Curious Minds: Legal needs to overcome its “imagination problem,” says Olga V. Mack, CEO at Parley Pro

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Curious Minds

We continue our monthly column, “Curious Minds”, created by Rose Ors to tap into the minds of legal innovators, disrupters, and out-of-the-box thinkers to learn what influences and inspires their work.

In this column, Rose speaks with Olga V. Mack, CEO at contract management platform Parley Pro, about where she finds inspiration, the value of imagination, and the lessons learned from her father.

Rose Ors: Who are the leaders and thinkers outside the legal industry that have most influenced your work?

Olga V. Mack: My father has been my biggest influence. He imparted three lessons that have had a huge influence on my life, my law practice, and the way I interact with others. One, is that the stories we tell ourselves define us, so we should be very choosy about what stories we tell. When my father took me to enroll in high school shortly after immigrating to the United States, neither of us spoke English. I told my father I didn’t want to ask anyone for help because I was afraid no one would understand me. He looked me in the eye and said, ‘Olga, those who want to understand you always will. You just need to assume they will, and everything will be fine.’ I find that lawyers consistently tell stories about themselves, such as they are risk-averse, they don’t like technology, or they are special. I think we should be more careful about placing such limits on ourselves.

The second lesson I learned from my father is that a lot of limitations we have are self-imposed. I had reservations about attending law school. I told my father, ‘You know, when people have big legal problems, they probably never would imagine that a girl named Olga with a Russian accent is going to come to their rescue.’ My father replied, ‘Olga, you will find people often have imagination problems. Do not let their lack of imagination limit you.’ When I talk to people in the legal industry, they all tell me they cannot imagine the profession adopting this or that significant change. Every time I hear someone respond with such incredulity, I can’t help but think they need to work on their imagination.


Everywhere I go, people tell me they cannot imagine lawyers adopting technology, using data, embracing other professionals. So, the big question for me is, when will we overcome the imagination problem in law?


The third lesson is that relationships and collaboration are important. When my father was mulling over a problem, he would share it with his friends and acquaintances, literally walking around town to discuss it with them. He always returned with numerous solutions. I really do find that when you interact with peers in your function or in different functions, you will find solutions that were not available to you before.

Rose Ors: What books have influenced how you think about business?

Olga V. Mack: After immigrating to the United States from Ukraine, I discovered the book, Drawing on the Right Side of the Brain by Betty Edwards. It is one of the world’s most widely used instructional drawing books. It reinforced two revelations I had as a child learning to become an artist. The first was that having the right mindset and the right tools can completely transform your abilities. The second was that skills are learned.

In my kindergarten class, our drawings were ranked from best to worst. Mine were always the worst. So, when I was older and told my mother I wanted to go to art school because my best friend was going, she was naturally skeptical. But she relented, and I was fortunate to have an exceptional art teacher. He taught me how to look at a three-dimensional world and put it in a two- dimensional space, in a precise way. He completely changed how I see the world and my ability to capture it through my art. I went from being artistically challenged to seriously considering becoming a fulltime artist with a portfolio to back up that ambition.

What I learned in art school I have applied to law. For example, there are those in the legal industry that assume that somehow lawyers are born. My experience learning to become an artist tells me otherwise. There also is a tendency among lawyers to accept things as they have always been. Seeing the world as an artist has debunked this narrow view. For example, at Parley Pro we are completely rethinking what contracts are, how they are negotiated, and what constitutes an appropriate, productive relationship with a contract. We are inspired to build the right tools and teach people new skills.

curious minds

Olga V. Mack, CEO of Parley Pro

Rose Ors: Where do you find your most creative ideas?

Olga V. Mack: I find inspiration in the intersection of doing the right thing, technology, and art. Many people go to law school because they have a definition of justice they want to pursue — I did. That pursuit has led me to be an advocate for women in leadership roles. To that end, I co-founded two non-profits — SunLaw and WISE — to help women in law reach leadership roles in their organizations.

Living in Silicon Valley has shown me how technology completely changes our lives — I love how it tickles your imagination and challenges your every assumption. Our relationship with technology forces us to have an open mind and continuously work on our imagination.

Art has a very special place in my heart. Not only because I was trained classically as an artist, but because I think the world is changed by artists. Artists are risk-takers, open and spontaneous. They challenge the status quo.

Rose Ors: What is a big-picture question facing the legal industry today?

Olga V. Mack: I am going to bring this back to a point I made earlier about imagination. Everywhere I go, people tell me they cannot imagine lawyers adopting technology, using data, embracing other professionals. So, the big question for me is, when will we overcome the imagination problem in law? It is time for us to imagine a better legal industry, one that serves everyone by using 21st century tools and adopting new behaviors.

This country was founded by lawyers who were agents of change, creating something amazing based on a radical idea. We should build on that legacy.

Rose Ors: Moving now to a top-of-mind question. How are you communicating to your team at Parley Pro and your clients during this pandemic crisis?

Olga V. Mack: While the crisis affects everyone, it affects everyone differently. Some members of my team enjoy the flexibility of working at home. Others miss not going to the office and feel a bit isolated. So, it is critically important that I communicate individually with each member of my team.

The same individual approach applies to our clients. All of our conversations with clients are focused on truly understanding how each of them has been affected. Only then can we fashion solutions that are tailored to what they need from us.


This interview has been edited and condensed by Rose Ors.