HBR On Leadership: Step Up from Middle Management to Senior Leadership
Release Date: August 5, 2025
Host/Author: Harvard Business Review
Description: Leadership isn’t a trait, it’s a set of skills. Whether you’re managing up or motivating a team, HBR On Leadership is your destination for insights and inspiration from the world’s top leadership practitioners and experts.

Introduction

In the August 5, 2025 episode of HBR On Leadership, hosted by Amy Bernstein and Amanda Kersey, the focus is on empowering mid-level managers, particularly women, to ascend to senior leadership roles. Featuring insights from career coach Cynthia Pong and seasoned COOs Megan Bach and Lauren Reyes, the episode delves into the challenges, strategies, and personal journeys associated with moving from middle management to the executive tier.

Feeling Stuck in Middle Management

The conversation begins with the recognition that feeling stuck in mid-level management is a common experience, especially for women. Cynthia Pong emphasizes, “00:03:20,” "There is a particular set of feelings that come with folks who are in the middle of their career... a feeling of both stuckness and also slightly a bit of being lost."

Challenges for Women in Middle Management

Cynthia Pong outlines the unique challenges women face in middle management roles:

1. Balancing Dual Expectations: Women often find themselves navigating between upper management's directives and their team's expectations, leading to frequent miscommunications and a "thankless job" ( 00:04:47).

2. Stereotype Biases: Women are stereotypically seen as communal and team-oriented, which can conflict with the assertiveness needed for leadership roles. Pong states, “00:05:24,” "There's always going to be people upset at you from both sides continually."

3. Pipeline and Numbers Game: The scarcity of senior roles compared to the abundance of middle management positions makes the leap to senior leadership particularly daunting (00:05:47).

4. Visibility and Networking: Women often underutilize strategic relationship-building outside their immediate organizations, which is crucial for sponsorship and advancement (00:07:36).

5. Fear of Rejection and Self-Doubt: Cynthia highlights the internal struggle women face, “00:08:07,” "We feel extremely accountable to our word... the hyper self-criticism can prevent us from saying certain things out loud."

Strategies to Move to Senior Management

Visibility and Networking

Both Megan Bach and Lauren Reyes stress the importance of building a strong external network. Lauren notes, “00:42:52,” "Networking... has been a big part of how I'm in the seat that I am in today." Megan adds that increasing visibility beyond current roles can open doors to senior positions (00:40:33).

Taking Risks and Career Mapping

Megan Bach shares her journey of taking calculated risks, including switching industries and seeking executive coaching to pivot her career (00:29:43). Lauren Reyes discusses the importance of career mapping, aligning each career move with long-term goals (00:34:49).

Overcoming Self-Doubt and Fear of Rejection

Amy Bernstein relates to the fear of rejection, sharing her own experience of hesitancy in pursuing desired roles. Cynthia Pong advises, “00:10:07,” "You have to be visible to enough of the right people so that enough of those people will become your sponsors or champions."

Personal Stories: Megan Bach and Lauren Reyes

Lauren Reyes’ Journey

Lauren Reyes recounts feeling undervalued despite long-term dedication at the YMCA. She encountered a pivotal moment when a peer was promoted over her, leading her to confront leadership about her value. “00:25:07,” she explains, "I realized I wasn't going to change their opinion on that. And so... I told him, I'll be gone by the summertime."

Lauren's strategic relocations within the YMCA and her commitment to building nationwide relationships were instrumental in her rise to COO. She emphasizes the role of support systems in making bold career moves feasible (00:32:50).

Megan Bach’s Path

Megan Bach shares her frustration with being passed over for promotions in a large insurance company, leading her to seek opportunities externally. By moving to a technology company and engaging executive coaches, Megan was able to redefine her career trajectory. “00:29:07,” she states, “...having the courage to take the risk is absolutely a factor.”

Her proactive approach in establishing a consulting organization post-transition highlights the importance of continuous growth and learning in leadership development (00:31:31).

Advice for Listeners: The Maggie Case

In a practical application, Amy Bernstein presents the case of Maggie, a mid-level manager feeling stagnant after 19 years with her company. Despite excellent performance reviews, Maggie receives indirect feedback that she's too nice and not ready for senior roles.

Lauren Reyes' Perspective

Lauren advises Maggie to evaluate her satisfaction with the organization's current valuation of her. “00:47:51,” Lauren suggests, "I would say it's not worth, it's no longer worth my energy and effort. I'm gonna just go on to other places."

Megan Bach's Insights

Megan concurs, encouraging Maggie to seek opportunities elsewhere if her current organization does not recognize her potential. She also recommends Maggie develop new skills through self-initiated projects to enhance her leadership profile (00:49:07).

Conclusion

The episode concludes with a consensus that proactive measures, such as strategic networking, taking calculated risks, and continuous self-assessment, are essential for mid-level managers aiming to ascend to senior leadership roles. Both Megan Bach and Lauren Reyes exemplify the courage and strategic thinking required to overcome the barriers that often leave women feeling stuck in middle management.

Notable Quotes:

• Cynthia Pong (00:03:20): "There is a particular set of feelings... a feeling of both stuckness and also slightly a bit of being lost."

• Cynthia Pong (00:05:24): "And you're in a position where inherently, intrinsically, there are going to be people upset at you from both sides continually."

• Lauren Reyes (00:42:52): "Networking... has been a big part of how I'm in the seat that I am in today."

• Megan Bach (00:29:07): "Having the courage to take the risk is absolutely a factor."

• Lauren Reyes (00:47:51): "I would say it's not worth, it's no longer worth my energy and effort. I'm gonna just go on to other places."

This summary encapsulates the critical discussions and insights shared in the episode, providing a comprehensive overview for those who haven't listened while highlighting the experiences and advice of the featured leaders.