Ashley E. Lillesand-Leonhard - Waukesha, WI

Attorney Ashley E. Lillesand-Leonhard graduated from Marquette University and began working as a case manager in 110-bed residential facility for adults with disabilities. Having no prior experience working with individuals with disabilities, Ashley quickly learned that these individuals often needed advocacy and someone to go outside the normal job description to help them receive the services they needed. After a year in the residential field, Ashley went to work for a corporate guardian which was a non-profit organization providing Guardian of Person and Guardian of Estate services for adults and the elderly population. Ashley was promoted to Guardianship Director for Easter Seals and spent six years in that capacity. Under her tenure, the program grew from having 30 wards to over 200 in the Southeastern Wisconsin area.

It was working as an advocate in a guardianship role that prompted Ashley to go to law school. Ashley hoped as an attorney that she would be able to do even more for her wards and clients. She continued to work for Easter Seals and had her two older daughters while she juggled law school. After graduating, she worked for a small firm downtown before starting her own firm in 2010. Ashley has been the managing partner of Lillesand Law since 2010 and continues in that capacity as the firm transitions to Lillesand Leonhard Law LLC in 2025.

Ashley has fine-tuned her practice over the years to focus on estate planning for both young families and clients reaching retirement age who need guidance with asset protection strategies. Additionally, Ashley represents clients with Probate and Trust administration and Medicaid applications. Ashley also hasn’t forgotten what brought her to law school in the first place by continuing to represent family members in guardianship matters which require knowledge of guardianship laws and the practical ins and outs of serving as a guardian. Ashley serves as a guardian ad litem in guardianship and probate matters in Milwaukee County as well.

Ashley often jokes that she tries to be the “least lawyerlike lawyer you will ever meet.” She strives to make clients feel comfortable and educated about their issues and options. She believes that her days as a case manager and guardianship director make her uniquely qualified as someone who has a law degree and hands on experience.

Ashley is married, and along with her teenage daughters, has two young children. Three girls and a boy make their lives busy with sports and their involvement at St Charles. Ashley plays golf, loves to read, and competes in running races and triathlons.