Meet the Boss Who Could Change the Way We Work

Lawyer Mae Tai O’Malley was fed up with the choice too many women in her field were forced to make between a competitive career and motherhood. In 2006 she founded a firm with a new model.

Photo by Harry Who Photography

At Paragon Legal, where most of the 
70 employees are 
women with little kids, attorneys 
decide when and where they work while handling cases for big-name clients, like Facebook and Autodesk. O’Malley, 43, spoke with Real Simple about her 
 path, her family, 
and reimag­ining the way we do business.

What was your 
childhood like?

I was born in southern Illinois, and when I was about 12, we moved 
to San Francisco. My 
parents were both very career-oriented, so 
my older brother and I often ended up taking care of ourselves.

What fields were 
your parents in?

My dad was a professor of linguistics. My mother had a lot of different little ventures, which created some family angst, because she was constantly gone. I probably 
picked up some of her entrepreneurialism. But I knew that whatever I did, I wanted 
to be more present in my own kids’ lives.

Tell us about Stanford.

I went there as an under­grad and majored in political science, music, and Japanese. 
I rowed crew and was recruited as a coxswain for the men’s team.

What was that like?

It was a huge part 
of my life there, and 
it shaped a big part 
of who I am today in terms of how I handle a lot of my interactions.

How so?

Many years ago, I was sitting in a conference room, pitching to a group of potential clients who were all men and all Caucasian. I realized that for years as a coxswain, that was my world. As a coxswain, your whole job is to motivate. You have to find a way to be compelling to that crowd. You’re literally shouting at them and hoping that they listen to you. At first [being coxswain] was terrifying. But after a while, I had no problem with it.

What was your 
career path?

I started at a large, traditional law firm. Later I worked part-time for various technology companies. I got asked to do some work for Google in 2006. I had three kids at that point and couldn’t take on all the work, so I thought, I’ll just hire one other mom. In looking for that person, I met a number of attorneys. That was the start of Paragon. The demand for work was there, 
so I started bringing them on.

How does it work?

We start the interview process asking, “What kind of hours are you looking for, ideally? How far are you willing to travel? How long a project are you willing to do?” Once we get all that information, we look at what we have and try to match accordingly.

Your lawyers are 
generally moms with school-age children.

Yes. It’s not uncommon for our attorneys to take a two- or three-hour window at 5 o’clock to pick up their kids from day care, get them home, and spend a little time with them before 
getting back to work. 
As long as you’re getting the job done, it shouldn’t matter where or when you’re doing 
it. We’re very focused on the needs of the attorneys, knowing that when they do good work, that will bring us more clients.

Tell us about your management style.

I think I’m very good at distilling problems, getting past the emotions and all the other stuff. That’s been super-
helpful in my job. When resolving disputes, I like to ask, “What is it really that’s making 
you unhappy? Let’s get to the core of that.”

You and your family recently moved 
from San Francisco 
to Taiwan.

My dad moved back 
to Taiwan many years ago, and my three boys have been educated bilingually since they were born. Every summer since 2006, I’ve been bringing them
 to see my dad and to spend time in the place where their 
roots are. The kids enjoy it so much, and with our businesses, we could do it. (My husband runs his 
own online financial-
services company.) 
 So we decided to live there. The kids are now 13, 12, and 10 and in school in Taiwan. I travel monthly [to San Francisco] for work.

How does your 
company flexibility policy play out in 
your own life?

Especially because 
I’m in Taiwan right now, I do a lot of 
work at night and a lot of work in the morning. I take off from my office at, say, 3 o’clock to go pick 
up the kids, take them to their sports, and make dinner. Then I get back to work.

What does success look like to you?

For me, success is doing things for 
both my family and 
my community that will have a lasting impact—anything 
that could influence how women and 
girls might approach 
a career. I tell my kids that ultimately we’re put on this earth 
to help other people.