Thursday, August 6, 2026

Selling with shortcuts

 Offering a shortcut to a human in an AI-led sales process makes business sense.



“Can you please repeat that? I am writing it down,” requested the elderly caller, but the sales agent from the assisted living facility (ALF), who identified herself as Ashley, clearly did not understand that he was really asking her to also slow down so he could note down the facility’s street address.

I have been a part of many sales pitches, either leading them, or listening in when my team is making a sales pitch. I have also been privy to startup pitches of tools to help sales teams get a leg up on their competition. Today, I got an opportunity to not only listen in on the buy-side, but to also observe it.

I got to listen to an elderly person trying to obtain information from a sales representative on a phone call, a surprisingly impatient and indifferent representative. This was not the first time I have heard the same elder making calls to customer service representatives. Those calls usually start with banter, move on to a bargain and then, a buy. It took me a few seconds to realize he was speaking with an AI agent, an AI agent not trained to listen. It was not the near lack of latency in the conversation. It was the lack of emotional intelligence. It was an apparent lack of kindness and warmth. If your AI does all the talking, who will listen to your customer?

Last fall, I had the privilege of watching kids and teens react to the demo of an AI product that small businesses can use to never miss a customer call, day or night. One of the questions from a teenager in the audience was how the AI agent would handle a customer who knows only to speak in Mandarin or Spanish. Live-translation is probably easy to add with existing technology. However, it’s what’s unsaid that can be missed.

The apparent lack of empathy in Ashley’s voice when taking a customer’s call would soon cause frustration and abandonment. For an effective sales conversation, Ashley had to compensate for the impatience of the octogenarian customer with an extra dose of patience and some humor.

That is the bigger challenge for a sales agent to overcome, regardless of whether the sales agent is human or not. It is a listening challenge. It is listening for the unsaid, the hesitation in the voice of a prospective buyer, the pause, the sigh, and the repeated interruptions when the sales agent is talking.

For a marketer, the opportunity to observe prospective buyers while they are interacting with a product, a brand or a sales team carries more valuable insights than all the number crunching done at one’s desk. An opportunity to gauge the prospective buyer’s emotions through their expression, the tone of their voice, and everything expressed or bottled carries more weight than a list of the product’s features or benefits.

A successful AI sales agent is the one that helps a prospective customer breathe easier at the end of the sales call, even if that means constantly offering the prospect an opportunity to speak to a human.

It reminds me of my general reluctance to enter a mega furnishing store when I know what precisely I need to buy as a gift for my college-bound niece, when the store’s layout aims to keep me wandering and wondering about dorm decor. When I must walk in, I look for the quickest way to check out or ask for help to exit. On my last visit, for the first time, I saw signs for shortcuts to the checkout area. That is thoughtful.

An effective AI sales agent must be kind and thoughtful by listening for signs of impatience in the voice at the other end and before it turns into frustration, offer a shortcut to a human, so buyers never lose the joy of shopping.

When asked if she was an AI, Ashley said she was a virtual agent and would be happy to have the Director of Sales return the call. Luckily for the ALF company, even though the call ended abruptly, the shopping wasn’t abandoned.