In an era where technology was not at the point it is today to help drive accessibility, Michael was highly resourceful and adaptable. Even though he could not see, Michael’s disability did not get in the way of him being a great lawyer. I spent a lot of time with Michael during my second year of law school and got to know him well. To better serve him I needed to experience the world through his perspective and have a rich appreciation for his unique challenges. Looking back, Michael supplemented my law school education by not only inspiring me to work in the legal department for a technology company, but he taught me the importance of being empathetic. Fast forward 20+ years later Michael continues to be at the forefront of my mind as my team and I work hard to embrace empathy to deeply understand our customers, our partners, our business clients and my Microsoft legal team colleagues so we can better serve them.

My Wife

My wife Simona was born in Romania and after graduating college she made the difficult decision to leave her family and immigrate to the United States due to a lack of job opportunities. When she arrived in the United States, she did not know anyone, had only $100 in her possession, had a temporary job and was not fluent in English. Despite these challenges – and the discrimination that she and other immigrants typically face – she persevered. Over a short period of time Simona progressed from being a hotel housekeeper to a salesperson at a high-end retailer to a store manager at that retailer to a district manager at that retailer to her current role as a leading realtor in Chicago. During her swearing-in ceremony as a new US citizen in 2011, she told me that she now hoped she would no longer face discrimination.

My wife has taught me a lot about resilience, strength and the ability to navigate through change. We all have faced – and will continue to face – challenges in our lives. However, what is critically important is our ability to have grit, to remain positive, to learn from our experiences with a growth mindset and to move forward. Witnessing how Simona successfully navigated through changes and obstacles in her life has inspired me to do the same – whether it be having 3 different jobs in the Microsoft legal team over the past 4 years to coping with the loss of my father last year to having to build a trusted advisor relationship with my new Microsoft Corporate Vice President business client this fiscal year. As I often remind my team, “the only constant is change” and we need to be ready, willing and able to embrace change rather than fear it.

My Teammates

Since July 2018 I have had the privilege to lead a team of 14 outstanding lawyers and legal professionals and we provide a wide range of legal support to Microsoft’s Enterprise Commercial and Small, Medium and Corporate sales teams across the US.  Our team’s rich diversity is one of our greatest strengths and I have learned – and continue to learn – so much from my teammates. One of the most important leadership lessons they have taught me is the importance of earning their trust so we can be more inclusive and better serve our business clients. I have learned that being authentic, checking in with them on a regular basis, consistently sharing important business information from senior business clients, providing them with “air cover”, and being highly transparent goes a long way in building trust. This is one my favorite quotes from Microsoft CEO Satya Nadella: “Trust cannot be claimed. It must be earned.” While this quote of course applies to our customers and partners, in my opinion it is equally applicable to our relationship with our teams.

As lawyers many of us work too hard, have too much stress and don’t focus enough on our wellness. One way to invest in our wellness is to take “real” vacations versus “fake” vacations so that we have time to unplug from work, give our brains an opportunity to recharge and spend quality time with family and friends.

My family and I just returned from a terrific two week vacation in the beautiful Scandinavian cities of Copenhagen, Denmark and Stockholm, Sweden. Although I typically write about the intersection of technology, business and the law in this blog, I am taking a detour to write a trip report about our “holiday” in these incredible Northern European cities. Here’s some thoughts on Copenhagen and Stockholm:


Bicycles, Bicycles, Bicycles

Suffice to say that I felt I was at the Tour de France in these two cities as I have never seen so many bicycles in my life. In fact, I could not get the Queen song Bicycle Race out of my head. People were riding bicycles everywhere and incredibly these cities are so well designed to accommodate cars, bicycles and pedestrians (and increasingly scooters) with wide and appropriate lanes for a seamless and orderly flow of traffic – which is a bit different between the interplay of motorists and bicyclists in my city of Chicago. Perhaps one of the reasons why many people in these cities seem to be in such great physical shape is because so many are riding their bicycles to get around.


These cities are also starting to see the California influence of electric-powered scooters – and there seemed to be more scooters in Stockholm than Copenhagen. It will be interesting to see how the scooters and bikes get along in the near future – perhaps they will have a relationship similar to skiers and snowboarders? In any event, I was not bold enough to ride a scooter as I was afraid I would fall and break something.

Great Mass Transit

Each of these cities had very impressive and very clean transit systems to get around town and outside the city. While we flew from Copenhagen to Stockholm, in hindsight we probably could have just taken the fast train – especially since our hotels were close to their respective central stations. I wish the United States had transit and train systems that are on par with most of Europe.

Kid Friendly

These cities are also very family friendly and my seven year old son had a great time. Copenhagen and Stockholm are well-known for their amusement parks – which reminded me of the “vintage” Playland Park in Rye, New York that I used to go to as a kid growing up in the NYC area. The amusement park in Copenhagen is named Tivoli Gardens and we went there three times with my son – which was way too much for me – but not for my son. There was even a Tom Jones concert the final time we attended – which was a bit bizarre as he was a big deal when my parents were young. The name of the amusement park in Stockholm is Grona Lund and fortunately we attended that park only once. In my opinion Tivoli Gardens was better than Grona Lund as it was a much larger venue and much more aesthetically appealing. Going on the rollercoaster rides with my son at these parks probably took a few months off of my life.


During a rainy day in Copenhagen we also took our son to an incredible aquarium located on the outskirts of Copenhagen (via the train) called Den Bla Planet and the National Museum of Denmark has a terrific children’s museum. Also of course the birthplace of Lego is in Denmark and if you have small kids no visit to Copenhagen is complete without a visit to the Lego store in Copenhagen – where they even have some fake facial recognition.

There are also several kid friendly things to do in Stockholm. Some of our favorite activities involved going to Skansen – the first open-air museum and zoo in Sweden and the Vasa Museum – home of a well-preserved 17th Century ship.

Long Days

An insightful person once observed that the “days are long and the years are short.” This is especially true in Copenhagen and Stockholm during the summer as it did not get dark until 10pm or so while we were there. The beauty of this is that you can sleep in, rest up and still have plenty of time to explore.

Crisp Weather

One of the reasons we traveled to these Nordic cities during the Summer was to escape the heat and humidity of the Windy City. I’m a huge fan of early Fall/late Spring weather so the summer climates in these cities – including their fresh air – were perfect for me.

Day Trips

Each of these cities have nice day trips which provides an escape from their respective urban areas. In Copenhagen we took the train to a very pleasant town called Roskilde and felt like we went back in time to the Vikings era. In Stockholm we took a boat for a great day trip to Fjäderholmarna – Stockholm’s closest archipelago island.


Jogging Friendly 

I try to go for a 5+ mile run three times a week – including when I’m on a vacation/travel for work. I continued my jogging regimen while in Copenhagen and Stockholm, these cities are very running friendly and I found some running routes online. My favorite route in Copenhagen was near our hotel and around The Lakes (which was almost 4 miles in length around the lakes) and my favorite route in Stockholm was around the island of Kungsholmen – which is home to their City Hall and the venue of the annual Nobel prize banquet.

Interlocking NY Yankees Logos Everywhere

As some of you may know I’m an avid New York Yankees baseball fan so it was pure joy to see so many people wearing caps or having backpacks with the traditional interlocking NY New York Yankees logo. While I’m not sure if the folks wearing those hats or backpacks know much about the storied history of the greatest sports franchise on earth (and the Yankees even played a series in London against the Boston Red Sox while we were there and swept them), in my opinion the extensive footprint of these caps and backpacks throughout Copenhagen and Stockholm underscores the range, depth and power of the vaunted New York Yankees brand. As an aside, I saw exactly just three lost souls wearing Red Sox hats while I was there.

