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How to Ace Cold Calling and Win Deals in 2021

How to Ace Cold Calling and Win Deals in 2021

Ananya Mallya
Ananya Mallya
August 19, 2021
5 min read

Cold calling has long been the bread and butter of sales when it comes to prospecting. But it’s also become the most controversial, to say the least.

Some say that it’s dead while others swear by it.

“Cold calling made sense in an age where a telephone call or door knocking were the only ways you could connect with buyers directly. But relying on cold calling today to boost sales makes about as much sense as pulling out a typewriter to send someone a letter,” says Colleen Francis, one of LinkedIn’s top sales influencers and bestselling author.

But Jason Bay argues, “The truth of the matter is that cold calling is one of the most effective tools for breaking into an account and getting a hold of the prospect. The reason they fail is because they’re too cold.”

Whether too cold or too hot, at the end of the day, B2B companies use cold calling to win multi-million dollar deals. But that’s beside the point. 

The million dollar question is...

How do you make cold calling a successful channel?

We all know that we have to prepare before a cold call, but nobody tells you how. 

Let’s be clear: this involves a lot of planning, but it’s worth the effort.

Warm up your cold calls

Sure this article is not titled "How to Ace Warm Calling and Win Deals," but it's important to address this. A popular way to get your prospect's attention before your cold call is to send over a cold email or a message on LinkedIn before actually calling them, so your call doesn't get the knee-jerk 'how dare you?' reaction. 

This clip from Seinfeld sums up how people feel about cold calls:

That aside, the best way to plan and carry through your cold call is by dividing it into three parts: before the call, during the call and after the call. 

Sounds scary? Don’t worry, we’ve got your back. 

Before the call 

You need to have a proper outreach system set in place for outbound work, whether this is by yourself or as a team effort.

As Anupreet Singh writes for Wingman, "Splitting the work of one Account Manager to two teams: a team of Sales Development Representatives (SDRs) that exclusively reach out to and qualify prospects before handing them over to the Account Executives (AEs) that work only on closing sales is a great way to divide the labor to improve the efficiency with which your team functions."

But even if you're handling this without the help of other sales professionals, here's how you can take care of the research:

Set up a cold calling list 

You need to have a list of potential clients that you will call. A cold calling list is, just as the name suggests, a list of people you think can be buyers for your product, but you haven't had prior contact with them. This list is important so you can keep track of who you've contacted and who you haven't. For every contact, you should have their name, job title, company and phone number, so you know who they are and why you're calling them. 

This task may seem tedious if you’re sifting through hundreds of leads. So, we’ve got a present for you. No, really! Don’t mention it.


Who doesn't love presents? Source: GIPHY


Here’s a bunch of tools that you can use to create your cold calling list:

For finding potential leads

LinkedIn Sales Navigator

If you’re looking for prospects, you’re probably already on LinkedIn. You can stop glancing at your open tab now. To help salespeople prospect better, LinkedIn launched LinkedIn Sales Navigator, which provides a lot more information on your leads, more advanced search filters and a way to speak to them through InMail credits, which warms up your cold calling process.

For qualifying leads 


Need a huge database of all the information you could need on a prospect? ZoomInfo is your answer to qualifying your prospect. Apart from the company information, you can use it to find the contact details of your prospect.

For contacting prospects


Apollo provides you with unlimited email addresses for every contact who could potentially buy your product. They also provide you with a sequencing platform that allows you to A/B test your emails, record your calls, automate your follow-ups, and create a repeatable process of setting up sales conversations. 

Narrow down your targets 

Wriggling your way through the company might not be a very effective way to close deals. You’ll end up making more phone calls that might not be worthwhile. Instead, call the people who are involved in calling the shots and are one of the decision-makers.

Research about your prospects

Before the call, check your lead’s profile on social media like LinkedIn in order to appeal to their interests. You might be able to find what issues they are currently facing and what kind of solutions they are seeking as well.

Why is this important?

