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.


Yesterday I delivered a keynote presentation on the critically important topic of Security & Privacy at the Association of Legal Technologists Ctrl ALT Del 2019 Conference in sunny Scottsdale, Arizona. As a huge baseball fan I unfortunately just missed the opening of Spring Training in the Arizona Cactus League.

My primary message point was that in our world of rapid technology advancement that has generated and will continue to generate massive amounts of data, data privacy and data security are the big issues of our time in the technology space – especially as cybercriminals become more sophisticated, bolder and also include some nation-states.  Every company is increasing transforming into a data company and in order for all organizations to continue to earn trust with their clients and customers, we all need to be even more laser focused on data privacy and data security.

During my keynote I highlighted these “Top 20” cybersecurity best practices for ALL organizations to embrace – regardless of their size or industry:

  • Set the “Tone at the Top” for Cybersecurity: Senior leaders in all organizations need to appreciate, understand and embrace the importance of privacy and security in our data-first world so that they and their organizations can make the appropriate cybersecurity investments.
  • Get Help: As the data privacy and security landscape continues to change and grow more complex, don’t be shy in seeking out the assistance of subject matter experts.
  • Conduct a Cybersecurity Audit: If you haven’t already done so, consider having a highly reputable cybersecurity expert conduct an audit on your organization’s technology infrastructure to help identify security gaps and areas for potential vulnerabilities.
  • Focus on Data Classification: Be sure to clearly understand, classify and conduct an inventory of your organization’s different data types.
  • Develop Thoughtful Written Information Security Policies (WISPs): Develop meaningful and easy to understand WISPs for your organization – and make sure you follow them.
  • Employees & Data Access: Carefully consider which employees need to have access to certain types of more sensitive data and when they exit your organization be sure to immediately shut off their access to your company’s network and data.
  • Conduct Cybersecurity Training: Periodically deliver meaningful privacy and security training to your employees either in-person or online – but make it interesting to capture their attention.
  • Transparency: Be very proactive in communicating to your customers the specific steps that your organization takes to protect data. As an example at Microsoft we embrace this type of transparency via the Microsoft Trust Center.
  • Use Strong Passwords: It seems like we live in a password world. Make sure to avoid reusing old passwords, generate strong passwords, consider using a password manager and as technology continues to advance, we will increasing become passwords free as passwords will probably become a relic from the past.
  • Embrace Multi-Factor Authentication (“MFA”): Many cybersecurity experts agree that simply using MFA or two-factor authentication practices can go a long way to preventing cyber-related intrusions.
  • Be Careful of Phishing Attacks: Be wary of emails from financial institutions, social media sites, etc…that seem legitimate, but upon closer inspection are imposter emails that seek private information from you and which may contain malware. Microsoft Office 365 Advanced Threat Protection provides protection against phishing attempts.
  • Download Security Updates: Don’t ignore installing the latest versions of technology solutions that may contain more robust data security protections.
  • Work with Hyperscale and Trusted Cloud Services Providers: Generally speaking, large, hyperscale and trustworthy cloud services providers that operate state-of-the-art and highly secured data centers can do a much better job at protecting data than organizations who seek to secure data via their own servers in a traditional “on-premises” computing environment.
  • Conduct Careful Evaluations of Technology Providers: It’s always important to conduct thorough due diligence on the privacy and security practices of any technology provider, vendor or third party that may have access to your data.
  • Be Social & Secure: We are all spending a greater part of our day using social media so please be sure more to be cyber smart when using Twitter, LinkedIn, Facebook, etc….as social media is a key vector for cybercriminals.
  • Be Cyber Aware in Public: Leading technology increasingly enables many of us to work remotely, but when you use public WiFi, always be sure to use a Virtual Private Network (VPN) and be careful not to disclose confidential information in public places.
  • Develop Your Incident Response Plans: Build a clear playbook for what to do in case your organization suffers a significant data loss incident and stress test that response plan like a fire drill.
  • Consider Acquiring Cybersecurity Insurance: Another risk-mitigation technique is to acquire cybersecurity insurance from a reputable provider – but please be sure to clearly understand the scope and limitations of any such insurance.
  • Careful Emails & Texts: Unfortunately our digital worlds may eventually be compromised at some point in time so always, always be careful with the contents of your emails and texts and assume they could one day appear on the front page of The New York Times.
  • Learn from Others: Embrace a “growth mindset” mentality in this area by understanding the lessons from companies that have endured significant data loss incidents and learn from organizations like the International Association of Privacy Professionals (IAPP), the Cloud Security Alliance, the National Cyber Security Alliance and the Microsoft Secure Blog.

