Leadership in Phase Three of This Lawyer's Life

Sigalle Barness | July 20, 2022

On this week’s episode of Lawline's Lawyers Who Lead podcast, Sigalle interviews David Mann, Angel Investor at Launchpad Venture Group and former Chief Legal Officer for Dunkin Brands and General Counsel for Marriott International, Inc. David discusses what leadership looks like in phase three of life, a time where he focuses his experience on helping his children grow, funding startups, and mentoring first-time entrepreneurs. Listen to the full interview or read highlights of the interview below! Transcribed answers were edited for readability.



Interview with David Mann


On a Piece of Gratitude

Having Breakfast with His Three Kids


My favorite thing that happened today is I had breakfast with my kids and I talked to them about their day and I sent them off to school. And that's a great way to start your day. 


On What Drew Him to Being a Lawyer

An Accidental Lawyer With a Curious Mind


I was one of these people who was an accidental lawyer. In college, I didn't really know what my major was gonna be. I was really interested in philosophy, which prepares you for either teaching philosophy or becoming a lawyer. You have to read a text very closely. You have to be prepared to argue it one way or the other. And you have to be a skilled communicator. It's a good place for a curious mind. It's a good place for learning about learning. I do think that was a good way to prepare, but I think almost any undergraduate degree in liberal arts can prepare you for law school or business school or similar degrees like that.

Then I spent a year after college trying to get a job and not being successful. And then I took the LSAT. Did pretty well and went to law school

And even in law school, I wasn't sure if I wanted to be a lawyer, but I knew that law school could be a springboard to many things and it turned out to be true for me. But I really fell into it for lack of a better thing to do and I'm glad I did because it's been a very rewarding career and I've made a lot of great relationships through the law. And so it's just a great platform for doing almost anything in life. 


On His Time in Private Practice

Great Training and Fast Paced, But Ultimately Wanted to Go In-House


At my law school, you were invited by a lot of law firms to interview and it was the thing to do. So I learned how to tie a tie and went to a bunch of on-campus interviews and, you know, it's very enticing. They fly you to whatever city for an interview and put you up at a nice hotel and take you to a nice dinner. And it sounded like, wow, that's a pretty cool lifestyle to have and the money wasn't bad. So I just again fell into that one. I figured that would be great training to work in a law firm and move to a big city. I'm from a small town. So moving to Washington, D.C. was very exciting to me. 

I'm from Southfield, Connecticut, uh, small town in Northern Connecticut. So I was intrigued with living in a big city and meeting people from all over the country, all over the world, and it was exciting and fast-paced. 

It was a corporate practice. It was M&A, it was finance, it was securities. It was a very small group so whatever client came in the door, whatever work had to be done, we would be assigned to do it. So it was a lot of holding your breath and trying to breathe underwater, while learning at a very rapid pace. But I think that set me up well to have the confidence to tackle almost anything, even with no background. You realize you can come up to speed faster than you think on almost any topic that's not technical in nature.

And I learned a lot and I still have a lot of great friendships from my time at the firm, but ultimately I needed to have a life. So that's why I left, went in-house.


On Advice For Lawyers in Private Practice

Keep Your Options Open, Return Every Recruiter's Call, and Inquire About All Opportunities That Come Your Way


I would just say keep your options open. I would return every head hunter's call and ask questions about every opportunity that came in the door. Some people love private practice and stay in it their whole careers and I know a lot of successful lawyers who've made that a career and they're very happy at it. 

But it's very challenging from a personal point of view to manage, getting clients, keeping clients happy, managing lawyers, managing an office. It's a very time consuming career. So it just depends on what you want out of a career.



On Working for Marriott International Inc. for 23 Years

Culture of Long Term Employee Retention, Growth, and Vast Opportunities


It was a cold call from a recruiter. I'd never done any work for Marriott. I didn't know anybody who worked there. I was so busy at the law firm that I actually had to cancel my first interview. Which ironically, I think made me more interesting as a candidate that I was so committed to my job that I would cancel an interview to make sure the work got done. So maybe that's something people can use as a strategy. 

But in any case, I came in not knowing anyone and found a terrific culture and a very interesting company. Lodging is just so fascinating and rewarding in so many ways including as a traveler, most people listening will have stayed at Marriott hotels or hotels like Marriott. And it's just a great group of people to work with. 