Only 37% of prospects in a HubSpot survey feel sales reps who’d made cold calls to them had given information relevant to them. Yet, nearly 75% of salespeople thought they were spot-on with what they knew and pitched. 🤷‍♀️

Sharpen your sales pitch   

Within 10 seconds of calling someone, you need to win their attention. You have to use empathy and emotional intelligence to show you understand the challenges they face. Remember they’re more interested in the benefits you can offer than who you are as a person or organization.  

But apart from that, how do you ensure that you say what you’ve been meaning to say? 

Useful plug alert! 

Wingman is a conversation intelligence tool that provides you with discreet pitch points and battle cards that you can refer to while on call, so you can nail your cold call with ease.

Use local numbers for calling

A vast majority of people will hesitate to answer calls on their phones if they get a call from an unrecognized area code. So, if your salespeople call your prospects from a number with an unknown area code, most of your calls will not be answered, leaving deals lost before they’ve even begun. It’s always a good idea to use local numbers to call your leads, as it will have a higher connection rate.

During the call

You’ve got to be on your toes during the call, even before you're dialling the lead's number. Everything you say or don’t say has an impact on your prospect. What you do here creates the chance for your prospect to turn to a potential customer. 

You have to nail your key message. The message is the reason why a salesperson calls. The suggestion here is to write a marketing text and then rewrite it from your prospects’ perspective. Focus on the one big thing that will matter to them. You would definitely know this if you've done your homework while prospecting.

What if we go to voicemail?

Now, if you're afraid of going to their voicemail, don't sweat it. Here’s how our CEO Shruti Kapoor broke down how to tackle the voicemail pitch for you.

Relevance: Start with their favorite topic and make it sound like this isn’t 1 out of 500 calls you are making that day. Make them feel special.

New idea: Offer them value – two new ideas that might help in something very meaningful to them. You might not have credibility with them yet, but this is a step in that direction of being consultative rather than sales-y. 

Pattern interrupt: Leave it hanging. No phone number. No company name. 

This kind of pitch is unusual for cold callers, to say the least. This break in monotony is what will make your voicemail stick out from the hundreds of others in their inbox. Want more tips? You can check out this article with cold calling tips.

Ok, so they pick up your call. Breathe! 

We can get through this, no matter how daunting it seems. Here’s how:

Follow a flexible cold calling script

This also includes sales scripts for situations when the call goes south, like for sales objections that you find difficult. Before any cold call, you want to know how you will handle it, no matter what mood your prospects are in or what questions they may have. 

But what makes a sales script flexible? A script is a template, of course. But you can make it flexible by adding open-ended questions that you can gently probe the prospect on to get more details. 

On introducing yourself 

This is a controversial point, but some believe that you don’t explain what your company does at the very beginning, because a pattern interrupt is important to set yourself apart.

But you have to introduce yourself, duh. 


No prospect will tell you this. Ever. Source: GIPHY

Ask them about how they’re doing

According to, asking your prospect about their day has a 6.6 times higher success rate compared to baseline. It shows that you care, especially when said in a cheerful tone. More on this later.

Never use these phrases (debatable)

  • If you ask a prospect, “Did I catch you at a bad time?” there’s a high chance they will say yes.
  • “When can I call you back?” might be met with “How about never?” Always have the details like time, place and date, set straight.
  • “Are you the one making the purchase decisions?” This shows that you haven’t done your research and honestly, it just comes off as rude and pushy.

We mentioned that these phrases are controversial because while some believe that they can kill your chances of closing a deal, others like Belal Batrawy believe that they can catch your prospect’s attention. 

He's got a point. Source: LinkedIn

P.S. Adding pauses to your cold call script will help you recollect yourself without panicking during the call.

P.P.S If you're worried about forgetting information that you need, you can set up Wingman to get real-time sales battle cards on your screen while you're on call with your prospect. No more regrets after your call.


You, after using Wingman 😁 Source: GIPHY

 Master modulation and responsiveness

Sure, the content of your pitch is really important. But at a time when virtual meetings and voice calls are the norm, your prospect will not have the entire picture to rely on. This means that you will have to, you guessed it, ensure that your tone and modulation are on point.

