The Power of the Ask: When It Hurts and When It Doesn’t

The knees quiver. The heart quickly beats. The hands palpitate. All of those symptoms can arise when you're about to ask. Whether it's approaching that beautiful girl for a first date, petitioning your boss for a raise or, in this case, requesting funds on behalf of thousands of teachers, asking takes courage.

It's exactly this courage that Donorschoose CEO Charles Best had when he asked Ripple for 29 million dollars to fund every project on the crowdfunding site, After a story like this hit the media, I kept hearing people comment, "Goes to show, it never hurts to ask!"

Or does it?

Seth Godin, the famous marketing guru, believes it does hurt to ask. It hurts when you "ask the wrong way, ask without preparation, or ask without permission. It hurts because you never get another chance to ask right." Godin makes the point that before you ask, you must do the work.

This includes the work of preparing, the work of connecting, and the work of investing into the person of whom you are asking.

Godin's point resonated with me because I was the one to use that phrase 'It never hurts to ask!' as the fuel to make big requests, often without taking the time to do the work.

As the teacher rep on the Donorschoose Board of Directors, I get a front row seat of watching Charles and the Donorschoose team 'do the work.' Their partnership team does major research on potential partners before they approach a prospective organization, business or funder. Before they roll out a program, they carefully A:B test it to see how well it would do locally before they introduce it on a national scale.

They do the work.


Educator Genein Letford welcoming our partners to the Summit!

In April, Donorschoose is hosting their fifth 'Partner's Summit', an event where they invest cutting edge information to the organizations, businesses and large donors that support our Donorschoose. They build relationships, they make connections and they invest in the people who invest in you; our Donorschoose teachers.

This Ripple request was no different.

In this article, Charles talks about how Ripple founder, Chris Larsen, has supported Donorschoose teachers for years. He knew Larsen was 'someone who had done a lot in his career on the frontlines to enable people to do big things with small sums of money." That is what Donorschoose is all about; equipping citizen donors with the power to do big things with any amount of giving.

But his first point of contact for this request wasn't Larsen, it was Brad Garlinghouse, another longtime supporter of Charles Best knew the relationship was present and the connection was strong. Donorschoose did the work for this rare opportunity to make this BIG ask:

Would Ripple be willing to fund every project on the site?

Charles hesitated at first to send the email, thinking he might offend Mr. Garlinghouse, but his dedication to us teachers overrode this hesitation. He found the courage to send this 'wildly ambitious pitch'.

I know thousands of teachers who are happy he pressed send.

Donorschoose Board Member, Stephen Colbert announces the 29 million dollar donation!

It was the click of that button that manifested into a 29 million dollar donation funding over 35,000 projects. It was the click of that button that affected over a million students nationwide. It was the click of that button that made the work they did beforehand pay off.

So as we celebrate this major milestone for and their teachers, let's not forget the important lesson here. Instead of haphazardly making big requests without preparation, let's find the time to do the initial research, build relationships and invest some time and resources to earn the right to ask.

You'll be glad you did.

And who knows? It just might become another #BestSchoolDay ever.