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Asking Big: Communicating Big Needs FOR Big Dreams

By Jeff Henderson | February 2, 2023
Asking Big: Communicating Big Needs FOR Big Dreams

I see a great book as the start of a great conversation. So, when I finish a book I love, I try to reach out to the author.

That includes Mr. Warren Buffett. When I finished his biography, I wrote him a letter asking for 15 minutes of his time, to answer three questions, if I would fly down to Omaha to meet with him. 

15 minutes with him was a big ask.

Mr. Buffett runs Berkshire Hathaway, a company purported by Forbes to be the largest in the world. His personal net worth is more than $100 billion.

Not long after I wrote him, I got a letter back: he declined (as you might expect).

But I didn’t let that stop me from also asking civil rights leader and former Atlanta mayor and United Nations Ambassador Andrew Young when I read his book a few years later. My ask was even bigger this time: would he come speak to my staff and myself?

He said yes.

And after he spoke for us, Ambassador Young and I went on to have a lot of talks that never would have happened if I hadn’t asked.

Don’t Let Fear Keep You from Asking Big

We often undercut our ask because we expect rejection.

I’ve done this a lot as a leader of three nonprofits over the last 17 years. We needed to raise money for new buildings, and as excited as I was about the project, I still had to battle the fear of asking big.  

I found myself thinking, “I probably shouldn’t ask them.  They might not be in a position to give at this time.”

What I eventually realized is that I was speaking for them without even asking them. But it’s not my responsibility to answer for them – it’s my responsibility to ask. 

My responsibility as the leader was to make the ask. 

Their responsibility was to provide an answer. 

I couldn’t confuse the two. 

Since then I’ve seen that asking big will net you a lot of nos. They’re inevitable. And they are more common than yeses. But by asking big, I make a lot of big yeses possible.

When you ask, just keep these three things in mind:


What are you asking for? Do you need their time, their money, their resources, their connections, their support? Be specific. Make their “yes” easy on them by letting them know exactly what will happen if, and when, they give it to you.


Asking big demands boldness.

When my daughter graduated high school, our family took a trip out to San Francisco to celebrate. She loves Pixar movies and the studio HQ is in the San Francisco area, so I wrote Ed Catmull, the CEO, and asked if my family could have a private tour of Pixar.

Another big ask of a “big man.” Mr. Catmull runs one of the world’s leading animation studios. They’ve picked up an Oscar nomination for almost every film they’ve released, and a total of 18 Oscar wins. I thought, “They’ll probably never even read the letter.”

But five months later, I was standing in Pixar headquarters with my family staring in awe at all those Oscars.


Be bold in your big ask. Be clear about it. And then, be quiet.

It will be awkward. You’ll want to break the tension by speaking. But stay strong and stay silent. You’ve done your part by asking; now, they need the room to do their share by giving you their answer. 

When you make your ask, they can only say one of three things: “yes,” “no,” or “let me think about it” (which also means “no”). I wish I could say you’ll get more yeses than nos, but what I can say is that you’ll get bigger yeses – yeses that will send you on your way to being your best FOR the world.

What big asks will you make for your mission?

Zig Ziglar famously said, “Success occurs when opportunity meets preparation.” Prepare yourself to ask big by writing down the name of one person whom you’re going to ask for help. And if you’re looking for more ways to live a life of substance for the world, my book Know What You’re FOR might be a helpful resource for you. You can get a copy here.

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