Dialing Through Time: A Cold Calling Odyssey

The year was 1996, a year of change and opportunity, I accepted a new position at an ambitious international bank.?The role of Wealth Generation and Preservation Counselor was a perfect fit for my skills and aspirations.

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As I bid farewell to my previous job, I felt a mix of relief and gratitude. The send-off party was filled with pizza, cake, and well-wishes. Amidst the laughter, there were whispers of "Take me with you, please" and "Don't forget about me." With that chapter behind me, I was ready to embark on a new one in my life and career.

To give our younger readers a glimpse of what transpired in 1996—and refresh the memories of those who lived through it—let’s take a moment to revisit that vibrant and transformative year. It was a time filled with events that would soon leave a lasting mark on history. Bill Clinton secured a second term in office, only to become embroiled in a scandal, with cigars becoming an unlikely talking point.

Then, there was Viagra—the little blue pill that gave a whole new meaning to "rise and shine," proving that staying power wasn’t just about batteries anymore.

Technology also made its mark. Motorola's StarTAC flip phone landed, fulfilling the dreams of every wannabe Captain Kirk, "Beam me up, Scotty, there's no sign of intelligent life down here". Meanwhile, Pokémon burst out of Japan, and suddenly, kids everywhere were glued to their Game Boys.

And let’s not forget the pop culture storm that was?The Macarena.?This dance craze turned every dance floor into a chaotic sea of flailing arms and awkward hip thrusts, making everyone look like they were swatting invisible bees while having multiple spasms in their groin area.

Of course, not everything was a party. The UK was grappling with Mad Cow Disease, and suddenly, everyone was eyeing their burgers with suspicion, wondering if their meal was about to develop a British accent and talk back to them.

In this dynamic and ever-evolving landscape, our area country manager, a seasoned banking executive who probably couldn't close a deal to save his life, gathered us all to unveil the grand strategy. He declared with a voice brimming with authority—and perhaps a whiff of garlic—"We shall employ a multifaceted sales approach infused with data-driven analytics, segmentation, and customized marketing endeavors. We aim to increase market share by proactively engaging potential customers, offering tailor-made financial solutions, and leveraging advanced customer relationship management techniques to build lasting relationships and drive sustainable growth." What a mouthful.?

My overly enthusiastic and?combustible?new line manager—whose qualifications seemed more rooted in his?contacts within the bank than any?actual sales expertise—had called for a?department?meeting.?He then launched into a long, repetitive monologue, trying to?rally the troops. It was the?weakest?and?most comical?form of?sales huddle?I have?experienced, highlighted by?this.

Mr. Laddy, as he liked to be called, looked like a villain straight out of a Cartoon Network show. He was the kind of guy who wore cheap, ill-fitting polyester suits that were?too big for him, with no concern for color coordination. His hair was?drenched?with so much oil that?he?had to wear?a disclaimer not to dispose of your cigarettes?in?proximity?to him,?sharply?parted to the side, creating a trench of oil-soaked dandruff. He reminded me of Snidely Whiplash—the kind of slimy, greasy villain?you'd expect to see tying someone to the railroad tracks.

?"As Mr. Laddie tried his best to rally everyone with what he thought were martial arts analogies, he squirted phrases like:

'Sales is like sparring in a dojo, except the opponents are rejection letters, and the goal is to land the knockout punch.'

And, 'Closing a deal is like breaking through a martial arts opponent's defense and delivering the decisive blow.'

He then dropped his final analogy on cold calling, intending to steer the meeting—and his bewildered team—in that direction. 'Cold calling is like throwing a flurry of punches, hoping to land a lucky hit,' he declared."It sent a ripple of unease through the room,?planting fear in the hearts of the team.?I was still pondering why I was part of this meeting and why every time he mentioned the word "cold calling," he would look in my direction and give me a sly smile like a used car salesman about to close a deal.

?Cold calling. I could hardly believe it. The term felt like a relic from a bygone era, yet here we were, and he was glorifying it like some sacred sales scripture. Just when I thought I’d never hear those words again, they echoed in my ears. Little did I know, I was about to become part of a much larger plan in his grand design.

