Fundraising Friday: This Five Word Phrase Changed How I Fundraise

When I first started fundraising, I was pretty bad at it.

I was good at the relational aspects and the follow-through, but when it came to talking about giving and actually asking people to give, I struggled.

Do you know what finally helped?

It wasn't some grand strategy or better collateral. It

didn't involve making more calls or going on more visits.

It was five simple words:

"Would it be okay if...?"

Here are a few places where this simple phrase can change the way you experience fundraising.

Setting the Stage

Imagine you're in a meeting with a giver. You’ve spent some time connecting and catching up. And now you’re ready to talk about giving.

Instead of launching into your carefully crafted spiel, what if you paused and asked:

"I always like to start by trying to understand the impact people want to have when they give. Would it be okay if I asked you some questions about the difference you want your giving to make?”

Suddenly, the dynamic shifts. You've given the other person control, showing respect for their time and preferences. You've set a tone of collaboration rather than solicitation. You’ve put them at ease.

Deepening the Conversation

As the meeting progresses, you want to understand more about the donor's motivations.

Instead of unexpectedly launching into a series of questions, you ask:

"Would it be okay if I asked you about what inspired your interest in education?"

By seeking permission, you're acknowledging the personal nature of the question.

You're giving the other person space to decline if they're not comfortable, which paradoxically often makes them more likely to open up.

Before Making the Ask

When it's time to actually invite someone to give, many fundraisers feel their anxiety spike.

But what if you approached it this way:

"Would it be okay if I shared an opportunity to give that I think aligns with your interests in supporting students?"

You're not pushing. You're offering. You’re asking permission to share. You're treating the person you’re asking as a partner, not a target.

Following Up

Even after a successful meeting, these words are powerful. As you’re leaving, you might ask:

"Would it be okay if I reached out next month to update you on the project's progress?"

You're respecting their time, giving them the option to set boundaries.

Handling Rejection

Not every ask ends in a gift. But even when someone says "no", these words still apply:

"I understand. Would it be okay if I came back to you in the future with other opportunities that might interest you?"

You're respecting their decision while leaving the door open for future engagement. You’re turning a “no” today into the possibility of another conversation tomorrow.

The Brain Science Behind the Phrase

There's fascinating brain science behind why this phrase is so effective.

When we hear a question like "Would it be okay if...?", our brains interpret it as a safety signal.

This type of language activates the prefrontal cortex, the part of your brain responsible for logical thinking and decision-making, while simultaneously calming the amygdala, which governs your fight-or-flight response.

In essence, by using this phrase, you’re creating a psychologically safe environment for the people you’re talking with. You’re signaling respect for their autonomy, which helps put their brains at ease. And when our brains are at ease because they perceive a situation as safe and familiar, we're more likely to respond positively.

This state of comfort allows people to engage more fully in conversation, be more open to new ideas, and make decisions from a place of clarity rather than stress or pressure.

By consistently asking "Would it be okay if...?", you’re creating a pattern of respectful interaction that donors come to expect and appreciate.

When you use this phrase, you're not only being polite, you're actually helping create an optimal neurological state for a productive, positive conversation about giving.

The phrase "Would it be okay if...?" does several things when used throughout a conversation:

1. It shows respect for the autonomy of the person.
2. It creates a collaborative atmosphere.
3. It reduces pressure on both people.
4. It gives the other person control while still allowing you to guide.
5. It clarifies your intent and never leaves them wondering what's happening.

When you consistently use this phrase, you'll change more than your language. You may actually find your entire approach to fundraising starting to shift.

You may find yourself naturally moving from transactional to relational fundraising.

True story. I've seen it happen.

Would it be okay if I give you a challenge?

(see what I did there???)

Over the next month, can you try to incorporate "Would it be okay if...?" into your fundraising conversations?

As you do, pay attention to how it changes the dynamic with your donors. Notice how it makes you feel as a fundraiser.

You might just find that these five simple words not only improve your results but also make the entire process more enjoyable for you and everyone else involved.

Let me know how it goes, and keep up the good work friends!

-Michael