Have you mastered the Art of Asking?

By Nina Kaufman, Esq.

I’m sitting in a café with my good friend—mental health stigma expert, keynote speaker, and professional drummer—Mike Veny.

We’ve been chatting up a storm, both having to be somewhere else soon, but pushing the departure envelope because one topic so naturally tumbles into another, like the gentle cycle of clothes in the dryer.

The check finally arrives. We scramble for our wallets. I dig through my tote bag. Thinking, “silly women’s handbags—whatever you need always falls to the bottom.” My hand blindly gropes at objects—Android phone, eyeglass case, Moleskine notebook—but none of them have the texture and heft of my wallet.

“Could I have missed it?” I wonder. I begin to take out objects one-by-one and put them on the table so that I don’t re-grab what I’ve already dismissed as “not-wallet.”

I scrape the bottom of the bag with my fingernails. No wallet. A hot flush creeps up my neck. I feel like a complete mooch. A deadbeat. Here I had cavalierly ordered a healthy salad and full glass of wine … and don’t have the means to pay for it.

“I’m so sorry,” I stammer. “I must have run out without my wallet. Can you spot me?” I ask Mike. He laughs and says, “Sure!”

And then I find the courage to ask for even more. I c-o-u-l-d walk the 2 miles to my meeting and back home (although at 15 degrees F., who would want to?). I c-o-u-l-d make my way back home, get my wallet, and then get onto the subway, but I’d be terribly late for my meeting. Would he buy me a MetroCard for the subway? (Yes).

That got me thinking about asking.

As my mother says, “When you don’t ask, you don’t get.” And when you don’t get what you want, what you do get is resentful.

Amanda Palmer knows a thing or two about asking. When she left her record label to strike out on her own, she asked her fans to support her in making an album, leading to the world’s most successful music Kickstarter. You can find out how she did it in her TED talk.

But how often do you ask for what you really want? I mean, really really want, not just what you will accept, or what you think the other person would agree to without too much fuss?

When was the last time you asked for what you wanted while:
• Negotiating with a client
• Making strategic decisions with a business partner
• Setting performance expectations with an employee
• Requesting services of a vendor

And how did it go?

Have you mastered the Art of Asking?

About Nina Kaufman, Esq.