LEADing San Diego

Executive leadership coach Amanda Flisher and two-time LEAD alum Lucy Romero explore why so many women struggle to see their own strengths and what changes when women stop competing for “one seat” and start extending the table. Lucy shares how Advance was the first space where she felt safe to be vulnerable and truly supported by other women and describes the lightbulb moment that shifted everything: stop fixating on weaknesses and start leading from strengths. Amanda brings the coaching lens, her mission is to help women become the best versions of themselves, own what they bring, and step into the rooms where decisions are being made. Together, they offer practical ways to name your strengths, advocate for yourself, and uplift other women along the way.

Jay Henslee reflects on moving from a small Northern California town to San Diego and finding his voice professionally and personally. A LEAD Impact 2017 alum, Jay shares how the program expanded his understanding of the region and connected him to a lifelong civic network. In this conversation, Jay goes deeper on what leadership means to him: creating environments where people can perform their best, having one-on-one conversations that draw out what others bring to the table, and helping people pursue goals that feel genuinely rewarding. He also shares how early involvement in church shaped his sense of being part of something bigger and why giving back, arts advocacy, and advancing equality remain central to how he leads across San Diego.

Kristen Diggs shares how moving to San Diego and joining LEAD Advance helped her find community, deepen her leadership, and build a network rooted in real support. She tells the story of taking a leap early in her career, going for an HR role at an organization that had never had HR before, and becoming the first HR hire in its history, and why she now passes that lesson on to the people she mentors. We explore the full-circle power of mentorship: what Kristen gained from her mentor as a new San Diegan, how those relationships shaped her career, and how she returned to Advance to mentor others, proving that the strongest networks are built on belonging, reciprocity, and showing up for each other.

Author and CEO Jamie Moraga shares how growing up in a Navy family shaped her resilience and drive and how LEAD San Diego was a goal she chased for years. In this episode, Jamie reflects on the perspective shift of Impact 2011, building and scaling companies in the defense space, and leading a fast-paced acquisition. She also opens up about the mindset work behind her success: becoming more reflective, giving herself more credit, quieting her inner critic, and staying intentionally uncomfortable to keep growing. Now, through her book REVERED: The Power of Female Leadership, she’s championing women-owned, founded, and led businesses, and sharing the lessons learned.

Tana Lorah, Chief Operating Officer for Snake Oil Cocktail Company, reflects on a leadership path shaped by service, curiosity, and bold career pivots. A three-time LEAD San Diego alum (EMBARK, Impact, Influence), Tana shares why LEAD feels like family, what cross-sector executive leadership looks like in San Diego, and how she brings service leadership into every room she enters.