After the team meeting, Mr. Laddy pulled me aside to unveil my role in this so-called 'insurgence.' His plan was straightforward: I was to be the primary weapon. Yes, weapon. As the expert in investments and wealth management, I was expected to lead by example—by picking up the phone and cold-calling. And this wasn't a friendly suggestion; it was a direct order that caught me off guard.

That's how it all started. And let me tell you, I was livid. So much so, I wrote him a poem that echoed my frustration and anger.

Mr. Laddy, Oh Laddy How you became a manager is a mystery to me. Why don't you go back to where you came from and let me be? You asked me to hit the phone with no script in hand. You have no clue—you don’t understand. Who made you a manager, for God’s sake? That must be the bank’s biggest mistake.        

GATEKEEPERS: Gatekeepers are not mythical creatures or mighty sorcerers guarding ancient civilizations or entrances to other dimensions, although I used to think of them that way. They're usually receptionists, secretaries, personal assistants, or office managers who filter out unwanted calls and visits from sales gladiators trying to reach someone important or hold a decision-making position.

With no training and zero guidance, the idea of cold-calling strangers terrified me. So, I came up with a survival strategy of my own. To keep my manager off my back, I’d pick up the landline, put on my most "confident salesperson" voice, and dive into imaginary conversations. I’d throw in dramatic pauses and say things like, “Absolutely, sir, I’ll get that info to you right away!” or “Thank you for appreciating my expertise!” It was a one-man show, but hey, it kept the boss happy… at least for a while.

"Finally, I summoned the courage to make those first calls.?My trusty tool? The Yellow Pages—the quintessential cold-calling instrument of the pre-digital age. I targeted professionals in the blue section, specifically focusing on medical clinicsThe goal was clear: to win over the nurse and secure a callback from the doctor.

In my youthful optimism, I assumed the nurses would kindly help me reach the doctors.?Little did I know that doctors were constantly bombarded by pharmaceutical sales reps, with nurses acting as the ultimate gatekeepers, blocking access at every turn."

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Given my strategy's short lifespan, I shifted to making random calls, hoping something would stick. To get past gatekeepers, I'd exaggerate my Yankee twang and deepen my voice to sound authoritative. I even changed the second letter in my family name to resemble "Jerrar," hoping it would evoke strength, leadership, or wisdom. Although my actual family name possessed those qualities, they were within a different cultural context.

Even though I was suffering and failing miserably, I had a better chance than my colleagues from the personal banking department. Not only were they also sifting through the brutal combat of cold-calling, they didn't have much to offer as a "hook" to keep the phone conversation going. All they had were bank deposits, while I was using fancy words like "structured notes" and "feeder funds."

Fortunately, it didn't take long for our line manager to realize his grand strategy was backfiring. Instead of driving results, it was demoralizing his core team and costing him a few senior members. Their parting words were priceless, with remarks like, "I'm a banker, not a call center agent," and the ever-popular, "I didn't sign up for this!"

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As the week came to a close, I made a personal commitment: if I ever found myself on the receiving end of a cold call, I’d respond with patience and understanding. It’s more than just professional courtesy—it’s about empathy.

My role in cold calling has evolved from hands-on execution to strategic guidance. I now partner with organizations and their sales teams, leveraging my experience to help them overcome obstacles and optimize their outreach efforts.

Recently, a leading real estate developer, grappling with low conversion rates despite a strong lead generation program, sought my expertise. They tasked me with conducting a 'lead forensics' assessment, a thorough examination of their CRM and sales processes to uncover the root causes behind their team's hesitation or lack of success with cold calling.

I began by carefully analyzing the company’s sales process, honing in on key areas that often reveal hidden issues. First, I reviewed the lead generation process to ensure that the leads being acquired were of high quality and aligned with the company’s ideal customer profile. Next, I took a close look at how the sales team was utilizing the CRM, checking that they were effectively managing leads and following up as needed.

I evaluated their follow-up cadence—the flow and structure of how they engaged with leads. This cadence is crucial, encompassing the number of touchpoints, the timing between each interaction, and the content delivered at every stage. When any part of this process is out of sync, potential customers quickly lose interest before a meaningful sales conversation can even start.