All in-house counsel have a tremendous opportunity to help their organizations earn more trust with their customers by actively encouraging their organizations to embrace leading privacy and security practices.  Also a big thanks to Legaltech News for publishing an article about my keynote.

Earlier this week I had the good fortune of leaving the remnants of Chiberia for sunny Miami to spend time learning from some of the best and brightest in the data privacy space at the annual Privacy Law Salon Roundtable Event.

This was my second time attending this fantastic event, Microsoft served as a proud sponsor and since Artificial Intelligence (AI) is such a hot topic in the data privacy law arena, we were also provided the opportunity to distribute copies of Microsoft’s book entitled The Future Computed: Artificial Intelligence and its role in society. 

While I learned so much at the Roundtable and had a terrific opportunity to network with many data privacy leaders, here were my primary takeaways: (1) the Roundtable provides a great “blueprint” for the legal and compliance community on how to produce an outstanding and high-impact event; and (2) as we are well into The Fourth Industrial Revolution that has resulted in leading technologies generating massive amounts of data that can help us achieve more but which needs to be properly used and protected, data privacy considerations needs to be top of mind for all in-house counsel.

Over the past several years I have attended my share of legal and compliance industry events, seminars, continuing legal educations, etc… Some have been excellent, some have been good, some have been mediocore and some have been a waste of my time.  In my opinion the Roundtable was better than excellent and here’s some reasons why:

  • No PowerPoints: There were no traditional presentations delivered during the Roundtable. As a result, instead of only a few people talking at you, everyone was talking with each other.
  • “Off the Record” Discussions: Attendees participated in various private group discussions – approximately 20 people per group – on leading data privacy topics. Participants have the opportunity to become acquainted with each other in such a smaller setting and these discussions are based on the Chatham House Rule so people feel more comfortable actively contributing to the conversation and learning from each other.
  • Highly Skilled Facilitators: The leaders for these group discussions are leading law professors who have outstanding credibility and privacy law subject-matter expertise. They are well skilled at keeping the conversations moving forward and drawing upon the insights of the participants to generate an even more robust dialogue. In fact, when I was in law school back in the day I wish I had professors just like them.
  • Built-In Networking Time: The Roundtable agenda is smartly designed with plenty of opportunities to network both between the group discussions and during meals/refreshments.
  • Great Venue: My wife is a realtor in the Chicago-area and she is constantly reminding her clients that real estate is all about location, location and location. In order for an industry event to be successful, the location also needs to be top-notch and you can’t get much better than being in Miami during February at The Four Seasons Hotel.
  • The Attendees: The Roundtable attendees are privacy leaders from a mixture of companies, law firms, cybersecurity practices, academia and the non-profit world. I’ve been impressed with the diverse nature of the attendees and their passion for the privacy space – which also rubbed off on me. After being at the Roundtable for a few days I’m fired up about the increasing importance of data privacy in our ever-changing world and I look forward to continuing the conversation during my keynote on Security and Privacy at the ctrl-ALT-del Conference in the Arizona desert next week.

Last month in a LinkedIn blog post, Microsoft President & Chief Legal Officer Brad Smith identified privacy as a Top Ten Tech Issue for 2019. In addition, here are some trends we are seeing in the data privacy area:

  • The “Internationalization” of Data Privacy: Countries across the globe have been leading the establishment of new data privacy laws. Last May the widely anticipated and transformative General Data Protection Regulation (“GDPR”) became effective in Europe and a few months afterwards in August Brazil enacted a new data privacy law that is GDPR-like.
  • The United States & Data Privacy: It will be interesting to see whether Congress is ready, willing and able to enact any sort of federal privacy law in the near future. Historically United States federal privacy law has been more industry focused with the Health Insurance Portability and Accountability Act (“HIPAA”) and the Gramm-Leach-Bliley Act (“GLBA) focused on the financial services sector. In the meantime, California passed the California Consumer Privacy Act which goes into effect next year and other states are actively considering enacting their own data privacy laws.
  • Rise in Data Breaches:  Cybercriminals are becoming more and more sophisticated and as depicted in this graphic below from an article in The Economist magazine last month, data breaches in the United States continues to increase across various industry sectors:

  • It’s AI All the Time:  AI requires huge amounts of data to help train AI algorithms – and such data needs to be properly used and protected. Facial recognition technology can also present some unique challenges and late last year Microsoft published principles that it will adopt for Microsoft’s facial recognition work.
  • National Security Versus Privacy: Balancing the need for law enforcement to have access to key data in order to protect citizens in the interest of security with the data privacy rights of individuals can be very difficult. At the end of last year Australia passed a law providing law enforcement access to encrypted data.

