As a pastor, she was hailed for not shying away from speaking about topical issues of the time, and is credited with getting people interested in the faith with her popular sermons.

[6][7][8] In Woolley's article in The Open Court, she discusses the success of the Congress of Liberal Religious Societies, an organization of which she was a vice-president alongside Susan B. Anthony and other notable figures.

Woolley cultivated close relationships with many prominent Chicago figures of the time, including Fannie Barrier Williams, a Black unitarian civil rights activist and educator; Jenkin Lloyd Jones, a popular unitarian minister and Frank Lloyd Wright's uncle; Ida B.

[13] Fannie Barrier Williams became the first Black member of the club in 1896 with the help of Woolley's intense lobbying and Jenkin Lloyd Jones' support.

[10] In 1904, she moved with her husband to Chicago's South Side to do social work, because she was concerned with issues of racism and human rights.

[12] Louis George Gregory spoke there in April and August 1911,[16] and was one of the keynote speakers of the 1912 NAACP conference in Chicago,[17] and hosted ʻAbdu'l-Bahá, then leader of the Bahá'í Faith, at the Center in September during his journeys in the West.