Copenhagen versus Stockholm: My Verdict

Both cities were absolutely terrific, I highly recommend visiting them and I think it’s hard to say that one is technically “better” than the other. However unlike “neutral” Sweden, I will pick a side and choose Stockholm to visit again over Copenhagen largely because I found Stockholm to be a unique combination of a city and a country environment that is spread out along an archipelago. Plus Sweden is the home of ABBA – one of my favorite groups of all time – and they have a great ABBA Museum in Stockholm.

Two months ago I had the opportunity to speak about Artificial Intelligence (AI) at the 68th Annual Meeting of the Seventh Circuit Bar Association and the Judicial Conference of the Seventh Circuit in Milwaukee at the historic Pfister Hotel and at the Judicial Conference of the Fifth Circuit in New Orleans.  Both myself and James Dempsey – the Executive Director of the Berkeley Center for Law & Technology – were invited to speak and we did a similar presentation last year at the Sixth Circuit Judicial Conference in Nashville.

In my experience, the audiences for these events are typically federal judges, federal magistrates, their staffs and leading lawyers from their local areas.  They all have different degrees of sophistication about technology and how it can be used to better serve the public and their clients. As technology continues to change our lives, the Federal Judicial Center seems very focused on improving the technical competence of the federal judiciary.

As we were assembling at the speakers table in the front of the room for our presentation on AI at the Seventh Circuit Judicial Conference, I noticed a very familiar-looking man heading to the front row to be seated. It was new US Supreme Court Justice Brett Kavanaugh as Justice Kavanaugh serves as the Circuit Justice to the Seventh Circuit and he attended the conference.

Shortly afterwards, the President of the Seventh Circuit Bar Association introduced James and I as speakers and also specifically thanked Justice Kavanaugh for attending this session. I was the first speaker so I took a deep breath and approached the lecturn knowing that as a “paper pushing” corporate lawyer I would have may proverbial “day in court” with a sitting US Supreme Court Justice to deliver a presentation on a leading technology that has the potential to reshape the entire legal profession.

Several years ago I am not sure I would have been confident enough to deliver a presentation in front of a US Supreme Court Justice – let alone so many federal judges and magistrate judges. It has been a long journey for me to gain greater confidence in public speaking – and that journey still continues.

In no particular order, here are some of my public-speaking “lessons learned” through the years:

Public Speaking Fear & Anxiety  

It has been extensively reported that people fear public speaking more than death.  While I find that to be incredible, it is also not surprising to me. Over the years I have had my fair share of anxiety and fear before delivering presentations – and I continue to be nervous before a presentation. However I have grown to realize that while some level of nervousness is okay, being overly nervous and/or having anxiety is simply not productive and will inhibit my ability to deliver a high-quality presentation. Please keep your presentation and public-speaking activities in proper perspective as it really is not a very big deal in the larger scheme of things of life. Try not to over-engineer what public speaking is all about because at its essence it is really just about having a conversation – which is something we do all the time. The difference is that this conversation is to a group of people versus just one person or a few people. Also try not to be overly fixated or obsessed in what your audience may think about you and your presentation. While of course you want to do your best and be appropriately prepared to deliver your presentation, in my experience the less you care about what your audience thinks about you and your presentation – the less fear you will have. In my experience embracing this type of mindset can be liberating.

Get Repititions & Grow Confidence

To be an effective and confident public speaker you need to actually do it as it does not happen by magic. As we know regardless of our profession, we all need to constantly work at our respective crafts in order to improve – and the same holds true for public speaking. Actively look for opportunities to speak in front of people – whether it be in the workplace or outside of the workplace – and do not shy away from delivering presentations. In order to keep my public-speaking skills sharp I make sure to speak publicly at least one a month – whether at work or as part of an external presentation or participation on an external panel discussion.

Create Your Slides

Not all presentations require visual slides but I am a big fan of using slides for talks that are greater than five minutes of length. Of course being a Microsoft employee, I am partial to using PowerPoint – but we all still need to avoid the proverbial “PowerPoint by Death.” PowerPoint is an excellent presentation tool and while I consider myself very proficient in using it, there are still so many PowerPoint features that I still do not use. In fact, PowerPoint just released some new AI-powered features to help make you a stronger presenter. When I need to deliver a presentation I try to begin to construct my slides a few weeks in advance so that I can take the time to properly develop a story (or stories) for my presentation. When I develop my slides I also add just a few words per slide at most. Many lawyers like to add lots of words to their slides, but I find that by doing so your audience has a tendency to read the words on your slides versus listening to your message and there is more of a temptation for a presenter to read her/his slides as a “safety-net” – which is one of the worst things a presenter could do – instead of telling a story. I view each of my slides as a mini-presentation and most of my slides contain interesting pictures and/or graphics that aim to capture the attention of my audience. Being a big user of social media and Twitter, I also make sure that my Twitter handle is on the bottom right hand side of each slide so that people have a way of connecting with me as needed. Finally, I am somewhat of a control freak with my slides as I prefer to develop them on my own rather than having someone else do it – and possibly screw them up.

Practice, Practice, Practice 

Before you deliver a presentation – even if it is only a few minutes in length – you should invest the time to appropriately prepare for it. Doing so will provide you with more confidence and in my experience it never makes sense to try to “wing” a presentation without the appropriate preparation. As to how much time you need to prepare that all depends on the individual presenter and her/his comfort level with the subject matter of the presentation. When you practice your talk be sure to time yourself so that you can stay within the allotted time of your talk and practice under the same conditions under which you will be delivering a presentation (e.g., using a clicker to advance slides, standing up if you are expected to stand during your presentation). You should also be mindful of overpreparing. In the past I have over overprepared with too much practicing during the day of or the day before my presentation – which resulted in my voice being overly tired, raspy and not strong enough for my presentation.

Presentation Logistics

Invest the time to understand your presentation environment and the technology associated with that environment (and always prepare for the worst and assume that technology will not work during your presentation). Be sure to arrive well in advance of your presentation timeslot and here is a checklist of key logistical considerations for your presentation:

  • Try to check out the presentation location/room in advance.
  • Will you be speaking from a lecturn, a podium or can you walk around?
  • Do you need your laptop/device to present the slides? If so, is the laptop/device charged up and do you have the appropriate adapters?
  • Will there be microphones? If so, are they handheld or lavalier microphones?
  • Will there be confidence monitors?
  • How many people will be in the audience?
  • Have a back-up copy of your presentation slides on a thumb drive.
  • Will the audience have access to your presentation slides?
  • Will members of the media be present?
  • Will conference organizers be videotaping or audiotaping your presentation? If so, they should first obtain your express written consent to do so.
  • Print out copies of your slides in the event you cannot glance at your slides via a laptop/device or a confidence monitor.

The Shorter Your Talk, the Better

I have been asked to deliver presentations at conferences or work-related events for 45 minutes or an hour in length. In my opinion that is way too long to speak. First, our attention spans as audience members are very limited – especially when presenters are competing with an audience’s smartphones. Also I do not know of many people who want to listen to someone speak for that long – especially a lawyer (and while my business may like me, they expect me to embrace the 3 B’s: Be Brilliant, Be Brief and Be Gone). Secondly, it takes a lot out of a presenter to speak that long in a compelling fashion – and to also invest the amount time to prepare for a talk of that length. Ideally I try to speak for no more than 15 minutes tops for a presentation and if an agenda requires 30 minutes, than I will speak for 20 minutes and have 10 minutes for questions and answers from the audience.

Know Your Audience

It is very critical to understand the make-up of your audience and their backgrounds so that you can create a presentation experience that connects you with them and is memorable. Several years ago when I traveled to various cities across the United States to deliver presentations to customers on how Microsoft inspires trust with its cloud solutions, my slides included images to local landmarks and sports teams so that I could develop a better rapport with my audience. Presenters should serve their audiences by earning their attention and providing them with useful content they can easily absorb.

