An Incredible Man (and the Making of a Champion): TIM Initiative featuring Matthew O’Leary

Seven years ago, when Matthew O’Leary and I were still fresh out of law school, wide-eyed and swimming with big sharks, we ran into each other at a wine festival. Two brand new lawyers talking shop in the summer sun. Somehow the discussion turned to women in the law and Matthew informed me that “women in the law are now equal--just look at law school enrollment!--and they just need to catch up in the partner ranks.” Full stop. Whaaaaa?

I vowed NEVER to do business with him.  

Two months ago, Matt and I opened O’Leary Wallace LLP. I’m going to tell you why at the end of this post, but first, let’s chat with him.

So, Matthew, do you remember telling me that women are equal in the legal profession and just need time to “catch up” in the partner ranks?

Wow! Why does my chair feel so warm all of a sudden?

Vaguely? Sort of? Maybe?

Sorry to put you in the hot seat, partner! What changed your mind?

I would say, not really in self defense but as an explanation, that in law school I was surrounded by awesome, accomplished women, including my law school best friend (shout out to you, AK!) and observed the women to be having a seemingly equal experience.

Since law school I have seen that the real world is not a university setting nor is it a collective of open-minded 20-somethings.

One of the real eye-openers for me was hearing a story from an accomplished female colleague. In a deposition, opposing counsel used several demeaning terms toward her and then, at one point, slammed his hands on the table, jumped out of his chair, and literally touched her face with his finger in an aggressive manner. I talked with her about this right after it happened and she was still very rattled. I could hardly believe such a thing was happening in 2010+. Just as much of an eye-opener as knowing such things still happen, was recognizing that I could not even relate to such an experience. I will never have to go through what she did.

After becoming a father and watching my wife juggle all the demands, responsibilities, and pressures of motherhood while also maintaining her own career gave me a front row seat to watch not just how difficult it is to do both things, but how there are a lot of societal pressures working against the woman trying to do so.

Also, I'm no longer drinking wine with you on summer days if you're going to call me out on Ms. JD.

Ha! This is all for good. Once we decided to open a firm, you got a real-life picture of some implicit bias. It was maybe the first time you’ve seen this sort of thing first-hand in our profession. Tell us about that.

Well, Janet, after we told people that we were leaving our respective firms, many people said that you probably didn't want to work in the big firm model because you were too focused on being a mother. We both have young children, but not a single person said that I wanted to be self-employed so that I could focus more on being a father. The double standard and the silly presumption was open and obvious.

We’re a small firm--just the two of us (at least for now)--but you’ve already said and done some things that demonstrate your commitment to diversity. As one example, you suggested that we not use a certain professional service company because they did not show a commitment to diversity on their board of directors.

I am a huge fan of Justin Dillon and the Made in the Free World movement.  If you don't like what an organization does, refuse to give it your money. This is the best way to affect organizational change. At O’Leary Wallace, we will choose service providers and support causes that reflect our values. Among those values are commitments to diversity and inclusion.

Do you think some men are afraid to have an open dialogue about gender equity in the upper echelons of the legal profession? If so, why? What can women do to encourage that conversation?

Part of the problem is that men simply don’t know. I don’t have to worry about another attorney aggressively touching my face during a deposition. Nobody suggests that I make work-related decisions because I’m focused on raising children. Frankly, I was not fully knowledgeable about the implicit and explicit prejudices women face in the workplace and I suspect that many men are in the same boat. So, what can women do to encourage that conversation? I think by initiating--nay, requiring--the conversation in the same way you have, Janet (i.e. fully informed, with kindness but determination), other men, ignorant to some of the challenges women face, will demonstrate tangible change as they become more aware.

You’re definitely an incredible man (I wouldn’t partner with you otherwise), but it’s my goal to turn you into a true champion for the advancement of women in the profession. On that note--are you so excited to attend Ms. JD’s Conference on Women in the Law next year?

DEFINITELY! And I really hope the Conference location is near a warm beach. We only get to the beach 1-2 times a week around here in San Luis Obispo, which is not nearly enough. 


Turns out, Matt’s okay. Better than okay. He’s truly incredible. He’s an excellent attorney, a phenomenal law partner, a steadfast advocate, an exceptional parent to his children, and one of the kindest people I’ve ever known, hands down. Like many male attorneys, the issues we are passionate about at Ms. JD simply were not on his radar--but a lot has changed in six years. He’s always been good, but now he’s better than ever because he gets it. Maybe, someday, he’ll even be a Frank-Kimball-level champion for women (is it even possible? We're talking grandmaster status.).   

First step in getting Matt to true champion status? Induct him as a bona fide member of the Argentine Beverage Society. I’ll print up a membership card and, in the tradition of TIM Initiative’s namesake, Tim Miller, I’ll send Matt down to the market to buy some Malbec. Stop by our office anytime--we’re toasting to incredible people and new adventures!

Ms. JD launched The Incredible Men (TIM) Initiative in 2014 to celebrate men who are active champions for women’s advancement in the legal profession. These men not only value equality and diversity in the profession, but earnestly and enthusiastically support women and women’s initiatives. Ms. JD’s TIM Initiative was named after Timothy Miller who served on the Board of Directors of Ms. JD.  

O'Leary Wallace LLP is a community-based law firm dedicated to providing a personalized experience for each client. Find us at www.olearywallace.com. We’re also on Instagram @OlearyWallace & Twitter @Oleary_Wallace.

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