☀️ 45% of enterprise AI projects are failing. Your deal gets compared to those.

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GM to the Top 1% ☕

A director stopped me in the middle of a demo last year and asked a question that had nothing to do with the product.

"Who owns this when it does not work?"

I gave a decent answer about support tiers and success plans. It was the wrong answer, and I could see it land wrong. He was not asking about support. He was asking whether he would be the person standing in a room in nine months explaining another one of these.

Roughly forty five percent of enterprise AI projects are now failing to deliver on what they promised. CIOs have responded exactly the way you would expect, by demanding ROI clarity, security posture, and defined governance before anything gets signed.

💡 YOU ARE NOT COMPETING WITH VENDORS

Every seller builds a competitive battlecard against the other logos in the deal. In an AI-adjacent purchase in late 2026, those logos are not your real competition.

Your competition is the buyer's own graveyard. The pilot that ran for two quarters and never left one team. The platform that got bought at the executive level and never got adopted at the desk level. The project that produced a dashboard nobody opens. Those are live, specific, painful memories held by the exact people sitting on your call, and several of them are personally associated with a failure they are still paying for socially.

This changes what a good deal looks like. The buyer is no longer trying to select the best option. They are trying to avoid being wrong again. Those are different jobs, and they reward different sellers.

The rep who wins does not have a better feature story. They have a more credible failure story. They can say, with specifics, here is how this goes wrong, here is what it looks like at week six when it is going wrong, here is who inside your organization has to own it, and here is the point where we stop and you get your money back. Naming the failure mode out loud is the single most trust-generating thing you can do in a market where forty five percent of these things fail. Everyone else is still pitching upside into a room full of people who have been burned.

🔧 THE SURVIVOR BRIEF

Build this once per account. It replaces the battlecard.

1. Excavate the graveyard: Ask directly. "What AI or automation work has been tried here in the last two years, and what happened to it?" Then stay quiet. The answer is the most valuable thing you will hear in the cycle.

2. Name the failure mode first: Before they raise it, state the two most common ways this specific deployment fails. Adoption stalling below a usage threshold, or ownership never landing on a named person. Buyers do not trust vendors who have never seen a bad outcome.

3. Assign a human owner: Every surviving project has one named person inside the customer who is accountable. Get that name on paper before contract. If nobody will take it, you do not have a deal, you have a pilot with a purchase order.

4. Define the stop condition: Agree in writing on the metric and the date at which the customer can declare this is not working. Sellers think this weakens a deal. It closes deals, because it is the only thing that makes the sponsor safe.

🎯 THIS WEEK'S HOMEWORK

On your next discovery call, ask what AI work has already been tried and what happened to it. Do not connect it to your product. Just find out who got burned and how. Then build the rest of your cycle around making sure that specific person is never in that position again.

❓ QUESTION OF THE DAY

In your biggest open deal, can you name the last internal project that failed and the person associated with it?

Reply with yes or no. No is the most useful answer here, because it is fixable this week.

See you tomorrow.

Edward

Founder, Morning Sales

P.S. Asking a buyer about their failures is easy to say and awkward to actually do without sounding like you are hunting for pain. The 500 AI Sales Prompts manual has the discovery and risk-framing prompts I use to run that conversation, including how to name a failure mode without talking yourself out of the deal. 27 dollars: https://store.edwardgorbis.com