Free self-assessment

The Enterprise AI Readiness Checklist.

12 questions every leadership team should be able to answer before their next AI investment. Answer honestly: for each question, mark whether your organisation's position is Clear, Partial, or Unclear. You'll get your result immediately, and Ricky will personally review your answers.

0 of 12 answered

Where should Ricky send your result?

Section 1: Governance & Risk
Where governance gaps usually hide.
01
Who actually owns AI governance in your organisation, and do they have the authority to say no to a deployment?
Most organisations can name a committee. Few can name a person who can stop a project. Ownership without authority isn't governance, it's paperwork.
02
Can you list every AI tool currently in use across your organisation, including the ones procurement never approved?
Shadow AI adoption moves faster than any policy cycle. If the honest answer is "no," that's the first gap worth closing.
03
Is your AI use POPIA-compliant by design, or are you relying on a vendor's word for it?
Data protection isn't a checkbox on a vendor's website. It's a question you should be able to answer for every tool touching customer or employee data.
04
When an AI system gets something wrong, is there a named human accountable, and do they know it?
"The AI did it" is not an incident report. Accountability has to sit with a person before the first incident, not after.
Section 2: Organisational Readiness
How to read your organisation's real readiness.
05
Do your people understand what AI can and can't do, or is their sense of it shaped by headlines?
Fear and hype are both forms of misunderstanding. Readiness starts with a shared, accurate baseline, not enthusiasm.
06
Is adoption being driven top-down, bottom-up, or not at all, and does leadership actually know which?
These three situations need completely different interventions. Treating them the same is where most rollouts stall.
07
Have you identified the roles AI will change first, and have those people been part of the conversation?
The people whose jobs shift first are the people who decide whether adoption succeeds or gets quietly resisted.
08
What's your plan for the skills gap AI adoption will create over the next 18 months?
Tools arrive faster than capability does. Without a plan, that gap becomes the organisation's actual bottleneck.
Section 3: Board-Level Scrutiny
The questions your board will ask you first.
09
What's the ROI case for your AI investment, beyond "everyone else is doing it"?
Competitive pressure is real, but it isn't a business case. Your board will ask for one.
10
If a competitor moved twice as fast on AI, what would break first inside your organisation?
This question exposes the real bottleneck: usually it's not technology, it's process, skills, or governance.
11
How are you measuring adoption: usage, output, or outcomes?
Login counts feel like progress. They rarely correlate with the results the board is actually asking about.
12
Who reports AI risk to the board, and how often?
If the honest answer is "no one, yet," that's not a failure. It's the most useful finding in this checklist.

Sent straight to Ricky. No spam, no mailing list you didn't ask for.

Please answer all 12 questions and fill in your name and email.

Your result
0/24

Your answers have been sent to Ricky. He reviews every submission personally.

Book an AI Strategy Call