Self-Care Before Your Presentation 

It is so important to be well-rested and in the proper positive mindset right before your presentation. Getting a good night’s sleep before your presentation is incredibly important and if you need to travel for your presentation try to arrive the day/night before if possible so that you can become properly acclimated to your environment, be rested and not be rushed. Also doing some physical activity earlier on the day of your presentation may be beneficial to you. I am a big fan of going for a run a few hours before my presentation as it serves to clear my mind, it calms me down and it makes me feel great. Also consider embracing some mindfulness practices such as using deep breathing techniques immediately before your presentation – and of course remember to breathe properly during your presentation. I also avoid drinking too much water/coffee immediately before my presentation as I may have a sudden urge to go to the bathroom. In addition, I try to avoid eating too much food prior to my talk so that I can avoid potentially having an upset stomach and I am careful to not eating something that has a higher likelihood of getting stuck in my throat during a talk (that has happened to me before). Finally just like a professional baseball player has his favorite “walk-up song” that the stadium plays before that player heads to the pitching mound or at-bat, consider listening to your own “walk-up songs” before your presentation that will make you feel good and put you in a positive frame of mind. Here are a few of my own “walk-up songs”: Feels Like the First Time, Thunderstruck and Gonna Fly Now.

Don’t Seek Perfection 

Remember that it is virtually impossible to deliver a “perfect” presentation and the definition of “perfection” as it relates to presentations is highly subjective. Most of us are not professional presenters, we will make mistakes during our presentation and our audiences do not expect perfection from presenters. It is okay to make mistakes, just move forward with your presentation when that occurs and if you have to quickly correct an error or mistake, you should feel free to do so.

Control the Slides

Whenever possible make sure that you have a clicker/slide advancer available so that you can move the slides forward at your own pace and for a smooth and professional presentation versus having to tell someone else to do so on your behalf.  Also practice on advancing the slides prior to your presentation in the proper order in which you want them displayed.

Say Thanks

I am a big believer that presenters should always be gracious and should begin their talks by thanking both the people who have invited them to speak and the members of the audience who have taken time out of their busy schedules to listen to you speak.

Start Strong

Open your presentation in a strong manner that grabs the audience’s attention and builds positive momentum for the duration of your talk. Avoid wasting valuable time introducing yourself – hopefully your bio will be provided to attendees by the organizers of your talk or perhaps someone else will introduce you. Instead, work hard to capture the audience’s attention in the first few minutes of your presentation or you risk losing them. Consider opening your presentation with a provocative question, a memorable story or another technique that makes your audience want to listen to you versus checking out their smartphones.

Be Authentic & Energetic

Please be yourself – and not someone else – when delivering your presentations. I find it refreshing when presenters display their own personalities and styles when delivering presentations as they come across more authentic and genuine. I have seen too many presenters come across very robotic-like and stiff during their presentations. In my opinion, if you deliver a presentation in a monotone fashion, if you speak just like everyone else, if you speak in the language known as “corporate speak” or if you are just reading from your slides like a news anchor, you risk losing your audience very quickly. Also while we can all learn a lot from great speakers, still be sure to develop your own unique presence and style. Also please bring some energy and passion to your talk. The last thing people want to hear are presenters who are boring and lethargic like this teacher from the movie Ferris Bueller’s Day Off.


Make it very easy for your audience to digest and understand your presentation as the best presenters are highly skilled at “decomplexifying” topics. Avoid using verbose words, acronyms or corporate jargon. Also consider highlighting the main takeaways from you talk at both the beginning and end of your presentation.

Add a Video 

We are all visual people and incorporating a compelling video into your presentation is a great way to convey messaging to an audience during your presentation – and it provides the presenter with a few minutes to catch her/his breath and regroup. In my experience I have seen many senior executives weave in videos into their presentations. Just make sure that your video works properly so that there will be no glitches during your presentation – and if you are presenting at an external conference/event please let their information technology people know in advance that you plan to show a video during your presentation. During my presentations on AI at the Fifth and Seventh Circuit judicial conferences I played a Seeing AI App video which demonstrates a unique application that was created by Microsoft and powered by AI to improve the lives of people with visual impairments. In fact, even Justice Kavanaugh liked the video and applauded along with the other attendees at the Seventh Circuit judicial conference after the video was finished.

Be Smart 

In our smartphone and social media driven world always assume that whatever you say during a presentation can be easily recorded or quickly shared via social media. So if you are speaking at an external conference or event please be very thoughtful in what you say as you will be viewed as an ambassador of your employer or industry whether you like it our not.


Always try to leave some time at the end of your talk to answer questions from the audience as that provides additional opportunities for others to learn from you and it also demonstrates your transparency. Also if the audience is small, consider fielding questions during your presentation. However, if you do take questions during your presentation try to avoid going down the so-called “rathole” by spending too much time answering a specific question as you can always get into a deeper discussion with the person asking the question after the presentation is over. Remember to repeat the specific question from the audience member so that others can hear it and do your best in trying to address a question. If for whatever reason you do not know the answer to a particular question simply say that you do not know the answer, you will research that issue and get back to that person as soon as you can.

Seek Feedback

After your presentation is over proactively seek the feedback of attendees and ask them what you could have done to make your presentation more impactful. Usually at external conferences and events attendees are asked to provide formal feedback on all presenters so be sure to obtain such feedback from the conference/event organizers. Learn from such feedback so that you can become an even stronger presenter in the future.

Get a Coach 

When needed do not be shy to enlist the support of an executive coach or trainer to help you be a stronger presenter. It is not a sign of weakness to do so, many senior executives have such coaches, and if your employer is unable to absorb an expense for a coach consider doing so on your own nickel as it is an investment in yourself and your career.

Embrace Diversity & Inclusion

Over the years I have been asked to speak at external conferences and panels where unfortunately the event’s organizers did not do a very good job at having a diverse slate of speakers – which is totally inexcusable in my opinion. Nowadays I refuse to participate in all male panels AKA “manels” and I am performing better due diligence with conference organizers to help ensure that the event I am speaking at will include an appropriate amount of diverse speakers before I commit to participating in such event.  If you are a frequent speaker at events please be a strong advocate for greater diversity of speakers at industry events like Dr. Francis S. Collins, the director of the National Institutes of Health.

Best of luck being a stronger and more effective presenter. Remember that it is a journey, stay positive and never ever get discouraged.


This is my first Father’s Day without my dad, Dennis P. Garcia (I was named after my dad and he was named after Dennis Chavez – the first Hispanic person elected to a full term of the US Senate from the state of New Mexico). My father passed away on Saturday September 29, 2018 at the Memorial Sloan Kettering Cancer Center in New York City where I was with him for the final two weeks of his life. The picture above is from Father’s Day 2018 with me, my dad and my son Sebastian.

Since my father had a huge impact upon my life it is still very surreal that my father is no longer around and the grieving process has been very difficult for me – and was similar to my grieving process when my mom passed away 23 years ago so unfortunately I knew what to expect.

While this Father’s Day will be very emotional for me, I feel extremely lucky that I had my dad for as long as I did. This realization dawned upon me during one of the very long nights when I stayed at Memorial Sloan with my dad. Late one evening I went to the family area on the hospital floor where my dad was staying to try to clear my mind. In the family area I saw a young boy – who was similar in age to my son – playing a game by himself and he was accompanied by his grandmother who looked very distressed. I said hi to both of them and the grandmother – who spoke little english – looked at me with tears in her eyes and cried, “My daughter, my daughter!!” I gave her a hug and I told her that my dad was also on this floor in the hospital and was very ill. Since I learned a few days earlier that many of the patients on this floor at Memorial Sloan unfortunately had terminal conditions, I quickly surmised that this women’s daughter and this young boy’s mom may also have a terminal condition. I looked at this young boy with tears in my eyes and prayed to God that he would not lose his mom at such a young age. At that moment I realized how fortunate I have been to have my father with me for my entire life.

