This one simple question led to a $40,000 gift.

It was supposed to be a normal stewardship visit.

Show up. Say thank you. Report back on impact. Ask a few questions. Deepen the relationship a bit. Nothing out of the ordinary.

Within a few minutes, my agenda flew entirely out the window.

After a little small talk, he asked, “How much have we been giving you all the last few years?”

Before I could answer, he stood up, walked quickly across his large office, and pulled a file folder off his bookshelf with the word “GIVING” scrawled in magic marker on the cover.

He walked back my way and answered his own question, “$20,000 a year.”

What happened next took me totally by surprise.

Without really thinking about it, I asked, “Is that the right amount to be asking you to give?”

He paused, “You know... no one’s ever asked me that before.”

He then gave me a masterclass on what it’s like to be on the giving side of a major gift relationship.

He told me that most of the time, the fundraisers who showed up in his office asked him to give LESS than the amount he was considering giving.

“Sometimes I’m thinking about giving $10,000 when they ask me for $2500. When that happens, they get $2500.”

Almost no one ever asked him for too much.

He said it was nearly impossible to offend him by asking for too much.

“If you ask for a LOT more than I can give, I’ll either laugh because I’m flattered you think so highly of my financial position, or if it feels slightly out of reach, I’ll try to find a way to make it work… Usually, I can.”

The conversation continued for a few minutes, and then I realized he still hadn’t answered my original question.

So I bolstered my courage and asked, “Is there a different amount we should be asking you to give?”

What followed felt like one of the most awkward and protracted silences I’ve ever experienced.

It was probably only 7 seconds, but it felt like 7 minutes.

He finally responded, “You could ask me for $50,000, and I wouldn’t blink.” ?? ??

[he paused before continuing]

“I’m not telling you I’d say yes, but you could definitely ask.”

And so I did.

“Would you consider a gift of $50,000?”

He smiled and told me he’d think about it, and get back to me.

How much did he end up giving?

$40,000.

It was not the $50,000 he gave me permission to ask for, but it was the largest gift he’d ever given us.

The day that $40,000 check arrived, something hit me.

Up to that point in my fundraising career, I’d been playing it safe. I hadn’t been bold or courageous enough in my relationships with givers.

I’d been too worried about offending people.

Not anymore.

Over the next few months, I asked several people I’d been building relationships with a similar version of the same question.

Without exception, they all answered the same way and gave me permission to ask for more.

These conversations weren’t limited to $$$ amounts either:

“You’ve been giving to a specific program. Is that the right thing to be inviting you to support?”

“You’ve sponsored our gala for the last four years. Is that how you want to continue giving?”

“You’ve given every year for the last ten years. Many people who give as regularly as you have included us in their will. Is that something you’ve ever considered doing?”

“We normally ask you to support the ongoing work of existing programs. Is that right, or would you ever be interested in helping launch something new?”

One couple told me they preferred to make 3-year commitments and asked if we might be open to them doing that with us! ????

(in case you’re wondering, the answer was yes!)

Clarifying questions like these aren’t intrusive or offensive.

If asked in the context of a relationship, they communicate care and a desire to help someone make the most of their giving.

Are you too worried about offending people?

Try asking clarifying questions about their giving the next time you visit with a giver, and see what happens.

The odds are good you won’t offend them.

And who knows?

You might even end up with a 3-year gift commitment.