A thought leader in prospect development with over two decades of experience in the field, Ruthie Giles is currently the Director of Advancement Operations at Springfield Technical Community College and Partner, Prospect Development at Staupell Analytics Group. Ruthie added "published author" to her resume this year with the release of Prospect Management: The Essential Guide for a High Functioning Nonprofit Prospect Management System. We sat down to discuss how she transitioned from a prospect development practitioner to an industry expert, and what it takes to "ship" your expertise to the wider world:

Was there a specific moment when you realized the skills you use every day in prospect development could translate into something you could offer to others—a book or training? What did that look like?

I don't think there was a moment where I was sitting around and it dawned on me suddenly. It was more of other people asking me things: I had put together a prospect management system, and my supervisor said “You should present this at NEDRA,” the New England chapter. So I did that, and people started calling—back when you called people more often than you do now—to ask me questions about it.

And the more questions I got, the more I thought, well, I should just package this information up because I kept getting asked for it anyway. In our industry a rising tide lifts all ships, so If I know something other people don't, let’s just share it. I remember struggling with certain things early on myself and not having anyone to go to, because I was just sort of blindly blazing my own trail—so if I can help someone not have to go through that particular pain point, then absolutely I’ll help them.

Making the leap from "I'm good at my job" to "I'm an expert people should hire" is a big mental shift. Did you wrestle with that at all, and what helped you get past it?

Oh, yeah—I always have imposter syndrome. I don't think I'll ever outgrow that, and I think that's okay because it keeps you from getting too much of an inflated sense of self.

It was more other people telling me that I was their “person,” their expert to go to. There was one woman at a conference several years ago who gave me what I consider the highest compliment ever, she said: "You are to prospect management what Elizabeth Crabtree is to prospect research." And I thought, Oh, probably not, but that's a really nice thing to say—I wasn't going to say no, but I was like, I don’t know that I am, even though apparently to her I was! In that moment I certainly felt like an imposter—like, Elizabeth Crabtree? That’s where the heavens open up and the light shines down, and I didn't feel like that. But apparently, to her, I was.

You wrote a book on prospect management and are a partner at Staupell while still working full-time. How do you actually make that work day-to-day?

The good thing about me in this instance is that I'm a workaholic. I'm always doing something related to work, volunteering on a board, freelancing, so for me it wasn't hard to juggle things around, because I already knew how to parse out my time doing multiple things at once.

When the pandemic hit, that's when I really started writing the book, because we weren't getting as many consulting clients in my specific niche. So writing the book actually made sense during that time. But it was also chaos—I was working full-time, doing small projects with Marianne [Pelletier, Managing Director, Staupell Analytics], and my mom was dying while all of this was happening. I was her primary person.

And sometimes just sitting down to write the book was the calm I needed in the day. I'd focus on it for an hour, and that's all I had. It was a nice escape, and it was productive, which is in line with exactly who I am.

When you sit down to write, what does that actually look like? Are you a meticulous outliner, or more of a "figure it out along the way" person?

It's funny because sometimes I get super laser-focused, and I'll get lost in something for four hours. And then other times my ADHD kicks in and it’s like, nope, squirrel, something shiny—

I was hoping you were going to talk about ADHD!

Some days it's my superpower and some days it's my downfall. Some days I'd stare at the same three sentences for twenty minutes and nothing was happening, then I would sit down on a Saturday and just write for six hours.  

I started with an outline that sat on a virtual shelf, as it were, on a USB drive, for a couple of years. I'd first drafted it around 2018, and then it sat around for a while. When I started working with Marianne Pelletier at Staupell in 2021, I said, “I’m thinking of writing this book I started,” and she said, "You should finish that." And it wasn't really a question. So we started talking about how we would get to that finish line of having it done, and set up timelines and everything. […] She just said “It's going to be successful.”

So I dug out the old draft, took a look, and realized “Oh, this is terrible,” because my thinking had changed in the years since. So I grabbed it, pulled it apart, and made a big outline. Marianne and I went through it virtually—she was my partner in crime, she'd say, "What about this? You should probably talk about this." So we bounced ideas back and forth, and then I just picked a spot and started writing.

I didn’t set out to write a book, because I was writing the way I talk—I was used to teaching a webinar or a workshop and saying the same thing four different ways, because I know one of those will resonate with someone. And she kept writing "too hammery" in the margins—I’m like, "What does hammery mean?" And she'd say, "You're pounding the same point home too many ways, just pick one and go with it & they can reread it."

I joke that I probably wrote at least twice as much as made it into the book, because once I realized it I started editing myself as I was writing before I gave it to Marianne—because I didn't want to keep seeing "too hammery" in the margins!

For prospect development, there's the weeds and then there's the rabbit holes: there's always one more source to check, one more angle to explore. How did you finally draw the line and say, "This thing is ready to ship"?

So trying to figure out how much or how little to include was challenging because to me, it's all interesting; any one chapter in that book could have gone on for a whole book unto itself. I talk about things like lead management and total quality management—there are entire books just about those things, and I have them as a sliver of a chapter. But someone who just needs to build a prospect management system at their job doesn't really need the entire history of prospect management, since they may not find it as fascinating as I do.

Some sections were just harder to write because they weren't interesting to me, and those were the painful ones because I'd start thinking, “Maybe I need to go clean a closet.” And sometimes you just have to let it happen!

Did you set out with a specific need in mind from the start, or did your target audience find you as you started putting things out there?

I was definitely writing for someone who was trying to do prospect management—whether they were moving into it, or already doing it and needed help. And I made sure to include areas where, if you aren't yet doing prospect management but want to, there's a whole section that helps you make the case to your leadership.

In a big shop, it's easier to justify the time and effort, but in a small shop, it's harder because you have to make choices about what you're working on, and I leaned in that direction because they need the strongest tools.

How do you pitch the value of prospect development to organizations that may not fully appreciate what we're doing before they've seen the results?

I think first you have to get a feel for the culture: you can't go in like a bull in a china shop and say, "You need this, everyone else is doing it," because you sound like a lunatic when you do that.

You have to assess who’s going to be the hardest to convince: “Why should we implement one more thing, one more system, one more process?” And then make the case for how it’s going to benefit them—if it's not helpful to people, they're not going to adopt it.

For the people higher up on the org chart, you have to answer how is this going to help them bring in more gifts and engage more of their constituency; for the folks at the hands-on level, they want to know how this is going to help them manage their data, pull better reports, have fewer meetings and better meetings.

That sounds like a pretty good selling point. For other potential entrepreneurs out there in prospect development with a great idea, what's the very first thing they can do to start making it real?

Talk to other people who work in our industry, and find out what people actually need, and how they want it presented. If  you’re writing a blog, writing a book, building a service, or building some kind of vendor solution, anytime you can solve a problem, someone's going to be happy, right?

Can’t argue with that! What's the one thing you wish someone had told you before you started building something outside of your 9-to-5?

Cite your sources as you go! When I was writing the book, I had to go back more than once trying to remember where I heard things and then trace them back. I've been doing this work for 25 years, so trying to remember “What was that webinar that I went to?” or “What was that presentation?” or “Who was the woman who said that stuff?”—that was probably the hardest piece.

There was one person I emailed and asked, "Do you remember a presentation you did in, like, 2012?" And he said, "That's over ten years ago!" Fortunately he still had a copy, but those moments of trying to get back to the origin so you're not accidentally stealing material were a real challenge. So cite your sources.

Ruthie's book, Prospect Management: The Essential Guide for a High Functioning Nonprofit Prospect Management System, is available now.

Join Apra Carolinas as we host Ruthie on her virtual book tour on June 9, 2026! Register here.