[Worked there for] 23 years which, believe it or not, is not that unusual at Marriott until you hit your 10th anniversary, you're still considered a newbie at Marriott, at least in the old days. And I think it's still largely true that people stay there and make a career there. Because lawyers are given a lot of opportunities at Marriott, that I guess is a little bit unusual. I think over my career at least one lawyer per year would go and take a job on the business side as we called it. So you had lawyers doing development deals, becoming hotel general managers, becoming regional managers. A lawyer even became CFO and then a CEO of the company. So lawyers really were almost like a training ground for senior executives in the company. So again, back to that idea that being a lawyer can open up doors and you really could create possibilities for yourself at Marriott. 

I never did that. I always, uh, stayed in a legal role, but I felt like lawyers were given such latitude of responsibility. And we're listened to on non-legal matters. If you establish your credibility, you could be sitting at a table discussing something that has nothing to do with the law, but you're just there as another person thinking about how to solve a problem and come up with the best course of action. 

It was very much a matrix organization. And so you had a team working on almost any project and the team would involve business people, accountants, lawyers, communications people. You would get a lot of exposure to other groups in the company. There was obviously a lot of travel, a lot of conferences. Very much a team based and a committee based process. So you got to hear from a lot of experts. You got a 360 degree perspective on the business if you were willing to patiently listen and ask questions. 

Lawyers were not put in a box. We weren't uh, a speed bump on the way to decision-making. We were really a part of the process from beginning to end. And that was the source of a lot of career satisfaction for me and many others. 

You might change your position or your role every two to five years, just as though you were changing companies, but you're still within the same company and there's that many opportunities. People do build great portfolios of knowledge across different organizations and parts of the business, which you really need because it's a more complicated business than a lot of people realize it is. 


On the Leadership Principle He Learned at Marriott

Watch and Emulate Leaders Who Want Others to Succeed


So many things. Not from being taught in a classroom setting, but from watching role models, watching good leaders in action. And there were a lot of good leaders at Marriott. So I guess what I would say is I tried to emulate the people that I admired the most, and that includes the senior leaders in the law department, some of the senior leaders in the clients that I worked with. Anyone from a general manager of a hotel to the general counsel of the company.

Lodging is largely about managing people, at the consumer end of it. Lodging tends to promote people and attract people who really wanna be with other people and wanna see other people succeed. And that was a great environment to be a lawyer in because you got exposure to that kind of person, that kind of personality.

And I really benefited from rubbing shoulders with really great leaders who cared about people, took the time to explain to them how their job fit in, and gave them the tools and the opportunity and the encouragement to keep progressing in their career and not be afraid of opportunities that seemed like they were beyond their capabilities. And I received that advice and I took that advice to keep pushing myself in my career. 


On His Move to Dunkin’ Brands

Wanted to be a GC at a Public Company and Also an Opportunity to Go Back Home with an Iconic Brand


I wanted to be the general counsel of a law department for a public company. I love consumer brands and it was like coming back to New England for me too cause I had lived in the Washington, D.C. area for many years. So it was a perfect opportunity to come back home. To lead a terrific team and work for an iconic company, which is sort of the equivalent of the Boston Red Sox. Here in Boston it's the home team when it comes to coffee and donuts. 


On His Experience at Dunkin’ Brands

Culture That Is People First, Consumer First, and of Serving Self Made and Often First Time Entrepreneurs


So I found another great culture in Dunkin' that reminded me a lot of Marriott. Really a people first culture, a consumer culture, a culture of caring and serving others. 

Marriott both manages hotels and franchises them. So it's sort of a dual system. Dunkin' is a hundred percent franchised. So a lot of the work at Dunkin' involves relationships with a wide variety of franchisees all over the country and all over the world. So that's another constituency that I was familiar with, and that brings a lot of great ideas and enthusiasm and dynamism into a business. 

A lot of people don't realize when they go to a Dunkin' that there's a local person, many times they're a first time entrepreneur. Most of them are self made and that's their livelihood. That's everything they own is in this store or series of stores. And that's exciting to be around. 


On Connecting Entrepreneurship and Franchising Work with Mentorship

Working for Entrepreneurs Provided Lessons He Can Pass to Others


Yeah, you know, I hadn't even thought of that. It's a good observation, but I guess I've been around entrepreneurs my whole career. Bill Marriott was an entrepreneur when he was a young man and always was. That is a family business. Dunkin' is largely a business of small family operators. So I guess I was familiar with the mentality. And some of the lessons that I learned from them, I can hopefully bring to other first time entrepreneurs. And a lot of it is just encouraging them that they can do it. 

