The Importance of Lawyer Mentoring: Perspectives From a Mentor and Mentee

In this interview, we talk to Cathy L. Cupp and Grant Ossler, a mentor and mentee in the Commission’s mentoring program. Cathy and Grant discuss how mentoring has helped them weather job changes and expand their career prospects as well as an attorney’s obligation to pass the torch to the younger generation. Cathy and Grant participate in the Commission’s mentoring program through the Chicago Bar Association. 

Want to jumpstart your professional development and earn free CLE? Become a mentor or mentee! Find out how to sign up here. 

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  • 0:08 – Why did you join a mentoring program? 
  • 1:36 – What opportunities have resulted from your mentoring partnership? 
  • 2:53 – How has your mentoring relationship evolved since the pandemic began? 
  • 4:34 – How does mentoring fit into your overall professional development strategy? 
  • 6:37 – How can mentoring strengthen the legal profession? 

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Cathy L. Cupp 

Cathy Cupp has executive management and general counsel experience for a broad base of companies including global publicly traded companies, mid-size global companies, small regional companies and tech start-ups. In these roles, she has also participated in Board management as Secretary.

Ms. Cupp is presently the Principal of CLC Legal Services providing general counsel services for small and medium-sized companies and tech start-ups. She recently served as Chief Administrative Officer, General Counsel and Secretary of the Board of Total Home Health, a Midwest leader in the home medical equipment space. Besides providing for the legal needs of Total Home Health she was responsible for executive management of key accounts and Board management. Prior to joining Total Home Health in 2013, Ms. Cupp served as general counsel and Secretary of the Board for Enesco, LLC, a global leader in the giftware and home and garden décor industry. Ms. Cupp also spent 13 years at Galileo International, an electronic global distribution company for the travel industry and guided the company through many transactions and corporate status. These transactions included an international merger resulting in a Delaware general partnership of 11 international airlines, taking the company public and a sale to Cendant Corporation. While at Galileo International, Ms. Cupp was Senior Vice President, General Counsel and Secretary managing an international legal department. Ms. Cupp began her legal career at the law firm of Chapman and Cutler.

Ms. Cupp received her J.D. from Valparaiso University after graduating with honors from Purdue University.

Grant Ossler 

Grant Ossler is an attorney at The Motley Fool in Alexandria, Virginia. Grant has expertise in digital media and the entertainment industry, particularly with regard to intellectual property, marketing, and advertising. Prior to his current role, Grant worked at The Onion, Inc. where he offered guidance through intellectual property matters related to copyrights and trademarks for branding and production services 

Grant received his undergraduate degree from William Penn University and his MBA and J.D. from George Mason University.  

This episode was recorded on January 19, 2021. 

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