Assistant General Counsel for Microsoft

Tell us a bit about yourself and how you came to be in (or a customer of) the legal business?

I have been in the legal profession for 20+ years and since my graduation from Columbia Law School I have worked in the in-house legal departments for these three technology companies: IBM, Accenture and Microsoft.

What do you do for a living right now?

I am an Assistant General Counsel for Microsoft based in Chicago and I have worked for Microsoft for 15+ years. I lead our legal support function to our US Enterprise Commercial group – which is made up of our world-class sales teams based throughout the US. My business clients are responsible for selling and delivering a wide range of Microsoft solutions to our large customers – and for embracing a “customer obsession” mindset as they serve our highly valued customers. I also have the privilege of managing a team of outstanding lawyers and legal professionals who are also located throughout the US.

What has been your greatest triumph and your greatest success in the legal services field and what did you learn from each?

I think my greatest success in the legal services field is my willingness over the past several years to be more open to change and to grow as both a lawyer and a leader. As an example, over the past three years I have had three different roles as a member of our legal team supporting our sales teams in the US. I wish I would have been more open to embrace change and “lean in” as a younger lawyer.

Do you think the legal industry is headed in the right direction, the wrong direction – or which direction?

While I think the legal industry is headed in the right direction, I do think it can accelerate its movement in the right direction by being more open to embracing (1) change, (2) technology, (3) a “growth mindset” mentality; and (4) greater diversity and inclusion.

Who – or what – inspires you – and why?

The people who inspire me the most are the very strong women in my family who have been a big part of my life – my mother, my wife, my 98-year-old grandma and my aunt. They have each faced significant challenges during their lives and they have taught me about the importance of health, family, hard work, grit, resiliency, empathy and the power of a positive attitude.

What advice would you give to the younger generation contemplating law as a career?

While I do think our profession will always need outstanding lawyers, nowadays attending law school is a huge financial commitment and finding employment after law school is not guaranteed. I would encourage our younger generation to carefully consider whether law as a career makes sense for them. If so, there are great opportunities to drive impact and serve others.

How ready for change do you think the legal industry is?

I believe the legal industry is beginning to demonstrate that it is ready and more open to change. As an example, I am encouraged by the growing #LegalTech movement and an increasing number of law schools are offering programs and classes to better prepare law students for the growing infusion of technology in the delivery of legal services.

Is more – or different – leadership required? In what ways?

In my opinion, to help drive success and better serve their stakeholders, every industry requires leaders who are empathetic, transparent, willing to learn, open to change, inclusive, highly committed to integrity and generate energy.

How deep do you think will be the inroads of technology in the industry?

I believe we are beginning to see more legal organizations adopt leading technology and that the inroads of technology in the legal industry will only grow deeper.

In ten years, do you see an industry much as it is – or do you see new players, new technology and an altered state?

In ten years, I think we will see a fair amount of change in the legal industry – especially as the competition for the provision of legal services increases and we see younger lawyers and legal professionals – who are comfortable with leveraging technology – assume more leadership roles within legal organizations.

Are consultants and lawyers looking increasingly similar? Should the distinction continue?

While I’m not sure of I have a real opinion if the distinction should continue, I do believe lawyers can learn a lot from consultants – especially in terms of the pricing and delivery of services.

What are your thoughts on the increasing availability of data to guide client-side procurement of legal services?

It has been said that “data is the new oil” and I think that data is a highly underutilized asset in the legal profession and that rich data can really help legal professionals make smart decisions.

Lawyers have typically regulated to keep non-lawyer investors out but that’s a two-edged sword these days. What are your thoughts?

I have not given much thought on this issue, but I am generally a believer in enterprises having access to available markets and capital.

What’s the one most significant factor that will drive change in your view?

In my opinion, fierce competition is a significant factor in driving change.

Are we seeing the demise of the “profession” and the real emergence of the “business” of law?

I believe a trend we are seeing is a movement away from the “practice of law” to the “delivery of legal services.”

What do you consider is the greatest challenge facing the industry?

Any unwillingness to change, adapt and transform.

What do you see as the greatest opportunity for the sector looking forward?

I think the greatest opportunity for the legal sector is to embrace more digital transformation – and to use leading technology and assets like highly trusted cloud computing tools, data, social media and artificial intelligence solutions – to help accelerate the delivery of higher value-add legal services to clients. In fact, here is some information regarding cloud computing and artificial intelligence which may be of interest to your audience: “Digital Transformation in the Cloud: What enterprise leaders and their legal and compliance advisors need to knowand The Future Computed: Artificial Intelligence and its role in society.

Do you think law can improve its track record on diversity and inclusion?

Absolutely. For lawyers to better serve their clients and the public, I believe that the legal profession – and senior leaders in the legal profession – needs to better reflect the increasingly diverse nature of our population.  How? Some things that legal organizations can do to advance diversity and inclusion include the following: (1) be more purposeful in recruiting and retaining lawyers from diverse backgrounds; (2) set the “tone at the top” of your legal organization about the importance of embracing diversity and inclusion; (3) provide training in the area of unconscious bias so that you can foster a more inclusive environment; and (4) learn from other legal organizations and the excellent legal diversity affinity group organizations. In addition, here is a link to some information that our Microsoft legal team has developed regarding advancing diversity and inclusion in the legal profession:

Will the current regulatory framework around law help or hinder it in the future?

I think it depends – but we need the regulatory framework to keep up with the rapid pace of technology change.

Who do you think are the greatest influencers on the industry these days?

I think the greatest influencers in the legal industry these days are our judicial system, large corporate in-house legal departments, large law firms, law schools, alternative legal services firms, and the growing group of #LegalTech providers.

If you had to do it all over again, would you?

Yes. As the immortal Hall-of-Fame baseball pitcher Satchell Paige once said, “Don’t look back. Something may be gaining on you.” Or what would you do differently?

If a law firm was a startup pitching for investors, would you be an investor?


Wildcard questions:

If you weren’t doing this, what would you be doing?

Perhaps I would have been a teacher, professor, sports coach or an architect.

What would you like to be known for?

For being a devoted husband, father, son, brother, uncle, friend and work colleague who acts with integrity and is always willing to mentor and help others.

What would surprise everyone if they knew (they may know).

I like to follow the ever-constant gossip in the world of pop culture and one of my favorite websites is

What’s your favorite hobby or activity outside of law?

I love to travel and this Summer I have already been to Vienna, Toronto, Las Vegas and Alaska. I also enjoy jogging three times a week along Chicago’s beautiful Lake Michigan.

What’s your favorite sports team?

As a Native New Yorker born in the Bronx, I’m a lifelong and avid fan of the New York Yankees baseball team.

What’s your favorite city?

My adopted hometown – Chicago – AKA the Windy City.

What’s your favorite food?

It is a tie between Mexican and Italian food.

What’s your nickname – and why?

I don’t have a nickname, but if I were a professional baseball player, I think my nickname would be “DGar.”