Cold calling is dead.

Or at least that’s what I was lead to believe — until recently.

Comedian Iliza Shlesinger coined the term ‘elder millennial’ to refer to those of us born in the early 80s. While some might raise an eyebrow when our crows-feet adorned faces proudly proclaim that we’re Gen-Y, we did make the cut — barely.

As such, us elder millennials share many characteristics with young millennials born in the early 2000s — except for an affinity for Snapchat.

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We Prefer to Text

Having had a cellphone in my pocket since I was 15 (a Nokia 5110 at the time, loaded with Snake and Tetris!), like many thirty-somethings, I developed a preference for texting over calling. It was just easier and safer. You could take the time to craft a well-honed message, and not deal with the real-time stressors of a phone call. You could put your best foot forward — or so it seemed.

Despite this preference, during my single twenties, whenever I scored a girls’ number, I opted to call instead of text, and most of the time it distinguished me and helped me to build stronger rapport than all those guys who were too afraid to call.

For whatever reason, the same boldness didn’t transfer into the entrepreneurial domain.

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A Convenient Belief

For years, I believed that cold calling was dead. Partly because in a world of digital marketing, I truly believed this to be the case.

“Why would I cold call when I could send tailored email drip feeds, follow my audience around the interwebs with display ads, and appear on page one of Google results?”

I also believed that cold calling was dead because it was a very convenient belief to hold — it meant not dealing with the difficulty, awkwardness, and rejection that comes with cold calling.

But the reality is, especially when it comes to B2B businesses, that cold calling is far from dead, and that it might actually be your blue ocean sales strategy in a world of entrepreneurs who are too afraid to pick up the phone.

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Hello Telephone

Having recently launched the Lemonade Stand K12 entrepreneurship ed-tech platform, my team got to work exploring myriad strategies including said emails, LinkedIn messages, inbound content marketing plays, and online ads. And we got a somewhat lukewarm response — not to mention the fact that most messages never got read, were addressed to the wrong people, or were blocked by email filters.

We were urged to start making cold calls by our advisor in the K12 space, and despite the initial dread that this suggestion filled my body with, I reminded myself of Marcus Aurelius’ famous maxim that ‘what stands in the way becomes the way’, swallowed my pride and picked up the phone.

It worked.

Here’s what I learned.

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5 Reasons to Pick Up The Phone

1. Rapid Learning

Speed is absolutely fundamental to success when it comes to innovation and entrepreneurship. The faster you learn what works and what doesn’t, the faster you get to product-market fit. There’s nothing quite like the real-time feedback that cold calling offers. Instead of pontificating about your target market around a whiteboard for days and weeks on end, how about calling them and learning there and then whether or not your offer is remotely of interest?

Complete with the subtleties of tone of voice that teaches us more than a kindly-worded rejection email, or worse, non-response, ever does, cold calling is one of the fastest ways to learn.

Just some of what you will learn includes:

• The roles you should be targeting at said companies
• How they make purchasing decisions
• What time of day you should call / day of week
• How they prefer to communicate
• How much budget they have to spend on offers like yours
• Whether or not your value proposition is unique or compelling
• When budgets become open
• What common objections to your offer might be (and therefore, how to get around them)

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2. Character and Resilience Building

As Wired founder Kevin Kelly told me on the Future Squared podcast, in today’s fast-changing world, we are all newbies. As a result, adaptability and resilience are keys to success.

Nothing develops character more than having to try and sell something to people who aren’t expecting your call and developing a thick skin to withstand the almost inevitable rejection that follows — especially when you’re making 50 calls in a row.

Getting comfortable rejection and ambiguity — the essence of cold calls — is a great character builder that you can transfer to all aspects of life; learning new skills, job hunting, capital raising, and even finding a mate!

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3. Honing your Elevator Pitch

Given the cold nature of the call, you’ll need to grab your audience’s attention immediately. As a result, your pitch needs to be succinct and snappy. You’ll want to clearly articulate what problem it solves for them or how it makes their lives better, any social proof you’ve earned, and leave them with a compelling offer and easy-to-execute call to action…all in under 30 seconds.

The more calls you make, the more you’ll learn which aspect of your pitch work, and which don’t, and craft it accordingly. The learnings from this exercise can then be transferred into your copy, whether that be in emails, your website, your online ads, and so on.

