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4 Words?


I remember that meeting so clearly.

The prospect was new. His foundation had money to give away. The potential was tremendous.

I had brought in my organization’s founder to make his pitch. Now, I watched him as he spoke. He was doing a wonderful job. Yet I had the sense that the time wasn’t yet right for him to make his actual ask.

After a few minutes, I decided to make a bold move. I stepped in and asked the prospect, “How does that sound?

That short check-in was probably one of the most valuable sentences I’d say in my entire previous fundraising career.

Why? Because it cleared the way for a tremendously successful solicitation.

Here’s what happened next. Because of my check-in, the prospect voiced an uncertainty he had about our project.

Because he voiced that uncertainty, we had a chance to make our case better. And, from the look on his face as we did, it seems like we had cleared things up.

Just to be sure, I checked in a second time. “Is there anything else?”

There wasn’t.

That was the moment I chose to go in with the solicitation.

It was no small ask. We were aiming for a multi-year commitment at a high level.

The silent wait began. Those ten quiet seconds that often feel like a decade.

Finally, the prospect responded. With a six figure donation. The largest I’d ever facilitated.

For many of us, making our pitch is easy. We’re passionate about our work, and we’re happy to talk about it.

It’s transitioning to the actual ask that gets tricky.

First of all, asking for money isn’t generally a comfortable thing to do. Secondly, with this type of request, timing is everything. Ask too early, and you lose the donation. Ask too late, and you miss your opportunity.

So how are you supposed to determine the right time? 

My four-word check-in - “How does that sound?” - can bring you tremendous clarity. This little question helps both you and your prospect wordlessly figure out, “Where are you at here? How are you feeling about helping us? Is there something holding you back - some objection that we can clarify before I make my ask?”

Because often, donors do have hesitations. Questions or objections that keep them from wholeheartedly buying into your cause. But they may not voice them unless you give them an opening.

Sometimes, they’re not even clear on what’s bothering them. They need you to help them uncover their uncertainties. Then, you can work on assuaging them.

Objections aren’t something to shy away from. In fact, they’re a powerful ally. They help you transition smoothly - and successfully - from pitch to ask.

These four words - “How does that sound?” - are my gift to you. Use them well.

Have a wonderful fundraising week,



© Avraham Lewis & Co.