Welcome back to Burning Questions, where we tackle the most common (and often unspoken) challenges in fundraising. In this bi-monthly feature, Lisa tackles burning questions from across the nonprofit world — from donors seeking clarity, to fundraisers facing tough choices, to board members striving for greater impact.

Each column offers practical, candid insights to help everyone in the philanthropic ecosystem better understand one another — and do more good, together.

(Why Burning Questions? Why Philanthropy 451? See bottom of the article for an explanation.)

Have a question for Lisa? Let us know - share it in the Substack comments below, email it to greer.team@lisagreer.com, or message Lisa on LinkedIn and your question may be featured in an upcoming column.

This Month’s Questions

This month, we’re diving into two big ones — questions that nearly every fundraiser wrestles with, whether they’ve been in the field for six months or 25 years.

Q1: How do I balance meeting fundraising goals with building genuine relationships?

Q2: What’s the best way to talk about money without making donors feel uncomfortable?

Let’s get right to it.

Q1: “How do I balance meeting fundraising goals with building genuine relationships?”

This is the nonprofit sector’s eternal tension, which we only experience when something about our strategy is misaligned.

Here’s the reality:
Fundraising goals and genuine donor relationships are not competing priorities. They fuel each other.

The problem arises when goals push fundraisers into transactional behaviors — more asks, quicker asks, templated messages — rather than long-term engagement. That’s when donors disengage, trust erodes, and meeting goals becomes even harder.

Here’s how to realign:

1. Shift the mindset: donors are partners, not targets.

When we treat donors like numbers on a dashboard, we create a self-fulfilling prophecy: they give once and don’t give again. Instead, when we treat donors like collaborators in our mission, retention rises and goals become far more achievable.

2. Prioritize meaningful touchpoints — not just “check-ins.”

A relationship isn’t built on updates that say nothing. It’s built on:

• Showing impact

• Asking for input and authentically listening to the answer

• Being transparent

• Sharing progress as well as challenges

• Celebrating wins together

These touches are how fundraising goals get met without harming trust.

3. Don’t assume relationships slow you down — they speed you up.

Organizations with high retention and high donor satisfaction often close gifts more quickly than those with low retention rates. Why? Because trust eliminates friction. Donors don’t have to “think about it” when you’ve already shown you value them.

4. Be honest about goals.

Donors know you have goals — hiding them creates distance, not closeness. Bring them into the process: “We’re trying to raise $200K this quarter (in order to ... fill in the blank*). Your support, at any level, genuinely helps us get there.”

Transparency strengthens relationships and inspires giving.

*The answer can’t be just to meet our numbers this quarter – it should be more specific about what that money will actually impact.

Q2: “What’s the best way to talk about money without making donors feel uncomfortable?”

Talking about money becomes uncomfortable only when the conversation is vague, pressured, or disconnected from the donor’s motivations, or when the fundraiser is just plain uncomfortable talking about money (a common problem, unfortunately).

The good news? There are simple, practical ways to make these conversations comfortable for everyone — including you.

1. Start with purpose, not dollars.

The fastest way to create discomfort in a donor conversation is to jump straight to the amount of money you want from them. Doing so can be jarring, off-putting, and can end the conversation right then and there.

Having said that, some donors specifically want to know the amount that you want from them right away, and if you have an authentic relationship with them, there’s nothing wrong with telling them the amount you’re asking for.

For donors that you don’t yet have a relationship with, anchor the conversation in the mission: “Here’s what we’re trying to solve, and here’s why it matters.” When the purpose is clear, the money discussion becomes a natural next step.

2. Use honest, donor-centered language.

Try replacing:
❌ “We need you to give.”
with
✔️ “Knowing your interest in (XYZ), we’d love to partner with you on this important work.”
or
✔️ “Would you like to hear more detail on this project, along with the opportunities and challenges related to it?”

Clarity + respect = comfort.

3. Ask permission before talking numbers.

A simple: “Can we talk about how you might want to support this?” allows donors to opt into the money conversation rather than be dragged into it.

4. Normalize the conversation.

Most donors with means are likely to be comfortable talking about money, especially if they have agreed to take a meeting with you. Any awkwardness in the conversation usually comes from the fundraiser, not the donor. When you approach your discussion with confidence and transparency as opposed to discomfort or fear, both you and the donor will likely relax and be able to have a comfortable conversation — without any awkwardness.

5. Always leave room for “no.”

If you feel passionate about your mission, and you think about your profession as bringing joy and purpose to people, you will engage the donor more deeply. In doing so, the donor will be more likely to hear your story and want to support your organization.

Even the most dedicated donors may have a moment – based on their personal or business life – when the time just isn’t right for them to make a financial commitment. In an authentic, long-term relationship between a donor and a fundraiser, a donor will feel they can say “no” without damaging your relationship.

Final Thought

Fundraising isn’t about scripts, tactics, or formulas. It’s about human connection, clarity, and trust. When you build real relationships and talk about money with honesty and ease, donors feel valued and stay committed to ongoing support of your nonprofit.

Which means:
Better experiences for fundraisers and donors.
More sustainable revenue for nonprofits.
And ultimately, more impact for the world.

See you in the next Burning Questions edition.

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Inspired by Fahrenheit 451, the classic novel about a world where books are burned to suppress ideas, Philanthropy 451 is about igniting the opposite — sparking bold conversations in a field that too often avoids them. Philanthropy shouldn’t be on fire for the wrong reasons; it should be burning with curiosity, honesty, and change. This newsletter is a place to challenge assumptions, question outdated norms, and reimagine what giving can be when we’re not afraid to turn up the heat.

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