Just Ask.

Get What You Want By Asking For It

I stood far away from Sharmeen, mortified at the intrusion. Like a mob wife, I took no part in the crime but waited to benefit from the goods. 

The lights in our favorite bakery in Noe Valley were already dimmed, the neon OPEN sign shut off. Tapping on the glass, Sharmeen peeked inside, trying to get the attention of the people closing down. 

Someone in an apron came to open the door. 

“I know you're closed, but I love the fruit tarts here, could I still get one?,” she asked.  

A few minutes later, we sat on a nearby bench eating our precious crumbly prize. 

“I don’t know how you do it,” I remarked between bites. 

Sharmeen paused mid chew, licking raspberry juice and crumbs off her lips. She shrugged, popping the final piece into her mouth, “You just have to ask”.

Simply asking for things did not come naturally for me. My immigrant Indian parents have a lot of pride and don’t like the idea of receiving things from other people. When I buy them presents, I have to pretend like I happen to have an extra pair of headphones or I’m throwing away a new sweater. Otherwise, they won’t accept my gift. 

My perspective shifted my freshman year of college when I started a job calling alumni asking them to donate money. The phone would ring and ring in my ear as I waited for someone to pick up. When they did, I’d ask them to donate $250 to the university. 

“I lost my job, how could you be so insensitive?”

“Please remove my number.”

“Sure, can I put it on my credit card?”

Calling people and asking for money should be a form of exposure therapy for the fear of rejection. Cold calling builds the perseverance muscle. 

When I moved into tech sales after college, I said in my job interview, “I can hear ‘no’ a hundred times and still go back to work after.” 

The art of asking for something is overblown in my opinion. There’s a myriad of books in the world like FBI negotiator Chris Voss’ Never Split the Difference. This book teaches you to say “it seems…” and “we” instead of “you”. I’ve even tested out his late night DJ voice. There’s something to it but I find my high pitch, over excited voice is also effective. 

The importance of simply asking is lost in all this content.

People like Chris Voss have these tactics because he is negotiating with high profile criminals.

The most difficult person everyone else negotiates with is their manager. Often, it’s two empathetic people, trying to understand what the other wants. 

Over-preparation is a security blanket that does not tackle the root problem, which is fear. Fear of rejection, fear of judgment, fear that asking is in some way immoral. 

However, we ask for the little things we want so that we train our muscles to be ready when we need to ask for the big things, like a higher salary. 

Feel free to take this strategy: talk less, ask for what you want. 

When I hesitate to ask for something, I feel the fear of rejection and judgment creeping inside of me. Often, I don’t want to lose something important. 

My weak point is my dating life. The last guy I dated took me on cool dates to things like a Grateful Dead cover band concert, the Banff film festival tour and most importantly, a beach day with his friends. 

But the in-between communication was non-existent. As I grew to like him, I wanted to see and hear from him more than once a month. 

A friend (my therapist) finally gave me a script: “Hey, it’s been nice getting to know you, but I’d love to hear from you more often.” 

Simple and direct, perfect. I practiced my lines for the month it took for him to reach out to me, and when he texted to see me again, I was ready. 

“It’s so nice we get to spend time together,” he said. 

I froze. I couldn’t say my lines. I didn’t want to ruin our date and convinced myself this time was different. 

After that, he ghosted me. 

Next time there’s something you want, instead of losing time to over-preparation, just ask. Whether you get a yes or a no, you learn something.

Sometimes, the guy isn’t interested. Knowing that early means I can move on sooner and don’t need to spend hours searching his social media to see if he’s alive.

Sometimes, people say yes, and your prize is a fruit tart that tastes even better because you did something others don’t: you asked.