Read part one, Judgment, Early Careers and the Age of AI, here.
In part one last week, I argued that judgment used to be built almost accidentally — through proximity to pressure, consequence, and the small daily tasks that quietly trained an entire generation of professionals. AI has dismantled much of that apprenticeship. The instincts that protect a business haven’t become obsolete; they’ve become harder to develop. Which raises the practical question early-career professionals keep asking me: if no one is going to hand you judgment, how do you build it yourself?
Judgment starts early
Here’s the part students rarely get told explicitly: you don’t have to wait for authority to start developing judgment. You can begin building it deliberately, right now.
Judgment develops through a loop: making decisions, living with the consequences, and reflecting honestly on what happened. Earlier generations fell into that loop by accident. You’re going to have to step into it intentionally.
Start by slowing yourself down before you act. Not outwardly — mentally. When you’re given a task or a problem, ask what happens if nothing is done. Ask who gains and loses influence from this situation. Ask what could go wrong—not catastrophically, but plausibly.
Practice second-order thinking. Don’t stop at “What should we say?” or “What should we do?” Push yourself to ask, “What happens after that?” Then ask it again. Over time, this becomes instinct.
Creating artificial pressure
Create pressure before reality does. One practical way to do that is to use AI and real business news as your training ground. Take a recent business event — a product failure, an earnings miss, a recall, a cyber incident, a regulator letter, a labor issue — and freeze it before the outcome. Ask: What decision has to be made right now? What do we know, what don’t we know, and what can’t we say yet? Who actually has authority, who has influence, and what are the constraints?
Then use AI to role-play the stakeholders you’re likely to face: the skeptical customer, the angry employee, the board member, the journalist, the regulator. Let it challenge your assumptions and force tradeoffs. After you choose a course of action, fast-forward and compare your decision to what the company actually did and how it played out. The goal isn’t to guess right. It’s to build the habit of framing, pressure-testing, and reflecting — because that habit is judgment.
Take ownership seriously, even when the stakes are small. Own a piece of work end-to-end. Own the outcome. When something doesn’t go as planned, resist the urge to explain it away. Ask what you would do differently next time — and actually change your behavior.
Reflect deliberately. After decisions — good or bad — ask which assumptions held and which didn’t. Ask whether timing mattered more than content. Ask whether restraint would have served you better than speed. This reflection is where experience turns into judgment.
Pay attention to your emotions under pressure. Decisions are rarely made in calm environments. Fear, ego, urgency, incentives, and reputation are always in the room. Most bad decisions aren’t caused by ignorance — they’re caused by anxiety, pride, or the need to appear decisive. Notice when fear is driving urgency. Notice when ego is pushing certainty. Judgment improves when you can recognize those signals in yourself and compensate for them.
Where bad decisions begin
Watch, too, for whether ethics show up before a crisis forces them to. Most operational failures I’ve seen didn’t start with bad intent. They started with small rationalizations under pressure — because something was technically allowed, because speed felt necessary, or because no one would notice in the moment. Building judgment means catching those rationalizations early, in yourself, when the stakes still feel low.
Judgment doesn’t require authority to begin forming. It requires intention.
AI can help you explore options, test scenarios, and accelerate learning by exposing you to patterns faster than experience alone would allow. But it will never replace responsibility. You will still be the one whose credibility is on the line, whose decisions affect real people and real outcomes, and whose judgment will be remembered.
The truth is simple. Judgment isn’t something you wait for. It’s something you practice.
You don’t need to recreate the work of the past. You need to recreate the pressures that made that work matter.
AI doesn’t replace judgment. It reveals whether you’ve begun to build it.
That’s the work that lasts.
David J. Chamberlin is the managing director of the Strategic Communications Advisory Team at Orrick, where, alongside Orrick’s lawyers, he advises clients on reputation risk, communications strategies to address those risks, and global business operations issues. He previously served as the head of global communications at Nortel Networks, the chief communications officer at PNC Bank, and the chief marketing officer at SonicWall.
Illustration: Daria
