Ongoing Series · 5 essays so far · 2026

On Judgment

What do we actually mean when we say someone has good judgment?

I kept using the word judgment across product, data, AI, strategy and leadership.

Eventually I realized I was asking it to describe too many different things.

Reasoning. Evaluation. Taste. Decision-making. Authority. Accountability. The ability to interpret incomplete evidence. Even some of what I thought would remain distinctively human as AI became more capable.

So I decided to take the word apart.

On Judgment is an ongoing inquiry into what judgment actually is, what makes one judgment better than another, how people develop it, how organizations shape it, and what changes when machines become capable of making more of the assessments we once assumed belonged to humans.

This is not a finished framework presented one piece at a time. The argument changes as the questions get sharper.

Start with Part 1 ↓

The inquiry so far

Five questions, each moving from the individual toward the organization

Part 1Definition

I Keep Talking About Judgment. What Do I Actually Mean?

I had argued repeatedly that organizations need to preserve, improve and scale judgment. Before making that claim any further, I needed to understand what I was actually talking about.

The first essay traces how judgment entered my thinking through product decisions, data, AI and the Semantic Supply Chain, then starts separating assessment from reasoning, preference, decision, authority and accountability. It ends with a working definition rather than a finished answer.

Read Part 1 →

Part 2Boundaries

Judgment Is Smaller Than I Thought

The counterexamples made the definition thinner.

This essay treats judgment operationally as an assessment about something, then asks what follows once we stop using the word as a container for every valuable part of a decision. Judgment is separated from reasoning, preference, generation, decision and authority.

The practical question becomes much more precise: What exactly is the assessment inside this decision?

Read Part 2 →

Part 3Outcomes

Was It Good Judgment, or Did It Just Work?

Once judgment is separated from decision, another problem appears: how do we know whether an assessment was actually good?

A successful outcome does not prove that the original judgment was sound. A bad outcome does not necessarily prove that it was poor. The essay treats outcome as evidence about an earlier assessment rather than the verdict on it, and asks what a decision system needs in order to remain correctable.

Read Part 3 →

Part 4Formation

Where Does Good Judgment Come From?

Experience does not automatically create expertise.

This essay looks at informative experience, expert intuition, domain transfer and the organizational conditions that shape judgment: what evidence people see, whose expertise counts, whether disagreement survives long enough to surface unique information, which standards define “good”, and how consequences are interpreted.

It ends by moving the problem from the individual to the organization: What happens when a company tries to make an assessment or standard durable after the person who formed it is gone?

Read Part 4 →

Part 5Scaling

What Happens When a Company Tries to Scale Judgment?

The inquiry now moves from how individual judgment develops to what happens when an organization tries to make it durable beyond the people who originally formed it.

Part 4 ended with exactly this handoff: some assessments and standards eventually become embedded in how a company operates. Part 5 takes that organizational question directly as its subject.

Read Part 5 →

Where the inquiry is now

The first five essays have moved through five questions: What is judgment? What belongs inside it, and what does not? How can we tell whether a judgment was good? Where does reliable judgment come from? What happens when a company tries to scale it?

Each answer has made the concept narrower and the surrounding system more important. What began as a question about an individual capability has now moved explicitly into the organization: how assessments are formed, challenged, tested, learned from, made durable and used beyond the person who originally formed them.

On Judgment is ongoing.