September 05, 2026 | Read online
Monday morning, a contract hit my inbox for a product the rep couldn't explain to me on Friday.
It was the end of one of the worst sales experiences I've had in a while, and I've been chewing on it all week because it's a perfect picture of where a lot of companies are right now.
It started innocently enough. I saw a promo video for a new AI feature inside a product I already use and pay for. It looked interesting, so I submitted an inbound lead to be one of the "first people to get access."
More than 24 hours later, I got an email from an SDR who "supports my account team" asking for a brief meeting. I'm assuming a human sent it, given the delay.
Side note - if you're a company touting your AI abilities and you're not using it to follow up with inbound leads immediately, can you even claim to be an AI company? That's the lowest-hanging fruit there is.
I emailed her back, told her I'm a 2-person company and probably not worth a meeting, and asked one specific question - How does the new product compare to what I'm already doing with my own version of Claude and the MCP connector?
She didn't even try to answer it. She looped in my Account Manager to find a time to talk, and two more emails later, I had a call on the calendar for Friday.
On the call, the AM (whom I'd never spoken with before) knew nothing about me or my business and went straight to asking what I wanted to know about the new offering. So I asked the same question I'd asked in the email.
Not only could she not answer it, she knew ABSOLUTELY NOTHING about the product. She fumbled around looking for a resource, then offered to send me a video. It was the exact promo video that made me submit the lead in the first place.
To her credit, she was honest. She said the company hadn't told the reps anything about the new product, and she found out about the release the same time I did. She also couldn't tell me what it cost and said she'd send a quote after the call.
That afternoon, she emailed to say the quoting system was down, which I knew was BS. They didn’t even know how to put together the quote yet because it was a different pricing model based on consumption.
Then, the cherry on top. On Monday, around noon, a DocuSign showed up in my inbox with zero context. It was a few line items and a price.
Seriously?
THIS WAS NEVER ABOUT THE PRODUCT
My first reaction was to blame the rep, and I want to be careful here because I don't think that's fair. She didn't know the product because nobody told her about the product. That's on the company, and I'll get to that in a minute.
What I do hold her accountable for is the conversation itself, because the conversation would have gone completely differently if she'd done even a sliver of discovery, and none of that requires knowing the product.
Two minutes on my LinkedIn or my website tells you I train sales teams, I've spent 25+ years doing it, and I talk about AI in sales constantly. That alone gives you a hypothesis about why a guy like me submitted that lead. A question like "what are you doing with AI in your own process today?" would have gotten me talking for ten minutes, and I would have handed her every reason I had for being curious.
Then she could have asked what I was hoping the new feature would do that my current setup doesn't, and what it's costing me right now to do it the way I'm doing it. Now she knows whether there's a real problem worth solving or whether I'm a tire kicker who saw a shiny promo.
At that point, not knowing the product is survivable. She could have said, "I don't have the details on this yet, but based on what you told me, here's who I'm going to get you in front of and when." I'd have respected that. I would have waited.
Instead, I got a video I'd already seen and a contract with no context, and it made me realize the entire conversation was designed to move me to the next step in their process instead of figuring out whether I had a reason to take it.
That's an order taker, and an order taker is 100% replaceable by AI. As a 2-person company, I should have been able to talk to a chatbot that knew my account, answered my question, gave me pricing, and sent the contract if I asked for it. If you're going to put humans in that process, they'd better bring something to the conversation a chatbot can't.
This is the whole reason I'm doing next week's Learning Lab on uncovering urgency. It's the meeting prep, hypothesis, and questioning section of Driving to Close, and it's the exact skill that was missing on that call. You walk in with a hypothesis about what's probably going on, you ask the questions that test it, and you get to what the problem actually costs before you talk about anything you sell. I'll show you how I'm using AI to do the prep in about twenty minutes instead of two hours, and I'll role play the call live.
It's on Wednesday at 11:00 am ET. Register here: https://us02web.zoom.us/webinar/register/WN_QwwIDuHIRguZjjtIDKdvzw#/registration
Everyone who shows up live gets the prompt pack I use for it.
THE PART COMPANIES DON'T WANT TO HEAR
Now, the company side, because this is the part that actually worries me.
I get that things move 1000 miles an hour in AI right now, and every company feels the pressure to ship something new to stay relevant. Investors love a release. The press release goes out, the promo video gets made, the inbound leads start flowing, the stock gets a bump, and everybody high-fives.
Meanwhile, the people who have to actually sell it found out about it the same day the customer did.
You get one shot at bringing something to market, in my experience. Whether it's your existing customers or net-new accounts, the first conversation they have about your new product is the conversation that decides what they believe about it, and the person having that conversation is a rep. If that rep isn't prepared, all the money and effort that went into building the thing gets burned on the front end where nobody's looking.
I'll probably never buy that feature now. I still have no idea if it's any good. What I do know is the experience told me the company doesn't have its act together, and that's the thing that sticks.
Trust is the currency of the future in this business. I believe that more every month. Buyers already have AI that can answer their product questions, compare options, and pull pricing in seconds. The only reason to talk to a human is that the human knows something, cares about the outcome, and can be trusted to tell the truth. Every conversation like the one I had spends that trust down, and you don't get it back with a discount.
Ready-fire-aim never really worked before AI, but it was tolerated because buyers didn't have a better option. Now they do, and the gap between reps who do real discovery and reps who send contracts is about to get exposed in a very public way.
Reply and tell me about the worst sales experience you've had this year. I'm curious whether it was the rep, the company, or both.
#MakeItHappen
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