The AI Readiness Gap
Nov 20, 2025 3:41 pm
Throughout the Fall—at MAICON, our IA•AI meetup, and dozens of conversations with leaders—one pattern kept surfacing: businesses want to use AI, but very few are actually ready to get value from it.
The issue isn’t tools or talent. It’s readiness—the structure that determines whether AI becomes a multiplier or another stalled experiment.
The Gaps That Are Showing
1. Unclear Problems
Teams jump into AI without defining the business problem first.
The organizations making real progress aren’t “trying AI”—they’re using it to solve something specific: a bottleneck, a workflow gap, or a customer pain point.
2. Weak Systems for Adoption
At recent tech & AI events I've attended, a common theme has been that AI struggles in messy environments.
If your processes aren’t documented or your workflows vary by person, AI has nothing stable to augment.
Readiness starts with systemization, not technology.
3. Messy or Fragmented Data
AI depends on data, and many organizations have it scattered across platforms, spreadsheets, and personal habits.
Before AI can help, businesses need cleaner inputs and a shared source of truth.
4. Limited Change Support
Most teams underestimate the amount of communication, training, and expectation-setting that AI requires to be fully embraced within a business unit.
Without that, fear or confusion slows adoption—even when the tech works well.
5. Undefined Success Metrics
In my discussions, leaders often asked, “How can I make AI actually work for my business?”
That question is impossible to answer without defining success, ownership, and measurement before a pilot begins.
What “AI-Ready” Looks Like
It’s simpler than many expect:
- A specific problem worth solving
- Clean, accessible input data
- Basic process clarity
- One accountable owner
- Simple, measurable outcomes
- A culture willing to learn and iterate
Get those pieces in place, and AI becomes practical.
Skip them, and even good ideas struggle to stick.
How Will You Use These Findings?
As we head toward 2026, this is the moment to pause, assess your readiness, and focus on the conditions that make AI truly useful—not just interesting.
I’m happy to share it to help you get started. Reply to this message with something like "AI Help!" and I'll send you a free AI Use Case Worksheet (PDF), and a link to the beta-version of my AI Use Case Brainstorm Bot (ChatGPT required, free account ok).
And/or, shoot me a note about your "roadblocks" so I can offer some ideas to get you past them.
Talk soon!
Your BizTech,
--Joshua
Disclaimer: I use AI to help write emails like these. I review & edit all AI-assisted work I publish.