What do you do when you walk into a new job and discover that the portfolio management system looks good on paper—but isn’t actually working?
Amy Modin, Director of Research and Prospect Management at the U.S. Air Force Academy Foundation (USAFA), found herself in exactly that situation. The organization had just closed a successful campaign. On paper, they’d raised the money. But when Amy looked closer, she saw portfolios with 300 names, ghost proposals tracking millions with no real conversations behind them, and a team of young fundraisers who’d inherited a system that was built for the campaign – not for forever.
As Amy put it: “They didn’t know it, but yes, they needed a new system.”
How She Built Trust: Humility, Skin in the Game, and Showing Up
Amy was hired, she was told, because she was “no nonsense.” She could speak plainly and communicate clearly. But that didn’t mean coming in with all the answers. It meant being willing to balance two things at once: meeting fundraisers where they were, and gently guiding them toward something better.
Some fundraisers were long-timers. They’d been doing things a certain way for years—and it worked for them. Others were young and floundering, trying to follow a process that had been half-explained before leadership left. Amy had to understand each person individually, demonstrate that reducing their workload was in their best interest, and show them a future they could work toward.
When Best Practices Don’t Fit Your Reality
Amy is refreshingly honest that everything she’d learned about prospect research and management was turned on its head at USAFA.
The intense research profiles she’d learned in healthcare philanthropy didn’t translate. The textbook processes didn’t match the reality of working with a graduate pool where 80-90% of donors are alumni. She had to make a choice to stay rigid and frustrated, or pivot and meet the organization where it was.
She chose to listen. Listen to fundraisers about what cues they were picking up in conversations. Listen to how they approached follow-up. Then figure out how to step in and help guide the moves management process so they could close gifts—or better yet, create new partners for the foundation.
Advice for the Solo Prospect Management Director Walking Into a Mess
Amy’s advice is simple:
First: Continually look outside your prospect development “box.” Network. Ask questions. Interview fellow researchers, prospect managers, and fundraisers. Fundraisers are a huge part of it.
Second: Open-mindedness. Come from a place of humility. The process you think it’s supposed to look like? It’s okay if it starts to bend a little bit outside the lines.
Because here’s the truth: having a seat at the table doesn’t look the same everywhere. If you create rigid parameters for what strategic partnership should be, you’ll end up frustrated when reality colors outside the lines. The excitement grows as long as you keep showing up.
Why This Episode Matters
If you’ve ever walked into a job where the portfolio management system was broken—or if you’ve ever struggled to get fundraisers to buy into a process—this conversation will resonate. Amy’s willingness to own the risk, to listen before prescribing, and to show up consistently even when it’s hard, is a masterclass in how to build trust and actually fix what’s not working.
Listen to the full episode to hear the whole story.
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