The trick to asking for what you want

I’m walking down Crosby St when I see something that makes me stop.

I’m on my way to Chinatown. I want to start doing Instagram interviews of New Yorkers in nature related careers, and I’m going to ask a plant store owner if I can interview him.

On the way, though, my plans change.

I see a team doing a live garden installation outside a restaurant. There’s a happy man with a big green top hat that seems to be directing the project — and it’s too good of an opportunity to pass up.

I interrupt him in middle of shoveling dirt to ask for a quick interview — and, surprisingly, he says yes.

It turns out it’s NYC-renowned gardener Tommy Little — responsible for many of the beautiful gardens outside the restaurants and hotels in the city (including the entire block outside Chelsea Market).

We have a wonderful little chat on how he got started and what he’d recommend to anyone getting into the profession — and then we part ways.

Just a few years ago that very interaction — approaching a stranger on the street to ask for a video interview — would have TERRIFIED me.

It would just feel so awkward and uncomfortable and cringy — and, most of the times in the past, if I’d ask “Can I interview you” — people would just flat out say no.

But then I started adding this little phrase before my ask — and it did wonders.

It’s this:

“I have a ridiculous request — it’s completely ok to say no.”

I initially got it from the book “Never Split the Difference” (and have since seen it in a lot of cold call courses). I think it works because

1. It takes the pressure off of saying yes — which lets people put their guard down and actually consider the offer

2. It piques folk’s interest — what’s ridiculous about the request?

3. It sets the expectation that the ask will be unreasonable, but when they hear it’s just e.g. a short interview — they’re more likely to be relieved and be cool with it.

It also helps having a go-to line in your back pocket so you don’t have to scramble for what to say.

My friends have heard me use this line about a 1000 times and have clowned me for it — but I swear it works.

Next time you have a request that you’re nervous to ask about, try it out. You’ll be surprised.

Till next week,

Mayank