A major part of my investigation focused on addressing "cold reluctance"—the hesitation or fear of making cold calls. I assessed whether the team had the right scripts, tools, and training to make effective cold outreach or if their reluctance stemmed from a lack of guidance or unclear direction.

After a thorough analysis,?it became clear that the follow-up cadence was inconsistent—there were too few touchpoints, and the time between follow-ups was too long.?Leads were slipping away before the team could engage them meaningfully.?Another significant discovery was the issue of cold reluctance.?The sales team hesitated to make the necessary cold calls,?a substantial obstacle in converting leads into opportunities.?This reluctance and gaps in the follow-up cadence contributed to their poor conversion rates.

I recommended that management implement a system to track key metrics,?enabling them to identify and address any weaknesses in their sales process.?These metrics included:

• Lead Response Time:?The speed at which the team responds to new leads.
• Number of Touchpoints:?The frequency of contact with leads before a decision is made to convert or drop them.
• Cold Call Success Rate:?The percentage of cold calls resulting in meaningful conversations or meetings.
• Conversion Rate from Lead to Opportunity:?The percentage of leads that successfully transition into qualified opportunities.
• Sales Velocity:?The speed at which leads progress through the sales pipeline to a closed deal.

By monitoring these metrics,?management could gain valuable insights into the team's performance and identify areas for improvement.

I was asked to share the insights from my lead forensics evaluation at their luxurious downtown office,?marking my third visit to the premises. This office was far from ordinary; its conference room boasted technology so sophisticated, that it felt more like a command center for plotting a covert operation in some unsuspecting, distant land than a corporate meeting space.

The meeting included key stakeholders like the CEO, CCO, and the head of sales. However, the C-suite's complete lack of interest throughout the entire meeting made me wonder if the root of the problem wasn't just poor sales execution, but a leadership vacuum at the top. After years of working both in the trenches and at the executive level, I've seen this disconnect time and again: a massive gap between what the C-suite believes is a brilliant strategy and what happens on the ground. This gap only widens as their egos inflate, and in this case, the CEO and CCO seemed more interested in stroking each other's egos than addressing the company's sales challenges. At one point, I was tempted to suggest they skip the meeting altogether and just get a room or a suite at the hotel next door.

After approximately 45 minutes of fidgeting - checking his watch three times,?glancing at his phone four times,?and doodling in his notebook what seemed like satanic symbols - The CEO politely excused himself and slipped out of the meeting, only to be followed shortly after by none other than the CCO.

The actual engagement came from Mick "The Hammer" Thompson, the head of sales. With his squared jaw, perpetual squint, and signature catchphrase, "Do you hear what I'm saying?" Mick exuded an energy reminiscent of an 80s action hero. From the get-go, Mick was fully invested, bombarding me with questions and delving into the specifics of my presentation. The discussion became particularly animated when we addressed the topic of cold calling.

Mick leaned in, his squint intensifying, and posed a question that's been on the minds of many in the sales world: "Is cold calling still relevant, especially with the rise of digital channels like social media? Do you hear what I'm saying?"

Hearing this from a head of sales who had just brought me in to advocate for cold calling was ironic. Typically, this question comes from hesitant sales reps, not their leaders.

I paused for a moment, searching for an objective answer, the echoes of past cold-calling traumas briefly surfacing.

"While some may question the relevance of phone prospecting in today's digital age, I see it as the sales industry's equivalent of martial arts training - a crucible where you sharpen your mind, hone your conversational skills, and forge the resilience essential in sales."

I then drew a parallel to Jari Bako, the Japanese martial arts practice of punching into a bucket of sand or rice. "Just like mastering martial arts demands relentless practice and refinement of technique, so does phone prospecting. It's about more than just making calls; it's about cultivating a mindset and skillset that will empower you in every sales interaction."

(Internally, I couldn't help but think, "Do you hear what I'm saying?")

"Mick," I continued, "as I see it, phone prospecting is more than just quick chats and connections. It's about something deeper. There are countless ways to communicate in this digital age, but none offer the real-time, direct human interaction of a cold call. The feedback you get is instant - you know immediately if the lead is interested, so you always know where you stand in your prospecting activity. It's a constant, invaluable engine for refining your approach and pitch, something that digital channels can't necessarily provide."

