Leona Thomas: Kids, career and tech

One of the reasons I started this column was to put the spotlight on people in the community who we might not know about and to get to know another side of folks that we see out and about who are in the public eye. This week’s Portrait falls in the latter category. I too am out and about pretty much and it’s not unusual for me to see this week’s Portrait, Leona Thomas, at the same functions. We’ve chatted briefly, but this week, I had a chance to learn more about the tech wiz. Thomas runs a business and digital transformation consulting company and has more accolades than I have room to publish: CIO, COO, CTO, and more.

Let’s start with the easy stuff. Are you a Philly original?
No. I grew up in Massachusetts, between Springfield, Boston and the Cape depending on the time of year. My parents were divorced so we would switch between families for vacations and between school years.

How did you manage to escape having a “Bahston” accent?
Well, western Mass and Boston have different accents. Western Mass is closer to that neutral accent people strive for. But if you get me home long enough, the accent will break through. 

How many in the family?
I have one sister, and then a lot of… you know I’m mixed race right?

I did not!
Yeah, I’m half Black and half white. I was born six months before the Loving decision, which lifted the ban on interracial marriages! So my parents’ marriage was illegal in about 17 states. I was actually born in PA before we went to Mass, and the nurses at the hospital took the time to correct my birth certificate to make sure it said “Negro.”

So we have a lot in common. I was the president of the Black Student Union at my school and when I went to events at other schools, people would do a double take, “You’re the BSU President?”
I grew up in Mass during the busing era and having that on my birth certificate affected a lot of things, like where I was allowed to go to school. My dad being Black limited where we were allowed to live, since there was still segregation in housing at that time, and as you know, if I had lived down south at the time, I would have been susceptible to the Jim Crow laws there, all of that crap. People forget this is not ancient history. These are lived lives, and we’re not that old. We’re talking one or two generations to know those of us who were subject to the laws and regulations against us. Part of the reason that it was so easy for me to come out is that I grew up mixed race in the ’60s and ’70s where you knew that someone wasn’t going to like you for just being you, so what’s one more thing!

Exactly, and with my family being mixed, you learned to be open to and to love people of all different backgrounds.
Yes, though on my dad’s side of the family, there were extended relatives who struggled with it at first. My great-grandparents were elders of the AME Church, which especially at that time, wasn’t the most accepting organization. So some of them took a little more time to get over it. It probably didn’t help that I came out on national television! My ex-wife and I did one of the first ever nationally televised shows on lesbian marriages. We were on Sally Jessy Raphael in the late ’80s. And that’s how some of them found out that I was gay. I was out to my immediate family and they were fine but it hadn’t gotten out to the rest. Looking back, I probably should have given them a heads up. [Laughing] Apparently, the promos for the show started airing and the family phone tree went wild! But I’m glad I did it.

You groundbreaker you! 

It was special, so many people came up to me later and said thank you or told me that they came out after seeing that episode. Not only were we unapologetically lesbian, but spoke about being married, which was rare at that time. As much blowback as we got, it was worth it knowing how many people said they made changes in their lives because of it.

Nice, so tell me a little bit more about the family.
Well, on my dad’s side of the family, my great-grandmother had nine kids and almost all of them had kids — six-plus in most cases — so it’s a very large extended family. There are a significant number of teachers and social workers, one of my aunts started the HeadStart program for the MD/Mid-Atlantic area. My grandmother was a teacher, business owner and ran the Boys & Girls Club for a while. She outlived three husbands so she was a single mom for much of that time, yet every one of her kids has at least a masters degree and she has a couple of PhDs thrown in there. Education was a priority in our house. You could do anything else, but you’d better keep those grades up.

So my father was a music teacher and when I learned programming, I taught him and he became a systems analyst. On my mom’s side, one of my aunts ran NARAL New Hampshire for over 20 years and was a big activist. There’s actually a day named after her. Her husband later became the state representative. My maternal grandfather was one of the initial founders of what they call “Operational Research,” which was originally part of the military. My sister is a physician’s assistant and I do business transformation and change, helping build and reshape companies.

Wow, that’s a lot. What were you like as a kid?
I was a super jock. I played multiple sports. I swam Junior AAU. I played basketball every chance I got, and soccer. I started playing baseball and then Title IX went into effect and they made me go play softball with the girls, “There’s a girl’s team now so you have to play there.” I would have preferred to play baseball. I played ice hockey. I ran and biked for a while, anything I could do to get outside and physical.

What was the best thing about it?
Honestly, the time spent with my teammates. Our high school was actually condemned while I went there. It was closed a few years later, but at the time, it was still open and the facilities were really bad, so we had to get bussed to another school for practice. So there was a lot of time together between traveling there and back, and during practice. We wouldn’t get home until 9 or 10 sometimes. You would always see me on the bus with my head in my books or on the sidelines sitting in the grass doing my homework! It’s funny. When I went to college, I played rugby, and there are all these pictures of me on the side of the field doing engineering homework! 

Good for you.
[Laughing] Yeah, it was crazy. The school was so bad that whenever it rained, they would move my AP math class to the gym in the basement because water would just pour in from the ceiling. 

Wow. Where did you go to college and what did you study?
I started at UPenn, in engineering, went a year and a half and ran out of money. I’d done an internship in a digital equipment company and they made me a nice offer to work for them but that would mean moving back to Mass and I didn’t want to do that. So I stayed here, did some biomedical research work and took night classes at Drexel. They were one of the only places to offer a BSE, Bachelors of Science and Engineering, so I graduated from Drexel. Many years later, I went back and got my executive MBA. 