I was incredibly lucky to have the best dad in the world and I learned so much from him. In memory of my father, here are just a few of those life lessons below – all of which I try to embrace as a father, husband, friend, lawyer and leader.

Be Confident & Fearless

My dad grew up on the tough streets of the South Bronx in New York City. As a Puerto Rican he faced discrimination at a young age and as a 23 year old he led soldiers in the Vietnam War as a First Lieutenant and was awarded the Bronze Star and Purple Heart. He had a larger than life personality and was highly confident. In hindsight, I think he needed that persona early in his life to survive.

While I did not have the same early life experiences that he did, my dad always instilled in me the importance of having self confidence, staying positive and being bold – something that I have increasingly embraced as I’ve become older.  I remember my first few days as a first year law student at Columbia Law School thinking that I did not belong there as I had attended Binghamton University (formerly known as SUNY – Binghamton) – an excellent state university in upstate New York – and I found myself surrounded by brilliant students from Ivy-league schools like Yale, Harvard and Princeton. As I walked around the Columbia campus with my dad during that time I remember him giving me a serious pep talk as to why I belonged at Columbia Law and that I needed to believe more in myself. Bottom line is self-confidence and being fearless can ignite both personal and professional successes.

Go Above and Beyond 

When I was a young kid and brought my report card home and if I did not get an “A” for a class, my father always highly encouraged me to go back to my teacher to see if there was more work I could do for some “extra credit” to help improve my grade. Of course, this is something that I never wanted to do.

Many years later I realized that this advice to me is so relevant to the business world and advancing in your career. In my experience during my career as an in-house lawyer for major information technology companies, we are all expected to perform the core part of our jobs at a high-level and that is considered “table stakes.” What sets us apart as professionals is our willingness, hunger and ability to really go “above and beyond” our core job responsibilities and drive a differentiated set of high impact for our respective employers.

Don’t Be Afraid to Ask

My father taught me not to be shy in asking for something. As a kid I was an avid baseball card collector and my dad used to take me to baseball cards shows in the late 1970s and early 1980s in New York City where I would spend my allowance monies on baseball cards. He taught me to negotiate hard and to never pay the asking price for something. The first time I did that was when I bought this 1957 Topps Baseball Card of Baseball Hall of Fame legend Willie Mays below which had an asking price of $30 back in 1980 and which I negotiated down in price to a whopping $25 – which was about a third of my savings at the time. There’s no doubt in my mind that I learned more about negotiation skills from my dad during these baseball card shows than in all of the professional negotiation trainings that I have taken in my career.

Never be afraid in asking for something in life or at the workplace.  You may be surprised with the answer to your ask and the worst someone can say is no.

Toot Your Own Horn 

My dad always encouraged me to sell myself to others and “toot my own horn.” This was something that he was skilled at doing for himself and on behalf of his two sons. For a long time I resisted doing so as I had a tendency years ago to be shy and introverted. As I entered the corporate world I also thought doing so was a form of “shameless” self-promotion that would be viewed in a negative fashion.

As I have become more senior in my legal career I have realized that we are our own best spokepersons on behalf of our ourselves and that we often cannot rely on others to do so. In my experience in the workplace those who promote or “sell” themselves to senior leaders and/or potential “sponsors” by articulating the positive impact they are driving are much better positioned for more opportunities versus those who stay silent.

Agitate When Needed

When I delivered my dad’s eulogy at his funeral I talked about how he had a “New York Edge.” What I meant by this is that when my dad felt that he, a family member, a friend, a work colleague, etc…were being wronged by someone else, he would “agitate” and/or “escalate” as needed to try to make the situation right from his perspective. When I saw my dad  “agitate,” he was very persuasive (and always sounded like a lawyer) and much more often than not he was able to resolve the matter to his satisfaction.

We all know that life can be unfair at times. Don’t be afraid to agitate.

Keep Perspective

Many years ago while I working as an in-house lawyer at Accenture I remember complaining to my father about my work and how demanding my job was negotiating very large and custom technology outsourcing agreements with demanding customers and the challenging law firms that represented them. My father gently reminded me that I was getting paid a lot of money for essentially putting words on a piece a paper and my job did not entail saving the lives of others. He was absolutely right and from that day forward I always tried to keep what I do in my job in perspective and to not take myself too seriously – which many of us in the legal profession have a tendency to do.

Be Transparent

My father actively cared for my mother for over 20 years as she lived with a disease called lupus. While my mom was in and out of hospitals for prolonged stretches of time, he was always open and honest with me about my mom’s up and down medical condition over the years. While those conversations could often be very difficult, I always valued his openness and honesty as he treated me like a man from a very early age.

Honesty and transparency are the keys to building trust in any relationship. From my perspective, in the workplace leaders earn greater trust and credibility with their teams and their customers by being authentic, avoiding ambiguity and being open, accessible, candid and telling it like it is.

Drive Inclusivity

My father was a role model to many Hispanics in the business world and before he became a senior executive at a major financial services company, he served as an Executive Director for a non-profit organization whose mission was to create business development opportunities for Hispanics. During his time he helped many Latinx people improve their lives and secure job opportunities. He understood many years ago why embracing diversity and inclusion made economic sense for all businesses and instilled that perspective in me at a very young age.

Always Be Networking

My dad was the ultimate networker and was often viewed as the “mayor” in the places that he worked. He was very personable, could make small talk with virtually anyone on a wide range of subjects and he encouraged me to try to meet one new person every day.

As I’ve become more senior in my career I’ve realized that who you know is more important than what you know. As a very smart person once said, our “network is our net worth,” so be sure to constantly network with others – and use social media tools like LinkedIn to do so.

Stay Actively Informed

My father would read The New York Times every single day – and every single article. He was incredibly well-informed and seemed to know everything about everything. He understood the power of information and the importance of staying actively informed about our ever changing world, trends, leading issues, etc…While he did not realize it at the time, it was his influence that got me hooked on craving the latest information on business, geopolitics, technology, my beloved New York Yankees, etc….which I consume largely nowadays via Twitter.

Embrace Change

Whether it be serving his country in Vietnam to coming home to his wife and new baby (AKA me) to returning to school to get his MBA to moving from the Bronx to the New York City suburb of Scarsdale, New York (where there were few Puerto Ricans) to changing his job several times to losing his wife of 25+ years to getting remarried and starting another chapter in his life, my father’s life involved a tremendous amount of change. He was very successful in navigating through the changes that life presents to all of us.

When I felt “stuck” in my career several years ago it was my dad who encouraged me that I needed to change as I was too comfortable. At that time he suggested that I do more to build my professional brand as a lawyer by writing articles for publication (and my first one was on the topic of cloud computing for a leading procurement organization that he was involved in) and to deliver external presentations on topics where I had expertise in. I followed through on his advice, these activities raised my visibility both within and outside Microsoft and I believe it was instrumental in helping me get promoted to Assistant General Counsel in 2014.

Be Healthy

My dad passed away from a rare form of skin cancer known as merkel cell carcinoma that originally looked like a small wart on his hand.  In hindsight, perhaps my dad could have done a better job in taking care of himself by immediately going to the doctor when this growth appeared on his hand.

While we all lead busy personal and professional lives, we all need to be extremely proactive in protecting our health and being laser focused on our wellness – and the wellness of our loved ones. This by far and away is the most important lesson from my dad so please do so in his memory.

