Do You Suck at Oral? A (Tongue-In-Cheek) Discussion on Why It’s Hard to Ask for Money

IN: Clients, Confidence, Money Talk, Success

My first sales call was the most disgusting thing I’d ever done.

I mean, I don’t even like talking on the phone with people I know, let alone people I don’t. My love for the phone ended after the 7th grade, when boys stopped calling and AIM instant messenger sank its teeth into our corsage-donning little hearts.

Back then, I was an instant messenger queen. I proved myself through my cat-like ability to manage multiple chat windows at a time AND simultaneously know, down to the second, exactly when Kristian (with a K, you guys) signed in, and then signed out, and then signed back in again. (Wait, did he just go invisible?! Wait, was it because of me? Wait, what if he’s talking to LiLBaBe8391?!)

The Buddy List was The Holy Grail. Song lyrics were the ying to away message yang. And that little yellow man—let’s just say he took our virginity in more ways than one.

But, that’s not the only thing he took away.

For half the people alive, communicating online via chat, message, text or email is the way you talk to people. Why pick up the phone and call customer service when you can hop on their live chat? Why call to confirm dinner plans when you can just text? Why call the girl you climbed Machu Picchu with when you can Facebook message?

And, you know, it’s not a terrible thing. (Assuming, of course, you’re not an arthritic senior citizen—or Captain Hook.) As a writer, in fact, I love that the written word is the medium of our time. I’m totally the asshole who puts a semicolon in a text message, and I can usually express creativity better in writing, too. For the record, this makes me incredibly sad I was never on Just THINK of the missed opportunities.

But, in the same breath, I can assure you that all of this keyboard pounding does have very real repercussions. Frankly, we’re getting dumber and dumber when it comes to using our mouths. (Unless there are gravy-dipped french fries involved.) If we thought awkward silences were awkward before, now they’re MAMMOTH. We’re forgetting how to talk to one another.

Certainly, while problematic in many areas (having “the sex talk” with your kids comes to mind as a fun example), one of the bigger ways the keyboard is handicapping us is around the one thing we had trouble talking about before:


That’s right—money!

You like that word, right? Scrolled right down to this spot on the page, didn’t you? That’s okay, I like money, too. The problem is that, more and more, we suck at asking for it. Why?

Because you don’t ask for money in an email. 

When’s the last time you asked your boss for a raise via email?

“Yeah, so, um, hey there, bossman! You think you could hook my paycheck up with a few extra bones?”

When’s the last time you pitched a prospective client via WhatsApp?

“Yo, yo, yo client! Cost will be $4200. I’ll assume the double green checkmarks mean this bid is approved.”

When’s the last time you discussed a rate increase via Facebook Messenger?

“Johhhhnnnnn. My mannnnn. Rate’s going up, buddy. Check it out on the next invoice!”

The majority of our most important business conversations happen orally while the majority of our everyday conversations happen in writing.

That means we’re not getting the practice we need in order to be able to have the conversations that will affect us most.

The only way you get better at talking…is by talking. Not typing.

However, despite my big gloomy whomp, whomp, whomp rain cloud over here, there is one advantage to the current state of affairs:


As more and more people become inept at oral—*wry smile*—that means that your odds just got better. You only have to become slightly more charismatic in order to seem significantly more charismatic.

And that’s called opportunity.

And we love taking those.

Because no matter how many pixels have claimed a piece of you, opportunity is still one thing the little yellow man?

Never can.