A Conversation with Dr. Lakeya Cherry

Annotated Outline

Episode Overview

This episode features a conversation with Dr. Lakeya Cherry, a social worker, executive

leadership coach, and former CEO of the Network for Social Work Management. The discussion

explores Dr. Cherry’s professional journey across multiple sectors, including nonprofit

leadership, clinical practice, and entrepreneurship. Through this conversation, the episode

highlights the diverse leadership pathways available within social work and examines how

leadership development, self-awareness, and emotional intelligence shape effective

organizational leadership. The discussion also explores structural inequities in leadership,

particularly within nonprofit organizations, and emphasizes the importance of supporting leaders

from historically marginalized communities.

Key resources informing this episode include: Cherry (n.d.), Brown (2018), and Network for

Social Work Management (n.d.).

Episode Annotation

This episode begins with an introduction to Dr. Lakeya Cherry and the host’s decision to

invite her as a guest based on shared interests in leadership development, vulnerability, and

psychologically safe workplace environments. The conversation highlights Dr. Cherry’s work as

a leadership consultant, executive coach, and Dare to Lead facilitator supporting leaders across

sectors.

Dr. Cherry then reflects on her professional journey into social work, including her early

interest in law and policy, her transition from law school to social work education at Columbia

University, and her early career experiences in nonprofit, clinical, and correctional settings.

These experiences illustrate the diverse pathways available within social work careers.

The discussion next explores her transition into leadership roles and the development of

her coaching and consulting practice. Dr. Cherry describes how leadership coaching supports

individuals and teams in developing self-awareness, emotional intelligence, and alignment

between their leadership behaviors and values.

The conversation also examines barriers that leaders may face in expressing their voice

and leadership potential. Dr. Cherry reflects on the ways suppression, structural inequities, and

systemic barriers can influence leadership trajectories, particularly for women and leaders of

color, and explains how her work seeks to support leaders navigating these challenges.

The episode concludes with a reflection on the broader impact of leadership development

within social work and human-serving organizations, emphasizing how leadership growth can

influence organizational culture and create ripple effects that benefit teams, organizations, and

the communities they serve.

Talking Areas

● Introduction to Dr. Lakeya Cherry, her leadership consulting work, and her professional

journey into social work

● Career experiences across clinical, nonprofit, and correctional settings

● The role of self awareness, emotional intelligence, and values alignment in leadership

development

● Suppression, voice, and structural barriers that shape leadership trajectories

● Racial inequities and leadership gaps within nonprofit leadership

● Ripple effect of leadership development, social entrepreneurship on culture and

community impact

Closing and Call to Action

The episode concludes with a reflection on the importance of mentorship and mutual

support among leaders and social workers. Dr. Cherry emphasizes the value of leaders

supporting one another in their professional journeys and encourages continued connection and

collaboration within the social work community. The conversation closes with the reminder that

leadership development is strengthened when individuals share knowledge and support one

another, reflecting the principle of “each one teach one.”