No one has ever read every decision a company has taken, and a kept record with an AI reading it would be the first

Jesper E. Thomsen · 24 October 2026

Organisations remember what they decided and lose why within a few years, and the people who could reconstruct it have moved on by the time it matters. A kept record of the reasoning, read across functions and years, is new, because no person has ever held all of it at once. The valuable part is the record; the judgment on it is still yours.

McKinsey has started calling an enterprise AI operating system the company's second brain. I have been running something with that name for a while, on my own material, and it is a different thing: a record of why decisions were taken, with a system reading it. The platform version connects data and decisions. The record version holds the reasoning, and a platform that does not hold the reasoning optimises whatever it can see.

I started with principles, board notes, meeting recaps and decision records, with the aim of a system that knows how I think and tells me when I am not acting on it. For the first weeks it was mostly noise. It raised questions that did not matter and found patterns that were not there. Then it told me that I was again spending too little time with the stakeholders who mattered most for what I was trying to do. It was right, and I changed my calendar. That is one correction, on one person, and it is the kind of thing a good chief of staff would have said. What made me take it seriously is that the chief of staff would have needed to be in every meeting for a year to say it, and the system had been.

The organisation remembers the decision and loses the reasoning

A transformation programme is approved because the rationale is compelling, the benefits are attractive and management believes it can deliver. The people put in charge are capable; that is why they were chosen. Three years later it is struggling, and the account changes: poorly managed, unrealistic targets, the wrong people. Some of that may be true. The questions that are rarely asked are who made the original assumptions, what was known at the time, what changed, and whether the organisation supplied the conditions it had promised.

There is a structural reason. Major initiatives are approved on optimistic assumptions, because the people proposing them believe in them and because an ambitious case is approved more often than a cautious one. When the assumptions fail, accountability travels to the people executing. The business case usually still exists; what is missing is what was known at the time and who assumed what, and nobody has an incentive to reconstruct it, since the people who approved are the ones who would be examined and the people executing are the ones still in the building. The organisation moves on, and the next initiative is approved on remarkably similar assumptions. Outcomes are measured; the reasoning that produced them is not kept.

The drift nobody decided

The larger version of the same loss is drift. A company states an ambition to become customer-led. Over five years its decisions on hiring, incentives, technology, structure and cost each make sense on their own and collectively move it toward internal efficiency. Nobody intended it and nobody noticed, because nobody was present at all of the decisions. A CFO sees the investments, a CHRO the appointments, a COO the restructurings. The pattern lives in the sum, and the sum has no owner. The CEO owns the whole in theory; in practice nobody has the memory or the attention to hold every significant decision of five years in view at once.

This is where a system with the record becomes interesting. It cannot decide better than the executive. It can be the one party with the whole record in front of it, every decision, the assumptions behind it and the corrections since, and the one that can be asked whether the sum has started to contradict the stated direction. The same holds for the long bets in the previous piece: a board asked to review whether a thesis still holds can only do so if the thesis was written down when the money was committed.

Record first, challenge second

I would separate two functions that are usually sold together.

The record is the dependable part. After an important meeting I write a short recap, or hand over the notes: what happened, what was decided, why, which assumptions, what remains open. It takes ten minutes. For a CEO the place to start is the executive committee: strategy papers, investment proposals, minutes, and the recaps of the conversations where the decision was actually made, which are usually before the meeting. Over time, mail and calendar can be connected under the confidentiality rules the company already has. The system gets things wrong at first; the corrections are what teach it which things matter.

The challenge is the less dependable part, and I say that from my own corrections. In a live session the systems I run generate forward and drop their own premises on the way: an assumption already in the conversation goes unused. Asking for a challenge while the system is working produces little. Given a closed record afterwards and one question, it finds the inconsistencies well. So the challenge works as a separate pass over the record, and it works best where the record is thickest. The judgment on what it finds stays with the person who owns the decision.

A side effect worth having: the system can tell which kind of decision is in front of you. Most decisions deserve less analysis and faster correction. A few deserve far more than they get; a senior appointment shapes capability and culture for a decade and often receives less scrutiny than a mid-sized capital request. The weight of a decision is rarely reflected in the process used to make it, and a record of past decisions and their consequences is the evidence for changing that.

Why this sits with the CEO

Strategic decisions play out over five to fifteen years; the people who made them rarely stay that long. The record is the one thing that can outlast them, and it outlasts them only if someone owns it. The CEO is the person responsible for connecting strategy, allocation, execution and the development of the organisation, and for whether the executive team learns at all. That responsibility is the reason to start there, and the reason it does not start as a company-wide programme. The CEO owns the discipline; the organisation has to end up owning the memory, or the record leaves with the person who kept it.

Where this does not hold

The record is only as good as what gets captured, and the decisions that matter most are often made in conversations nobody writes down; a thin record produces confident drift reports about nothing. A good decision can produce a bad outcome and a bad one a good outcome, and the system can separate reasoning from luck only if the reasoning was recorded in advance; recorded afterwards it is a rationalisation. And the challenge function is, on my own evidence, unproven beyond one user who corrects it daily. An executive team that does not correct it will get a sophisticated confirmation machine.