Dianne Yamashiro-Omi, Senior Program Officer at The California Endowment, is a big picture thinker. We were drawn to her many years ago when she began talking about boundary-crossing leadership. We felt very lucky to be a partner in this work, running a learning circle for her grantees so that we could all learn more about how to support leaders who can build bridges across boundaries. One divide that can be tricky is the one between funder and grantee, but Dianne brings a keen awareness of power dynamics. She frequently asked how her presence might alter a frank conversation and offered to attend (or even not attend) meetings to support candid learning. Dianne has been an invaluable learning partner asking the kind of tough questions we love about racial justice and the kind of leadership it would really take to tackle inequities in the health of Californians.