The cold-calling landscape has changed dramatically in the last few years, due to a number of factors, including (writes in broken record) AI. Jokes aside, though, we felt we needed to address the current state of cold calling, what’s different about it, what’s not, and, most importantly, what advice we can pass along to you. This blog is the third and final in a series in which we consult cold-calling experts. They come from different places, share views on some aspects of cold calling and differ on others. What they have in common is a razor-sharp understanding of the ways in which cold calling has changed and how vital it remains to sales. They generously shared advice, experiences, and keen assessments of cold calling today, yesterday, and tomorrow.
February 26, 2025
Our own cold-calling Maestros, Asad Ali, Mike Valade, and Will Fuentes started working with one another decades ago (really). Put together, their roster for training sales professionals runs well into the five digits. They’ve also made their share of cold calls. We wanted to impart some of their insights into a practice that is a rush for some and a horror for others. For quite a few salespeople, it has been both.
All three of them started their careers at Best Buy. Will Fuentes was the first to get hired. A year later he hired Mike, and a year after that, Will and Mike hired Asad, who was 16 at the time. It was there that they all learned the basics of having only seconds to convince someone to speak to you. We’ve all been approached by—or have ourselves been—the earnest salesperson asking aisle browsers if they need help. This was not Asad, Mike, and Will’s technique. They posed more specific questions, started conversations with potential buyers, and took them on an imaginative journey into what it would be like to be the owner—the winner—of a transcendent auditory experience (not just surround-sound speakers) or years of unforgettable family movie nights (not just a big-screen TV).
The next firm where the three worked together was Lemur, a B2B retail platform that Will founded. To understate it, there was a lot of cold calling.
By the time he got to Lemur, Mike had already logged hundreds of thousands of cold calls in a one-plus-year stint on Wall Street during what would quickly become known as the second worst time in the history of America to be a stockbroker.
Things looked very different at the time. He thinks back to 2009: “I got boxes of index cards from Dun and Bradstreet with the name, the company, the phone number on it. I’m on a corded phone. I am literally: card, dial, pacing, walking around, card, dial, pacing…I mean, zero in efficiency.” And yet, he says, “I would have just as many conversations then as if you are cold calling with the greatest tech stack in the world right now.” The reason? The ratio. Back when Mike was pacing, dialing, shuffling, rinsing, and repeating, the pick-up rate was in the neighborhood of one per every three dials.
By his own admission, Mike was unabashed. Nine a.m. phone calls on Saturday mornings, during what he assumed was kids’-soccer-game-o’clock. Not rarely was this tactic met with anger. “But the ones that liked the grind, that was fine. They were like, ‘I want this guy…to be my broker. I want the guy that’s working and hungry and gonna do anything for me, because I think my guy…I’m just a number to him.’”
About 10 years after Will hired him at Best Buy, Asad founded a software company in the event-marketing and ticketing space and was working there as a senior VP. Ask him, and he’ll tell you, though, that when Will hired him a second time at Lemur, cold calling was still new to him. He would have to learn quickly: other than Will and his cofounder, Asad was the company’s only salesperson. “I was Salesperson Zero.” Cold calling was a major part of his day-to-day work.
It’s not that Asad encourages people to jettison technology. He is a firm believer that today’s parallel dialers and other AI capabilities provide a valuable way to save time and cut to the important part of the job. “But I don’t think there’s a shortcut around that human element, that human touch, that calling directly is able to ultimately do.” It’s something he thinks people forget, which makes it all the more powerful for those who remember. It can be valuable to say, “I’m going to call because nobody else is—I’m going to connect—because people typically are not.”
He points to an article Peter Mollins, VP of Marketing at Nooks, published on Sales and Marketing Management that includes this behemoth of a stat: “52% of all meetings come from follow-up calls, yet only 21% of reps actually make those follow-ups when asked.”
Coincidentally, Maestro also obtained a quote about cold calling from Nooks’ co-founder and CPO, Rohan Suri. He said, “The future of cold calling will be human sales representatives supported by AI assistants. AI tools can handle the busywork—finding phone numbers, skipping answering machines, leaving voicemails, prepping talk tracks, and taking notes—allowing reps to focus on the strategic, human aspects of sales.” This aligns perfectly with Asad’s approach.
Of course, the dread cold calling provokes is not lost on Asad. “People get discouraged from making those calls and not having [the] level of success that they may have anticipated…” To him, the answer lies with leadership, which “needs to help manage expectations for people that are making these kinds of cold calls.”
It turns out that graduating from law school at GW, running multiple businesses, and training hundreds more doesn’t anesthetize you to the sometimes-unsettling experience of calling someone you don’t know. I asked Will, who has worked with hundreds of businesses to improve their selling capabilities and results, if he likes cold calling.
“No, actually, it’s funny, isn’t it? Do I like it? It’s a little bit nerve wracking…I’m a professional [but] I still have to get myself in the mindset of, ‘Hey, man, it’s gonna be okay. Just do the dials, just do the work. It’s gonna be fine.’” On the other hand, he says, “I do enjoy it…just because there’s a little bit of a thrill…”
He’s also sympathetic to the fact that, in many ways, cold calling can be even more difficult in the age of AI assists. “It’s one thing [to] make a hundred dials and have five conversations over the course of five hours, whatever it is. You get rejected like three times, right? It’s a whole other thing,” he says, “when you’re using parallel dialers and you’re getting multiple pickups, and you’re getting multiple rejections in a very short period of time. It’s one thing to go to the bar a couple of weekends in a row and not meet anybody. It’s a whole other thing to go to a speed-dating thing where everybody says no.”
His antidote to rejection? “Positive mindset and meditation. And I’m not trying to be funny here. I mean, I really do think it takes a lot of that. It’s a lot of that personal work of like, ‘These outcomes don’t determine the quality of person that I am.’”
Which is not to say that Will sanitizes his sales calls of his personality. Quite the opposite: he throws himself into the conversations he has with prospects, clients, and everyone else. He shares familial history and talks proudly about his son’s football team. He knows the AI sales-tool market thoroughly, but he also believes we are subtly approaching a kind of recoil. “We try to digitize our lives so much that I think there’s now been some sort of strong rebound towards: ‘Wait. We need more human interaction.’” He sees this borne out in the popularity of, say, cold-calling conferences today. But human interaction is something he understood as vital to sales long before he ever made a cold call. At Best Buy, he was known to sell obnoxious numbers of sound systems because of this instinct. (For more on that, see this.)
One thing the three have in common is a deep respect for the power of connectivity and the ability of cold calling to pierce certain membranes AI can’t.
Mike: “You can’t overcome the objection in email. You don’t know the objection. Cold calling is the communication where you get to learn the most about the client…The one where you get to separate yourself from the rest.”
Will: “What is more personal than actually a human-to-human interaction and voice?”
Asad: “The fastest way to get a door opened is to be able to call.”
Maestro has now trained hundreds of sales professionals on the science and art of cold calling—and sales, in general. Many of its selling strategies come directly from Will, Mike, and Asad’s histories, some of them from history the three of them share. Their sales trajectories have intersected for so many years, it makes sense that their cold-calling principles would align. High-ranking among these principles is that a good salesperson must be human—not just a human.
Do you need some help at the top of the funnel? Reach out at mastery@maestrogroup.co.
February 27, 2025 Zoey Weinstein
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