The Executive's Technology Readiness Checklist

Strategy

1. Can you name the business problem? If the goal is "adopt a new tool" rather than "cut invoice processing time by half," you're buying technology, not outcomes.

2. Do you know what it costs you today? Pick your top candidate workflow and put a dollar or hours figure on the status quo. That number is your business case.

3. Who owns the outcome? Technology initiatives without a single accountable owner become everyone's experiment and no one's result.

Data

4. Would your team bet on your data? If people already argue about whose report is right, new tools will amplify that noise, not fix it.

5. Do you know where your critical data lives? Systems, spreadsheets, and inboxes: you can't automate what you can't locate.

6. Is anything sensitive going into public tools? If staff are pasting client or employee data into free online tools today, you have a governance gap before you have a technology plan.

People and governance

7. Do your leaders share a working vocabulary? If key technology terms mean five different things to five executives, prioritization meetings will stall.

8. Have you set rules for acceptable use? A one-page policy beats an unwritten ban that everyone quietly ignores.

9. Who checks the output? Every technology-supported workflow needs a named human review point until it earns trust.

Action

10. What's your 90-day step? Not a transformation program, just one scoped, measurable pilot with a review date. If you can't name it, that's the first conversation to have.

How did you score?

7 or more "yes" answers: you're ready to pick a pilot.

Fewer than 5: start with a readiness conversation before buying anything.

Either way, the next step is a conversation.