Podcast Summary: Giving Done Right

Episode: "How to Get Boards to Help With Fundraising" (from The Chronicle of Philanthropy)

Release Date: November 6, 2025
Featuring: Host Stacy Palmer (Chronicle of Philanthropy), Kathleen St. Louis Caliento (CEO, Cara Collective), Nick Gronow (CEO, Freedom Fund)

Episode Overview

This episode dives deep into one of the most perennial challenges in nonprofit leadership: how to truly engage boards—in particular, how to motivate board members to help with fiscal planning and fundraising. Host Stacy Palmer is joined by Kathleen St. Louis Caliento and Nick Gronow, both seasoned nonprofit leaders whose organizations recently received significant unrestricted gifts from MacKenzie Scott. The discussion is packed with candid reflections, practical strategies, and actionable ideas for nonprofit executives and board members alike.

Key Topics and Insights

1. Understanding Board Dynamics: The Power-Knowledge Asymmetry [03:04]

• Main Insight: Boards wield significant power (e.g., hiring/firing the CEO, approving budgets), yet they often have less day-to-day knowledge than staff or executives.
• Nick Gronow: “There’s this big asymmetry of knowledge and power… when organizations get into trouble, it’s often because their boards were asleep at the switch." [03:04]
• Kathleen St. Louis Caliento: Adds that while boards have power, they also have access to critical resources—networks, skills, and expertise that nonprofits can draw upon. [05:13]

2. Building Strong Board-Executive Relationships [04:04 & 05:02]

• Key Elements:

  • Focus on the organization’s purpose rather than on personalities.
  • Maintain constant, respectful communication.
  • Ensure no surprises for the board by keeping them informed early and often.
  • Keep clear boundaries: boards govern, executives manage.

• Nick Gronow on communication:
  “I speak with our board chair… every two or three weeks. I want to make sure there are no surprises for the board. I want to make sure that they are fully informed...” [04:13]

• Kathleen: “We rely on our board members... for support we might not otherwise be able to access... not just financial but also strategic.” [05:13]

3. Engaging Boards in Strategy and Expansion [06:57]

• Case Study: Cara Collective’s expansion into the Englewood community.

  • Education: Regularly inform the board about community needs and opportunities.
  • Buy-in, not ‘Big Reveals’: Test ideas in committee before bringing them to the full board.
  • Broader Storytelling: Present the wider vision during board meetings after socializing the plan in advance.

• Kathleen: “We needed to educate the board on truly what is happening in the community. Our board members… are not thinking about this every day.” [06:57]

4. Learning From Others: Importance of External Expertise [09:34]

• Inviting outside leaders who have recently undergone similar expansions/fundraising campaigns can “help strengthen your argument” and provide “the good, the bad, and the ugly” firsthand. [09:34]

5. Demystifying Board Fundraising Discomfort [10:57]

• Barriers:

  • Many boards see fundraising as “extra” beyond attending meetings.
  • Some members lack networks or comfort with direct asks.

• Nick: “If you want board members involved... set expectations clearly upfront—during the recruitment process is the best time.” [10:57]

• Recognize diverse ways to contribute: personal giving, leveraging networks, corporate matches, or simply making introductions.

• Mapping Exercises: Map board members’ contacts to streamline and “lighten the load” for outreach. [12:59]

• Kathleen: “We try to be pretty explicit with our board members from the recruitment phase about the give-get and what that means... Even if you can’t give as much, can your company or network?” [13:24]

6. Creative Strategies for Board Engagement and Retention [15:09]

• Proximity to Mission:

  • “Mission moments” start every board meeting—stories from program participants or partners [15:09]
  • Annual one-on-one engagement meetings with each board member to discuss satisfaction, skills, and new opportunities.
  • Encourage board members’ personal and professional growth and networking with each other.

• Kathleen: “I think about proximity a lot and talk about it a lot with my board… If you’re proximate to the work, you’re much more connected to the mission.” [15:09]

• Building Relationships: “I make time to have drinks, breakfast, lunches… I truly want them to like each other because this work is hard.” [16:08]

7. Best Practices for Board Fiscal Planning [19:28]

• Have a treasurer or finance-savvy board member; in larger orgs, create a Finance/Audit/Risk subcommittee.

• Hold regular pre-board deep dives into financials and scenario planning, not just for current budgets, but looking years ahead.

• Transparency around risks and external shocks (e.g., government funding freezes).

