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This Lessons Learned Paper describes a yearlong faculty development pilot program that was designed to help a team of faculty de-risk their pursuit of wicked research problems. Wicked problems are extraordinarily difficult to solve due to their incomplete, contradictory, and at times changing requirements. They often include multiple stakeholders with competing interests and worldviews. As a result, they are risky by definition because they are difficult to fund, publish, and collaborate on. Presented here, a team of eleven faculty, from six different academic units, explored their personal and professional values during an initial off-site two and a half day retreat. These values were repeatedly revisited when discussing the implications of the team working together on their curriculum, tenure and promotion guidelines, hiring criteria, and pursuit of wicked problems. Faculty representation included all ranks from a brand new assistant professor to several full professors. This paper will discuss the background and implementation of our program, along with key lessons learned and how we are building on those lessons.