Coaching for Leaders: Episode 744 - "Where Being Selfish is Better" with Jenny Wood

Release Date: August 11, 2025
Host: Dave Stachowiak
Guest: Jenny Wood

Introduction: Redefining Selfishness in Leadership

In Episode 744 of Coaching for Leaders, host Dave Stachowiak engages in a transformative conversation with Jenny Wood, a former Google executive and bestselling author of Wild Go After What You Want and Get It. The episode delves into the often misunderstood concept of selfishness in leadership, advocating for a redefinition that empowers leaders to prioritize their own growth and well-being without compromising their dedication to their teams and organizations.

Selfishness: Beyond the Negative Connotation

Dave introduces the topic by challenging the conventional negative perception of selfishness. He states:

“The word selfishness we think about it and most of us bristle a bit... we can redefine it to make it work better for us, but also for the people around us.”
[00:35]

Jenny Wood concurs, sharing her journey through Google's ranks and how stepping back to prioritize her needs was pivotal:

“If you give everyone a leg up at your own expense, you'll end up getting trampled. So start showing up for yourself.”
[02:46]

Championing Your Agenda

A pivotal moment in the discussion occurs when Dave reads a powerful excerpt from Jenny's book:

“Being selfish doesn't mean seizing everything you can, like a treasure hoarding dragon. It means championing your agenda at least as strongly as you champion the needs of others...”
[03:13]

This redefinition emphasizes that advocating for oneself is not only beneficial personally but also attracts allies and fosters a culture of mutual success within organizations.

Balancing Big and Small Tasks: Saying Yes to What Matters

Jenny introduces the concept of "Yes to the Big and No to the Small," highlighting the importance of prioritizing tasks that drive business and personal growth. She differentiates between:

• Big Tasks: Strategic projects that align with organizational goals, such as developing an AI strategy or increasing customer satisfaction.

• Small Tasks: Non-promotable duties like organizing meetings or handling logistics, which she refers to as "nap work."

“When you write them down and you really articulate what's big and what's small, you're able to focus on what's going to move the business.”
[07:58]

Jenny shares a relatable example from her experience:

“I was a director of the project management office at a global consulting firm, yet somehow I still found myself organizing our in-person meetings...”
[09:00]

This clarity allows leaders to allocate their time effectively, focusing on impactful work that advances their careers and benefits their organizations.

Overcoming Guilt: Embracing Self-Advocacy

A significant barrier to self-advocacy is guilt. Jenny addresses this by linking guilt to fear and underscores the importance of pushing past these emotions:

“Recognizing that guilt and pushing past it... is where you're going to find yourself being the most successful.”
[06:57]

She provides practical advice on separating "truths" from "tales"—distinguishing factual realities from the narratives we create that hinder our progress.

“Truths are verifiable facts... Tales are the stories we tell ourselves to make sense of the facts.”
[19:15]

By identifying and reframing these narratives, leaders can make empowered decisions without the unnecessary burden of misplaced guilt.

Play to Win: Aligning with Current Needs

Jenny narrates her personal experience of declining a prestigious position at Google to focus on projects that truly resonated with her current aspirations:

“I had to play to win and recognize what I need now is to say no to this position.”
[14:09]

This decision not only allowed her to pursue her passion projects but also opened opportunities for others within the organization to step up, exemplifying how self-prioritization can lead to broader organizational benefits.

Second Dog Advantage: Leveraging Others' Pathways

Introducing the concept of the "Second Dog Advantage," Jenny contrasts the desire to be the lead dog with the strategic benefits of following. This perspective encourages leaders to recognize the value in allowing others to take the lead, thereby fostering a collaborative and supportive team environment.

“Other people paved the way for you... I got to draft in other people's wake. I still make a good living despite not being the trailblazer.”
[31:46]

This approach not only reduces personal stress but also cultivates a culture of shared success and mentorship within teams.

Personal Reflections: Redefining Success and Wealth

Jenny shares a profound personal shift in her perception of wealth and success. Moving away from the conventional high-earning trajectory, she prioritizes "memory dividends" and time spent with her family over monetary gain:

“I have dramatically lowered my desired annual income to about a fifth of what I thought I would want... investing in memory dividends now...”
[34:09]

This introspection underscores the importance of aligning professional pursuits with personal values and life goals, advocating for a balanced approach to success.

Conclusion: Embracing Selfishness for Collective Growth

The episode culminates with a reaffirmation of the idea that self-advocacy and prioritizing one's own needs are not antithetical to effective leadership. Instead, they are essential for sustainable personal growth and, by extension, for the flourishing of teams and organizations.

Jenny leaves listeners with actionable insights and resources, including a free guide on saying no without guilt, reinforcing the episode's core message of empowered, self-aware leadership.

Additional Resources Mentioned:

• Wild Go After What You Want and Get It by Jenny Wood
• Free Guide: itsjennywood.com/sayno

Related Episodes:

1. Episode 431: Align Your Calendar to What Matters with Niraal
2. Episode 596: The Ways Leadership Can Derail Us with Bill George
3. Episode 734: The Path to More Joy in Work and Life with Judith Joseph

For more insights and to access a library of leadership resources, visit CoachingforLeaders.com and activate your free membership today.

Edited by Andrew Kroger | Production Support by Sierra Priest