• Nick: “You need a board that takes its responsibilities seriously… I’ve been stunned how many new CEOs have come into the role only to find there’s a significant hole in the finances.” [19:28]

8. Managing Large, Unrestricted Gifts: The MacKenzie Scott Experience [22:18]

• Kathleen (Cara Collective, $8M):

  • Convened an ad hoc board committee (with finance and program expertise) to determine best use:
    • ~50% placed in sustainability investments
    • Infrastructure and capacity upgrades
    • Program expansion
  • “Engaging the board was really critical… it allowed them to really ultimately in the end be supportive of the way that we chose to implement those dollars.” [22:41]

• Nick (Freedom Fund, $35M):

  • Set parameters to spend the gift over five years, engaged all staff and board in planning.
  • Invested in capacity and program growth, but hit challenges in raising replacement funds (“we probably tried to do too many things” [28:05]).
  • Adjusted strategy mid-course to align income and spending.
  • Praises MacKenzie Scott’s unrestricted, multi-year approach for its ability to cushion against shocks.
  • “It’s enabled us to significantly increase our impact...” [25:49]

9. Innovative Board Retreats and Deepening Board Understanding [28:49]

• Cara Collective’s Retreats:

  • Annual, in-person, immersive, with agenda items and role-playing exercises to help board members “walk in staff’s shoes”
  • “Mission and proximity” as key themes
  • Social opportunities to deepen relationships
  • Now involving auxiliary boards to strengthen pipeline

• Kathleen: “We actually had our board members take on the roles of various team members on staff… hit with these challenges at every 10 minutes… really an opportunity for them to get so close... understand the herculean effort...” [28:49]

10. Self-Care & Board Camaraderie [32:44]

• Each leader shares their method for recharging:
  • Kathleen: Running (“Eight marathons… it’s my time for myself”) [32:44]
  • Nick: Swimming—ocean swims, even bringing board members along for organized swims (“...on at least a couple of occasions, have taken my board on it on long swims...”) [33:26]

Notable Quotes & Memorable Moments

• Nick Gronow [04:13]:
  “You need a relation of respect… I want to make sure there are no surprises for the board... but I also want to make sure they are focused on their responsibilities around governance and give me and my team the ability to focus on the day-to-day.”

• Kathleen St. Louis Caliento [05:13]:
  “We rely on our board members, right, because they are often much more resourced than we are… So they hold a lot of power, but they also hold a lot of resources for us as well.”

• Stacy Palmer [12:48]:
  “I’m not sure board members realize how much just helping you get in the room is what matters.”

• Kathleen [15:09]:
  “If you’re proximate to the work, you’re much more connected… There are a couple of things we do: we start every board meeting by grounding in what we call a ‘mission moment’.”

• Nick [19:28]:
  “You need a board that takes its responsibilities seriously. Management of finances, management of risk is among the top responsibilities...”

• Kathleen [22:41]:
  “It allowed them to lower their shoulders a little bit and breathe a little bit easier… engaging the board was really critical…”

• Nick [25:49]:
  “...one of the most joyful days of my professional life... we set up plans to engage all staff and mapped out capacity and fundraising priorities—but also had to adjust along the way.”

Timestamps for Key Segments

• Board power/knowledge dynamics: [03:04]
• Creating strong board-CEO relationships: [04:13]
• Leveraging board resources strategically: [05:13]
• Engaging board in major expansion: [06:57]
• Best practices—outside expertise: [09:34]
• Barriers to board fundraising: [10:57]
• Explicit expectations for fundraising: [13:24]
• Keeping boards engaged/proximate: [15:09]
• Board self-assessment and mutual growth: [16:08]
• Finance responsibility and scenario planning: [19:28]
• MacKenzie Scott grants—board engagement: [22:18]
• Engaging staff in grant allocation: [28:05]
• Immersive board retreats: [28:49]
• Leader self-care: [32:44]

Takeaways for Nonprofit Leaders and Board Members

• Set clear expectations with board members, especially regarding fundraising, at recruitment.
• Make fundraising easier for board members: provide lists, clear asks, and recognize indirect contributions.
• Bring boards closer to the work—through mission moments, site visits, and storytelling—to deepen motivation.
• Use retreats, role-playing, and peer learning as tools for board development.
• Involve boards early in major strategic decisions and grant stewardship, but provide the right information and support structures (committees, expert input).
• Value and encourage both the “treasure” and the “talent” that board members bring.
• Foster board relationships, camaraderie, and a sense of mutual growth.

For those who haven’t listened:
This episode is a masterclass for nonprofit leaders seeking to energize their boards and unlock their full potential. Real-world examples, concrete suggestions, and a tone of candor and encouragement make it both practical and inspiring.