How I Mastered Cold Calling

Glossophobia, or the fear of public speaking, affects about 75% of people. However, there’s one fear that often surpasses it: talking to strangers over the phone.

For me personally, this fear was very real. Coming from a background in Economics and Big Data, transitioning to software sales meant stepping out of my comfort zone, especially with cold calling. I knew mastering this skill was crucial—it’s what could connect me with anyone in the world with just one call.

I still vividly remember my first cold calls: the nerves, the shaky voice, and the struggle with rejections and objections to book meetings. Even after making over 7500 calls and spending countless hours speaking with prospects, I still occasionally battle insecurity on bad days. Phone anxiety is a genuine challenge, but it’s something that can be overcome with the right approach and mindset.

The mindset of cold calling & prospecting in general

Much of life hinges on your mindset and how you approach your goals. This is particularly crucial when feelings of insecurity arise; it’s vital to discern facts from emotions. This holds especially true for prospecting. Rejection is inevitable, and it’s common to feel disheartened, inadequate, or even disliked when met with negativity. Therefore, it’s essential to establish a solid mental framework.

It all starts with WHY

Relating to Simon Sinek’s, Start with Why, I believe this rings true: Without knowing your purpose, it can be tough to muster motivation for things that feel uncomfortable. Consider this:

  • For employees: Why am I in this profession? What are my personal and career goals?
  • For founders or business owners: What’s the purpose of my organization? Why do I want my mission to succeed?
  • What value do I aim to bring to my customers?
  • Why would someone be interested in my product or service? How does it specifically help them? – Check my article on account planing to help answer this question.
  • What’s the impact if I don’t reach out to this person? How would their life be worse off without me?

Prospecting can feel draining, often leading to avoidance in favor of more enjoyable tasks or distractions like LinkedIn or social media. But once you have answers to these questions, you’ll experience a shift in dynamics.

How to handle set-backs

When you’re in a good groove, a simple “No” won’t faze you much. But on off days, rejection can sting, making you feel insecure or personally targeted. That’s when it’s crucial to have a plan in place to bounce back.

The worst thing you can do is let it derail you entirely. Acknowledge it’s a rough day, but don’t let it spiral. Remember, failure is part of the learning process. It’s how we grow and build resilience. Avoiding a retry after failing only robs us of learning opportunities. Research by Jiao Wang and James R. Bettman from Kellogg School of Management backs this up.

Personally, what helps me is getting moving. I’ll take a stroll around the house or do some push-ups. It might seem random, but it helps me shake off the negativity instead of getting caught in a downward spiral. Others might find solace in a quick meditation or a cup of tea or coffee. Ultimately, it’s about regaining your focus, letting go of negativity quickly, and getting back on track.

Tools and processes to improve your cold calling and prospecting process

For me, insecurity about how to start and end conversations, understanding what matters to each person, handling objections, and maintaining productivity throughout the day were my primary challenges. Below, you’ll find solutions to these issues. Your challenges might differ, and if they do, please share them along with how you’ve tackled them—either in the comments or directly with me—so I can add them to this toolbox of strategies.

Insecurity how to start a conversation and get into a flow

Many people overlook call scripts because they seem “artificial.” However, having a clear structure for how to start and end each call is invaluable. Let’s face it: the entire situation is artificial for the person you’re speaking to. The more confident and secure you are, the better it will feel for your prospect.

I’ve personally tried numerous scripts and found some favorites. Below, I’ll share them with you for both opening and closing a conversation.

Opening a call – yes oriented scripts

The concept behind yes-oriented scripts is to establish a sense of dynamic rapport with the person you’re speaking to. This approach works particularly well with busy individuals at higher levels of organizations because it quickly sets the stage, provides context, and assures the prospect that you respect their time. However, with those lower in the hierarchy, it might come off as pushy.

Most importantly, using this framework empowers you with a structured approach. 

Example of a yes-oriented script:

>> “Hi [Name], this is Julian calling from [Company Name]. You probably don’t recognize my name, right?”

>> >>Yes

>> “Now, you may not know my name or my company, but I’m sure you’re familiar with [mention something relevant to the prospect’s industry or current events].”

>> >>Yes

>> “I understand if you’re still a bit puzzled about why I’m reaching out to you out of the blue. Is it okay if I get straight to the point?”

>> >>Yes

“The reason for my call is to arrange a meeting with you. The goal of that meeting is to [briefly explain the purpose of the meeting].”

→ Immediately transition to closing after pitching and book the meeting.

Opening a call – no oriented scripts

The challenge with yes-oriented scripts is that they can come across as overly salesy and may create tension with the prospect. This is because the prospect may feel pressured to say yes, which can be off-putting.

