Podcast Summary: What the Fundraising – Ep. 275

Title: The Heart Behind the Ask: Authentic Donor Stewardship with Hilary Dana Smiley
Host: Mallory Erickson
Guest: Hilary Dana Smiley, Assistant Vice President of Leadership Gifts at Boston Children’s Hospital
Date: December 23, 2025
Duration: ~27 minutes

Episode Overview

In this episode, Mallory Erickson sits down with Hilary Dana Smiley to explore what it means to build authentic relationships with donors at scale, why true stewardship goes far beyond transactional fundraising, and how to inspire and retain donors – particularly when it comes to unrestricted giving. Together, they unpack mindset shifts, strategies, and real-world examples for nonprofit leaders committed to moving past “fill the bucket” thinking and fostering genuine connection with every supporter.

Key Discussion Points & Insights

The Problem with Transactional Fundraising Models

• Donor Acquisition vs. Retention:
  Hilary emphasizes that not all donor acquisition is effective, especially when driven by incentives (“premium-based acquisition”), as those donors rarely stick around for the long haul.

  "We were seeing that those donors were just signing up to get the tote bag or get the decal for their car. So we pulled back from that. We saw a dip in acquisition. But what we're seeing is we're bringing on donors that are much more mission aligned." (Hilary, 00:38 & 15:16)

• Long-Term View:
  Hilary stresses the importance of thinking beyond immediate dollars and focusing on relationships that will sustain the organization.

  "Our job is not just about the money that's coming through the door today." (Hilary, 00:38)

Scaling Real Stewardship

• Personalization at Scale:
  Hilary explains how her team manages stewardship for 60,000 donors, emphasizing the need for both technology and a human touch.

  "It’s everything from technology enabling us to get to larger groups of donors in really personal ways. But it’s also not forgetting that we really should put people at the front of this..." (Hilary, 04:56)

• Key Tactics:
  • Use volunteer callers for thank-yous to $100+ donors.
  • Regular, personalized contacts for higher-value donors ($500+).
  • Tailoring communications by acknowledging milestones, gift types, and donor location.
  • Focus on “Thank you” more than “Please”.

Redefining Fundraiser Metrics

• Beyond Dollar Goals:
  Instead of pressuring fundraisers to hit monetary targets, Hilary’s team emphasizes quality interactions—tracking “significant contacts” and personalized outreach.

  “I focus on donor contact, significant contacts between donor and gift officers… being in front of each of their prospects in a personal way that creates a reciprocal relationship…” (Hilary, 08:15)

• Staff Mindset:
  Hilary argues that building relationships and trust will inevitably result in giving.

  “The gifts will come. That’s just my mentality. And they are, they do. The gifts come if we are doing these kind of personalized interventions along the way…” (Hilary, 10:59)

Retention: The Power and the Challenge

• Stewardship Wins Over Acquisition:
  Mallory articulates why retention is overlooked: it’s harder to measure and lacks immediate rewards.

  "We want that quick feedback loop ... we don't get it from retention activities and stewardship because it just isn't so cause and effect and it isn't so instantaneous." (Mallory, 13:58)

• Research-Backed Retention Value:
  Hilary points out the compounding benefits—higher donor retention leads to growth up the giving pipeline and future major gifts.

  “If you can get a donor to make that second, we know that their long-term value to the institution only grows.” (Hilary, 16:13)

Unrestricted Giving: Making the Case Clear

• Shifting Donor Perceptions:
  Hilary describes how they tackled the challenge of showing donors the tangible impact of unrestricted gifts.

  “When you gave an unrestricted gift, people ... thought that unrestricted giving did [nothing meaningful]. And I think it was really on us ... to think about, well, truly, what does unrestricted do? And how do we translate that to our donors in a way that feels impactful?” (Hilary, 17:38)

• Concrete Storytelling:
  The team ties unrestricted dollars to specific, compelling elements of the hospital’s mission, such as child life services, research, and health programs, using authentic messaging from leadership.
• Empowering Donor Imagination:
  By focusing on the vision for the institution rather than single, restricted projects, donors can see themselves as part of the hospital’s future and sustained impact.

  “You’re attaching their desire to the vision of the institution in a way that doesn’t ... make up some new thing they should care about each time.” (Mallory, 21:20)

Notable Quotes & Memorable Moments

• On Retention Over Acquisition:

  “...not all acquisition is created equal ... we don't do premium based acquisition ... we saw a dip in acquisition. But what we're seeing is we're bringing on donors that are much more mission aligned.”
  — Hilary Smiley | 00:38, 15:16

• On Donor Stewardship:

  "We should be saying thank you more than please."
  — Hilary Smiley | 09:37

• On Fundraiser Mindset:

  “The gifts will come ... if we are doing these kind of personalized interventions along the way and making sure that we’re reaching out to our donors.”
  — Hilary Smiley | 10:59

• On Unrestricted Giving:

  “Being able to talk to donors about concrete examples and not just making it a big black hole ... It’s really just drawing that line between institutional mission and our ability to pursue that mission through philanthropy.”
  — Hilary Smiley | 17:38

• On Motivation & Privilege of the Work:

  “It’s just a real privilege for us to be one of the helpers in this time ... It’s our own beliefs, our own passion that’s going to inspire others to give.”
  — Hilary Smiley | 24:21

Important Segment Timestamps

• 00:38 — Hilary on mission-aligned donor acquisition, and moving away from transactional strategies
• 04:56 — How Hilary and her team approach stewardship for 60,000 donors
• 08:15 — Shifting fundraiser metrics from money to meaningful contacts
• 10:59 — Letting personalization drive the dollars, not the other way around
• 13:58 — Mallory on why retention is difficult for organizations to champion
• 15:16 — Hilary shares how investing in retention paid off, despite risk
• 17:38 — How to communicate the impact of unrestricted giving
• 21:20-22:31 — Linking donor motivation to institutional vision rather than specific “things”
• 24:21 — The privilege and affirmation of working in nonprofit fundraising

Where to Connect with Hilary Smiley

• LinkedIn:

  “I would say LinkedIn is probably the best place to find me and I'd be happy to connect with anyone around any of these topics.” (Hilary, 26:08)

Final Takeaway

Hilary Smiley makes a compelling case for investing in authentic, heartfelt stewardship and relationship-building at every stage of donor engagement. Her leadership at Boston Children’s Hospital demonstrates that focusing on personalized touches, consistent communication, and an inspiring case for unrestricted giving not only deepens donor retention but fuels greater impact for the institution as a whole.

For further resources, episode transcripts, and actionable tips, visit MalloryErickson.com/Podcast.