While my dad was laying in his hospital bed during the last two weeks of his life he was constantly winking at me with his confident smile. When I was a young boy this wink and smile was something that my dad would do periodically and it was his way of letting me know that things were OK and he was happy with me. When he did this during his time at Memorial Sloan it was as if I was experiencing the “cycle of life” and I was immediately transported back in time to my earlier years in New York and the great memories that we created with my dad, my mom, my brother, my grandparents, the rest of our family and our friends. As Father’s Day 2019 approaches I plan on winking and smiling a lot at my son Sebastian.

A vital part of building a world-class legal team is not only recruiting and hiring great talent, but properly indoctrinating new legal professionals into your legal department or law firm – and also when they transfer into new practice groups or teams. Developing and executing upon a meaningful onboarding process for your new joiners will foster greater inclusivity, enable them to contribute immediately and position them well for future success. During my career I have had the privilege to help train – and be trained by –  many outstanding legal professionals. Here are some onboarding best practices for all legal teams:

Own the Onboarding Process

If you work in-house, do not simply outsource your onboarding processes to the human resources team or another group in your organization. While the new employee may of course participate in a company-wide new employee orientation program, the legal department – and the hiring manager specifically – should develop and take responsibility for the onboarding process for the new legal professional.

Deliver a Warm Welcome

When a legal professional joins your team, she/he needs to feel welcome in a new environment. Be sure to craft an email introducing your new legal teammate to your colleagues and clients. The new joiner should also review that communication before it is sent out and perhaps even add any personal information that she/he is comfortable in sharing with others. Senior leaders and colleagues on your team should also reach out directly to the new hire to extend a warm welcome. If you are a large legal department or law firm perhaps the General Counsel and/or law firm CEO/Managing Partner can record a welcome video/email for all new hires. Many years ago when I joined the Accenture legal department I remember being invited to  lunch with the then Accenture General Counsel Doug Scrivner just a few days after I started as he happened to be in the Chicago-area traveling for business. That lunch and personal connection with Doug went a long way to helping me feel a part of my then new team. Also be sure to encourage your legal teammates to connect with your new hire via LinkedIn so they can build deeper business relationships.

Develop a Custom Training Plan

I’m a big fan of the National Football League (NFL) – although my beloved New York Giants have unfortunately had several poor seasons in a row. Often times NFL coaches script the initial series of football plays that their teams plan to run on offense prior to the games. Similarly, a hiring manager should develop a training “game plan” for her/his new hire prior to that individual’s first day of work. This plan could be based on a schedule for an initial period – perhaps the new employee’s first month at work – that provides some detail regarding a slate of training and learning sessions that are applicable to the legal professional’s role. This roadmap can also take a forward looking view regarding significant anticipated milestones over the new employee’s first six months or so. You should provide your new hire with a copy of this plan on her/his first day of work and the plan should be flexible enough to adjust as needed.

Involve Your Colleagues

A hiring manager should not train the new legal professional on her/his own. Instead, embrace inclusivity and be sure to actively involve your legal team colleagues to help onboard your new joiner. Providing the new hire with the opportunity to learn from your legal group colleagues enables them to expand their network and helps to break down silos in any legal organization.

Introduction to Key Clients

Please take the time to introduce your new legal professional to your clients. When I have onboarded new teammates I have connected them with our clients from key parts of the business teams and they have graciously taken the time to describe their organizations, roles and responsibilities so that the new legal professional could gain a better understanding of the clients they would be supporting and the opportunities to partner with them to drive positive impact.

Periodic Check-Ins

Be sure to build in and schedule periodic 1:1s or “check-ins” with your new joiner as part of the onboarding plan that you develop. In my experience, for the first several weeks from my new hire’s first day of work, I would meet at least twice a week for formal 1:1 sessions with them. Also if you are unable to conduct those 1:1s in-person with your new hire because you are not co-located together, be sure to convene such sessions via Skype, Microsoft Teams or other suitable videoconferencing technology so that you can see each other and build a more personal connection with your new teammate.

Don’t Complexify Your Organization

Many organizations – including legal organizations – can have their own unique business, legal and technical lingo filled with acronyms and phrases that are difficult for new joiners to understand. Consider developing a glossary (which is periodically updated) that defines common acronyms, words and other “corporate speak” that new members of your organization will need to understand in order to be successful. In addition, always, always, always look to make your organization, its business, its opportunities and its challenges, super easy to understand for your new hire.

Leverage Leading Technology

Using and investing in the right technology tools can help create a high impact onboarding experience for your new legal professionals. Consider developing an onboarding OneNote that contains a digital collection of best practices that can help make a legal professional’s transition into your legal organization more seamless. Use Microsoft Teams as a way of collaborating, sharing knowledge and consider creating a “readiness” channel in Teams to store content that is of interest to new joiners. In addition, Microsoft Stream is an intelligent video service that enables you to produce and deliver learning and training content that can be easily consumed on-demand by your new joiners anywhere and at anytime.

Shadow Others

A great way for new legal professionals to learn is to be a proverbial “fly on the wall” by observing their teammates in action and performing their roles for a period of time.  Whether it be sitting in on a contract negotiation session to serving as a “third-chair” attorney in a courtroom to joining other legal professionals for important meetings with clients, always look for opportunities for your new legal teammates to learn by shadowing their new colleagues.

Assign a Buddy and a Mentor

Consider appointing a member of your legal team who is a peer to your new hire that can serve as a “buddy.” The role of a buddy is to be another resource – who is not an immediate manager of the new hire – that can serve as a “go-to” person on a wide-range of matters and help answer common questions and issues that may arise. Also consider asking another member of your legal organization to initially serve as a quasi “mentor” to the new hire that can provide more strategic and career-oriented guidance to the new joiner until she/he can develop mentor relationships on their own within your organization.

Learn from Others

Since other groups internal and external to your organization also need to train and onboard their new hires, be sure to embrace the growth mindset and learn from them. LinkedIn also provides us with opportunities via social media to learn about onboarding best practices for professionals.

Onboarding Feedback Loop

Please be sure to obtain feedback about your new hire’s onboarding experience 6 to 12 months after her/his first day of work – and encourage her/him to be brutally honest about it. Embracing and learning from such feedback can be invaluable to improving the transition of future new joiners into your legal organization.

New Joiner Group

Consider developing a team of legal professionals who have “graduated” from your legal organization’s onboarding process to serve as a “New to Your Legal Organization” group. This team can take the leading in constantly developing new best practices and  evolving your legal organization’s onboarding processes on a go-forward basis. Also be sure to rotate legal professionals in and out of this group over time to help ensure diversity of thinking.

Administrative Considerations

Develop a checklist of key items that needs to acquired or be put into process before a new legal professional begins her/his first day of work. Taking care of such matters before a new employee starts her/his job demonstrates your legal organization’s commitment to them. Some of those items may include the following:

  • Organization issued laptop, device and/or phone;
  • Organization issued corporate card for travel;
  • Securing appropriate office space and/or cubicle;
  • Organization badge/identification card;
  • Any necessary documentation that may be need to be completed by the new hire prior to her/his first day of work;
  • Business cards;
  • Creation of organization issued email address for new hire; and
  • Other necessary human resources-related information.

As we all know the greatest asset of any legal organization is its people. Please be sure to invest in your legal professionals by enabling them to get off to a “fast start” in your legal group.


I can watch old episodes of the iconic TV show The Office on Netflix all day long. In my opinion the actor Steve Carell was brilliant in his portrayal of Michael Scott – a fictional character on The Office who served as the highly dysfunctional regional manager of a paper company known as Dunder Mufflin in Scranton, Pennsylvania.

