What Your LLM Doesn’t Know
How general-purpose AI subtly leads CEOs astray
I’ve been telling people to think of AI as a brilliant new college graduate. It has a degree in everything—at least everything a university knows how to teach. Ask Claude or ChatGPT or Gemini about finance, and it answers like a finance major. Ask it about marketing, and it answers like a marketing major. Ask it about operations, law, medicine, coding and it knows the answer. It walked out of “graduation” with more knowledge than any human could absorb in a lifetime.
But here’s the problem CEOs encounter with AI: There’s no degree for being a chief executive.
Not even in business schools. In these schools, you find specialization in functional areas. You can take classes in finance, marketing, operations, and organizational behavior. These produce graduates who are genuinely good at their chosen function.
What you will not find in business schools is a department that teaches the job of integrating all of this knowledge into a practical theory of the organization. This is the essence of what the CEO job is—standing back and seeing the business as one interdependent system. To lead the whole rather than just one department, you need a bird’s eye view and a feeling for how it all works together. You must understand the inherent tensions between customers, shareholders, and employees. You must develop an eye for the friction that arises as a company builds, markets, and sells an offering. This is impossible to do from inside any one area, looking out. Taking the holistic view is the whole reason the CEO exists.
General-purpose AI, with its collection of specialized knowledge, isn’t much help when integrative leadership is your job. As the brilliant new college grad with a degree in everything, it’s eager to drag you back down into specialized knowledge. It’s completely uneducated in the actual discipline of running the organization as a whole. It has no model for where functions and stakeholder groups collide.
It can help you build a marketing plan. It cannot tell you what a CEO is supposed to do when marketing and sales and finance want three different things in the same quarter. It doesn’t understand the set of meta-disciplines that CEOs use to deliver results. Nobody ever taught it that.
As a CEO educator, I have been teaching these things for over a decade. The rapid rise of AI excites me because I think, when built properly, AI can be a major force multiplier for CEOs. In fact, I’m pretty convinced that those who don’t understand how it applies to their own job will be left playing catch-up.
Doing so requires more than having AI put on different specialist hats. This is why I have been working, together with specialists in LLMs, to develop custom skills for the CEO within a private AI environment. We call it ChatCEO. It’s an AI system that is actually trained on that holistic CEO degree no business school teaches.
Rather than trying to impress you by churning out 20-page docs full of specialized knowledge, this system is trained on the models and practices specific to the CEO role.
Imagine a CEO whose company’s revenue is flagging. This CEO decides to see if AI can help. What will a general-purpose LLM do? It will scan oceans of existing sales content (most of it not relevant to your company) and give you the average consensus take on how to grow revenue. It might then offer to draft up a plan for your sales team. Even if you spent a lot of time giving the AI all the context on your product and sales challenges, you’re still working within the paradigm of sales. AI is leading you to do your sales leader’s job for them. And when you hand off that plan, that sales leader is more likely to feel micromanaged and second-guessed than empowered.
Now imagine the same CEO with lackluster revenue and an AI partner that understands the CEO role. Rather than jumping straight into sales scripts, collateral, win rates, etc., it’s going to take a look at the whole context of your company. It’s going to work with you to look at larger questions, starting with your fundamental strategy. Are we having a sales problem, or is something else going on? Is our offering what customers want? Do they know about it? Do we have the right people in place to get where we want to go? And it will give you guidance and material informed not only by the data inside your own organization but by its structural knowledge of the CEO job.
The real question isn’t whether AI is smart enough to help a CEO. It obviously is. But being really smart doesn’t make someone a great CEO. General-purpose LLMs are really, really smart. The better question is: Do they know how CEOs deliver value at scale?
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