4. You Get Closer to “Yes”

The reality is that, no matter how good your product is, there will be numerous reasons for a “no” — lack of budget, other priorities, bad timing, lack of authority, existing contracts with like products, and more.

But as billionaire entrepreneur Mark Cuban likes to say, every no is one step closer to yes.

In the early days of any entrepreneurial venture, getting those first few yeses is critical to keeping making payroll, raising capital, and keeping team morale high. The more calls you make, the closer you will inevitably get to a yes, leaving you with a solid foundation to build upon.

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5. Relationship and Rapport Building

It’s a little difficult to build a human relationship through email alone.

Intrinsic to most B2B sales are human relationships — people like to buy from friends. Calling people on the phone and having a conversation, complete with laughter and the sense that the other person is smiling, helps to lower one’s defenses, humanise your product and get you closer to yes.

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6 Tips For Making More Cold Calls

1. Keep it Short and Disarm Them

I always start with a quick introductory spiel — “this is Steve from the Lemonade Stand entrepreneurship program” — and respect their time and disarm the prospect by asking “do you have two minutes for a quick conversation?”

Most people can spare two minutes, and it puts them at rest knowing that it will be a short call and won’t infringe on their time much. Not only that, but it’s common courtesy!

If they don’t have the time, I’ll ask for an email address to send some info along to, or a better time to call, and nine times out of ten, the prospect provides the requested info.

Finally, the opener “this is just a courtesy call to let you know that…” seems to work well.

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2. Personalise and Target Effectively

Nowadays, using tools such as Linkedin’s Sales Navigator, you can find out who you should be asking for when calling a company.

In our case, some of our example prospects are Heads of eLearning and Digital Technologies, among numerous other roles, at K7–10 colleges.

You can go a step further and leverage tools like BuzzSumo or Mention to target prospects who have been mentioned in the media either referring to problems and solutions like yours, or prospects who have recently started their roles as they will oftentimes be looking to get some quick runs on the board and your product might do that for them.

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3. Use Momentum

It all starts with one call.

As James Clear, author of bestseller Atomic Habits says, the best way to build a habit is by making it so easy that you can’t say no. Set yourself a target of making one phone call, and use the surrogate metric of learning, instead of selling, to cash in on the satisfying dopamine hit of accomplishment afterwards.

If you’re staring down the barrel of 50 phone numbers, just take it one a time. You’ll be surprised how quickly the anxiety wears off the more calls you make.

In fact, I’ve gotten to a point where I am actually so comfortable making cold calls that I need to fight the urge to make cold calls as a form of procrastination that prevents me from tackling other more challenging, intellectually demanding tasks.

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4. Combine Wants with Needs

Katherine Milkman, a behavioral economist at the Wharton School of the University of Pennsylvania, coined the term ‘temptation bundling’. It refers to bundling things you want to do with things you need to do, to help you build positive habits.

To take the edge off cold calling somewhat, pair it with something you want to do. Perhaps you could make those calls whilst going for a walk, to get some fresh air and exercise in? Or maybe you can make those calls whilst sitting by the pool with an Aperol Spritz — just cap it to one!

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5. Make It Easy to Say “Yes”

Few prospects, especially in the B2B world, will be in a position to buy something they’ve never seen or tried or spoken with their colleagues about, on the spot.

You need a call to action that’s not as all or nothing as buying your product or not.

It could be offering to send them some additional info, signing them up to a webinar, scheduling a demo visit, or giving them access to your free trial account (probably the best of the bunch).

In our case, we offer free trial accounts which to date, nobody has turned down on the phone. That way, they can jump into the platform, and effectively touch and feel it, and develop a visceral connection to it. Experiences, given our evolutionary nature, are far more likely to convert prospects than arbitrary words ever will.

It also gets them into our email database because more often than not, when it comes to B2B sales, it could be months or even a year or two before the prospect is in a position to buy.

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6. Outsource (Yes, this is cheating but…)

If you’re the head of the company or in a senior role, chances are you won’t have that much time and shouldn’t be investing that much time into cold calls.

However, before you outsource calls to a business development function, you’ll want to make sure you’ve done enough learning about how to effectively pitch the product to cold prospects, otherwise you might find yourself outsourcing a broken process.

Once you’ve outsourced the tough task of cold calling, it is advisable to learn via the bizdev team and still set aside some time to make calls yourself. This way, you keep your ear to the ground in terms of what customers want, especially as market forces change around you. The faster you learn, the faster you adapt and win.