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Confessions of a Former Cold-Calling Expert

· prospecting,future of sales

Today, when someone reaches out looking for sales prospecting workshops, I can't say "no" fast enough...then I refer those opportunities to others.

However, the answer was quite the opposite 15 years ago.

From 2003-2006, I was one of the experts in the field of cold calling (i.e., people paid me to come teach them). I owned & operated a sales training franchise in Chicago, and our expertise was “Cold Calling Techniques”.

I mean, I even owned the URL!

The franchise itself turned out to be a dog with fleas, but what we taught worked...theoretically.

I went from cold calling/prospecting being practically the ONLY thing I taught to being one of the few areas I don't teach today.

Two primary reasons:

First, there are others who can teach it better to whom I refer those requests.

Second, what I used to teach doesn't adhere to my fundamental foundation - where prospecting is the entry to creating customers who buy, but more importantly stay, buy more and advocate.

In other words, I definitely have opinions on the art & science of prospecting, given my nerdery for the behavioral science and the profession itself. But I recommend others do the teaching. With that in mind...

...when evaluating where your prospecting philosophy, investment and approach comes from, here are the two criteria I recommend you consider:

1) Empathy

Does what they teach sit on a foundation of true empathy for the prospect?

There's a stark difference between having empathy and having sympathy.

Imagine you’re getting ready to fly somewhere with a friend. The friend, hoping to get some work done on the flight, is assigned back-row-middle on an oversold flight.


“I’m so sorry. That sucks! I hope you’re able to get some work done when we go!”


Before you leave for the airport, you grab my step-daughter’s Nissan Juke hatchback, park it across the street right at the edge of our home’s Wi-Fi range. You grab your laptop, sit in the backseat and try to bang out a few emails. A few minutes in, you attempt to do so while also eating a Stroopwafel.

Since I shut down North Shore Sales Training, Inc. in 2006, I’ve been lucky enough to have held 7 leadership roles with 4 different companies, leading to 3 successful exits.

My days consisted of 100-150 emails per day in my inbox.

My weeks consisted of 30-35 meetings per week.

My priorities? They started with my team, my customers and my prospects. From there, they went to my boss, our investors and board, my peers,.....

Unknown potential vendors (i.e., you)? At the bottom of the list.

I couldn't possibly navigate my day through interruption.

As an unknown potential vendor making a cold outreach, do you realize that? Do the individuals who are teaching you truly understand that, and take this into account as a foundation to what they teach?

Some do!

However, many don't.

If you can't truly understand the world the individual you're prospecting into is living in, your efforts become harder. You're creating work for the prospect. Your efforts become unwanted. You're not helping.

It starts there.

2) Care & Homework 

Does what they teach focus on numbers & scale, or care & homework?

As a leader, I just couldn't say no to someone who (a) cared, and (b) did their homework.

How do you show a prospect that you care?

The first step is to actually care.

How do you show a prospect that you did your homework?

The first step is to actually do your homework.

The foundation for successful prospecting, which draws prospects in on a foundation of trust, which leads to higher win rates, faster sales cycles and less wasted time, must rest on this philosophical foundation.

Are these prospecting experts teaching you to scale, or are they teaching you to care?

Are these prospecting experts teaching you to focus on your numbers and ratios, or are they teaching you how to effectively do your homework?

This is why I can no longer teach what I used to teach.

I used to teach scripts, listening for the negative responses - prepared for direct turnarounds to those responses, and asking for the appointment. It focused on teaching voice mail techniques that leveraged the brain's desire for certainty to essentially trick the prospect into calling you back.

We looked at numbers - are you making enough calls? Are you sending enough emails?

We looked at ratios - is your ratio of completed calls to appointments schedule where it should be?

I'm a bit embarrassed that I taught this approach, based on what I know today, truly being on the other side.

And when you have empathy, care and do your homework, everything slows down and becomes easier. You stand out like a beacon in the night.

It stood out, because it so rarely happened.

You’ve seen my inbox in the book and in other posts I’ve written. Do any of these previews signal to you that the person truly cares? That the person has done their homework?

For example, in my last role as a CRO, recruiters called and emailed all-day every-day. All with the same message, focusing on my open job postings and how they could help, or trying to pitch a candidate.

While you may know who Amy Volas is today (founder of Avenue Talent Partners), and you're reading this, so you probably know who I am today, this was four years ago. I had never heard of her...and I was just one of many CROs.

Somehow, she stood out. She became a friend.

How? She taught me in every interaction. She never once tried to pitch a candidate, or pitch her services to fill a role. She led with advice. She cared and always did her homework.

Headline #2 on her website?

Every interaction felt like I was speaking with someone where I didn't need to do the homework, she did it for me. That's because she came from a place of knowing...and a true focus on empathy. Not sympathy...empathy!

The unquenchable thirst for scale is killing the sales profession. There's still time to save it. It must start with prospecting.

Find experts who can bring a perspective founded in true empathy. Find experts who can teach concepts and approaches grounded in care for the prospect, and centered on being the right fit starting with doing the right homework.

And if you want help on your presenting, positioning, negotiations and/or leadership, that's my focus today. If you want help with your sales prospecting, I would be happy to make a recommendation.

Bonus - some self embarrassment as I was looking into my old files. 😳

Pictured on the left: A guy who taught nothing but cold calling techniques.

Pictured on the right: A guy who aged like guacamole, teaches & speaks, but doesn't teach cold calling techniques. However, he's happy to make recommendations.

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