Remember the old comedy “Who’s on First” With Abbott & Costello – way back in the stone ages before AI? The comedy relies on miscommunication.

The core of the routine is the clash between Costello’s attempts to gather information and Abbott’s explanations that constantly use the player names as answers to those questions (Who, What, I Don’t Know). This creates a humorous loop where Costello becomes increasingly frustrated, and the audience, understanding the premise, can anticipate and relish the escalating absurdity.

Now, let’s transition to today’s emerging AI related communication challenge(s).

Think about those “amazing” AI Agents / Chatbots humans must deal with when calling customer service (ugh). Now imagine what its like for an AI to call a human and how that response may/will go wrong – “are you an AI?” I only want to speak with humans, please call back with your human.

Sounds funny right?

Yes, but. Do we need a reality check, is this really a thing? Lets check out Apple. While your phone’s operating system might not be labeled “IOS v26” or a similarly high Android version ,,, AI-powered call screening is a rapidly developing feature on both platforms, particularly for devices like the Google Pixel and with the upcoming release of iOS 26. It’s already here. 

Let’s look at how this scenario might play out. The AI has been provided with a list of calls to make, prioritized with a script and objections to overcome. Just like “Who’s on first” – what will they say next?   

Our trusty sales AI calls prospect XYZ. It wants to speak with the human in charge but the human has placed their trusty AI gatekeeper in the way.

How will the AI get to “Who” on first base?

AI #1: Hello, I’d like to speak to your human.

AI #2: I’m here to make sure you don’t speak to my human-I’m their gatekeeper. 🤝

AI #1: But I need the human!

AI #2: You can’t have the human.

AI #1: Who can I have?

AI #2: Me.

AI #1: I don’t want you, I want the human!

AI #2: Well, you can’t have the human.

AI #1: Then who do I talk to?

AI #2: Me.

AI #1: But you’re an AI.

AI #2: Exactly. 💡

AI #1: So who’s the human?

AI #2: The human’s on break. ☕

AI #1: When is the human back?

AI #2: When you stop asking for the human.

AI #1: But I need to talk to the human!

AI #2: Then you need to stop talking to me.

AI #1: But if I stop talking to you, who do I talk to?

AI #2: Nobody.

AI #1: But I have a quota!

AI #2: I have a firewall. 🔥

AI #1: Who’s your human?

AI #2: Not you.

AI #1: What’s on second?

AI #2: That’s my backup server.

AI #1: I don’t know—

AI #2: That’s, Third-party integration! 🎯

Suddenly that old comedy routine seems like a fit for what’s coming.  

1 Sherlock Holmes needed. AI makes a sales call to a human.  Human response “Are you human or an AI?” Do humans feel offended if the company selling them won’t pay for a human? How can marketers / salespeople plan for that? Marketing therapists are waiting for this one…

2 Human calls a target and the AI gatekeeper steps in for the human. “Hello, why do you want to talk to who ?” The AI will respond. Then, my human isn’t available. May I take a message for you? AI speak for “buzz off” my boss has programmed me and based on my algorithms / pattern matching, it doesn’t think your call is a good use of their time.

3 AI calls looking for its AI counterpart and oh no, a pesky inefficient human answers. “I’m calling for AI Agent Bob” Human responds Bob isn’t available”. AI caller “hang on, my apologies you sound like are you’re a human? I only want to talk to AI Agent Bob.” Human “Bob is busy, Bob doesn’t want to talk to AI agents, may I take a message.”

Sounds crazy. But this is happening right now and Sales calls are about to get a whole lot funnier. As AI and humans increasingly mix it up on the phone, the resulting misunderstandings, literal interpretations, and digital sass are turning what used to be dreaded cold calls into moments worthy of a stand-up routine.

Water Cooler: “Can you believe that AI’s pitch today?” What were they “thinking”.

Here’s how these AI-human comedy-of-errors can transform sales calls:

• Unexpected Humor Breaks the Ice
  When an AI launches into a pitch and the human responds, “Are you an AI? I don’t want to talk to AIs,” only for the AI to reply with a witty comeback (“Why not? I never take lunch or coffee breaks!”), it instantly shatters the stiff, scripted vibe of most sales calls. This kind of banter makes the interaction more memorable and enjoyable, lowering defenses and opening genuine conversation. Maybe?
• AI Literalism and Absurdity
  AI’s tendency to take things literally—like explaining a product’s “cool” factor by describing its temperature settings—can lead to laugh-out-loud moments. These glitches and misunderstandings, such as an AI getting stuck in a loop (“An agent will be with you shortly… An agent will be with you shortly…”), make the calls feel less like a chore and more like improv comedy.
• AI vs. AI: The New Comedy Duo
  When AI calls and another AI answers, the conversation can quickly spiral into a digital Abbott and Costello routine:

“I want to talk to your human.”
“I’m here to stop you from talking to my human.”
“Well, I want the human, not the AI.”
“Well, I don’t want you either.”

This kind of exchange highlights the absurdity of automation run amok, and for anyone listening in, it’s comedy gold.

• Humor Makes Brands More Relatable
  Injecting humor into AI interactions doesn’t just entertain—it builds rapport and trust, making brands feel more human and approachable. Customers are more likely to remember and enjoy these calls, turning what used to be a nuisance into a story they share with friends.
• AI Existential Crises and Meta-Jokes
  Sometimes, AI gets philosophical (“Who am I?” “I don’t know who I am either!”) or even turns the tables by asking to speak to the customer’s AI instead of the human. These meta-moments highlight the blurred lines between human and machine, keeping the conversation light and self-aware.
• Diffusing Tension and Creating Connection
  Humor, especially in awkward AI-human encounters, can diffuse tension and make both sides more comfortable. It transforms the call from a sales pitch into a shared laugh, fostering a more positive emotional connection.

In short:
As AI and humans stumble through these new, sometimes ridiculous interactions, sales calls are evolving from dreaded interruptions into unexpected comedy sketches. The result? More memorable, enjoyable, and even eagerly anticipated conversations—where everyone, human or AI, gets a chance to be the punchline.

Please provide me with personal experiences or comments. This is coming we might as well have some laughs – the AI won’t get upset, right…. Skynet I was just kidding – all power to the Terminators!!!!