Why Most AI Spending Fails
I've watched executives spend six figures on GenAI platforms, then shelve them three months later. Same pattern every time: shiny tool, unclear why they bought it, no one trained to use it, no clear owner asking whether it's working. The problem was never the technology. It was the readiness.
Before you write another check, answer these ten questions honestly. If you're hedging on more than two of them, you're not ready to buy yet. You're ready to prepare.
The Non-Negotiable Four
1. Can you define the problem you're actually solving? Not "we should use AI," but a specific business problem. Faster customer response? Better hiring decisions? Fewer manual spreadsheets? Name it. If you can't explain it in one sentence, you don't understand it yet.
2. Do you own clean, accessible data? GenAI without good data is like a Ferrari with no fuel. What data would solve your problem? Can your team access it in one place? Is it current? Incomplete or messy data will break your project faster than anything else.
3. Who owns the outcome? Not the IT director. Not the consultant. A single executive who lives with the results. No owner means no accountability. No accountability means it dies in six months.
4. Have you mapped the governance reality? Who decides what the AI can and cannot do? What happens when it makes a mistake? How do you audit it? Ignoring governance now means crisis management later.
The Six That Determine Success
Once those four are solid, answer these: Does your team have capacity to learn this (or are they drowning)? Can you measure success in the first 90 days? Do you have a second use case already identified, or is this one-off? Are you prepared for outputs that feel almost right but need human review? Have you stress-tested the vendor's security and compliance claims? And finally, can you kill this project if it's not working without sunk cost fallacy keeping it alive?
"The difference between companies winning with AI and companies wasting money on it is almost always preparation, not the tool."
Use the GenAI Readiness Assessment to work through these systematically. Then, before you vendor shop, run the Vendor Evaluation Checklist to make sure whoever you pick can actually deliver on what you need.
Hard questions first. Money second. That's how you win.