Community Colleges (CCs) have been particularly impacted by a deluge of "development" and "good" leadership frameworks removed from the very communities in which leading remains paramount. A paradigm shift is needed to support current and aspiring CC leaders in a manner that prioritizes the very essence of learning in the community. CCs are facing a variety of crises: (a) half of CC presidents will retire over the next decade; (b) leadership theories are so saturated that deciphering one from another becomes bewildering; and (c) the rapid changes in technology, economic conditions, and social reckoning require scholars to rethink how leadership is understood and supported. This study combined narrative inquiry and adult learning theory to investigate what and how leaders learn while leading, with particular focus on the contextual and relational elements connecting when, where, and with whom learning happens. From the analysis of the study findings, I introduced a new phenomenon termed "CC leader learning," including the transferable potential to additional domains and sectors. Lastly, I presented the 4 x 4 model for being a learning leader, which ignites leader learning as an embedded, iterative, and agentic practice. The study concluded with a call to action for current and aspiring leaders, and an invitation for anyone to use systems and methods that not only evaluate, but also respect, incentivize, honor, and resource the fundamental ways in which we learn together. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]