It’s that time of year—people want stuff.

Maybe your inbox looks like mine, flooded with unsolicited messages:

Would be great to hop on a call.

I’d love to have you on my podcast.

I could really use a portfolio review.

I’ve attached my book draft, and I’d appreciate any feedback you have on it.

Can you help spread the word about our product?

(It’s always that time of year.)

You shot your shot. Good for you. (Well, not quite, but close, and points for effort.)

I get it. I used to send messages like these, too. And I’ve learned something important: if you’ve sent a request like this to me—or anyone like me—it likely went straight to the trash.

Not because I don’t want to help. Not because I don’t care.

But because you missed the most important part of any pitch: what’s in it for me?

Asking Without Offering Is a Losing Strategy

Lately, I’ve started responding with that exact question: What’s in it for me?

And let me tell you—some people really don’t like it.

The mad ones tell on their own selfishness or self-centeredness. As Maya Angelou said, “When someone shows you who they are, believe them the first time.”

The surprised ones? They usually say something like, “Um, I don’t know. What do you want?”

And that’s the rub: why would I spend time and attention on your thing when you’ve spent little on mine? It’s a mismatch of effort. You’re asking me to invest in you without first showing me why it’s worth my time.

Sure, some people operate on an “Asker” model—they just throw requests out there, assuming it’s fine if people say no. Others, like me, are more “Guessers”—we prefer to sense whether a request is welcome before making it.

Either way, cold asks rarely work unless they immediately answer the one question every recipient is subconsciously asking: Why should I care?

Strategic Givers Win

In Give & Take, Adam Grant outlines three types of people:

1. Takers: People who always try to get something without giving back.
2. Matchers: People who trade favors, keeping things even.
3. Givers: People who create value for others without expecting an immediate return.

The research is clear: givers win—but only if they’re strategic about it.

That tracks when you think about the reciprocity principle—the psychological tendency that makes people feel obligated to return favors. When you give first, you make it easy for people to say yes when you finally ask for something.

But here’s the thing: figuring out what someone actually wants takes effort.

That’s why cold outreach as a lead generation strategy is a last resort—it’s hard to know what a stranger values.

Someone you already follow or admire, though? You probably know something about them.

If you’re trying to get something from me, a quick scroll through my social accounts will tell you that:

• Sixers floor seats
• A fresh pair of size 9 Jordan 1’s
• A reservation at an exclusive omakase

…will get my attention way faster than an empty request.

How to Ask the Right Way

Here’s how a little effort turns a cold ask into a compelling one:

See the difference? The first versions are all about the sender—what they want.

The second versions center the recipient—they make it clear what’s in it for them.

The Bottom Line

It takes time and effort to find out what someone wants. It takes time and effort to craft a compelling ask.

And that’s exactly why most people don’t do it.

Which is exactly why you should.

The next time you want something from someone, ask, but don’t just ask. Take ten minutes to figure out what’s in it for them first.

Do that, and your cold asks will start turning into warm yeses.

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