Dennis Garcia is an Assistant General Counsel for Microsoft Corporation based in Chicago. He is admitted to practice in New York, Connecticut and Illinois (House Counsel). Dennis is a Fellow of Information Privacy, a Certified Information Privacy Professional/United States and a Certified Information Privacy Technologist with the International Association of Privacy Professionals. He serves on the Board of Directors of Illinois Legal Aid Online and the Association of Corporate Counsel — Chicago Chapter. Dennis is also a member of the Illinois State Bar Association’s Standing Committee on the Future of Legal Services.

Tell me about the first piece of technology you owned that made you go WOW!

One of the first pieces of tech that I owned was an Atari video game console from the late 1970s/early 1980s that my brother and I received as a Christmas gift from Santa Claus. We played lots of Pac-Man, Asteroids, etc., back in the day. I recently purchased an Xbox One S gaming console and my 5-year-old son and I enjoy playing Xbox games — which of course are a bit more state-of-the-art than they were in my Atari days.

Now tell me about the latest tech that has made you go WOW!

I am excited whenever I participate in demos wearing the Microsoft HoloLens headset. The HoloLens technology involves mixed reality that brings people, places and objects from our physical and digital worlds together. This blended environment becomes our canvas, where we can create and enjoy a wide range of experiences. Here’s a link to an article that I wrote last year in Bloomberg Law Big Law Business regarding some potential use applications for virtual/augmented/mixed reality in the legal profession: here.

Where did you grow up and how much of your youth affects the decisions you make today?

I was born in the Bronx, New York and was raised in the suburbs of New York City. I was fortunate to be raised by loving parents and I also developed a very close relationship with my grandparents. My family instilled upon me values such as education, humility, hard work, empathy, diplomacy and always remaining positive. I have tried my best to continue to embrace those values and I believe they have served me well both professionally and personally.

What is it like being in-house counsel for such a large company? I imagine 100s of lawyers sitting in giant open spaces, conferring, although it’s possible I watch too many movies. What is an average day like?

It is an absolute honor to be part of the Microsoft Corporate, External and Legal Affairs (CELA) team. I have the privilege of working closely with and learning from so many outstanding lawyers and legal/business professionals in CELA. I am a member of our US CELA Field team and my colleagues and I provide a wide range of legal support to our world-class sales, marketing and operations teams across the US. Our US CELA Field team is scattered across various US locations and we are “embedded” with our business clients so that we are better positioned to serve as their trusted legal advisors.

Although our US CELA Field team is largely decentralized, we — and our entire CELA team — are power users of our highly secure and trustworthy Microsoft cloud computing solution known as Office 365. Office 365 provides us with anytime and anywhere access to key tools like Skype for Business, OneNote, One Drive for Business, SharePoint Online, Yammer and Teams, and these tools enable us to seamlessly collaborate, be more productive and achieve more.

An average day for me can range from serving as the lead negotiator on a high-profile cloud computing contract discussion with a large strategic customer to evangelizing Microsoft’s trusted cloud narrative to members of a customer’s legal team to sharing some best practices/lessons learned with my CELA colleagues who are located in other parts of the world to serving as a mentor to more junior members of our CELA team to providing legal/compliance readiness training to my business clients.

Microsoft has undergone a lot of changes over the years, certainly in the 15 years or so since you have been there. I am certain you and your team are often presented with new (and interesting) challenges as the company evolves. Please tell me about them.

prefer to view challenges as “opportunities.” Like any large organization, there is always the opportunity for Microsoft to be even more nimble and agile as we empower every person and every organization on the planet to achieve more. I believe we have made great strides in this area and as part of our continued customer obsession mindset, last month Microsoft transformed its sales organization to better enable it to align the right resources for the right customer at the right time.

Microsoft is moving towards AI and you have written about how people in the legal profession should prepare for AI. How about giving us the executive summary: Just how should this profession best prepare for artificial intelligence? And what will happen if it doesn’t?

I would not just say that “Microsoft is moving towards AI” — instead I believe Microsoft is a leader in the AI space. Microsoft’s vision for AI is one where machines and humans work together to enable greater societal progress and equality, and where the potential of AI is made available to every person and organization. This is a “humancentered” vision of AI — a future where machines augment and extend human abilities and experiences, empowering every individual to realize their full potential, and enabling new socio-economic opportunities. Microsoft has made significant investments in AI research and development, and is a major contributor to the advancement of these technologies. It is enthusiastic about the promise of AI to help understand and address some of society’s greatest global challenges.