What’s a favorite family tradition?
My sister and I have raised our kids together. We’ve adopted several along the way, and we try to do family vacations together. We have one that we refer to as “the trip of sevens,” — seven people, seven days, in seven different theme parks in Orlando. My uncle was an Outward Bound instructor and used us as guinea pigs, so I’ve summited all of the white mountains in New Hampshire and about half the green ones. But we could be hanging out in a box and have a good time. I grew up with two sides of the family who were 180-degree opposites — different races, different socioeconomic backgrounds, different sizes. At one point, there were 15 of us from one side of the family living in a single family home, while the other side didn’t even have 15 people and they had two homes. I’d get on the bus and my world would completely turn. 

When did you come out?
It’ll be 40 years next year. Growing up, I didn’t really see anyone LGBTQ. My dad’s wife at the time had a few friends but it definitely wasn’t something you heard about much, and rarely in a positive light. I didn’t know anyone in my age group. It wasn’t something you thought about. It just wasn’t on the radar as a possibility. But once I got here, I started playing with the Penn women’s ice hockey group, which was a club sport so there were a lot of alumni players on the team, a lot of whom who were openly LGBTQ. I started to hang out and make friends in the community. I went home after my freshman year and realized that I was missing one of my rugby teammates more than was ordinary for just a friend. 

Rugby too?
[Laughing] Yeah, the ice hockey team did that. One day, they offered me a ride home even though I lived three blocks from the rink. They basically kidnapped me by taking a long route home that somehow went through Germantown where the rugby team was playing and I got recruited for that team! 

But anyway, over that first summer, I started to think, “Maybe I’m gay.” And when I came back here, I professed my thoughts to the person who luckily turned me down, which saved our good friendship! But I started to tell people and eventually one of my housemates — a bunch of us rented one of those big houses in West Philly — she and I got involved and once that happened, that was it. I haven’t looked back since. 

I have kids, grandkids and even a great-grandkid and when I talk about them, people assume that I’m straight or was with a man at some point but that’s not the case. [Laughing] I like to say I’ve collected them over the years. As soon as we tag them and say, “You’re mine,” then you’re mine and you’re in. People used to be confused when I talked about being a parent, so it felt like I had to come out repeatedly, still do. It’s like, “Really? You can’t tell that I’m gay?” So I usually try to mention being a member of “Lesbians Who Tech” or something like that. 

How many kids?
I’ve helped raise six kids. Well, they’re not kids anymore. The oldest is now 45! Back then, they were attending MCC with their parent. I was 23 and they were 13, which when you’re younger, is a big difference. There was a point when they couldn’t live at home anymore so they moved in with myself and my wife at the time until they went to college. They were lesbians when we took them in. They’ve now transitioned, and it’s been great to see them continue to develop. We support them 100% but it is interesting to have someone you love transition, knowing them one way for many, many years and then finding yourself having to hit the reset button on your understanding and expectations so that you can fully support them. 

My next oldest is currently engaged to be married and has kids of his own. My sister and I have raised our kids together and she has three who live with her in New England. Basically, if there was a kid who needed us, we tapped them in and they become part of the family! 

That’s beautiful, so what groups are you a part of?
I was on the board of William Way for eight years, which I think is a record and I did their strategic planning for 10 years. I am now on the board of Philadelphia City Rowing, which provides public middle and high school students the opportunity to row and we also provide things like SAT prep, college counseling, tutoring, healthy living coaching, and mentoring. It’s a real wrap-around program to help them develop as a person, not just about what they can do in the water, though that’s pretty amazing. So far, 100% of our seniors in the program graduate and over 90% go on to post secondary education and complete it. I’ve had more than one parent tell me it saved their kid’s life. I’m also on the board of Philadelphia SIM, which is the Society for Information Management and the subgroup SIM Women as part of the National Leadership Summit Advisory Council and the National DEI counsel. I’m also involved with the ITSMF, which is an organization for African-American leaders in technology and I’m part of several other groups in the tech space.

And give me the quick version of what you do.
The best way to describe it: I do business transformation and strategy execution, so I help you build and redefine your company — what’s going on, why things are changing, and what you need to do when you’re negotiating a major change. I often work with them through the process. Right now, I have my own consulting company and over the years, I’ve also worked with some of the bigger companies like Computer Sciences Corporation and Slalom as internal executive leadership while running my consulting company as well. I’ve been doing this type of work for about 25 years and what’s great is that because it’s all about change, it’s never the same thing twice.

OK, two random questions. What is something you would like to learn how to do?
[Laughing] I’m about to show off my geekiness! With all the stuff that’s going on with AI, I would love to figure out how to create a framework and understanding of and how to help identify where there are gaps and biases in the data. Things that are driving misinterpretations that unintentionally — and intentionally — reinforce cultural and systematic biases. A lot of times people don’t even realize that there’s stuff missing in the underlying data and I haven’t so far found any consistent, structured way to correct it. It’s something I’m looking into. 

Your best birthday?
There are two that come to mind. The first was my 25th. I was living in Northern Liberties in a two bedroom, tri-level apartment and we had such a big bash. I almost got evicted! Luckily, I was smart enough to invite my neighbors but the landlord got wind of it and heard that there were over 200 people in the apartment that night through the wee hours of the morning. 

The other one was when I got to spend three-and-a-half weeks in South America. I was on an Olivia cruise and the morning of my birthday, we went from Buenos Aires to the Iguazú Falls so I spent the day hiking. The hike takes you on a seven-mile stretch that has three major drops the size of Niagara Falls, and 200-400 waterfalls depending on the rain. So I woke up and spent the day on the Argentine side and then went to the Brazilian side to watch the sunset. It was a pinch-me moment. As a kid growing up in the failing city of Springfield in a high school that was condemned, I couldn’t have imagined where my life would go.

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