The Asking Conversation: How to Ask for “Permission to Ask”

asking conversation with donor

asking conversation ask for permission to ask | Gail Perry Group

So much of fundraising comes down to the Asking Conversation, doesn’t it?

It’s inevitable — because we are simply in the business of raising money.

But asking can be tough: in worst cases – it’s full of fear and trepidation. Other times, it can be just plain awkward.  

Consider looking at it from the donor’s side during an ask conversation.

How do we want your donor to feel when we talk about the investment she could make in our cause?  Above all, consider: What does SHE want to do? How is SHE feeling right now?

Based on my own recent experience of being asked, I felt as awkward as the fundraiser across the table.

No matter what your asking style is, you need to prepare your donor. 

You can’t pop an ask on someone without preparing them.

When you just blurt out an ask without preparing the donor – it never really works.

It makes the donor feel uncomfortable – like they were not prepared for this conversation. Since the donor isn’t prepared, you certainly are not going to get a positive and quick response.

Moreover, if the donor feels taken by surprise, then they may resent you. Or be angry at you. Or at the minimum, feel put off.

Subsequently, you’ve really moved the relationship backwards not forwards. And you have to go into damage control.

By all means, use good manners. Let your donor know what to expect.

When you are visiting a donor, you don’t have to come right out and say ,“we want to ask you for financial support.”

But you can, at least, obliquely say,

“We’d like to discuss your interest – would you like to have that conversation?”

Five Ways to Introduce the Asking Conversation: 

For instance, you could ask:  

“Would you like to learn more about the project you have been so involved in?”  


“We have an opportunity to run by you regarding this area you’ve been so interested in.”


“Would you like to know about our new initiatives? Or the new projects we are planning? Or the expansion we are planning?

“I’d love to see if you might be interested in learning more and possibly supporting one of the projects.”

You can say,

“I know you are so enthusiastic about xxxx project, we’d like to talk more about it and see how you might like to be involved.” (I like this one because the donor feels completely in charge.)

Remember, the Asking Conversation is often a process, not a single point in time.

Above all, most major gifts are a series of conversations. You find out the donor is interested. You help them learn more about the project and get more engaged.

Most importantly, you use your judgement to decide when it might be appropriate to bring up the asking conversation.

And you open the asking conversation by asking for permission: ask the donor if they would like to have this discussion. Then you know where you stand. 

And, this goes for every single kind of asking conversation.

Here are some examples:

A major corporate sponsorship for an event –

You start out gently by inquiring about their marketing objectives or their philanthropic priorities.

And you only move forward if you get the green light.

A big foundation asking conversation –

First you start out by sending a letter of inquiry.

Or you have a conversation about whether there is a “fit” between their interests and your organization.

Usually you don’t move forward unless you get agreement to deliver a proposal.

An individual philanthropist – 

This person absolutely expects to be engaged and educated before any kind of ask is on the table.

The VIP donor will let you know clearly if they are willing to take the next step and discuss the possibility of a gift.

Bottom Line on the Asking Conversation:

To sum up: your ask is always more successful if you open the conversation like this: 

Is this something you might like to discuss?