The short answer
A serious AI readiness assessment looks at five areas: whether AI is a priority with an owner, whether the AI knows your business, whether using it is safe, whether your team is trained, and what work runs on AI every week. It also checks the structure underneath, because AI multiplies whatever you point it at.
This summer, I was at a dinner with a few business owners and corporate professionals. We ended up talking about AI for hours, and a couple of stories stuck with me.
Someone who works in a notary office told me that everybody there uses AI every day. And guess what? Everybody pays for their own pro subscription, if they need one. The office doesn’t cover any of it, and there is no governance around it at all.
Then a lawyer from a major international law firm told me about the AI legal tool his firm had just started to roll out. From what I understood, it came with very little training for the staff. His experience was bad: a lot of hallucinations and wrong assumptions, even though the tool had been fed all the codes and all the laws. It was not at the level the lawyers expected. So they started using it, and stopped almost immediately.
The notary office is what I call shadow AI: your team using AI tools you never approved, like an employee dropping confidential company information into a private ChatGPT. A recent Notion study of 2,000 SMEs found that 51% of business owners believe AI is used in an uncontrolled way in their company. People are using chatbots and feeding them information, with no control over it. It is a very common problem, in smaller companies and in larger ones.
The law firm is the other side. The firm chose the tool and rolled it out, and it still failed, because nobody trained the people who had to use it.
I tell you all of this because I want to show you how I run an AI assessment in a company, to find out whether your business is ready for AI. It covers five areas. Here they are, as questions you can ask about your own business.
The five areas
1. Foundation: is AI a priority for your business? Do you treat it as a real priority, or is it a nice-to-have? And is anybody responsible for it?
2. Tools and context: does the AI know your business? The better question is: have you documented your business? Have you fed it into your AI in a structured way, so the AI understands who you are, what you do and how you work? This is context management, and it is what I work on most. I call the result a second brain.
3. Governance: is AI safe in your business? This is the notary office. Do you know which client information has gone into which AI tool? Is there a written policy, even one page?
4. Team: is your team trained? This is the law firm. A tool arrives, nobody shows people how to use it, and they drop it. So I ask: do your people know how to use AI properly? Has anyone shown them?
5. Usage: what runs on AI every week? What is the biggest thing AI has done in your business, from start to finish? And how do you choose the next use case?
How I run it, and what you get
Every Operating Review I run now includes an AI assessment, automatically. It follows the same three views as the rest of the Review: a conversation with you, a short set of questions for your team, and observation of how AI is used in an ordinary week. I ask about behaviour. The last proposal you sent: did AI help write it? That question has a true answer. The gaps between the views tell me the most. A founder says the team uses AI everywhere, and the observation shows two logins opened each week.
Each area gets ranked, and you get an overview of how your business ranks across all the AI dimensions. I show it as a simple graph, so you can see at a glance where you are strong and where you are exposed. You also get a plan for what to do next. Sometimes the first step is “not yet”: if your processes are not written down, we fix that before we add AI.
So, is your business ready?
Back to the question: is your business ready for AI? You can ask yourself the five questions above today. But they are hard to answer about your own business. As a founder, you are immersed in the day-to-day of your business, and stepping back to see the full picture is very difficult, especially on a topic as new and shiny as AI. That is why an external view helps.
Feel free to book a call with me. We can talk about how AI is deployed in your business, or how to deploy it better.
