Meet HCBA Member Jennifer L. Olson

by Bethany Lenderink | May 14, 2020
HCBA member Jennifer L. Olson sees litigation as a storytelling practice. “You’re looking at the facts of a situation and putting them together along with the law in a compelling way to make your client’s case,” she said. Now a trial attorney with Best & Flanagan, Olson uses her passion and skill for storytelling to litigate complex business and commercial disputes. “I enjoy being in a courtroom. Just getting up in front of a judge or a jury and explaining your client’s case or their position—which ultimately is telling their story—and then matching it with the law and explaining why their position is the legally correct one. I enjoy the back and forth of the court room, when you get questions from the judge and are really thinking on your feet.”

Olson decided she wanted to become a lawyer early on. “Part of why I was interested in it was that I always enjoyed reading stories and telling stories. At the end of the day, that’s a big part of what litigators do.”  After studying English and political science at the University of Wisconsin – Madison, she attended Boston College Law School. 

Shortly after she started practicing, Olson’s HCBA story began when she began attending New Lawyers Section meetings. From there, she took on leadership roles within the section, including a position as the professionalism director, the events coordinator, and then the section chair. She was also part of the HCBA Finance & Planning Committee and is currently on the Board of Directors. Olson said, “For me [the value of the HCBA is] the people that I’ve met and been able to connect with. I think it’s so helpful to build those relationships with people outside your firm, with different practice areas, with people who have different levels of practice experience. It’s so helpful to talk through things with people, bounce ideas off them, and to get a different perspective. That is really why I’ve stayed involved with HCBA over the years.” Building strong relationships with colleagues and attorneys in other practice areas also enables one to ask for help, which is something Olson says is important to creating a healthy work-life balance. “Everyone has been in a position where they have too much on their plate and people are willing to help.” 


Olson encourages attorneys to be curious. She said, “One of the most important ways to learn how to be a good attorney in any practice area is to just be curious—curious about the world around you, curious about the people you meet, curious about your clients and their cases. Ask a lot of questions. Those two things will help you prepare a case, to develop relationships in the community and build business, to get out and involved in the community.” She also encourages litigators in particular to surround themselves with good writing. “Surrounding yourself with good writing makes you a better writer in turn.”

When she isn’t working, Olson is spending time with her husband and kids. She and her husband, who Olson says is an excellent cook, love hosting and are looking forward to starting that again. She also practices yoga and, of course, spends a lot of time reading.

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