This is a Panel held during ICIS 2021. The last 19 months have included a variety of grand challenges in Academe (i.e., Covid-19, cancelled international travel and study abroad programs impacting university income, unexpected expenses for constituent safety). Some questions that may have plagued leadership include: How do administrators ensure faculty are adequately trained for on-line course delivery? What options are available for maintaining university budgets with unprecedented expenses? How does a Dean navigate the storm waters of leading a school/college at the same time be supportive of mandates and leadership decisions from the President and Provost? How should the Dean navigate the increasing demands placed on faculty and staff considering elder and childcare during a pandemic? Fortunately, we have several women who have taken the helm as deans of business schools during this time of grand challenges and are willing to share their experiences.