Fail-Proof Cold-Calling Techniques from Becc Holland

November 19, 2019

Sara Howshar

Cold calling is the bread and butter for sales development reps (SDRs). It’s an integral tool for helping to fill the pipeline for account executives (AEs) and, of course, ensuring SDRs get paid.

Still, you’d be hard-pressed to find a sales rep who doesn’t wish that cold calling was easier.

Becc Holland, Sales Director at, has some time-tested strategies that can help make the cold calling process more strategic and effective and thus, a little bit easier overall. She and her team have some techniques for “warming up” their cold calls and smoothing the road to winning follow-up meetings.

In a recent episode of our webinar series “Flip the Script,” Becc unpacks how to structure and personalize a killer cold call.

Here are 6 ways to do just that.

1. Pick Your Premise

As Becc has explained in other episodes of “Flip the Script,” she’s a firm believer in the power of psychographic premises — key indicators of what prospects actually believe — over more traditional premises (demographic, technographic, firmagraphic) for enhancing personalization.

If you use the psychographic premise with a prospect, you’ll need to look for relevant details about the prospect in one of the five “buckets” that Becc has also discussed in earlier webinars. As a quick reminder, these buckets are, in order of effectiveness:

  1. Self-authored content (e.g., a blog post the prospect wrote)
  2. Engaged content (e.g., content the prospect liked or shared)
  3. Self-attributed traits (e.g., something the person does well)
  4. Junk drawer (e.g., a prospect’s hobby or a school they attended)
  5. The prospect’s company (e.g., relevant news about the company)

For an overview of the five premise buckets, see this blog post, “How to Personalize at Scale.”

2. Develop a Call Structure #

Once you’ve picked your premise, the next step is to set up the structure for your cold call. Becc says for many business development reps (BDRs) or even full-cycle SDRs, the first 30 seconds of the cold call are the most important. That said, you will still need to focus on structuring the entire call thoughtfully if you want to maximize conversion.

“Everything has a beginning, a middle and an end,” says Becc. “The key to warming up the cold call is to make each step as important as the last.”

“Hello, this is Becc. How have you been?” #

In Becc’s view, nothing says cold call more than opening with “How are you?” In contrast, try “How have you been?” That suggests a pre-existing relationship with the prospect. This approach may disarm the prospect, helping you overcome the ‘“fight or flight” defense they are likely to put up once they realize they’re talking to a salesperson.

Now, what if the prospect’s response is to throw a question right back at you, wanting to know who you or your company are, or why you are calling. If that happens, don’t address those questions (at least not immediately). Instead, stick to the script.

Becc’s approach is to say, “That’s a great question!” Then, she pivots back to the reason for her call, so she can launch into her postbound or outbound premise. That, in turn, shows the prospect that this isn’t really a “cold call” after all, because Becc has done her research.

Too often, though, reps drop the ball and leap to offer the prospect a product demo. Becc explains why this is a mistake: “If you know that a prospect downloaded a white paper on quota attainment, for example, why squander the opportunity to discuss that by asking if the prospect wants a demo? If they wanted a demo, they would have hit the convenient button that’s right on the same webpage where they downloaded the paper.”

“... but more importantly … ” #

In the case outlined above, Becc advises that SDRs refer to the postbound premise (i.e., the download of the white paper) for context and then quickly transition to the outbound premise summary: “I saw you had an article on your LinkedIn page about scaling teams effectively … ”

To make that transition, Becc also recommends using the phrase “ ... but more importantly … ” before presenting the outbound premise summary.

Becc cautions against self-imposed failure at this critical point in your interaction with a prospect. “If you reference an article, make sure you’ve read it,” she says. “I’ve seen situations where an SDR referenced a self-authored content premise and, when the prospect asked what they liked about it, they couldn’t answer because they didn’t read it. What’s the point?”

“So, I was curious if you’ve come across us before?” #

Having navigated the reason why she’s calling and making it clear she’s personalizing her outreach, Becc says she’ll then turn the call back to the prospect to see if she can glean some valuable information from them.

Once in a while, the prospect may respond with an objection (in which case, you’ll want to reference Becc’s tips for objection handling). But let’s assume the prospect hasn’t even heard of your company. “At this point, a lot of reps start talking quickly, trying to jam in as much information about the product or company into the time they think they have left,” says Becc.

Instead, she advises, take a breath and introduce an upfront contract to set ground rules that will benefit both you and your prospect.

3. Choose an Upfront Contract #

There are two versions of the upfront contract that SDRs should consider using at this point, says Becc. Each one asks for a commitment, sets an agenda, defines an outcome and requests the prospect’s consent. But one version requires reps to put themselves a little “further out there,” according to Becc. She refers to these two versions as the 30-Second Upfront Contract and the Two-Question Upfront Contract.

