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Kelly Friedman and Stellar Women on the Power of Persistence, Perfectionism, and AI

Blair Cohen

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Our Stellar Women community is kicking off 2023 with a bang. This month’s podcast guest is Kelly Friedman, senior counsel at Borden Ladner Gervais—and our first-ever winner of the Innovation Award for Artificial Intelligence.

For those of you who already know Kelly as a thought leader in e-discovery, buckle up to hear from a side of her you may not have heard before. Simply put, Kelly is an all-star and a problem solver in every aspect of her life—and she has some important, honest stories to share about starting out as a young woman in the law and technology, carrying on in the face of doubt, and building relationships along the way.

Check out a clip of our conversation in the transcript below, or listen to the full episode—here or in your favorite podcast app!—for all the insights.

Kelly Friedman

Kelly Friedman

Senior Counsel and National Leader, Beyond eDiscovery

Borden Ladner Gervais

Partial Transcript

Blair Cohen: How do you balance the fear of going all-in on a new technology versus sticking with what has always worked for your colleagues and clients?

Kelly Friedman: The concept of “all-in” is very interesting because when you say that, it sounds like you're putting all your eggs in one basket. I've never been one to do that. I'm really risk averse and cautious about that. So I think, intellectually, I'm all in on AI because I believe in it. I believe in its power. I believe in its importance in my industry, in the legal industry in general. So when a new tool comes along, I don't have the initial roadblocks that some people have of being scared of AI or skeptical about it.

The issue for me, and for my firm, is our return on investment and the cost-benefit analysis. At BLG, we don’t have skeptics at the leadership level—what they are is smart business people. So they said, “If you can prove the business case for this, then we'll go all in.”

The interesting thing about artificial intelligence, though, is when you actually get down to the brass tacks of working with it, that's when the skepticism creeps. So leadership was comfortable. But when you're working with, for the first time, a particular lawyer who's not used something like continuous active, they're very nervous, they're very skeptical, and you have to deal with that. While I had the benefit of very open leadership, I also have the reality check that, when you get down to brass tacks, lawyers are going to be concerned—quite rightly—that things are being done the right way. They want to make sure they are fulfilling their obligations.

They're kind of perfectionists in that way, right?

Oh, yes. Yes. It's a curse that we all bear.

Just as lawyers may underestimate AI, people have underestimated women in tech and the law since we got into this industry. What has it been like as a woman in law and then as a woman in tech for you?

It was very interesting being a young woman entering the legal profession. I quickly learned there were two sides of it.

One is absolutely you were minimized and underestimated. But the benefit of that is that you can prove them wrong quite easily. So if people have low expectations of you, great—let them have their low expectations of me, and let me blow it out of the water. I did experience all of that when I was a young lawyer, and tried to focus on building confidence so that I would prove them wrong.

I have so many examples of being treated poorly or inappropriately when we look back now. I think the hardest moment for me was during a case I had taken on when a lawyer from Philadelphia called me. He had a cross-border case, and there was a large Ontario component, which is where I practice. I worked on that case for months. And finally, the motion—it was a major contempt motion—was coming, and the lawyer from Philadelphia asked me to bring in “some gray hair.” That's the way he put it, but he was being quite clear that he wanted a man and someone who was older than me at that time.

That was really hard because I was raring to go. I had been working on it for a really long time, but then I had to go to senior lawyer I worked with at the time, who is was my mentor, and ask him if he would argue it for me. It was a bit humiliating. The first thing he said to me was, “Are you asking me because you're scared to do it yourself or you're not confident?”

I felt so small. I said, “Absolutely not. Please don't think that of me. The client wants this. And I think I need to give it to them because this is not a battle I should pick. If I do and I argue the motion, and if we lose, it's going to be blamed on the fact that I pushed back so hard on bringing in someone older who looked a different way.”

So what I had to do is take three days to teach him the case. I remember it was over a weekend, and I had to sit in a boardroom with this partner and teach him the file. I taught him everything, wrote the argument for him, taught him what I had been learning over the past few months on the case. And then I had to sit in the courtroom beside him while he made the arguments—and write him notes for him too.

Those types of things happened. And for the most part, I tried to let them roll off me because, like I said, I also had the positive benefit. I thought of being underestimated and then people being really surprised at how good I can be.

What's a piece of advice you would give to your younger self?

I can synthesize it this way: keep persevering. Take all the time you spend worrying and stressing about your future and put that into building relationships.

Luckily, my children don't seem to have this problem. They have really good relationships. But I'm very aware of it and I wish I had been like that. I was constantly stressed, so constantly worried—and it took me a very long time into my career to change that it's really important to not wait to live your life right.

So don't wait. I was always waiting to feel financially stable or get to a place where I could be comfortable in my career progression, and then have relationships.

I am so happy in my life now. I think I'm happier now than I've ever been in my life. And I think that's because I finally have slowed down and been able to focus on building relationships. I regret not having done it sooner.

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Blair Cohen is a brand program manager at Relativity, representing the company with enthusiasm, authenticity, and her flair for humor. When she isn't shining a light on women in tech via Stellar Women or cracking jokes on the main stage at Relativity Fest, you can find her running around Chicago finding the best places to eat with her dog, Goose.