How to Ask People for Favors, When You're Uncomfortable Doing It

I love helping people.

I am terrible at asking people to help me.

I have many reasons for this. I don’t want to be a burden. I don’t want anyone to feel obligated. I came up a rule in my head, which is that I have one ask of everyone I know. Like, one ask ever. So I better use it well.

But…

Then I wrote a book. I knew I’d need to rely upon my network — asking people to help promote it, or just to buy a copy.

So I made a resolution: I would finally start asking for favors.

It’s gone very well. Here’s what I learned.

1. When you ask for a favor, you’re doing someone a favor

I’ve done a lot of favors for people. I’ve made connections, given feedback, promoted their work — whatever.

Here’s what I didn’t realize: As a result, these people felt guilty. They really, really wanted a way pay me back, but I’d never given them a way to.

This reminded me of interesting research I’d come across, about the hidden benefits of birthday parties. The first parties in America began in the late 1700s, but most people considered them a ghastly overindulgence. They refused to celebrate their kids’ birthdays, thinking that they’d create self-absorbed children that will spurn the community at large. (I did a podcast episode on this.)

But now, as historians look at that shift, they see how birthday parties actually strengthened communities. Why? Because they created what York University consumer researcher Russel Belk calls a “lingering debt.”

It’s a self-reinforcing system: You’re invited to someone’s party, which means you must invite them to your party. And because birthdays are distributed throughout the year, this means the debt lasts for a long time. “That keeps the group spirit alive,” he said.

I found this to be true when I asked for favors too. I allowed my friends to feel better about their debt, but it’s not like we’re even now. This isn’t a financial transaction. Instead, I now feel great about what they did for me, which means I want to help them even more, and our beautiful lingering debt cycle will continue.

2. Asking for favors is a good reason to stay in touch with people

If you’re regularly in touch with someone, they’ll feel invested in your success. They’ll be happy to help you.

If you only contact someone when you want help, they’ll be annoyed. Maybe they’ll help once, but never again.

Podcast host Jordan Harbinger made that point to me a few years ago, when I interviewed him in Entrepreneur. You cannot take your network for granted, he said.

It’s why he actively keeps his network warm — and even uses a CRM to do it. (CRMs, or Customer Relationship Management, is a tool salespeople use to keep their leads organized.) “The CRM reminds me when I haven’t connected with someone in a certain amount of time — I set it for three or six months — and then I simply check in via text or email,” Jordan told me. “I’ll ask how they’re doing, share a little about me, and that’s it. It doesn’t take much time.”

I took that advice myself, though with a little less rigor. I created a spreadsheet called “Good Contacts” a few years ago, and now input anyone I want to stay in touch with. Periodically, I go through it and reach out to folks I haven’t talked to in a while.

This is nice! Yes, fine, there’s a selfish element to this — I hoped they’d help me with the book. But it also allowed me to keep up with interesting people, help them with their own projects, and build lasting relationships.

Oh, and Jordan and I kept up and became friends. I asked if I could be on his big and excellent podcast, and he said yes. Here it is!

3. Rejection gets drowned out by love

Here’s something I once couldn’t admit to myself: I didn’t ask people for favors because I was afraid of rejection.

I wasn’t actually afraid of the word “no.” I’ve heard that often enough. Instead, I was afraid of changing the nature of my relationships with people.

After all, rejection alters things! It’s like trying to kiss someone who’s not into you. There’s almost no going back from that moment. And I kept thinking — do I want to put this connection on the line, by asking the favor?

But then I did. So let me tell you what happened.

People were overwhelmingly happy to help. My best relationships were strengthened.

A few people said no, or just ghosted. These weren’t friends I knew well, but more like warm work acquaintances. For example, I have helped out a very large podcaster over the years, and we have exchanged many nice emails. But when I asked to be on this person’s show, they told my publicist no and never replied to me directly. I suppose that’s the end of that relationship.

But you know what? That’s OK. We have a lot of people in our lives — we don’t need to include the selfish ones.