As Albert Mehrabian found in his research, only 7% of how a message is perceived depends on the words that are spoken. 

Crazy right? 38% depends on how you say what you’re saying. If you’re not on a video call, the 55% that is dependent on your facial expressions is replaced by a heavier emphasis on tone.

Make pauses where you think you should

Sales reps often talk really quickly because they fear the lead will hang up before they have the chance to say what they want to say, so they rarely make pauses. But that's not how you should be tackling sales calls, simply because you have a target in mind and after all the research you've done, you know your outreach game.

Complete silence is not an option

Are you one of those people who usually keep silent when the other person is talking? Well, it’s not perfect for cold calling.

Using reassuring words like “Yes,” or “I understand,” or “Sure,” affirm to your prospect that you do care about what they are saying, and is a differentiator between bad cold calls and successful cold calls.

Talk: listen ratio is another factor that many believe is important to making your prospect feel comfortable and understood. According to the Harvard Business Review, “the amount of time and money spent listening reflects how much importance you attach to understanding customers and their needs. In this context, the talk-listen ratio is a measure of customer-centricity.”

Wingman just doesn’t record and transcribe your calls, it also provides valuable insights like your talk: listen ratio, which can help you prepare better for your next call and analyze your previous call’s performance. Need insights on your ongoing call? Wingman also gives you a monologue alert when you’ve been speaking for too long. 

We told you we’ve got your back. 

This image of us is as close to reality as it gets. Source: GIPHY

It’s good to be responsive

Responsiveness is the way you adjust your reaction to the words of another person. You can do this in three ways. 

  1. Echoing/Mirroring: You repeat specific phrases after the prospect to emphasize them, usually by stressing the right words.
  2. Rephrasing: You state what the prospect told you in paraphrased words.
  3. Summarizing: You provide a summary of the prospect’s words AND add valuable information for them, winning them over instantly. Hopefully.
But what if you run into a gatekeeper?

Gatekeepers. Hate 'em or mildly dislike 'em, they're around. You have to be prepared to handle bumping into them if you're serious about working on your cold calling game. But they don't have to be the bad guy. 

As Josh Braun puts it, "Rather than focusing on ways to get around gatekeepers, ask for their help. Gatekeepers can help point you to the appropriate person or even tell you the reason why it may or may not be a fit." 

Close by setting the next steps

Adding an action at the end of the call ensures that your lead remembers who you are due to the commitment and will hesitate before backing off the offer to talk again. 

Remember to add specifics like the time and date, like “Let’s catch up on Zoom at 3pm on the 21st,” instead of “Let’s set up a call to talk about this soon.”

Great! We’ve made it through the call. 

Time to sort out the last bit. Now, to the batmobile!


All we're saying is that you haven't seen Wingman and Batman in the same room. Source: GIPHY

After the call

So, you’ve made it to the end of your cold call. Now you can relax, right?

Enough said. Source: GIPHY

Send a recap email

Giving a recap after the call ensures that your prospect knows why and for what you are setting the next steps, especially if they give you a referral to someone higher up on their team.

This is usually sent in the form of an email after your call. In order to be able to send this, you would need to take notes during your call to understand your lead's pain points, actionables and any other important information. 

Follow up like your life depends on it

Who doesn't feel like Kermit these days? Source: GIPHY

Following up is critical to closing a deal, but most reps give up after just 1 follow-up. For reference, it takes at least 5 follow-ups to close a deal. Don't just leave your deal as another number on your CRM because they haven't responded to one of your emails. Maybe it just means you have to personalize your emails more instead of following a template to the T. 

Go over your performance 

Measure what works—and what doesn't. See what approaches help you actually land a meeting and then go through everything again. This is where you need...drumroll please... 

Wingman ✈️

Wingman is your best pal when it comes to performance review and conversation intelligence, among a ton of other things. Okay, that’s enough for a plug.

Now that you know the theory of how to ace cold calling, go put these tips into practice!

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