Author, CEO & Founder

Learn More >>

How to Cold Call Prospects Without Sounding Like a Tool

In: How to Sell Yourself

For those of you who don't know, in a former life I used to sell advertising for an international print and online magazine.

Think pencil skirts, a lot of telephone schmoozing, deal negotiations, contracts, national sales conferences and convincing a lot of fucking people they should give me thousands of dollars.

You can imagine the fun I had with this.

Particularly the day a prospective client named Lenny insisted we drink Long Island Ice Teas to talk business, and then proceeded to whip out a Polaroid camera and snap pictures of me without my permission. That wasn't awkward in the least. My director was calling me like a crazed Mexican boyfriend, worried since he hadn't heard from me in 82 years and wondering whether if I got the contract signed. We were thisclose to hitting some important revenue numbers that month, and this would put us over the edge. (For the record, I got the damn contract signed. And then I got the hell out of there.)

Or the time an overall-wearing man in the state of Delaware approached my car while I was preparing for a meeting, and straight up asked me if I wanted to be in a porno. Clearly he didn't notice I'D BE THE LEAST LIKELY PERSON TO DO THAT, EVER. I even had my fake spectacles on that day–you know, to add to the whole you-can-trust-me vibe.

So I drive off in a big fucking hurry, and overalls actually proceeds to follow me in his rusty blue truck, corners me at a traffic light, gets out of his car and runs toward mine to beg me to consider it. Twice. I couldn't lose him until I hit a straightaway.

And people wonder why I carry a knife.

And while, as it seems, one of the more salient skill sets I developed during those years was how to escape creepy men, I also learned a thing or two about talking to people.

And talking to people is important if you're in business, right?

I wanted to bring this up in particular, because a lot of the students that took my recent copywriting workshop were freaked out about how to get their first customers. And while I've developed an entire program dedicated to getting clients, sometimes, the easiest way is just by picking up the phone. Except no one wants to hear that because they don't want to have to talk to people on the phone. It's scary. And nerve-wracking. And what the hell do you say? 

And worst of all,whatever it is you're selling, people are going to be wildly, over-exaggeratedly afraid of you. They might even hold out their arms and make the X sign with their pointer fingers. Maybe they'll spray you with mace–I don't fucking know.

The point? Your prospects' barriers are UP, Berlin Wall style. And that's got to factor into the way you talk to them.

So what do you do when you've got to call someone who doesn't want to be called?

You ignore everything anyone's ever told you about sales.

:: You drop the bullshit jargon you're using that you know makes you sound like a tool.

:: You worry less about being perceived as the utmost of “professional,” and worry more about being human.

:: You ditch the Dick Clark voiceover tone you automatically use anytime you get on the phone.

You can still communicate authority, command respect and demonstrate that you know what the hell you're talking about without using a bunch of meaningless phrases like “We provide quality solutions for _________.” Well no kidding, bubbles. You mean to say your “solution” isn't the shitty quality I was hoping for?

These are the kind of phrases that people think make them sound more intelligent, when in reality, it makes them sound like they've sacrificed a few chromosomes to the gods of I-don't-know-what-I'm-doing-so-I'm-just-going-to-repeat-this-and-hope-you-buy-it.

And last but not least…when you call someone, you don't try to sell them. You aren't at that step yet; you just got on the phone, for christ's sake. At this point, you're just trying to get them to talk to you. That's always step one.

So that said, it's my recommendation to have another reason to be calling your prospect, if you can; a reason that's going to benefit them. This makes step one a whole lot easier because, remember, people are suspicious of people selling stuff. But if you have another reason why you're calling, then you aren't selling them stuff; you're merely helping them out.

For example, if I've just started a new business, maybe I'll decide to put on a free community workshop on X related topic. And maybe I'll call them about that, instead. Or maybe I've set up a fun new campaign around Y. Regardless, what I do will give me a reason to talk to the prospect…and not just try to sell them cold on my services.

The point, rather, is to sound natural. Be genuine. And be as anti-salesy as possible. You don't want your prospects' defenses to go up just at the sound of your voice–you want them to actually listen to what you're saying, instead of trying to figure out how to get rid of you.

And in order for that to happen, you've got to sound like a damn human.

Even when all you want to do is crawl under a rock because some lunatic is snapping Polaroids of you and you HAVE NO IDEA HOW TO REACT.

Not like I would know anything about that.

P.S. I don't really carry a knife. Then again, the first time I came to Chile in '09 I walked around the city with a butcher knife in my purse, just in case. So I guess I can't say that I've never carried a knife. You can just call me Ashley The Blade.