You don't need to have a degree. You don't need to have years of experience. You need to have passion and the capability to do hard work and to work well with people. That's really what it takes in almost any business like that. So I feel honored to have been able to learn those lessons and hopefully bring them to people just starting out.


On What Phase Three of Life Means To Him

An Opportunity to Try New Things and Chart Your Own Destiny


I don't think three is the last, so I don't know. I got that from someone else. I'm not sure what book I read, but phase one, you're growing up, you're educating yourself. Phase two, you have a career and family. And phase three used to be, you get the gold watch and you sit in a rocking chair and you take care of the grandkids. 

Well, that's changed obviously. Phase three, anyway, phase one and two haven't changed that much. But phase three people are retiring earlier. I retired younger than I ever thought I would. And my kids are still young.

So there's so many more possibilities as we're living longer and living healthier than there ever were before. I just thought this is an opportunity to just try new things, almost like going back to college again, try new things, see what you like to do, chart your own destiny. It's great to have free time and the ability to do new things.


On Making the Decision to Move to Phase Three of Life

Dunkin’ Acquisition Created Time to Reflect on What’s Next


Well, it was handed to me. Um, our company was acquired. A lot of positions were eliminated, including mine. And so I had a choice. Do I go back and look for another job or don't I? And I guess COVID and the great resignation influenced me, like so many others, to not just automatically go back to work and continue doing that. So I thought to myself, I'll have a test period and see how it goes. And it's been just a few months, but it's going great. 

And I found things to do that, again, came at me out of the blue. A law school classmate in Boston I hadn't talked to for 20 years, I got in touch with her and she introduced me to EforAll Roxbury, which is the mentoring program I talked about earlier. 

And that was terrific. I signed up as a mentor and through that connection, I met another mentor who, heads up, she's the executive director of Launchpad Ventures, which is a large angel investment group. And I just sort of cold called her. And she said, why don't you think about joining launchpad?

So I was on a few calls. I talked to some people and now I'm a member of an angel investment group. If you had asked me a year ago, if I'll be doing either of those things, I would've said, no. Why would I be doing those things? So I guess it's just only willing to open up your mind to new things and trying things out that are not in your wheelhouse or what you've done before is how I'm doing it. And so far so good. Maybe I'll be doing something completely different in three years and I'll be calling that phase four, who knows? 


On the Importance of Keeping Your Network Alive

Keep People in Mind, Plan Reunions, and Contact Those You Haven’t Spoken to in Awhile


So I have friends from high school, from law school, from when I lived in and worked in Atlanta. We just had a reunion here last summer. From Marriott, from Dunkin' and just keep the network alive, whether it's phone calls or texts or emails or social media, however you wanna do it. But the old fashioned phone call is very effective. And this podcast is really nothing more than a radio show, right? It's been around forever. So keep your network alive and you'll be surprised what comes to you.

I think you have to keep people in mind and make an effort to just catch up every now and then. And I'm a big believer in reunions. So we just had a family reunion for some cousins I hadn't seen in a long time. Now that COVID is somewhat more manageable it's more realistic to travel and get together again, especially as the weather gets nicer. 

So I guess keep a rolling set of reunions in mind. Uh, travel to see people, invite people to come see you. There's just nothing like face to face. Right? Nothing like it. So I haven't gone as far as making a calendar of catching up with people, but if I haven't talked to somebody for a year and there's somebody who I consider a friend, I'll just contact them and catch up. Simple as that.


On Becoming an Angel Investor

An Amazing Way to Become Part of the Entrepreneurial Ecosystem


I didn't really know much about angel investing myself until I started doing it, but an angel is someone who usually invests their own money in a startup business. Sometimes those startups are started by experienced entrepreneurs. Sometimes these folks are just outta college or even high school. Who have a great idea and a lot of passion. So we find, or people come to us, asking for not only money, not only capital, but also advice and counsel. Usually we'll put someone on the board of directors of a company and they'll stay with them for years and help guide them through all the obstacles and difficulties and challenges of being a startup.

So it's the opportunity to hear about maybe 4, 5, 6, 7 new opportunities and if you're interested, you can join a due diligence team and do more of a business due diligence, come up with a due diligence report, and then you get a chance to invest in these companies. And you can invest as little or as much as you want, but it's an amazing way to become part of the entrepreneurial ecosystem and a participant in it. And, boy, is it exciting. Talk about learning at warp speed. It's great. 