In terms of an executive summary of my view of AI’s potential impact on the legal profession, while AI may still be in its early stages, I do believe it is important for lawyers to gain a better understanding of AI, to begin to think about how AI can be used as a tool to both free up time to provide higher-value added legal services and to improve the provision of legal services and not to fear AI.

“I do believe it is important for lawyers to gain a better understanding of AI, to begin to think about how AI can be used as a tool to both free up time to provide higher-value added legal services and to improve the provision of legal services and not to fear AI.”

What do you consider a successful negotiation?

A successful negotiation is one in which both parties work together in a truly collaborative fashion, find opportunities to compromise, earn trust, remain highly respectful and build the foundation for a long-term successful business relationship.

And in an unrelated issue: RIP MS Paint — maybe? Please feel free to express your emotions openly over this news.

I am not sure I have much to say regarding Microsoft Paint other than sometimes tools of the past may not be so suitable for the present.

Microsoft is still being named to Top Innovative Companies’ lists after all these years. It seems impossible and yet here’s a recent article in Fast Company (here). How has the company managed to stay relevant?

Here is an interesting fact: Microsoft is the only company to be in the Top 5 lists for market capitalization in 1997, 2007 and 2017. Our CEO Satya Nadella has previously stated that “Our industry does not respect tradition — it only respects innovation.” I believe that Microsoft continues to be a marketplace leader and an iconic company because it embraces transformation, inclusion and a willingness to make difficult decisions when needed.

Microsoft is developing products that help people, from Minecraft: Education to apps that help the blind. Tell me about work your team is involved in that benefits the community and why that’s important to you?

Over the years Microsoft and CELA have done an incredible amount of work to better serve the community at large. That work is important to me because it makes me proud to be a Microsoft employee knowing that my company genuinely cares about improving our society and our planet.

One new exciting initiative that our Microsoft President & Chief Legal Officer Brad Smith announced last month involves Microsoft’s “Rural Broadband Strategy” to connect rural America to new opportunities. Today, 23.4 million Americans in rural communities lack broadband internet access. The time is right to set a clear, ambitious but achievable goal: to eliminate the rural broadband gap within the next five years. Microsoft believes the US can bring broadband coverage to rural areas within this time frame, based on a strategic approach that combines private sector capital investments in new technologies and affordable public-sector support.

I know you have coached a T-Ball team. My nephew once fell asleep on first base and I had to run out and carry him to second base when the next player hit — a blemish on our good family name for sure! Tell me one great story from your coaching days.

Here’s my best story: I’m a huge baseball fan — and as a native New Yorker I’m a lifelong New York Yankee fan — and I was so excited to be selected as head coach of my son’s T-ball team last year. However, I was then informed that our team’s name was the Boston Red Sox — who are the arch rivals and nemesis of my beloved New York Yankees. While I embraced the “growth mindset,” it was not easy for me to see my son wear a Red Sox uniform and for me to have to wear a Red Sox baseball cap for the very first time.

Fortunately, when I was selected as head coach of my son’s T-ball team earlier this year, our league assigned us to be a member of the New York Yankees team and my son was issued a Yankee uniform with a #2 on its back — which is the same uniform number of Derek Jeter — one of my favorite Yankee players of all time. I now call my son “Little Jeter”.

Here is a question I ask everyone I interview: What is one invention not yet in existence that you would want right now?

It seems like many of us in our society are becoming increasingly sleep deprived (including myself at times) and that can inhibit our ability to be our very best in our professional and personal lives. I would like to see an invention that could help ensure a restful night of sleep for all of us without that invention causing any negative side effects.

And finally, is there anything else you’d like to add?

I would like to thank you, [ROSS CEO/Cofounder] Andrew Arruda and ROSS Intelligence for the opportunity to participate in this profile. I had the opportunity to meet Andrew and serve on a panel about AI in the legal profession with him in New York City earlier this year. I learned so much about AI from Andrew during that panel session and I enjoy following Andrew on Twitter (@AndrewArruda). My Twitter handle is @DennisCGarcia if folks are interested in following me.

‍