However contrary to Michael’s own belief (and his coffee mug), he definitely was not the “World’s Best Boss.” Unfortunately we seem to be reading more news reports about senior leaders in well-known organizations across the business, political, cultural, academic, non-profit and sports worlds who unfortunately act like Michael Scott and are not good people managers.

While leading technology assets like software, cloud computing, devices, data and artificial intelligence can help law firms and corporate in-house legal departments digitally transform to provide more high-impact legal services to their clients, we can never lose sight that people are still the most important asset of any legal organization. As many of us know it is often the case that employees do not leave companies, they leave managers.

All lawyers can be better leaders and people managers. Leadership and management are key competencies that are generally not taught in law school and in continuing legal education programs that many of us may attend. Even if you do attend leadership/management trainings during your career, they are still vital skills that need to be  developed and honed over time.

It is important to remember that we are ALL leaders. Here are some guiding principles for lawyers to embrace as leaders:

Ethics & Integrity Are Non-Negotiables 

Leaders are role models and must always, always, always demonstrate a high-degree of ethics and integrity in their actions. Constantly setting this tone of the importance of embracing compliance and integrity will help make them part of your team’s DNA. Look for opportunities to share lessons learned when lawyers and business people have not acted in an ethical fashion.

Learn, Learn and Learn

Lawyers need to have a “learn-it-all” mentality versus a “know-it-all” mentality when it comes to leadership and management. Be sure to learn from the great, good, mediocre and poor leadership practices demonstrated by lawyers, clients and others that you observe over time. Also learn from the less than ideal actions that you have taken in the past as a manager.  Last July I assumed a new role leading 14 outstanding lawyers and legal professionals scattered across the US and I find myself constantly learning from my team, my peers, our customers, our partners and others on how I can improve to be a more effective and impactful leader.

Provide Recognition and Say Thanks 

Look for opportunities to recognize the great work of your team and get in the habit of continually thanking them for their hard work. Such recognition can range from informing your immediate management team of their great work to highlighting their accomplishments during team meanings to providing periodic awards to offering “Kudos” via LinkedIn. Also do not forget to congratulate them on their work anniversaries.

Be Empathetic

In my experience embracing a deep sense of empathy is a necessary skill for all lawyers. Lawyers can better lead their teams by being able to appreciate, understand and identify the needs of their teammates. Do you best in trying to “walk in the shoes” of your team members.

Invest in Your Team & Serve Them

Leaders need to have a service-first mentality with their teammates and should pose this question: “How can I serve you better?” When you hire new legal talent be sure to invest the time to train them. Develop a thoughtful on-boarding plan, introduce them to key clients/members of your legal team and provide them with opportunities to shadow you and others. Over time offer your team growth opportunities via stretch projects, mentor them (and suggest other potential mentors), provide them with chances to gain visibility with senior leaders, do not play any favorites and drive an inclusive culture free from Unconscious Bias.

Promote Wellness

The legal profession is filled with long hours, pressure and the wellness of lawyers is a growing and vitally important topic. Lawyers will only be their best in the workplace if they feel their best. Always be sure to emphasize to your team that they should take excellent care of themselves, excellent care of their families, and to take the necessary time away from the workplace to vacate their minds and recharge.

Have an Eye for Great Talent

Lawyers must have the innate ability to identify and attract great talent for their organizations. Leverage your networks to find such talent, avoid constantly hiring from the same sources (e.g., Top 20 law schools), seek lawyers from diverse backgrounds and do not rely solely upon your human resources team/recruiters. While hiring great talent is an inexact science, put a premium on the so-called “soft” skills and always go with your gut intuition.

Feedback is Fabulous

Take the time to periodically provide meaningful and constructive feedback to your entire team when applicable so they can learn and grow. Do not wait to share any feedback at a certain point in time like during a future performance review session – instead provide such feedback immediately. In addition, the best leaders always asks their team for specific feedback about themselves. 

Be Clear & Transparent  

Lawyers can often be vague, verbose and ambiguous in their communications. As leaders, we need to drive greater clarity, consistency and transparency in our communications to build trust with our teams and to better enable them to provide impactful advice to our clients. In my experience, lawyers and legal professionals crave and expect a high-degree of transparency from their leaders. Lack of clarity, ambiguity and inconsistency within legal teams can lead to confused and unsatisfied clients and legal team members.

Tough Conversations & Decisions 

On occasion being a leader will require you to have difficult conversations with members of your team and making tough decisions. When needed practice your delivery of those conversations with someone that you trust and be very thoughtful yet decisive in your decision-making process. Also do not worry about whether your team will still “like” you as managing a team is not a popularity contest. If you are unable to have these conversations or make difficult  decisions then you should not be a people manager.

Generate Positive Energy & Enthusiasm 

Whether we realize it or not, the energy and enthusiasm (or lack thereof) of senior legal team leaders is highly contagious. Like CEOs and other senior business leaders, lawyers also need to be positive motivators, passionate and inspiring.

Provide Air Cover

While practicing law is not an easy, it can be easy to second-guess a lawyer’s advice on difficult issues. Be sure to have your team’s “back,” never rush to any judgment regarding your team’s performance without speaking directly with your team and having a clear understanding of the facts and constantly reinforce your support to your team.

Put the Right People in the Right Place at the Right Time

Just like a head coach in sports, a legal team leader needs to be thoughtful as to how she assembles and deploys her team of lawyers and legal professionals to have the maximum positive impact. Doing so requires a deep understanding of the strengths/growth opportunities of team members, the specific requirements of clients and the business needs of your legal organization. 

Always Be Accessible & Responsive

While we are all busy, lawyers need to make themselves readily available to their teams to set them up for success. Be sure to have periodic high-impact 1:1 meetings with your direct reports, understand their preferred modes of communicating, and never ignore your teammates (and be quick to respond to their emails) as leaders must be super responsive to their team’s needs.

Be Present

During discussions with members of your teams be sure to focus on them, make eye contact, do not be distracted, avoid multi-tasking and engage in active listening. We owe it to our team to always “be present” when we connect with them. Leading psychologist Dr. Michael Gervais has spoken and written extensively that “being present” is a key attribute of high performing teams.

Stay Humble

On occasion I have seen lawyers promoted to senior leadership positions who have let their new responsibility, power and influence “go to their heads.” While it is important for people managers to exude confidence, it is equally important to remain humble and well-grounded as a leader.

It is always a shame when lawyers and legal professionals decide to leave organizations because of their managers and leaders. Remember to always work hard to continually develop your leadership skills so that you can help build the next generation of great lawyers and legal professionals – and leaders – within your legal organization.


Last week I was invited to speak about LinkedIn to the legal department of a highly strategic Microsoft customer and partner. My presentation was entitled “LinkedIn and You: Increasing Your Visibility with LinkedIn.”

I love talking and writing about LinkedIn – and other social media platforms like Twitter – as they can help us establish and deepen professional relationships, build both our personal brands and the brands of our organizations and they can help us learn. LinkedIn is a highly powerful social media tool that I believe is an underutilized technology by lawyers.

Ever since Microsoft acquired LinkedIn in June 2016, LinkedIn continues to grow. Statistics indicate that there are now over 600 Million LinkedIn users, 45% of those users are in upper management, two people join LinkedIn every second and 3 Million American jobs are posted on LinkedIn every month.

When I graduated law school during the 1990s, we were still in the midst of the Third Industrial Revolution – which was led by iconic technology companies like my former employer – IBM and my current employer – Microsoft. Exchanging business cards were the primary way of initiating professional relationships during the Third Industrial Revolution. Here is a business card of mine from back in the day when I was a “baby shark” lawyer for IBM working in the foothills of the Rocky Mountains in beautiful Boulder, Colorado.