Unfortunately, such feedback comes with its share of rejections, brush-offs, and many other words ending with the phrase 'off.' But that's part of the game, and it only makes you more robust and adaptable. So, despite all the digital alternatives, phone prospecting remains essential.

Mike concluded the meeting by outlining a timetable for me to start a two-week workshop series, addressing the main pain points first with the Sales Managers, followed by a separate workshop for the Sales Representatives.

Exiting the meeting, I realized that before my upcoming gig, I needed to research how phone prospecting is currently conducted in the Real Estate industry, specifically within the context of a developer's sales team. I aimed to gather firsthand insights into the methods, tactics, and readiness levels. The most effective way to achieve this was to place myself on the receiving end of the phone prospecting call.

Over one week,?I intentionally provided my contact information to sales representatives,?whether through online registration or by visiting their sales booths at the many shopping malls that dotted the city.?My goal was to gain firsthand insights into their follow-up practices.

Within a short time, the floodgates opened, and a barrage of calls overwhelmed my phone. I was bombarded with enticing offers, from dream homes promising instant happiness and prosperity to investment schemes boasting astronomical returns in no time. One particularly memorable caller even insinuated that buying the off-plan apartment he was peddling would significantly improve my chances of attracting the opposite sex. How he managed to translate the features of a property into an improved love life remains a mystery to me. Each caller seemed determined to make a quick sale, providing minimal information in the process.

Amidst this barrage of calls, I couldn't help but notice several recurring patterns in the sales representatives' approaches, not to mention their unique interpretations of the English language. A symphony of colorful pronunciations, peculiar speech patterns, and unexpected intonations often made the already challenging sales pitches even more difficult to comprehend.

It was like a bizarre cartoon network audio reunion, with classic characters pitching over the phone, each in their signature and unique style. There was Droopy (Looney Tunes), his slow, drawling voice stretching every word beyond its elasticity until it practically snapped. Then there was Speedy Gonzales, a blur of words and barely comprehensible sentences, his pitch delivered at breakneck speed. And, of course, there was Pinky (Pinky and the Brain), his hyperactive ramblings and nonsensical tangents leaving me wondering if he was even aware he was on a sales call. The?Piglet?(Winnie the Pooh) type was timid and nervous, their voice barely a whisper, desperate to end the conversation as quickly as possible. And then there was the Gaston (Beauty and the Beast) archetype, full of bravado and self-importance, convinced they were doing you a favor by gracing you with their sales pitch.

Disclaimer:?No salespeople were harmed (emotionally or otherwise) during this experiment!

Afterr this colorful insight into the state of phone prospecting in my part of the word and a profound insight of the humen mind and condasions when to put to the test of phone prospecting I new how to structure my upcoming worckshops.

The Conclusion

Phone prospecting shouldn't be a nightmare for the caller or an ordeal for the recipient. With proper preparation, practice, and coaching, it can be a professional, human interaction. It's one person talking to another, not a script-driven monologue. It's a conversation – sometimes brief, yes, but still a conversation.

It's crucial for everyone involved to understand the importance of not overcomplicating the process. It's already challenging enough. This applies to everyone, from management to sales professionals to those on the receiving end of the calls.

First and foremost, management needs to recognize that their sales reps are the front-line ambassadors of the company. A well-trained, supported, and equipped sales team can make a world of difference in creating positive first impressions and building lasting relationships.

On the other hand, sales professionals should view phone prospecting as an opportunity for growth, not a dreaded task. It's a chance to sharpen their skills, refine their pitch, and build resilience. And for those on the receiving end of those calls, a little empathy goes a long way. Remember, that salesperson is just doing their job. A brief, polite interaction might even lead to something beneficial for both sides.

Ultimately, successful phone prospecting hinges on mutual respect and a willingness to connect. It's about recognizing the human element on both sides of the line. So, let's strive to make those interactions a little more human, a little more empathetic, and a little more productive. Whether you're a manager, a salesperson, or a prospect, remember that a simple shift in perspective can transform a dreaded chore into a valuable opportunity for connection and growth.