The Ten Moments Buyers Hate (and Where They Go When They Hit One)

I'm in the middle of evaluating an outbound stack. An email platform, a couple of secondary sending domains, enrichment data. Nothing exotic. The kind of purchase that happens ten thousand times a day in B2B.

None of the vendors know it's happening.

No demo, no form, no chat widget. The whole evaluation has run inside one ChatGPT conversation. It told me which tools fit a five-person company, whether I need multiple sending domains, and that I don't need a CRM yet. When it dumped too much on me at once I told it to go step by step, and it did, which is more than I can say for most discovery calls I've sat through. I skimmed a few vendor websites, mostly to double-check what it had already told me.

Midway through, I asked it a different kind of question: forget the tools for a second. You sit inside millions of conversations like this one. What do buyers actually hate about buying?

The answer was better than most buyer research I've paid for, because it isn't a survey. It's pattern memory from the place buyers now go to complain. Here's the list, with my own scar tissue where I have it.

1. Not knowing if it's for you.

This one I hit personally, on this exact evaluation. I read one vendor's entire site, every page, and still could not tell you whether the product was built for a two-person company or a two-hundred-person sales org. I sell B2B software for a living. If I can't self-qualify from your website, your actual buyers have no chance. "Is this for someone like me" is the first question every buyer asks, and almost no site answers it.

2. Doing the vendor's job.

The other one I hit. To understand what one product actually did, I went through their docs, then their subreddit, then asked ChatGPT to explain their own product to me. It did a better job than they did. When a buyer needs three sources and an AI to understand your product, you didn't simplify anything. You outsourced the work to the buyer.

3. Being handed to sales before you're ready.

Buyers don't hate salespeople. They hate being qualified before being helped. There's a real difference between talking to someone whose first goal is to answer your question and someone whose first goal is to establish whether you deserve an answer.

4. Waiting.

For pricing. For a demo slot. For the follow-up. For legal. Every pause gives doubt a vote. Momentum is the most underrated force in a purchase, and most sales processes are built out of pauses.

5. Repeating yourself.

You explain your company to the form. Then to the SDR. Then to the AE. Then to the solutions engineer. Then, if you buy, to customer success. Five retellings, and the vendor had the information after the first one.

6. Feeling worked.

Buyers can smell process. The discovery questions read off a script. The discount that materializes on the last day of the quarter. The "just checking in" email that checks on nothing. None of it is dishonest, exactly. All of it says: you are a row in our pipeline.

7. No straight answers.

Ask a simple question, get an invitation. "Great question! Let's set up a call to walk through it." The distance between a buyer's question and a vendor's answer is where trust goes to die.

8. Selling it internally.

The hardest part of buying was never picking the vendor. It's the meeting after: finance, security, IT, your own boss. The vendor gets a signature; the buyer carries the risk into a room alone. Very few vendors ever help with the part of the purchase that is actually hard.

9. Procurement.

Weeks of paperwork that begin after everyone has already decided. Nobody defends this. It persists anyway.

10. The fear of being wrong.

Underneath everything else. Nobody gets fired for the demo they sat through; they get fired for the tool that failed. Every unanswered question, every vague page, every dodge compounds into the buyer's real math: if this goes badly, it's my name on it.

Now the uncomfortable part. I make software for marketers, and I'd love to tell you our own funnel commits none of these. It commits some. Every vendor's does, ours included, and always for reasons that sound sensible from the inside: the pricing says "it depends" because it genuinely depends, the demo is gated because the team wants context before the call. All of it defensible. All of it friction. The inside of every company is full of good reasons that the outside experiences as this list.

For twenty years, these ten moments were simply the price of buying software. Buyers paid it because there was no other door.

That's what changed. There is another door now, and buyers found it before vendors did. My evaluation didn't route around vendor websites as a protest. Asking an AI is genuinely the better way to buy: it answered the "for someone like me" question, it never made me wait, I never repeated myself, and it has no quarter to close. Whenever I do pay, the winning vendor will learn I exist at the moment the money arrives, and not one second earlier.

We can watch this happening from the other side, on our own site. Over the last 90 days, AI agents fetched pages from salespeak.ai roughly 37,000 times. 72% of those were ChatGPT or Claude pulling a page in real time because a human, mid-conversation, had just asked about us. That's about 25 times the number of humans who opened chat on the site in the same window. Our data; I doubt your site looks much different.

Each of those fetches is one of the ten moments not happening. Somebody wanted to know whether we were for a company like theirs, and instead of enduring the list, they asked the thing that answers straight, instantly, without a form.

The ten moments used to cost vendors time: a longer cycle, a grumpier buyer. Now they cost the conversation itself. The buyer still gets their answer. You're just not the one giving it.

Which leaves the question I haven't been able to put down since my own evaluation went this way: somewhere in a conversation I couldn't see, my product got explained, compared, maybe shortlisted, maybe cut. I don't know what was said about us when someone asked, "Is this for a company like mine?"

Neither do you, about yours.