While many of us still exchange business cards, we are in a new era called The Fourth Industrial Revolution.  When I meet people nowadays I usually do not provide them with my business card (in fact, I’ve been meaning to order a new batch of business cards for the last several months). Instead, I search for them via the LinkedIn app on my smartphone and I send them a request to connect on LinkedIn. In my opinion, LinkedIn is our digital business card of the Fourth Industrial Revolution.

I have been a power user of LinkedIn well before the Microsoft acquisition, here is my profile and I have learned a lot (and continue to learn a lot) about LinkedIn. Here are some of my LinkedIn best practices:

Build a Thoughtful LinkedIn Profile: A key foundation of using LinkedIn is to make sure you take the time to construct a strong profile that reflects your authentic professional self. Your profile is in essence how you brand and market yourself to the business world.  Developing your profile is not a “one and done” proposition – instead it is a journey that requires frequent updating. Check out the profiles of people you admire on LinkedIn as you may be able to pick up some tips on how to structure a compelling profile.

Here are some key focus areas for your profile:

  • Profile Pictures: Please be sure to include a relatively current professional headshot of yourself as your primary photo on your profile. As an example, I would not use the dated picture above of myself flexing in a black cowboy hat as my primary photo on LinkedIn. It is worth spending a few bucks for a nice headshot of yourself by a professional photographer – and I’ve attended many legal conferences where they have someone on-site taking headshots so that may also be an option for you. In addition, since you may leverage LinkedIn for work-related purposes, do not be shy in asking your manager if your employer would be willing to reimburse you for the costs associated with your headshot. Also do not forget that LinkedIn allows you to have a secondary/background photo on your profile. I have seen a range of secondary/background photos from company logos to picturesque sceneries to uplifting quotations to other interesting pictures.
  • Headline: The headline area is right below your primary photo and name – and you have 120 characters to provide a short description of yourself via compelling keywords. Your headline is a very valuable piece of “real estate” as it occupies an important section of your profile that is one of the most visible – especially since people are often viewing profiles on their smartphones. Be sure to give special thought and attention in constructing a headline that is Twitter-like to briefly summarize you as a professional and serves to differentiate yourself. As lawyers we have a tendency to develop headlines that are somewhat boring – so figure out how your headline can really “pop” and capture the attention of a reader.
  • Summary: Your summary is basically an executive overview of yourself as a professional. In many respects a summary is similar to your professional bio. While LinkedIn limits your summary to 2,000 characters, in my opinion your summary should just be a few short paragraphs long.
  • Experience: The experience section is akin to the work experience section of a resume and should contain appropriate and accurate information pertaining to your jobs experience.
  • Education: This section is fairly straightforward to depict your education. You may also want to consider capturing any executive education-level coursework that you have completed.
  • Licenses & Certifications: Please be sure to list your various state or local bar-related licenses in this section. Also do not forget to identify any unique certifications (e.g., privacy, compliance, technical) you have obtained during your career.
  • Volunteer Experience: Most everyone appreciates people who volunteer their time to help non-profit organizations and other worthwhile causes so do not be shy in listing out those experiences in this section – and it could be a source of similar interests with other LinkedIn users.
  • Skills & Endorsements: I think this section is of limited value to LinkedIn users as your skills can be highlighted elsewhere in your profile. I also do not routinely endorse the skills of other LinkedIn users.
  • Recommendations: I remain torn about the value and importance of recommendations on LinkedIn. On the one hand they can be useful – especially for people who are interested in seeking new jobs. On the other hand, I do not think I have ever seen a negative recommendation about someone on LinkedIn since the person seeking a recommendation would not be doing so unless she/he knows that the recommender will be providing a positive recommendation.
  • Accomplishments: This is a very valuable section that is often overlooked by LinkedIn users. I am a very big advocate of adding applicable content to the “Publications” area of this section – and not just for articles, blogs, etc…that you may write but to also include your external speaking engagements, presentations and panels that you may participate in. The “Honors & Awards” area also provides an opportunity for lawyers to amplify the various honors/awards that they may have be recognized for during their careers.

LinkedIn Connections: A fundamental premise of LinkedIn is to be connected to or “linked” with other professionals for networking-related purposes. I have heard from some LinkedIn power users and recruiting professionals that LinkedIn users should strive to have at least 500+ LinkedIn connections. While I am not sure that there is any sort of magical number associated with how many LinkedIn connections you should have, LinkedIn limits users to have a maximum number of 30,000 1st-degree connections (which is a LOT of connections). While I consider myself a very active user of LinkedIn, I have almost 4,000 1st-degree connections.

  • Who to Connect With?: A question always arises as to who should you connect with? While of course that is ultimately up to you, here is a suggested list of professionals that in-house counsel may want to think about connecting with:
    • Other members of your legal department.
    • Members of your outside counsel law firms and alternative legal services providers.
    • Your internal business clients.
    • Legal counsel and business professionals representing your customers, partners, vendors and competitors.
    • Law professors, deans and other law school personnel.
    • Legal professionals focused on legal technology.
    • Legal recruiters.
    • People you meet at legal-related conferences, continuing legal education events, etc…
    • People you may volunteer with.
    • Your college and law school classmates.
    • Your friends, neighbors, parents of kids who attend the schools of your kids, etc…
    • Your relatives.
  • Personalize Your Invite: Whenever possible try to send a personalized invite to connect with someone via LinkedIn. While doing so certainly takes more effort than simply pressing the “Connect” icon in the LinkedIn App on your smartphone, sending a personalized invite will help you stand out in the eyes of the invitee, provides a warm bespoke “touch” and increases the likelihood that someone will accept your invite.

  • Find Nearby: The “Find Nearby” feature of LinkedIn is great for legal conferences, continuing legal education events, etc…as it enables us to discover other LinkedIn members that are near you.
  • Be Bold: Sometimes we may be reluctant to send invitations to professionals who are very senior in our organizations or other organizations. My advice is do not be shy in connecting with these senior leaders and make sure you personalize your invites to them.
  • Follow Others: Keep in mind that there is always the option to “follow” people on LinkedIn versus actually connecting with them. For example, I follow several people on LinkedIn who have been designated as LinkedIn “Influencers” and although I am not technically connected to them, I can see their LinkedIn activity.
  • Thoughtfully Accept Connections: I used to always blindly accept connections from other people. While I accept most of the connection requests that come my way, nowadays I have become a bit more cautious and I always check out profiles before I accept any connections. Over the past few years I’m seeing more profiles that look suspicious/stealth in nature and I have become more reluctant to connect with people who seem to just want to sell something to me. That said, as a “seasoned” lawyer who prides myself in serving as a mentor to “junior” lawyers and law students, I think it is important for senior lawyers to connect with the younger members of our profession (who quite frankly we have a lot to learn from).
  • Unfollow/Block Users: Keep in mind that connecting with someone does not mean you cannot get separated or divorced in the future. It is easy to unfollow someone (but still remain connected to that person) so that you do not see their LinkedIn activity and you can also formally block a LinkedIn user via your privacy settings.

Evangelize, Evangelize, Evangelize: LinkedIn provides us with terrific opportunities to highlight our respective organizations and to showcase our personal brands as lawyers via posting content. As you share and post content think about how such content provides value to your audience of LinkedIn connections (and their connections). The more valuable content you share, the more people will want to connect with you, the more people will like/view/comment on your posts/comments and you may soon receive formal requests to speak publicly and write – which in turn helps to increase your visibility, credentials and brand. Active evangelism via LinkedIn can help you get noticed by others in the legal industry (and even in your own legal department if you are part of a large legal department), develop relationships with professionals that you will not have met but for your LinkedIn usage and grow your professional network.

