In this time of overwhelm, where many staff and leaders of nonprofit organizations are leaving the field or those who have stayed are truly running on empty, I went looking for leaders who have figured something out.

The good news is: I found them! This series, How Smart Nonprofit Leaders Create Lasting Impact, shares the insights of amazing people who continue to navigate the ups and downs of nonprofit leadership to create lasting impact. This is one of the many ways our clients at Development Without Limits keep their amazing staff doing great work without wasting time, energy and money on quick fixes that fail.

What a joy to speak with Penn Sheppard from Girls Inc. Driven by passion, Penn has led girl-centered nonprofit work for 40 years. In our interview, she shares her core philosophies that have kept her motivated and making an impact over time. She also discusses the key to navigating the toughest challenge she’s faced: navigating change.

Q: What is the biggest factor in your success in creating lasting impact?

I’ve got a couple of philosophies that have carried me through the years:

1. Stay mission focused. As I’m pondering a decision, or working with the group around a decision, the central question is: how does this further our mission? I’ve been with Girls Inc. for over 30 years. Prior to that I worked for Girl Scouts. What has helped ground me is making sure that we’re really centralizing what we’re doing and why we’re doing it.

2. People first, employee second. I think one of the other things that became super apparent during the pandemic is to see the people that I work with, specifically the staff that I supervise as people first and employee second.

I’ve always had really good relationships, and connection with my team. I care about them, their families and what they do outside of the job. But I think the pandemic really taught me that you’ve got to let people know that you care about them as a person, and not just what are they going to do for me in the job. That has been so apparent.

Approaching people as individuals and knowing that different things work with different people is really key. For example, having a leadership style that is flexible enough to go with the groove. In thinking about specifically youth development and youth work which has been my career, the people and the relationships really are the key. We can sit down and write these great, dynamic curricula that we’re excited about, but how they’re delivered, how they’re facilitated… what those relationships are–that’s what is essential.

3. Keep learning. Another area that has carried me through is that I’ve always found myself in a constant state of learning. Even after 40 years as as a leader I’m still open to reading, learning and developing. I ask myself:

• How can I be stronger?

• How can I be more inspiring?

• How can I be more compassionate?

I always feel like there’s more that I can learn. And it has helped as my career has gone on. Over time, I’ve shifted more into training and development, probably because I have been so interested in that. But you know, even as a trainer, and a learning leader, I want to continue to learn. I think that includes both the formal learning opportunities, and also our experiences by saying: How do we look at the things that went really well and say, why did it go well? And also about the things that we failed or didn’t go how we thought they would. How can we reflect on those? How can we process that? What can we learn from that?

Those are parts of my philosophy, so to speak, that I feel like I’ve kind of grown into and have carried with me over the last part of my career.

Q: I love hearing about relationship-building and really thinking about how you build and sustain relationships with staff… So they are able to turn that into how they build relationships with their teams and then in turn, build relationships with young people. Do you have any particular strategies that you use on a regular basis to build relationships with your team?

I feel like I’m in this really unique situation because I have a lot of tenure on my national team. My associate director, I’ve known for 30 years; I have two assistant directors, one has been with me for 22 years, another’s been with me for almost 16 years. I have a senior learning manager who has been with me for over 15 years. She is actually leaving this week to spend time with her kids. I have other team members who’ve been with us for 12 years. So, we have this incredible tenure. The newest person on my team has been with us four years this fall.

I attribute that to just taking that time to get to know each other and to spend time doing whatever people feel like they know is going to be enjoyable. One of the things I did before the pandemic was once a month, we would take an hour, and I called it mental recess. At the time, we were all in the same office. (We’re not all in the same office now. So some of us are in the office sometimes and some of us are not.) But we would just come together and there wouldn’t be an agenda. Sometimes we would just sit around and talk about movies. Other times, we’d play Pictionary. We just did whatever we wanted to do. Sometimes there were snacks, sometimes there weren’t. But it was me saying to them:

It’s okay for us to take a break, and to get to know each other and to laugh together and have a good time together.

I also understand, we don’t do direct service. And so we do have that privilege and that luxury to say we’re going to take an hour of our time. But, you know, just carving out just a little bit of time makes a big difference. And even if people didn’t want to come together as a group, you could take an hour for yourself, take a walk. Have some self-care, as we’ve all been learning more about as we’ve experienced the collective trauma of the past two and a half years.

