Curiosity Over Persuasion: How to Find Recruiting (or sales!) Magic
Summary
What if the secret to great recruiting, sales, or product development isn't about being more persuasive, but about getting better at listening for what people need and what matters to them? Caroline Fitz-Roy's approach to recruiting shows how curiosity, layered research, and willingness to adapt create those magical professional connections that feel effortless—and how the same skills apply to any situation where you're trying to create the right match.
What’s in it for you:
You want to understand how to actually find those "perfect fit" candidates
You're curious about what makes some recruiting processes feel magical while others feel transactional
You want to apply research-driven, learning-focused approaches in your own world
Helia’s Perspective
I've been lucky enough to know Caroline for about 15 years now. We met when she was leading cold calls at Revolution Foods, and when she scheduled meetings for me, folks would be disappointed when I showed up, as they were really hoping to meet with Caroline! This happened constantly—and not just with me, but with everyone she worked with.
When I hired her as a recruiter (both at Think of Us and at the YWCA of Glendale/Pasadena), I started to really understand the difference between a recruiter and a search firm! Caroline’s incredible people skills are founded in listening and learning, and they’re something that every human she comes into contact with appreciates. Every conversation teaches her something. Every “yes” and every "no" reveals new information. She is constantly paying attention and iterating, sometimes on how to better structure the process or on new ways we might think about the role or candidates beyond our initial definitions. Caroline’s listening, learning, and iterating constantly expanded our definition of what was possible.
All of this curiosity and listening makes it possible for Caroline to figure out what folks need and what matters most to them. She’s not just listening to check off a list of candidate skills; she’s listening to understand what is going to make a candidate say “HELL YES” to a role. This is her brilliance in recruiting AND it's a powerful foundation for most things. Whether trying to find product-market fit, close a sale, or build the right team, success comes down to curiosity, listening, and willingness to adapt based on what you're learning.
How I spend my mornings!!!!
Caroline’s Story
"The true story is that I did not know I wanted to go into recruiting," Caroline told me. "I did a temp job as a recruiter in San Francisco, and a woman I worked with said, 'Oh, you're really good at this.' I didn't really know I was good at it. I was just doing it."
So, she cold-called every recruiting firm in the San Francisco Yellow Pages (yes, the Yellow Pages!) until she landed her first job. From there, she moved through corporate recruiting at Gap and Charles Schwab and learned how showing up for humans as an employer attracted candidates and built loyalty.
After this early-stage career, she left to pursue her passion for food access and healthy eating in schools, which eventually brought her to Revolution Foods as employee number four. "They said, 'We want you to recruit schools,'" Caroline laughs. "So my job was to cold call and recruit schools. And they were like, 'Why are you so good at this? How are you finding this information?"
The answer, she realized, was always the same: "I was good at research and I was good at listening to what people were saying. I would connect the dots across what they're saying about their RFP process, what they need, what matters to them."
What this looks like in practice
-
Most people think research is pulling lists and finding names. But Caroline builds four layers that help her understand not just who people are, but what they need and what matters to them. Let’s imagine she’s recruiting for a Healthcare AI Company:
Level 1: The Foundation: Quantitative research — aka basic market mapping. For a healthcare AI search, this meant identifying five different categories of companies: health tech startups, companies that shifted focus, traditional tech companies, insurance companies, and direct competitors.
Level 2: The Intelligence: Qualitative research to understand the nuances that indicate someone is actually viable. For doctors interested in preventive medicine startups: who's following Peter Attia, commenting on longevity blogs, attending specific conferences?
Level 3:The Context: This means market research across the entire ecosystem, both for a specific role, but also building and paying attention to role after role. "Five years ago, doctors were willing to take full-time jobs at startups. In 2025, they want to consult for multiple companies. They have the leverage—they're never without a job." This shift in the market means you need to change your approach.
Level 4: The Adaptation. Real-time learning about what's actually working is a must. Caroline and her team track not just response rates, but quality of responses, language that resonates, reasons people say yes or no. "Every week we're adjusting based on what we learned."