The 30-Second Upfront Contract #

The first type of upfront contract might look like this:

“Give me the next 30 seconds to give you my best dog-and-pony show about why Chorus might be a good fit for you and if, after that time, you don’t want to hear more, I will leave you alone. Fair?”

It’s a straight ask and gives the prospect the comfort that they can get you off the line in just 30 seconds. In many cases, this approach works in getting the prospect to listen, Becc says.

The Two-Question Upfront Contract #

The second version of the upfront contract goes something like this:

“If you let me ask just two questions and, after you answer them, you feel I’m still not relevant to you or your team, I promise I won’t call you again. Deal?”

The latter version is higher risk/higher reward in Becc’s experience. It’s designed to get the prospect talking and perhaps, lead more quickly to a meeting.

“Either version of the upfront contract will receive a positive response,” says Becc. “So, you just have to decide which one is the best fit for your situation.”

But wait, there’s more: Becc also has tips for what to do after you make an upfront contract offer to the prospect and they accept it:

4. Cast the Net #

If the prospect takes the 30-Second Upfront Contract offer, Becc says your next steps are to:

  • Stay on the personalization track by circling back to the outbound premise: “As I mentioned, I was really drawn in by your article … ”
  • Then, zero-in on your buyer persona and show you’ve done your research. (But don’t be the authority!): “At the end of the day, and correct me if I’m wrong, VPs of sales care about quota attainment … ”
  • Next, describe your typical buyer in a hero way and in doing so, cast a net — one that is so wide, your prospect will be caught: “We work with VPs of sales who want to drive quota attainment higher but just don’t know what their reps are saying on the phone. So, they can’t tell them when they need to pivot … ”
  • Finally, give the prospect a key to jump in and, hopefully, tell you about their pain points: Are you running into this, or am I just rambling here?”

5. Expose the Pain Points #

As for the Two-Question Upfront Contract, Becc explains what you should get from asking the two questions:

  • The first question lets you dig deeper into the prospect’s business while also engaging the prospect. Becc suggests asking something like: “Who is your top performer?” She explains, “There’s no way I would know the answer to that question myself from browsing LinkedIn or other sources. It’s something only the prospect can really tell me.”

The second question follows on from the first and can help you expose the prospect’s pain points and open up the discussion further. For example, suppose the answer to the first question is: “Nick is the best salesperson.” Question two then becomes: “So, what is Nick doing that the rest of your reps aren’t?”

“Nine times out of ten, the prospect can’t put their finger on why Nick is the best salesperson. They just know that he is. Inevitably, that leads into a longer discussion, ideally about 90 seconds, about pain points, which is exactly where I want to be,” says Becc.

To get as far as possible beneath the surface to expose the prospect’s pain points, Becc recommends asking as many strategic questions as you can in the time you have, using a technique known as the Sandler Pain Funnel. This technique comprises a series of questions — general, specific, intellectual and emotional — designed to uncover the reasons behind a prospect’s pain, as well as the impact of that pain on the prospect or their organization.

However, Becc recommends using general overview questions first to tease out more information from the prospect, rather than more specific situational questions. A question like: “I hear that a lot, what does that mean?” is more likely to keep the prospect talking and less likely to turn them off than a potential qualifying question such as, “What kind of CRM are you using?”

6. Closing Time #

If after 90 seconds of discussing pain points you start to get into a detailed conversation about how you can help and what you can do for the prospect, you need to move quickly to a neat close and start moving the deal into the pipeline. Otherwise, the prospect may not want to do a follow-up meeting with the AE.

Becc suggests transitioning by saying something like, “I know that I called unannounced … ” and then trying to get the prospect to commit to another call at a specific time and date. If the prospect questions the purpose of the next call, repeat back all the pain point information you’ve noted, telling them you want to dig a little deeper. Then, unpack the elements of your product that you feel will help them address that pain.

Lastly, solidify the next meeting by offering an additional upfront contract that addresses what the prospect likely fears most: that you are going to keep hammering them with calls. Becc suggests a contract like this: “So, if after that call next Tuesday, you don’t think we’re a fit, we can part ways as friends and I promise I won’t hammer you with follow-ups.”

It’s also a good idea to get some buy-in from the prospect by asking if they would like to add anything to the call agenda. Becc says, “The more they add, the more invested they are, and the more likely they will be to show up.”

Once the cold call has warmed, Becc says the only things left to do are to thank the prospect, let them know you’ll send a call invite, and encourage them to reach out to you for help in the meantime, if they need it.

Otherwise, consider your mission accomplished.

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