Ep 253: Still Figuring It Out: An Honest Take on People Pleasing and Leadership

by Glennda Testone

For a long time, Glennda Testone’s people-pleasing nature shaped – and sometimes complicated – her leadership. In this honest, personal solo episode, she shares her journey from people pleaser to recovering people pleaser. Plus, five practical strategies for leading well when you’re wired to make everyone happy.

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There’s a moment every nonprofit leader hits eventually: You realize that if you try to keep everyone happy, you are going to fail your staff, mission, or yourself.

And if you’re wired – as many nonprofit leaders are – to make everyone around you happy, that reality can be genuinely paralyzing. 

In this episode, Glennda Testone, CEO of Nonprofit Leadership Lab, gets honest about her journey as a self-described recovering people pleaser and how that instinct kept her from making some of the most important leadership decisions of her career. 

This isn’t a conversation about becoming cold, tough, or uncaring. 

In fact, Glennda argues the opposite: empathy, attunement, and caring deeply about other people are often the qualities that lead people into this work in the first place. 

But unchecked, people pleasing can quietly wreck your leadership.

Especially when:

  • staff are looking to you to protect them
  • donors want one thing and your mission demands another
  • power dynamics make “keeping the peace” feel safer than telling the truth
  • you find yourself tap dancing instead of leading

Plus, Glennda will walk you through five hard-earned strategies that helped her move from reflexive people-pleasing into values-driven leadership. Including how to decide whose voices matter most, why peer accountability matters, and why some leadership decisions are not either/or.

If you’ve ever avoided a hard decision because you didn’t want someone to be upset with you, this episode will hit close to home.


TUNE IN TO LEARN:

  • Why people pleasing isn’t all bad, but needs boundaries in leadership: How the same instinct that draws many people into nonprofit work can quietly undermine their ability to lead well when left unchecked.
  • How to start with yourself before looking anywhere else: Why figuring out your core values is the essential first step for any recovering people pleaser – and why this one is a solo journey.

  • How to decide ahead of time who you are willing to disappoint: Why making this decision explicitly – before you’re in the heat of the moment – changes everything about how you lead.

KEY QUOTES:

  • “What I mean when I say I’m a people pleaser is that my first instinct from very, very young, the first thought I have when I sense…that someone else might be displeased, is to tap dance as fast as I possibly can to make them happy again.”

  • “[T]here’s no way I’m going to avoid disappointing people. I just have to decide who are the people I’m willing to disappoint.”

  • “I can’t continue to be a people pleaser for everyone, that’s not going to serve anyone.”

ABOUT GUEST:

Glennda Testone is a nonprofit leadership expert who spent 14 years as the Executive Director of New York City’s Lesbian, Gay, Bisexual & Transgender Community Center. Over the course of her tenure at The Center, she tripled the organization’s budget, strengthened its programs, and completed a $9M capital building renovation to transform the LGBTQ community’s home on West 13 Street. Additionally, she partnered with Google to launch the virtual reality experience of Stonewall Forever, celebrating the 50th anniversary of Stonewall, and helped lead a racial equity transformation of the organization.

Testone previously served as Vice President at The Women’s Media Center and Senior Director of Media Programs for the Gay & Lesbian Alliance Against Defamation (GLAAD).


RESOURCES:

Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”


Sponsorship

Donor Perfect

Sponsored By DonorPerfect

DonorPerfect provides nonprofits with powerful fundraising tools to drive success. Built on a foundation of integrity and innovation, the company prioritizes its clients over investors, cultivating a culture of collaboration, continuous improvement, and a commitment to making a difference. 

Check out their resource(s) below.

  • The Nonprofit Leadership Workbook for Women
    Less than half of nonprofits have women in senior leadership, so we called on established women in the nonprofit space to share their wisdom. For actionable career advice and exercises, download your free Nonprofit Leadership Workbook for Women.
  • The Clean Data Checklist for Nonprofits
    Messy data slowing you down? DonorPerfect is here to help! Grab our free Clean Data Checklist to keep your CRM organized and your team working smoothly together. Start your checklist.


Sponsored By DRG Talent Consulting Experts

DRG Talent Consulting Experts partners with nonprofits to help them build thriving teams and cultures. With a focus on integrity, collaboration, and continuous learning, DRG supports organizations in finding and developing the right leaders. Their work is grounded in compassion, accountability, and a commitment to helping clients make the world a better place. Check out their resource(s) below.

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    Bias is sneaky. It creeps into hiring decisions within minutes, shapes how we evaluate candidates, and can keep truly great people out of the door — even when we think we’re being fair. This one-page guide breaks down the most common unconscious biases that derail interviews (from halo to “like me” thinking) and gives hiring teams a clear, research-backed way to make better, more equitable decisions.
  • Navigating Founder Transitions
    Founder-led organizations often face a unique and delicate moment when it’s time for leadership to evolve. This one-page guide breaks down the key pieces every board and leadership team needs to think through — from honoring the departing founder and separating their identity from the organization to creating a clear succession plan and setting up the next leader for success. If you want transitions that strengthen mission and culture (not shake them), this is a must-read.