This post was inspired by a recent webinar we hosted with AI strategist Tristan Day and Workiro President Dave Owen. It wasn’t a product pitch. It was a frank, 60-minute conversation about why so many AI projects fail before they start, and what real AI readiness looks like in the messy reality of day-to-day business.

Here are the actual questions business leaders are asking us (and what we told them in the webinar).

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Q: How do I know if we’re ready for AI?

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A: Start with this question instead: What would AI actually help us do?

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If you can’t answer that without using the phrase ‘stay ahead of the curve’, you’re not ready yet.

Tristan Day put it perfectly: “Even if you can do it, should you? Not everything needs AI. Sometimes it just needs a decent workflow.”

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Q: What makes a business AI-ready?

A: It’s not about having AI tools. It’s about:

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1. Clean, consistent data
2. Integrated systems
3. A culture that doesn’t panic every time something changes

If your team still uses spreadsheets called "final_v5_budget_draft_REALLY_FINAL.xlsx", you're not there yet.

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Q: Where do most AI projects fall apart?

A: Right at the beginning.

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Dave Owen nailed it: “The smartest AI in the world is useless if your team can’t find what they need.”

You can’t automate chaos. Start by fixing the stuff that should have been fixed years ago.

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Q: What should I fix first?

A: The bottlenecks that hurt most.

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Look at your:

1. Document management (Are things filed automatically? Are they searchable?)
2. Email approvals (Are they lost in someone’s inbox?)
3. Systems (Are they connected, or duct-taped together?)

Then fix the simplest, highest-impact gap first. Don’t aim for AI. Aim for progress.

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Q: Is there a way to check how AI-ready we are?

A: Yes. We built one.

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Take the AI Readiness Scorecard to get an honest read on your current setup.

👉 Run your readiness check [link]

You’ll know exactly where you stand, and what to do next.

Catch the full on-demand session with Dave and Tristan here [link]. It might just save you from another doomed AI pilot!