Lookingglass Theatre Company (2019)

Lookingglass Theatre Company (2019)

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Less than two years into her tenure, Lookingglass Theatre Company’s executive director, Rachel Fink, faced both a challenge and an opportunity when the organization acquired new space in Michigan Avenue’s Water Tower Water Works complex. This opportunity came in the wake of two hectic years for the company. Since 2017, Lookingglass had experienced a transition in leadership with the departure of long-time executive director Rachel Kraft and the arrival of Fink. It had also suffered both a financial and emotional blow when a remounting of a previously successful adaptation of Hard Times by artistic director Heidi Stillman fared poorly at the box office. Early in 2019, the company renewed a lease with the City of Chicago for its home in the Water Tower, which included the acquisition of a larger amount of space in the building.

Lookingglass celebrated its 30th anniversary in 2018, an opportunity to reflect on its history and consider its future. What had begun as a group of college friends had become a $5 million, Tony Award-winning regional theater located in the middle of one of the most heavily trafficked areas of Chicago. Many of the company’s founding ensemble members had achieved notable careers in Chicago and beyond, but all remained committed to Lookingglass as an artistic family and home.

Fink was concerned that Lookingglass was still functioning as it did when it was a scrappy, young ensemble company just starting out. She saw how elements of its culture were at odds with the realities of its present staff, budget, and national reputation. Both Fink and Stillman acknowledged challenges in the company’s new work development pipeline and season planning practices, as months-long production runs put immense pressure on every production to be a box office success. Even when shows sold well, Lookingglass’ flexible performance space was often configured in a way that kept audience sizes small, preventing even the most popular shows from generating maximum revenue. Furthermore, although the company was fortunate to a pay nominal fee of $1 a year for a home on Michigan Avenue, it had a complicated relationship with the space. Limitations on outdoor signage, unwelcoming interior architecture, and a cramped lobby kept the company from providing the sort of holistic hospitality theater patrons increasingly expected.

Fink saw the footprint expansion as an opportunity to address some of those concerns, but the company needed to decide how the space should prioritize artistic programming, other programming and general hospitality. More importantly, Fink, a relative newcomer to the organization, needed to determine how to lead the organization through this process—one that would require Lookingglass to agree upon a vision for its future that was in alignment with its current financial realities and culture.

Publication Date: 2020-11-16

Suggested Citation: Emma Rose Perrin, "Lookingglass Theatre Company (2019)," Yale Theater Management Knowledge Base Case 19-101, November 16, 2020.

Keywords: Chicago, Growth, Leadership, Capital Project, Nonprofit

Teaching Notes: Yes (contact yaletmknowledgebase@yale.edu)

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This case is from the Theater Management Knowledge Base, a body of arts management material created by Yale School of Drama Theater Management students and faculty, overseen by an editorial board of leading practitioners. For more information or for help in selecting cases suitable for your educational or organizational purposes, please email yaletmknowledgebase@yale.edu.