The Ultimate Guide to Selling When you Hate Sales

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I sat at my desk, hands folded on my lap, staring at my phone.

I sat for a long time like this. It’s as if I was waiting for the phone to give me a pep talk.

Then, a brilliant thought came to mind. Maybe I should check Facebook…after all, one of my posts might have gotten a LIKE. My eyes shifted to the pile of paperwork that had been sitting idle on my desk for over a month and I contemplated organizing it. Then I noticed that my index finger nail was chipped and I thought maybe I should find my nail file.

Do you catch my drift? I wanted to do anything other than pick up the phone and make my first cold call.

Ugh – Cold Call. Those two words responsible for more anxiety and cold sweats than “hungry dinosaur” and “disgruntled mailman”.

Fast forward 1 year. Would you believe that I had been responsible for bringing in $3.5MM in opportunities for the small business I worked for?

How did an introvert with no cold calling experience, a crippling fear of selling and a total adversity to becoming a smarmy douchebag become…well…an effective salesperson?

I shifted my mindset.

What really sent shivers down my spine was the thought of bothering someone (quickly followed by being rejected). Let me ask you this. If you felt you had a cure to what ails someone wouldn’t you want to share it?

Would you feel bad about sharing your cure? Of course not. You’re solving a problem. You’re helping. You’re being of service. The moment you stop thinking of selling as…well…selling and instead think of it as connecting someone to a solution they need, you’ve leapt over the biggest hurdle to cold calling.


You can’t serve if you’re not offering service

In order to shift your mindset from selling to serving you have to know who you’re calling, their problems and how you add value.

Without this, your focus is on you, not them. And, here’s a little secret. No one wants to hear about you. Do your research. Learn about your prospect. Try to uncover what motivates them. I used to do tons of research. I’d do the rudimentary Google search and website audit, but I’d also do some sleuth work.

My #1 secret weapon was to find out what suppliers they worked with and, provided I had an in, I’d call and learn as much as I could about how they worked, what they valued, what their pain points were, etc.

That, my friends, is liquid gold.


You can’t give up in the first go around

When I first started my calls it was almost a relief if I didn’t connect with a live person.

I had to fight my flight mentality. I wanted to use non-connection as an excuse to move on. Cue the Family Feud strike one buzzer. If you want to be good at sales you must be persistent.

One of my favourite stories was calling someone who at the time worked for Extraordinary Events in California. I had done my homework. I wanted to work with this company. They did GREAT work. They needed us. I called the decision maker, ready to make my connection. I got her voicemail. So I left her a short and friendly message asking her to call me back. A few days later, I noticed I hadn’t yet heard from her, so I called again. No answer. So I left her another voicemail. So sure I was that I had a solution for her that I didn’t mind being steadfast. A few days later, still no response. So I tried again. Voicemail. Ugh. This time I switched my tactic. I left her a message that was friendly but firm. I told her that, “I had left 2 voice mail messages and I would like it if you would please respond to my call”. Ballsy. But it worked.

She called me that same day.

If I was selling something to her, I’d feel apologetic for bothering her. Instead, I was persistent because I knew I had something she needed. Me. I’ve heard her recount this voice mail message, and it sparking her to action, to many people over the years. As a side, she became one of my very best friends.


You’ve got to feel it in your toes

I’m going to make this part really quick and to the point.

You’re talking to a real human being. Someone who’s probably received quite a few calls, just like yours. If you’re not excited about the prospect of working with them, I guarantee they’ll feel it. Your call will be meh. Your connection will be meh. Your results will be meh.

Call people that excite you. Your heart should be beating hard in your chest at the thought of screwing up. If it’s not, move on to the next.


You’ve got to become an expert at closing

Imagine a sprinter who invested all of their training into sprinting but never learned how to cross the finish line. That’s like a salesperson who never mastered the art of the close.

The idea of becoming a great closer is to never, ever, ever leave anything on the table. You never want to walk away from the call asking yourself any of the following questions:

  • I wonder if they want to work with me
  • I wonder if they had questions I didn’t answer
  • I wonder what they’re thinking

The entire point of you calling is to connect your prospect to a solution. But if you never confirm if they agree it’s a solution they need you’re going to have an excruciating few days of ambiguity ahead of you.

Want to know the one sentence I’ve used for 20 years that has an almost 100% success rate?

“Is there anything you’ve heard that would prevent us from working together?”


1. You’ll find out just how much they want to work with you, and

2. You’ll get a chance to address any issues that you might not have anticipated


Bottom line is that sales is a necessary skill to have if you want to grow your business. It’s more important than your ability to work a tradeshow booth and definitely trumps your penchant for writing a good Facebook post.

Hating to do something doesn’t absolve you from the need to do it. So, learn it. Master it. And, start it.


eNews February 2015

Originally posted on

About the author : Lara McCulloch

Lara McCulloch

Lara McCulloch is the Chief Shift Disturber for She teaches event companies how to elevate their businesses so they can get back to doing what they love. A brand strategist and marketing consultant for almost 20 years, she’s worked with big brands like Cadbury Adams, Shell, Benjamin Moore, ConAgra and Scotts. Lara also been named Industry Innovator by BizBash Magazine, featured in both Connect and Rejuvenate Magazine’s Top 40 under 40 issue, awarded Best Industry Blog by CSE and has been honored with Dedication and Leadership awards from ISES Toronto. A living well passionista, when she’s not working, she’s making her own body care products and trying out new raw food recipes.

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