Q: What kinds of challenges or obstacles are you still working on as a leader?

I would say the big thing, in all with capital letters is CHANGE. We’ve experienced a lot of senior leadership change here at Girls Inc. that came with the pandemic. We have a relatively new CEO who has been with us for three years. And now she’s at a point where she wants to see some different things. The way we support our affiliates across the United States is different because they’re struggling in ways that they never had before, just in terms of staffing. Training staff looks really different. The way our fundraising team is fundraising is a little bit different.

The trauma that staff had been through–I kind of attribute that to change, too. How people are approaching their work is very different than anything that I’ve ever experienced–different than most what most people have experienced. The things that worked even 10 years ago, you can’t assume that they’re going to work anymore.

That’s the challenge: just navigating all of the change that’s coming to us.

Q: And so in your role, what are you currently doing to help navigate the change?

I would say: communication. Transparency just keeps coming up for us–especially for those who aren’t in leadership or senior leadership positions. It’s one thing to say we’re going to start doing this, or we’re going to change the way we’ve been doing something. But if you don’t give the explanation on how you reached that decision, what the decision was based on, then people are either going to fight it or they’re going to be upset.

It’s important to start early and communicate everything including what you’re anticipating is going to happen and helping people understand what the change is. And, if it’s a decision that they’re not going to have an opportunity to provide feedback, then I think even telling them that like, “the Board of Directors is going to make this decision.”

That’s what I keep hearing–we need to be transparent. To me, that means communication, and even over communicating. I feel like I spend the majority of my time communicating, figuring out what do I need to communicate to who when I’m in this meeting? Who do I need to share what I learned in this meeting? What do I need to make sure is documented? So when I’m gone, that information is still there. Communicating, which is really the basis of change management, is helping people understand the why and helping them through whatever their reaction is going be. That’s all communication.

Q: To wrap up, I’d love to know what, in your opinion, is the secret sauce to being a smart leader in a nonprofit organization that’s making a lasting impact that many other folks miss?

I think it’s finding your passion. What do you really really care about? I have found myself in organizations that support girls and really advocate for girls. I think that’s from my personal experience growing up. I was in a very stereotypical role. I have four brothers and I was the one who had to pick up their dirty laundry! I felt like, why? I just found doing what I’m doing — both starting with the Girl Scouts and then with Girls Inc.– I really, really care about the work that we do. I still get energized by reading, you know, something that a girl has experienced or having a staff member share the results and the impact of their programs.

Even though I’m a leader of the national team, I can still see the impact that we’re having, and still keep my eye on that. Because that’s why we do what we do. That passion is still there for me after all these years. It’ll still be there after I retire.

It’s one thing to come out of school with the skills, the book knowledge and whatever internships and practice you’ve had, but if you don’t have that passion, you’re probably not going to stay with what you’re doing very long. You’re going to be drawn to whatever your passion is. So for me, that really is the secret sauce of success, longevity and impact.

Thank you, Penn, for sharing your passion and wisdom with me and our readers.

Penn Sheppard is the Vice President, Learning at Girls Inc., a United States 501(c)3 nonprofit organization that encourages all girls to be “Strong, Smart, and Bold” through direct service and advocacy. The organization equips girls with the skills to navigate through economic, gender, and social barriers and to grow up as independent individuals. Learn more: https://girlsinc.org/

She has over 40 years of non-profit experience, specifically in the out-of-school time youth development field with girl-serving organizations. Her career started with Girls Scouts, spending three years as a Field Executive
and nine years as part of a summer resident camp staff working for 3 different Indiana councils at 3 different camps, with five years as a summer resident camp director. She has been with Girls Inc. for 32 years with 7+ years as a Program Director at Girls Inc.of Greater Indianapolis and 24+ years on the Girls Inc. National staff. Penn currently leads the team that provides support and resources around girl learning and adult training. She has been part of the Indiana Afterschool Child Care Association, is currently a member of the National Afterschool Association, and has presented professional development sessions at the local, state, and national levels. Sheppard holds a Bachelor’s degree in Education from Ball State University.