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How to Overcome the Dark Side of Cold Calling

Cold calling sucks.


It’s the only tactic that you can turn on any second of any day and start having conversations with prospective customers.

And in the website sales game—conversations lead to business. So how do we wrangle this idea of cold calling, and make it work for us to sell more websites and internet marketing deals?

You Fail

A lot of people think they are bad at selling…but really they are bad at prospecting. They aren’t having enough conversations with enough people. For most of us, when we sit one-on-one with someone and have an authentic conversation there is a good chance it will lead to business.

But most of us aren’t talking to enough people. How many leads did you actually communicate with this week? 1, 5, 10? I bet it wasn’t enough.

That’s what was wrong with my business. I would be head down in a project for two or three weeks and wouldn’t talk to a single lead. Then I would pull my head up from projects and realize my pipeline was completely empty.

It wasn’t that I was bad at sales (although that needed some work too), but that I wasn’t out there telling people what I did. And I definitely wasn’t trying to figure out what they did.

Then it hit me.

“I need to talk to more people.”

“But where do I start?”

“I know. I’ll start cold calling.”

(Yes. I just had a conversation with myself in this blog post.)

First I Googled. I found a list of businesses that didn’t have very good websites. I picked up the phone and dialed…

“Hi, this is Brent Weaver from HotPre…[click]…ss Web. Damnit.”

[dial next company]

“Hi, I noticed you don’t have a very good website.”

“What are you selling.”



And so it went. Totally painful. Excruciatingly depressing.

But after enough dials I got a meeting. Then I got a deal.

Cold calling works. There is no question about it. With the right script, experience, and thick skin, anyone can smile and dial their way to financial success.

My question to myself was simple though…

“Is there a better way?”

Change the Definition

When I started selling, I had a very narrow view of what cold calling was. I thought that it was getting a list and dialing on that list. And I thought because that was really hard, and I had no interest in being turned down so often, that I wasn’t very good at cold calling. I didn’t understand how to get better…so I gave up.

But then a mentor taught me a very powerful lesson:

“Brent, any unscheduled interaction is a cold call. You already do cold calls all the time. Whenever you call someone or they call you and there isn’t a meeting on the calendar, that’s a cold call. You need to develop your script and practice it on every one of these calls all the time.”


“Wait a minute…so when someone refers me and introduces me in an email and I call that referral, I’m really engaging in a cold call?”


“Or what about when I follow up with someone I met at a conference a week later?”

“Yep, cold call.”

“I know, how about when I call an existing customer to check-in and see how they are doing?!”

“As long as it’s unscheduled (even if they are expecting you), then yes, it’s a cold call. Even if the person is calling you…any time it’s unscheduled people have the same reaction. They have a defense mechanism that goes into play: what does this person want? Should I invest any time in this conversation? Etc. Now, the more warm a call is, the easier it is to get the next meeting, but the mechanics are always the same. Imagine when you’re at a party and you walk up to someone you don’t know, chances are, they have some armor up. It’s a human response to be defensive toward someone when they sneak up on us.”

Cold Calls Can Be Warm?

When you accept this definition:

Any unscheduled interaction is a cold call.

Then the next step is to understand the spectrum of types of cold calls.


  • Your mother (comfy like grilled cheese)
  • An existing account (comfortable)
  • A referral (butterflies)
  • People on a list (uncomfortable)
  • A girl for a date (pins and needles)

Obviously, you can get more granular on that list when you start thinking about calling people you met at a conference, someone you follow and interact with on Twitter, and so on.

But the idea I want to get you to grasp here is that cold calling is a lot of things. And when we accept the wide spectrum of things that it is, we can begin to get good at it without having to jump directly to the toughest calls.

For instance, if you want to practice the process of creating a script, developing a habit of calling a business every day, and trying to book a meeting, then a good exercise might be to start on your existing client list.

If you don’t have any existing clients, then call everyone in your family and friend circle. Use anyone you already know and have a relationship with as a person that you can practice on. You can even be upfront about it and tell them that you are practicing your script and pitch.

As you get good at cold calling a friend, calling a stranger you’ve never met will feel more natural.

Or, you might never need to call a stranger at all if you network often and are able to regularly get cards from people. Maybe you are able to ask your existing clients, friends, and family for referrals.

Whatever your strategy for getting phone numbers, any time you call someone and they aren’t expecting your call, you can classify that as a cold call. Measure how well you book meetings and whether they turn into deals. See how good at cold calling you really are.

But It’s Just Too Hard

Okay. Fine. You don’t like calling friends, clients, referrals, or even your mother. You are one of those tough cookies that only wants to receive inbound leads that are interested in buying today. So what do you do?

The alternative to getting up in the morning and hunting for new business is to become a farmer. And farmers plant crops. They tend to their crops. They wait for an entire season before they can harvest.

Too much metaphor?

If you don’t like cold calling, then you need to become a recognized expert at your craft. You need to blog, speak, eBook, workshop, and webinar your way to riches. And that takes time and a lot of energy.

I did it.

But first I started with cold calling.

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