Here are some evangelism strategies:

  • Likes: Consider actively using the “thumbs up” like feature of LinkedIn – which is a quick and “low touch” way of using LinkedIn. During the course of any given day I will typically like several LinkedIn posts/comments – especially those posts by my Microsoft legal team colleagues and those posts that serve to demonstrate Microsoft’s leadership in the technology marketplace. I have often found that by liking the posts of various LinkedIn users, many of those users may provide a form of “reciprocity” back to me by liking my own posts.
  • Comments: Consider providing a comment (or two) on posts/comments to share your opinions, demonstrate your knowledge and to keep the conversation moving forward on the topic of a particular post/comment.
  • Posts: Periodically posting content via LinkedIn is fundamental to increasing your professional visibility. I try to post information that reflects positively upon both my employer Microsoft and my own brand as a lawyer. I try to post content that I am passionate about or which may be of interest to my professional network and provide value to them. I will also post about external presentations that I deliver, panels that I serve on at legal industry events or articles/blogs that I write. For example, knowing that artificial intelligence is of great interest to me and one of the hottest topics in the business world nowadays, I shared this post about serving as a co-chair for a Practising Law Institute program entitled “Artificial Intelligence Law 2019” in New York City a few weeks ago. One way to measure the “impact” of your posts is to see how many views, likes and comments that you receive.
  • Be Visual: To attract more people to view your posts be visual by adding interesting pictures to your post. Take care in adding pictures that are clear, have proper lighting, are well-centered and are appropriately cropped. LinkedIn also enables you to add videos to your posts – which is another excellent way to deliver messaging to your professional network in a compelling format. While I have only posted this one video on LinkedIn when I traveled to Shanghai last November, I look forward to incorporating more videos into my posts in the near future.
  • Use @Name Feature:  When you want to recognize someone or give them a “shout out” in your posts/comments, use the @name feature to specifically reference them and their name will appear in blue highlights that then links to their LinkedIn profile. The @name feature is not limited to individuals as you can also use it for organizations. Doing so provides a nice personal touch.
  • Give Thanks: Get into the habit of thanking people that may have some association with your post and use the @name to reference them. Also if someone provides a positive comment on your post or comment be sure to like that comment and reply back to that comment with a thank you.
  • Careful Cadence: Some social media marketers may disagree with me, but I think you should develop a very thoughtful frequency as to how often to post content via LinkedIn. While I generally do not limit myself on my likes, I do limit the amount of my comments and I typically do not formally post items more than a few times per week. In my opinion if you post way too often, people in your professional network may start to ignore you or “tune you out.” There have also been a few people in my network that I stopped following as I thought they were “over-posting” content. In addition, you need to be very sensitive and careful about potential perceptions of “over-posting” as some in your management team within your organization may be of the view that you spend too much time on LinkedIn/social media and not enough time doing your job.  In my opinion if you want to constantly post social media content then use Twitter.
  • Be Current: I also believe that when you post content it should be based on relatively current events/initiatives/information to help draw maximum attention otherwise it may be viewed as being stale and dated.
  • Be Positive: There is already so much negative energy on social media so I always try to remain positive, upbeat and complementary in my posts. I also try to avoid responding to any social media trolls that try to draw people into negative discourse.
  • Use #Hashtags: Consider using #hashtags for key trending words and phrases in your posts to help increase their visibility with others.
  • Write Articles: Since many lawyers love to write, a neat feature in LinkedIn is that it allows you to write your own articles so you can serve as your own author. A few years ago I wrote this article about the importance of taking a “Real Vacation” after spending a fantastic family vacation in spectacular Jackson Hole, Wyoming and not looking at any work emails or taking any work-related calls.

  • Edits to Posts/Comments: Please do not be afraid in making any mistakes in your posts/comments as they can easily be changed by you afterwards.
  • SlideShare: SlideShare is a company that was acquired by LinkedIn in 2012 and is a feature that you can use to add content in the form of PowerPoint presentations – and of course lawyers deliver many PowerPoint presentations.
  • Increase Team Morale: LinkedIn can also be used to build more “esprit de corps” on your team. When a member of my team posts content on LinkedIn, I try to support and encourage them with a like and a positive comment. LinkedIn also has a nifty feature where you can provide a “Kudos” to someone.

Learn via LinkedIn: LinkedIn offers plenty of opportunities for users to embrace the growth mindset and to learn from others as there is a wealth of information at the fingertips for all LinkedIn users.

Here are some examples:

  • Insight on LinkedIn Users: In my role I work closely with the legal and compliance professionals who represent our customers and partners. It is important for me to try to develop relationships with these professionals so I spend time reviewing their LinkedIn profiles to better understand their backgrounds, I connect with them via LinkedIn and I try to begin to develop and sustain a professional relationship with them. I also try to do the same with my business clients – and I try to like the posts of many of my more senior business clients.
  • Business Intelligence: LinkedIn is full of incredible information that is available in our news feeds. Increasingly LinkedIn has become one of my primary sources of business-related information where I can learn a lot about the technology marketplace, Microsoft, our customers, our partners and our competitors. Having this wealth of information at my immediate disposal helps me provide more high impact legal counsel to my business clients.
  • Follow LinkedIn “Influencers”: You can follow business and world leaders who are officially designated as  LinkedIn “Influencers.” For example, two LinkedIn Influencers that I closely follow are Microsoft CEO Satya Nadella and Microsoft President & Chief Legal Officer Brad Smith.
  • Follow Companies: LinkedIn also enables you to follow companies and other organizations. To help me embrace both a customer and partner obsession mindset in my role as a lawyer, I follow several Microsoft customers, partners and competitors on LinkedIn so that I can have visibility to the content these organizations are sharing via LinkedIn.
  • Follow #Hashtags: You can follow various #hashtag words or phrases via LinkedIn. Some of the favorite #hashtag words that I follow are #cloudcomputing, #artificialintelligence, and #digitaltransformation.    
  • LinkedIn Learning: LinkedIn Learning is an excellent resource where you can have access to world-class on-demand video courses taught by industry experts.

Miscellaneous Considerations: Here are some additional considerations to keep top of mind as you use LinkedIn:

  • Office 365 & LinkedIn Integration: LinkedIn has now been integrated with Office 365. If you are an Office 365 user (and thank you for being a Microsoft customer) consider taking advantage of features like Profile Card to build relationships and Resume Assistant.
  • LinkedIn Messaging/Email: Remember that it is very easy to send messages/emails to your connections – including composing group messages/emails.
  • Find Great Legal Talent: LinkedIn is a tremendous resource for lawyers and legal teams to help identify great legal talent.
  • Help Resources: LinkedIn has very robust and easy-to-use “Help Center” resources that can assist users in troubleshooting issues and addressing common questions. Do not be shy in leveraging those resources.
  • Cybersecurity: Make sure to be cyber aware when using LinkedIn as social media has been an area that has been increasingly targeted by cybercriminals. Embrace strong password protection practices when using LinkedIn.
  • Social Media Policies: Many organizations have policies governing social media usage by employees. Please be sure to follow those policies when using LinkedIn.
  • Legal Ethics: Many national, state, and local bar associations have legal ethics opinions, rules and guidelines in connection with a lawyer’s ethical usage of social media. Please be sure to follow these applicable opinions, rules and guidelines.
  • No Confidential Information: Never ever disclose or post any confidential information on LinkedIn.
  • Be Smart: As I like to tell my business clients, assume that whatever you convey in a digital format can find its way to the front page of The Wall Street Journal. Please embrace a similar practice when posting on LinkedIn and always “be smart” with your LinkedIn usage.

Just like any leading technology you need to use LinkedIn on a regular basis for it to have a positive impact for you. I routinely check my LinkedIn news feed first thing in the morning, during my lunch break and in the evening. Best of luck in using LinkedIn as a valuable tool to achieve more.