Dec 9


Running a Holiday Sale? Memorize This by Heart.

Dec 9, 2014

So the other day I’m Christmas shopping here in Costa Rica, which is automatically hilarious because, first of all, because they spell “Ho Ho Ho!” like “Jo Jo Jo!” which never gets less funny, and second, because Santa was dressed in a royal blue suit. (I still haven’t decided if this is posh or ridiculous, […]

In: How to Sell Yourself


Aug 28


“Hire Me” versus “Listen To Me”

Aug 28, 2017

If you’re a freelancer, there are two different power dynamics: Hire me! Please hire me! I’m shitting my pants, over here, because I’m depending on you entirely and I’ll do anything it takes, even work for peanuts, because I need you to take mercyyyyy onnnnn meeeeee. Listen to me. I’m great at what I do, […]

In: How to Sell Yourself


Aug 14


Lots of Inquiries But No Sales? Help Is Here.

Aug 14, 2013

I get two questions all of the time: 1. How do I convert more email inquiries into actual customers & clients? (Who ideally have zero credit card limit and maybe even a mullet because wouldn’t that be fun?) 2. How do you manage to stay looking so young? Obviously no one really ever asks me […]

In: How to Sell Yourself


Jun 4


Are You Sorry About Charging Money?

Jun 4, 2017

I was talking to a client yesterday, who, bless her heart, is LITERALLY working for free. She feels bad charging. And my goodness, she’s one of the smartest, most qualified women in her industry! She’s out there helping people every single day, in person, face-to-face! She’s spearheading an entire movement in Canada! And now the […]

In: How to Sell Yourself


Jun 12


How to Sell a $250,000 Diamond Ring

Jun 12, 2015

You know how when you want to sound professional on the phone, you do that thing where you clear your throat, steady your voice, and then inevitably start talking THREE OCTAVES HIGHER in that sickening sweet, Southern-Belle-esque manner, almost as if you were speaking to a priest, or maybe the sheriff, all while using words […]

In: How to Sell Yourself


May 4


How Do You Make People Care About Your Work—Even When Your Work Is Lofty, Intangible, and Abstract as F***?

May 4, 2017

I’m working with a client, right now, who wants to sell emotional intelligence. That’s the result you get when you work with her. EQ, instead of IQ. And emotional intelligence is actually really, really important. It’s one of the biggest predictors of success, believe it or not. She’s read the literature. I’ve read the literature. […]

In: How to Sell Yourself


Sep 14


If you’re both killer & poet, YOU GET RICH.

Sep 14, 2014

“Most good copywriters fall into two categories: Poets and Killers. Poets see an ad as an end. Killers, as a means to an end. If you are both killer & poet? You get rich.” Ogilvy once said that about copywriters, but that’s just because he wasn’t around long enough to see the internet blow up. […]

In: How to Sell Yourself


Dec 15


List Your Prices (THE RIGHT WAY) (Calling All Photographers.) (Hedgehogs Welcome, Too.)

Dec 15, 2011

As an entrepreneur, sometimes you fall flat on your face. Figuratively–and, apparently, literally–namely when you’re traveling in the South of Chile pretending to be in better shape than you actually are while attempting to jump over pathetically small streams that you really should be able to fucking clear, but somehow, don’t, and manage to fall flat […]

In: How to Sell Yourself


I'm a Bad Influence on Women

Hey, I’m Ash! Twenty years ago I was a small town girl growing up in a trailer park in rural Pennsylvania. Fifteen years ago, I lost my family and everything I knew right as I became the first to graduate college. Fourteen years ago, I found myself leaving everything behind for a new life in the city where I could be “normal.” Ten years ago I realized normal was the most disappointing thing that ever happened to me. Nine years ago I quit my job in advertising and pursued my dreams as a creative writer. Eight years ago, I built a 6-figure business doing what I love using nothing more than the Internet and my voice. And now, today, I’m the founder of The Middle Finger Project, an irreverent media co. that helps other women find their voice and teaches them to use it to build whatever the f*ck they want to. With a book coming out with Penguin Random House in February 2020 (YASSS, WE’RE A PRODUCT IN TARGET!) I’m proud to be a bad influence on women and guide them into doing something disobediently brave with their life and their career.

Enter your email address and I’ll send you my advice column every week sharing everything I’ve learned—and so much more.

But no serial killers. I promise I won’t send those.

Privacy Policy Info Here