There's still a wide variety, [but] they tend to want companies that are business to business focused, not so much consumer companies. Often with a technological or software advantage or component to the business. But that's still a lot of categories of business. Also, I should say life sciences and health sciences are also in their wheelhouse and with 170 members, you have, in almost every case, someone who's an expert in that type of business who can come along and give you their two cents and even serve as an advisor to the companies. It really is amazing, to see all the energy in a place like Boston and New England that's going into entrepreneurial activities. 


On Mentoring First Time Entrepreneurs With EforAll

Providing People from Underrepresented Communities with Guidance and a Network 


EforAll started out in Lowell and now there's EforAlls in a lot of different communities around New England and even around the country. So this is volunteer mentors, who have typically had a career, are either still working or retired. And each entrepreneur applies and is accepted into the program and has an intensive three month period of classroom study, as well as regular meetings with our mentors. So with the mentor's assistance, create a business plan, create goals, put together a strategy for one to two years ahead. And you're helping to guide them along the way and it's very powerful. These are mostly people from underrepresented communities who don't have a network in their life.

And this is providing them with the kind of network that everybody wishes they had. So it's powerful, it's exciting and a lot of these entrepreneurs are gonna create jobs in their communities and they're empowering themselves. It's a great program. I encourage anybody who has an interest in this to reach out for the local EforAll chapter.

I've been a lawyer my whole career. I'm a little bit of an oddball in that group. But as long as you're willing to put in the time to understand the business and their challenges, a lot of the advice is non-technical. It's about hanging in there. It's about sticking with your strategy. It's about overcoming obstacles and a lot of it is just about supporting them, telling them they can do it. They have what it takes. At this stage of development, they need a cheerleader.


On Where the Desire to Help Entrepreneurs Comes From

Growing Up Watching His Inventor Father Help Entrepreneurs Take Ideas to Market


Well, probably from my father. He was an inventor and he was a very creative person. He wrote music and poetry and so forth and he created a business where he would help entrepreneurs take their ideas to market. That was his business. And so I just grew up in a house where he was always inventing things and tinkering with things. I can remember as a young kid giving him my two cents on this or that invention that was in the basement. Comes from a family background. 

If you play tennis, there's a different grip for the forehand and the back hand. And you have to constantly be shifting your hand a little bit this way or a little bit that way. So he invented a tennis racket where the grip would actually, uh, rotate. It would click one way or click the other way. And so you would be spared the need to keep changing your grip. We had a working prototype. It never took off, but it could have. Who knows? That's one example. 


On Being a Stay-at-Home Dad

It’s Consistently Listening, Being There, and Helping Them Grow


Well, it's a little bit mundane. It's a lot of driving to soccer games, preparing meals, making sure they get to where they need to go and doing their homework and practicing their piano. 

That's the day-to-day nuts and bolts, but really it's about being there for them and listening to them and helping them grow. So I think that's one of the most important things I'm doing right now. Is being there for them on a consistent basis. I'm always here when they come back home from school with a snack and unfortunately I have to hide monitors and phones so that they're not constantly on social media or playing video games. So it's a little bit of a policeman function too, but this is an age where they need their parents. More than they want to admit. So I'm really thrilled to be there for them. 

And just giving them a hug every day, multiple times a day saying, I love you, just makes everything worth it. 


On Starting at the Harvard Institute for Learning and Retirement

Continuous Learning with Community Teaching with Other Retirees 


I just recently learned about this by doing Google searches and as far as I can tell it's a unique program, they have their own building in Cambridge at Harvard University. And this is entirely made up of retired people, about 500 of them from all different backgrounds. Some have academic careers, some have had business careers, teachers, engineers, scientists, you name it. The courses are taught by the students. So after you have a few courses under your belt, you're expected to teach or co-teach a course and you don't even have to be an expert in it.

These are all retired people and mainly just so you have the time to devote to it. Not, not necessarily that you're a retired person, but that you have that kind of time. You sign up from year to year, but it tends to be the kind of thing where people just keep on doing it year after year. And they have a lot of extracurriculars as they call them. So you could be in a play. You could speak in a foreign language. You can go to restaurants with other people, go to performances. They even have their own literary magazine. 


