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In this episode of So Many Questions, Moses Singer CEO Rebecca Goodman-Stephens speaks with Ashley Fina, co-CEO of Oxygen, to unpack what it truly takes to develop great leaders. Ashley reflects on stepping into a CEO role at 25, leading her family’s global recognition business, building and selling an HR tech company, and ultimately co-founding Oxygen, a company dedicated to equipping managers with the skills and support they need to succeed.

Rebecca and Ashley explore a challenge seen across industries: high performers are frequently promoted into management without the behavioral, communication, or cultural training required to lead people effectively. They examine the increasing pressures on middle managers, the critical role of clear expectations, and how coaching, therapy, and consulting are converging in modern leadership development.

This episode provides a practical roadmap for cultivating leadership at every level through value-driven behaviors, ongoing manager support, and cultures that embrace learning and asking for help as strengths, not weaknesses.

In This Episode

 00:29 – Guest introduction
 01:53 – Becoming CEO at 25
 06:36 – Coaching and leadership development
 08:33 – The leadership skills gap
 12:55 – Coachability and values alignment
 15:33 – Turning values into behaviors
 20:30 – Navigating family business dynamics
 23:18 – Partner selection and expectations
 27:30 – Strength of community and learning
 29:24 – Why asking for help matters