How to Cold Call: The Definitive Guide (Now with .GIF’s!)

Since the early 80’s, cold calling has been the fastest and easiest way to turn ordinary people into laser-focused selling machines.  Turning technology into dollar signs, this guide will teach you how to cold call like a pro– unflinchingly confident, wildly successful.  First– a bit of history.

Cold Calling Was Born of Technology

When it was born, cold calling was cutting edge.  The status quo for getting new business was through social connection– formal meetings, dinners, drinks, and subtlety.  It was an art form that took years to master, cost inordinate amounts of money to perfect, and often backfired.  Cold calling changed the game.  Rather than putting highly-paid, highly-trained salespeople in front of customers, why not use technology to have the same conversations in an abbreviated fashion over the phone?


The strategy turned the business world on its head, and was wildly successful.  Organizations that invested the time and resources in the technology and people who could effectively use it succeeded, while those who clung to the rigid ways of the past slowly faded into obscurity.  The idea was genius, the timing perfect, and the execution flawless.

Customer Confidence

Initially, cold calls worked.  People answered the phone because the person on the other end usually had something important to say.  Getting phone calls from important businessmen was thrilling, like getting a thousand likes on your Instagram pic in the first 5 minutes.  Quickly, however, the luster began to fade.  Turns out when you don’t have to look a person in the eye, you can lie to them with much greater effectiveness.


Salespeople from increasingly dubious organizations picked up (pun intended) on the practice, finding an easy way to mass produce their swindle attempts.  Soon, even legitimate cold calling found hit rates in the single digit percentages.  What was once a way customers wanted to be contacted was now a nuisance.

The Safe Bet

Despite the declining effectiveness, detrimental branding, and increasing cost– cold calling was so successful initially that over time it became (and still is) a ‘safe’ bet.  Risk-averse organizations had a tried and true formula for generating new sales.


Put bodies on phones, tell bodies things to say, repeat as much as possible.  It became an integral part of a salesperson’s repertoire known infamously as– the ‘hustle,’ playing the ‘numbers game,’ or ‘putting in the work.’  As with all things, what was once cutting edge became widely used, and what was widely used became standard practice.  While the smart players moved on to other means (email, then social media, then inbound content), safe-betters could still see success.

The Problem

Today, cold-calling is still widely used.  C-suite professionals can expect their public-facing phone numbers to ring continuously every day as increasingly desperate and burned out salespeople try to reach “decision makers” to peddle their goods.  Organizations still report wild success with cold calling, but a problem in each lies just beneath the surface.  Cost.


Let’s look at some of the numbers, with percentages taken from actual results of a successful Minneapolis SaaS company that relies heavily on cold calling:

Sales Dev Group A makes 1000 calls/day.  Their list is good and their strategy sound, so of those calls, they get 300 people on the phone.  Of that group, the highly skilled SDR’s find 50 that are relevant or convinced enough to agree to a follow-up of some kind.  A very solid 5%.

Through an above-average qualification process, 30% of those follow-ups have the need, ability, interest, and time to investigate the solution and are passed off to inside sales and account executives.  30% of 50 is 15, so there are now 15 qualified leads to work.

Those 15 leads get worked, and a highly trained, highly capable team of reps does a great job and generates 7 qualified opportunities from the 15 leads.

Those 7 opportunities are worked diligently, bringing in engineering resources, doing demos, everything needed to close the business– which is successful on 4 of them.  Overall, 4 wins out of 1000 contacts, or 0.4% success.

I think everyone would agree that those numbers, while somewhat sustainable, are far from ideal.  The problem is this:  Cold calling costs too much.  It sucks money from everywhere– marketing, product development, leadership… everywhere.  The opportunity cost of continuing to blast cold calls outweighs the benefit.

How to Cold Call

So.  You came here for a guide on how to cold call, and here it is:  Don’t.  Real success in sales doesn’t come from what was cutting edge 40 years ago.  You wouldn’t allow IT to give everyone Apple II’s, so there’s no reason you should allow your sales department to live that far in the past either.  Success in sales process comes from the same question that spawned cold calling in the first place:  how can we reach more prospects where/how they want to listen with less effort?  Go back to the beginning, and find where your prospects want you to be.  Learn what gets them excited to interact.  Steer that interaction to your business needs.  Find a way to do it en masse, and for goodness sake put down the phone.





How to Find the Best Sales Jobs (for you!)

Whether you’re just starting to look for a career or are a seasoned pro looking for a change- knowing where and how to find your next sales job requires a unique set of skills.

First: Preparation

Going into a job hunt like Officer John McClane vacations around the holidays is a good way to end up underutilized, underpaid, and unhappy.
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On the other hand, a little planning and preparation really goes a long way- especially when looking for a new sales position.  Here are a few steps to plan like a pro:

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How to Use CRM to Ruin Your Sales

Let’s face it- you’re too busy.  You’ve been working hard and your account list is starting to look like the yellow pages for your territory.  With all that work and money you’re making- how are you supposed to have time for the important things- like napping under your desk?  Here’s some tips so you can use your CRM tools to decelerate your sales and free up your time for more important things- like bowling with your high school gym teacher.


1. Complain about having to enter details and data for your opportunities.

Say things like “I’m a salesperson not a data entry specialist!”  This draws attention away from the data-driven sales acceleration tools your CRM tool provides.  These tools will likely boost your win rate as you spend time learning what’s working, where, and why- time better spent in the hammock you put up in the broom closet last year.  Your win rate is high enough already (single digits, baby!), why would you want to cause yourself more stress by having more happy clients?

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The Fundamentals- Sales Skills for 21st Century Selling

Thanks to Cole (@COLESLAW927) for this week’s topic.

I’ve talked before about core sales skills and how to develop personal sales strategies– and today I want to talk about tools and processes.  The most persuasive, highly skilled salesperson in the world will do a poor job without the tools and habits that lead to success.  Here are a few lessons to get you on the right track.

Lesson 1: Don’t be a tool, use one instead.

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How to Negotiate (the boring, effective way)

Negotiation as a sales skill is commonly thought of as the ability to sway your customer onto your way of thinking- regardless of needs.  Sleazy salespeople are experts at this.  They use cheap conversational tricks and common logical fallacies to try and force agreement and get the win.  Fear tactics and selective inflexibility are their friend- and once the transaction is closed they disappear.  They treat sales meetings like hostage situations, and focus on getting rather than helping.  They’re obsessed with position and power- thinking only of themselves.  They make for really good entertainment on TV and in movies, but they’re just awful in real life.  I’ve written about them before- they’re scumbag salespeople.

Don’t be a scumbag.

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