The vendor‑industrial complex.

A mid-market CIO I work with keeps a single spreadsheet. In it, twenty-seven rows. Each row is an AI vendor her team has evaluated in the last eighteen months. Seventeen of them pitched “co-pilots.” Nine of them pitched “agentic workflows.” Twenty-three of them used the phrase “your team will be 10x more productive” in the deck. Three of them could answer the question “what does your product actually do in production?” without a handoff to a sales engineer.

I am not anti-vendor. Some of the best software in the world is vendor software. The problem is that the current AI vendor ecosystem is optimized to extract a budget line item, not to deliver an outcome. It is a market in which the demo is the product.

What to read before the meeting

A short pre-reading list, useful before any AI vendor call:

1. Their last two product changelogs. If they don’t publish changelogs, that’s a data point. If they publish changelogs and the changes are all “improved accuracy,” that’s a stronger one.
2. Their SOC 2 or HIPAA posture. Not because you’ll read the full report, but because the answer to “can you send us your SOC 2?” tells you how seriously to take everything else.
3. One customer reference outside their featured logos. Ask to talk to a customer who is not on the marketing site. If they won’t produce one, you have learned something.

The three questions to ask on the call

Forget the feature tour. Ask these, in order:

1. “What’s the worst a customer has said about you in the last six months, and what did you do about it?”
2. “If we signed tomorrow, who on your team would I be working with day-to-day, and what’s their background?”
3. “What happens if we decide to leave in six months? Show me the off-boarding flow.”

None of these are trick questions. All of them are answered well by good vendors and answered badly by the other kind. The goal of the meeting is not to understand their product. The goal is to understand how they will behave in eighteen months when you have something stuck in production and their account manager has rolled to a new territory.

What to say to the board

Mid-market boards, in my experience, want to hear one of three things about AI: that you have a plan, that you are spending responsibly, and that you are not being embarrassed by a competitor. The healthy version of the vendor conversation produces answers to all three. The unhealthy version produces a list of logos and a request for more budget.

If the answer to “what did we get for the AI budget this quarter?” is a list of tools procured, you are losing this game. If it’s two sentences about what changed for your customers, you might be winning.