From 1995 until 2002, Lenny served as an Assistant Public Defender for the Broward County (Florida) Public Defenders Office representing clients in criminal cases. Lenny has served as lead counsel representing both juveniles and adults charged with felonies and misdemeanors and has participated in more than 100 judge and jury trials. Lenny has served as a Guardian ad Litem and Juvenile Mediator, ensuring that the rights of children in dependency and criminal matters were protected. Lenny also serves as a Judge Pro-Tempore in Thurston County District Court and presides over civil and criminal matters.

Lenny is currently the Secretary of the Thurston County Bar Association Board of Directors and is a member of the Ukrainian American Bar Association, and the Family Law Section of the Washington State Bar Association. Lenny has been named a "Rising Star" lawyer by Washington Law & Politics in 2005 and 2006 and has received recognition from the Washington Satate Bar Association for his pro-bono work in the community every year since 2007.