On What Leadership in Law Means 

Live Your Values and Be a Role Model


You know, I just think it means to live your values. To be the kind of person that someone would wanna imitate. To be a role model. I think so much of what we learn is not formal instruction, but it's observational. You know, think about a teacher that was very important to you. It was usually how the teacher behaved and thought and cared about you. And not so much the formal education that you got in that classroom. So, I guess it would be to try to be a person that others want to emulate that can help them succeed. 


On One Thing to Change About the Legal Industry

Private Practice Should Reduce Hours, In-House Should Get More Paid Leadership Training


Oh, that's a tough one. In private practice I think they need to reduce the hours and make it more of a manageable lifestyle. I think that's the number one problem in private practice and it has been for eons. So I think getting rid of the billable hour has to be part of the solution. 

And in house, I think more attention needs to be paid to leadership education. Especially in larger law departments, but even smaller ones. I think there just has to be more of a curriculum for leadership. I think it would be based on case studies of specific challenges that we all have, hiring, giving feedback, disciplining folks, dealing with, having to terminate someone, how to encourage people to take on difficult assignments, how to encourage people to grow beyond what they think they can do. 

So it really is about managing people and that's an endlessly fascinating topic no one has completely mastered yet. And as a matter of fact, I think budding lawyers in law school should be exposed to a leadership segment that maybe as first years or third years.


On Something People Misunderstand About His Work

Lawyers Aren’t Just Litigators, They Are a Trusted Advisor


Most non-lawyers think you're always in court, arguing like you're on a TV show. I don't think that people understand that lawyers are advice givers and counselors. Many times it has to do with legal issues, but many times it doesn't. You're a counselor. You're someone who is a trusted advisor. And often you come at problems with a different perspective. You don't necessarily have a stake in the game. You can be a voice of reason or impartial reason. And I think a lot of people don't understand that it's a function that lawyers serve and fulfill beyond their technical skills.

A lot of people think lawyers go around looking for loopholes. Most lawyers are telling their clients how to comply with the law. Doing a public good as a result. 


On Practical Advice to Leaders in Law

Never Underestimate the Advice of Others and Seek Advice from Trusted People Who Know You


I would say, never underestimate your own abilities. I tended to do that as a young lawyer, I tended to only want to do what I had already succeeded in. So I would say, push yourself and ask others, whether you think you're capable of doing something because a lot of times they'll see something in you that you don't even see. So really listen to the advice of others as to what you're capable of, but only listen to people who really know you. Don't listen to people who put you in a box and judge you. 


On the Person Who Shaped His Life

His Mother as a Role Model of Calm, Trust, and Good Judgment


I would have to say my mother. She was someone who was calm. Was trustworthy. Had impeccable judgment and really participated in our community. Whether it was in education or she was in local government, but she was someone who people came to for advice and counsel, and always had time to listen and was a great role model for me.


On Self-Care

Exercise, Get Outside, and Untether from Tech


You have to exercise, whether it's taking a walk in the woods, cycling, doing a sport, even just walking, you've gotta exercise. You've gotta get outside. And especially now you have to unplug. I know people are plugged in listening to this, but you've got to get in the habit of turning your phone off, putting it in a drawer and leaving the house and doing something. I really believe that because I found myself putting my phone next to my bedside table and I felt like I was mentally always tethered to it. So I would say untether yourself for quiet contemplative time.


Lawyers Who Lead is a weekly podcast that celebrates lawyers who are making powerful changes through extraordinary leadership. Each week, Lawline’s Chief Storyteller, Sigalle Barness, interviews a lawyer who is driving meaningful change in the legal industry. Guests represent a diverse and exciting range of experiences but with one common thread, the pursuit of bettering the legal profession. 

Each episode explores the guest’s journey to leadership, the underlying principles that helped them make an impact, and devises ways listeners can apply these concepts in their own lives.

Subscribe or follow on Apple Podcasts, Spotify, Google Podcasts, Audible, or anywhere you listen to your favorite podcasts. You can also follow @lawyerswholead on Linkedin, Twitter, and Instagram.  Let's celebrate and continue to build a community of leaders in law together.

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About the Author

Written by Sigalle Barness

Sigalle champions and grows Lawline’s brand awareness through impactful stories that are authentic, meaningful, and thought provoking. She designs communications strategies that underscore the why and how behind Lawline's work. Sigalle is an avid lover of music, video games, blogging, asking questions and all things food. She is also fluent in Hebrew and enjoys writing fiction, traveling and scuba diving.


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