Chris Voss, a former FBI hostage negotiator, suggests using no-oriented questions instead. This approach gives the prospect more freedom and a greater sense of security. You can learn more about his technique on his website.

In my personal experience, no-oriented scripts work particularly well with individuals lower in the organizational hierarchy. These individuals may have more time to engage in conversation and may respond better to a softer approach aimed at building rapport and trust rather than appearing overly assertive.

Example of no – oriented script

>> Hi {Name} this is Julian, I know I call unexpectedly, is this a bad time for you to talk?

>> >>No

>> Start with your pitch & Close

>> >>Yes

If it is a bad time to talk, it’s perfectly fine to ask when would be a better time for a conversation. Once they confirm a better time, politely ask for their email address so you can send them an invitation with a video-call link. If you don’t already have it, this is a good opportunity to gather that information. Typically, this is when they might inquire about the purpose of the call, giving you the chance to pitch your proposal.

Closing a call – Way to get calendar opened

A final step in overcoming obstacles is to ensure that the person you’re speaking to is actively opening up their calendar and checking for a suitable date and time. While this should ideally flow naturally, it can be helpful to guide them through the process in a way that feels natural and enjoyable.

One approach I particularly enjoy using, integrated into my pitch, adds a touch of fun and humor to the process, making it less formal and helping to establish a personal connection.

How to find date and time in a fun way

>> “Before we wrap up, as I mentioned earlier, I’d really like to delve deeper into your specific situation and explore whether similar benefits could be achieved for you. Quick question: what day of the week falls on the 15th of January?”

>> >> “The 15th of January? That’s a Monday, right?”

>> “Exactly! So, we’re on the same page. Now, would 11:00 or 14:00 o’clock work better for you?”

How to handle objections?

What matters to the person you call – be specific and crisp

Let’s be honest, often when you’re working with a lead list provided by marketing or from a Business Development Rep who did the research for you, it’s not always clear why you’re reaching out to a particular person. Many just start dialing without a clear plan, and when they do get on the phone with the customer, they’re not fully prepared or intentional about where the conversation should go.

In my view, this is a missed opportunity bordering on a mistake. You risk alienating potential customers and damaging your credibility when they could have been valuable additions to your client base. To avoid this scenario, I came up with a solution: I developed a card game for myself. This, along with the next section, formed the cornerstone of my personal prospecting productivity.

I created game cards for each person I called, printing and preparing them in advance. This boosted my productivity significantly because I didn’t have to think on the spot once I picked up the phone. Writing them out by hand forced me to slow down and carefully consider my approach, making it more effective and easier to remember.

Game Card, to increase effectiveness when cold calling potential customers
PG Game Cards

I’ve put together a PDF for you to download and print so you can try this approach yourself!

How to have productive cold calling days the “fun” way?

Cold calling gamified in a group

Start by setting goals for yourself, and consider sharing them with others to create a healthy sense of competition and accountability. Even if it feels a bit uncomfortable at times, remember that your co-workers, friends, and family all want you to succeed. Use their encouragement and support to motivate yourself.

Whenever possible, warm up with your peers by gathering in a group and practicing pitches together. Just like professional athletes warm up before a game, preparing yourself mentally and emotionally before making calls can help you perform at your best.

At the end of each day, take time to reflect on your performance. Share not only the outcomes, but also the personal efforts you’ve made. While you can’t control how many people answer the phone, you can ensure that you consistently put in the effort.

Cold calling gamified alone

Another strategy that significantly boosted my productivity was making the abstract concept of “dials” and “calls” tangible. I purchased 50 marbles and divided them into groups of 5 (later 10). For every dial I completed, I moved one marble into a “done jar.” Once I finished a group of 5 or 10, I took a short break to stretch, grab a coffee, or decompress for 5 minutes. During this time, I reflected on what I did well in the last set. This approach allowed me to learn continuously and break down the daunting task of making 50 dials into manageable chunks. As a result, I felt more motivated to tackle each small pile of marbles, knowing there was a small reward waiting, rather than feeling overwhelmed by the thought of 50 dials looming ahead, especially on low days alone at my desk.

These are just a few of the tools, techniques, and “gamifications” I used to make cold calling enjoyable and develop a skill that will benefit me in various situations throughout my life. Whether it’s building a pipeline of investment opportunities, networking with potential hires, or selling products/services, it all boils down to connecting with people, building relationships, and helping others find solutions to their problems.

Feel free to share your experiences in the comments, whether you’ve tried any of the ideas I’ve shared or if you’ve found other strategies helpful in mastering cold calling.

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