Words by Meher Khan | Photos by Marie Ketring

At the August YNPN Twin Cities Leadership Breakfast event, Trina Olson, executive director of the PFund Foundation, packed into an hour enough leadership advice for a lifetime. Trina makes this kind of rapid fire learning experience possible through her incredible amount of energy, focus, and smarts. It’s not hard to see how she’s accomplished so much—an evolving career in political advocacy and running a nonprofit—at a young age. By the end of the morning event, I felt more sure about the concrete steps I could take to further my career, but I also just believed in myself. (It felt great!)

Trina’s ability to instill confidence in others is just the beginning of her long list of qualities that make her a great leader. Luckily for those at the event, and now for you, Pollenites, Trina distilled her key pieces of advice into memorable, useful nuggets, while making us feel sure that we could put them to action.

Trina’s own confidence comes in part from a background in advocacy work that was often challenging. She always knew she was interested in politics and rhetoric, so she was naturally drawn to working in political advocacy. A lesson that she learned early on while working with a group advocating for Medicare was that she would encounter resistance. She would have to be careful, and she would come across people who made her afraid. Trina counts this as incredibly valuable experience, because it taught her to talk to everyone, give everyone an opportunity to have a dialogue with her, and that she was always in control of the conversation.  When Trina thought about having those scary conversations, she learned how much of that she had to internalize, and to analyze what she was really afraid of in the situation.

Trina became interested in leadership, mass mobilization, and “building to scale” in effecting policy change when Washington, the state she lived in, elected a woman as governor. It was the only time two female senators and a female governor were elected at the same time, which inspired Trina to head to Washington D.C. where she could increase her involvement in political work. 

At one point in the conversation, Trina answered a question about how to care for yourself when doing advocacy work. To connect with voters and be authentic meant having to be extremely vulnerable, and this meant Trina had to pay special attention to her own well-being. She credits her own success to having a solid team around her.

“I never did anything alone. I made fundraising calls with them, I did everything with them, not because I couldn’t do it alone, but because doing it alone is bad for you.”

Reflecting on her career trajectory, Trina pointed out that she never set out to be an executive director. Always having a supportive team around her made it easier for Trina to continue saying “yes” as opportunities came along. She emphasized the importance of surrounding yourself with people who are smarter than you (so you can learn from them), and making sure your team includes members with as many skill sets as possible. Trina also shared this important reminder: you don’t have to do everything, and for the skills you don’t yet have, there’s always on-the-job training and coaching. Early on in your career, Trina advises against siloing or specializing too much.

“Being a jack- or jill-of-all-trades is how you lead nonprofits.”

Some key factors to Trina’s quick advance through her career (she was in her mid-20s during many of the leadership positions she’s held) included her being a good follower. She trusted the leadership around her and followed their lead, rather than trying to claim everything for herself. “There are lots of different ways to reach the same outcome,” Trina says. “Be open to what that might look like.”

She was not, however, a passive follower. She took initiative and supported her leaders, making their lives easier, which in turn made those leaders create opportunities for Trina.

She reminded us to be proactive in working on what you want to learn, your plan to learn it, what access you want, and to start asking for it.

Finally, to be a good executive director, Trina advised to first learn to be a good manager. In a field where most resumes that cross her desk look the same (and Trina maintains that past experience is important, especially in establishing confidence in your field), Trina hires based on attitude, curiosity, and smarts.

In true leadership fashion, Trina inspired everyone in the room to chase after their goals with tenacity. The best part of Trina’s talk wasn’t how much valuable advice she gave us (and as you can see, it was a lot), but how possible she made it for us to follow that advice, and how capable she made us feel.