-
Caroline turns every conversation into intelligence gathering about what people need and what matters to them. She's not trying to convince people—she's curious about what would actually work for them.
"A lot of it's listening and looking for openings and taking that information to either get you to another person or follow up with this person."
Example: An executive mentioned she wasn't happy in her new job. Instead of persuading her to start an interview process immediately, Caroline simply noted the executive was unhappy and ended the conversation. When a CEO later wanted to talk to that candidate, Caroline approached her with: "The CEO saw your background and would love to just have a conversation." That led to a successful match because Caroline had listened for what mattered. While the executive was unhappy with her current job, she had some concerns about job-hopping so quickly because she was still new to the role. By framing it as a “conversation” rather than the first step of a full interview process, Caroline gave the unhappy executive a way to overcome her job-hopping concerns in order to explore something that might be a better fit.
-
Caroline constantly tracks and adjusts based on real-time feedback. Are people not responding to the specific role but interested in staying connected about opportunities in the field? Do they want full-time jobs or consulting arrangements? What words and examples get them excited versus the ones that make them tune out?
"Every week we're adjusting based on what we learned. They didn't respond to this specific role, but maybe they'll respond to broader outreach about joining our community for consulting opportunities. We're listening for what people want in the market."
This isn't just about changing your messaging, it's about fundamentally understanding what people need and what matters to them, then adapting everything from your approach to your offerings based on what you discover.
Secret Sauce & Takeaways
Listen for what people need and what matters to them: Whether you're selling, hiring, or building products, success comes from understanding motivations, not just demographics.
Layer your research beyond the obvious: Go deeper than lists and basic facts to understand context, nuances, and what actually drives decisions.
Adapt based on real feedback: Track not just whether your approach works, but why it works (or doesn't) and adjust accordingly.
Curiosity beats persuasion: Focus on learning what would actually work for people rather than convincing them to want what you're offering.
Every interaction teaches you something: Turn conversations into intelligence gathering about needs, preferences, and changing conditions.
Enough said!
Questions to ask yourself
How are we capturing and applying learnings from our processes (hiring, sales, product development, partnership building)?
What market intelligence are we missing about the people we're trying to reach?
Are we listening to learn, or just hoping our standard approach works?
How could we turn any process we're running into a continuous learning laboratory?
When have you experienced that "magic" in professional relationships - what made those interactions different?
Want to Try This?
Templates & Guides:
Caroline’s Sourcing Strategy Guide — a systematic approach to building a strong candidate pipeline
Caroline’s Job / Market Fit Framework — approach hiring like product/market fit
Caroline’s Health of the Pipeline Tracker - captures both hard data AND qualitative observations. You review it weekly and it grounds you + the team in all the ways needed for a great search.
Intentionally build your pool with The Management Center’s worksheet for building a diverse pool of high performers and connector email template.
Recommended Reads:
Helia's Interviewing: Finding Your People, Hiring with Heart and Strategy and The Why Interview — helpful reads to understand who you're looking for AND creating a solid hiring practice/approach
Management Center's hiring resource hub — practical tools for systematic, equitable hiring processes
Subscribe to First Round Review - wealth of job specific frameworks for hiring AND interview questions. Some of Caroline’s favorites:
Connections
Helia can make connections to folks like Natalie to help bring this to life (one-time set up OR ongoing)
About the Contributor
Caroline Fitz-Roy is the founder of FitzRoy and Associates, a recruiting firm specializing in purpose-driven organizations in healthcare, nonprofits, and social ventures. She cold-called every recruiting firm in the San Francisco Yellow Pages to get her start, worked at Gap and Charles Schwab, then followed her passion for food access to Revolution Foods before launching her own practice. She believes that great recruiting is equal parts science and art — and that the magic happens when you never stop learning from every conversation.
This article comes from a conversation with Caroline Fitz-Roy in June 2025. These conversations form the heart of the Helia Library – because I've learned the most from doing and from talking with other doers willing to share their wisdom. We don't need to start from blank pages or do everything alone.
As always, take what's helpful, leave what's not, and make it your own.
Article & Resource Tags