As organizations increasingly use data to help enable their digital transformation, I believe that both understanding and keeping up to speed on the constant evolution of data privacy/cybersecurity law is an absolutely necessary and foundational skillset for all in-house lawyers – regardless of their company or their area of legal practice. As you look for more opportunities to better serve your clients and earn their trust, think about how you can “skill up” on data privacy and cybersecurity.




The epic Academy Award winning motion picture “The Godfather” starring Al Pacino as organized crime family leader Michael Corleone is one of my favorite movies of all time.

An iconic scene in The Godfather is when Michael informs the family’s longtime consigliere Tom Hagen (portrayed by Robert Duvall) that Tom is “out” as consigliere. Michael is brutally honest with Tom and tells him, “You’re not a wartime consigliere, Tom. Things may get rough with the move we’re trying.” Ouch.

Our clients always deserve the very best from us as lawyers. In fact, I think our clients want us to be “wartime consiglieres.” Here are some guiding principles based on the spelling of the word C-O-N-S-I-G-L-I-E-R-E on how we can all be wartime consiglieres so we can better serve our clients:


A wartime consigliere needs to be an outstanding communicator. This means effectively communicating to our clients in less legalese and breaking down complex legal issues into more easy-to-understand layperson’s terms. Wartime consiglieres also do not write lengthy memos or long emails – instead they know when to tailor their mode of communication to their client by picking up the phone, connecting in-person, using Microsoft Teams, texting, etc…and they craft emails that are no longer than the screen size of a laptop. They also excel at delivering presentations that are not long and boring – but are short and full of energy and enthusiasm.


Wartime consiglieres also pride themselves in being open, honest and transparent. They understand that the foundation of any relationship is built upon trust, are always available at anytime to their valued clients and are always open to receiving and providing meaningful feedback.


Networking and building relationships with others is part of the DNA of any wartime consigliere. She/he is a schmoozer and knows how to “work a room” in order to create, develop and maintain relationships with the right people. Wartime consiglieres also leverage technology and they use leading social media platforms like TwitterLinkedIn and Facebook to develop meaningful relationships with clients, colleagues, partners and competitors.

Smart Risk-Taker

To be considered a wartime consigliere, a lawyer needs to constantly demonstrate excellent judgment when dispensing legal advice to clients. She/he should not focus on theoretical risk when counseling clients – but instead a wartime consigliere provides practical, easily digestible and “street smart” advice to clients. Here is a link to an article that I wrote about the art of Smart Risk-Taking.


Wartime consiglieres are viewed as business enablers and not as business inhibiters. They invest time to understand the business needs of their clients and are problems solvers who drive positive impact by proposing solutions that are aligned to these business needs. They are also skilled at measuring the impact of their work in a tangible and quantifiable fashion to help demonstrate their high-value add to their clients.


The willingness to embrace change and to stretch professionally is another important attribute of wartime consiglieres. As Winston Churchill once said, “To improve is to change, to be perfect is to change often.” Wartime consiglieres are “learn-it-alls” and not “know-it-alls” as they continue to adapt and grow so they can better serve their clients. The growth mindset” mentality as outlined in the book “Mindset” by Dr. Carol Dweck is embraced by wartime consiglieres.


Being an active listener is critical to the success of any wartime consigliere. Listening to your clients, asking the right questions and understanding their important needs positions wartime consiglieres to be customer obsessed and impactful problem solvers.


In order to provide more thoughtful legal counsel wartime consiglieres understand they need to consider diverse and different perspectives on a particular matter. They also recognize that diverse and inclusive teams are higher performing than teams who are less diverse and inclusive in nature.


Embracing a non-negotiable mindset of high integrity and ethics is vital for any wartime consigliere.  They do not “cut corners” and instead they lead by example to promote a culture of compliance within their respective organizations and on behalf of their clients.


Wartime consiglieres are lightning fast when responding to their clients and colleagues. Even if she/he cannot provide an immediate answer to a client’s or colleague’s request for assistance, at a minimum a wartime consigliere acknowledges receipt of the request, let’s them know that she/he is working on it and provides a realistic timeframe as to when a meaningful response can be provided.


During an Association of Corporate Counsel – Chicago Chapter Board of Directors annual retreat I was pleased to learn via a StrengthsFinder assessment that empathy was my number one quality since being empathetic is an underrated and important attribute for all lawyers.  When providing legal counsel wartime consiglieres put themselves in the shoes of their clients. They do their best in identifying with and being empathetic to their client’s specific needs so they can offer bespoke and differentiated legal services.

Always be sure to be a wartime consigliere so you can avoid being “Tom Hagened” by your clients.