Thought Leadership

How do we build judgment if AI does the work?

AI is compressing the work that traditionally built professional judgment over years of repetitive, increasingly more complex work. Firms must intentionally redesign the learning journey or risk creating a generation of professionals who can review AI outputs without understanding them or knowing how the outputs affect their own clients.

In audit and tax work, the profession’s apprenticeship model historically relied on repetition: preparing workpapers, tying out schedules, drafting memos, receiving review notes, and building judgment through iterations. AI threatens to remove or compress precisely those repetitions, especially at the early career stage, because many of the tasks most amenable to automation are also the tasks most likely to be assigned to new hires.

This is the paradox accounting firms must confront: AI can help the firm meet capacity constraints and client expectations, but it can also erode the “learning engine” that turns bright graduates into reliable seniors and future partners. Not to mention how leadership skills shift dramatically when your first “staff” to manage is a piece of software.

The ladder is shifting: what happens when entry-level work disappears

A growing body of accounting-industry guidance describes a restructured “first rung” of the career ladder: entry-level roles increasingly require not just accounting fundamentals, but AI fluency, because the work is moving from manual production to AI-assisted analysis and review. CPA.com has framed this shift as the rise of “AI-ready associate” expectations and new training models that blend domain fundamentals with AI-tool competence.

But apprenticeship was never just a staffing model; it was a cultural contract:

• New staff did repetitive work, often under pressure.
• Seniors and managers developed coaching and review skills.
• Partners relied on a pipeline of people who had earned judgment through structured exposure.

This is what my firm calls “The Covenant.” As a new hire, I agree to join your firm and do my absolute best to learn and grow and reach my fullest potential with you. And you, as the firm, agree to support me as a new hire, giving me access to all the tools available, so that I can reach my fullest potential while I am with you.

Now, when AI drafts the first version, summarizes the evidence, and suggests conclusions, the firm must redesign how people “earn” competence and expertise. Otherwise, the firm risks creating professionals who can present technical work before they can validate it with their own deep understanding and mastery. Learning and growth and expertise are thwarted.

Imagine a future senior manager who has reviewed thousands of AI-generated tax returns but has never actually built one from scratch. They may know what “looks right” without understanding what is right.

That is dangerous.

So how do we build judgment?

A first-year accountant in 2030 may not spend hours preparing a tax return or footing a workpaper. But if we are intentional, they may actually develop judgment faster, just through a different path. But we have to be prepared to give them that path.

I think future-ready accounting firms will intentionally create five new developmental experiences:

And perhaps the most important addition:

The “explain it to me” rule

Every first-year accountant should routinely be asked:

• Why do you agree with the AI?
• Why do you disagree?
• What assumptions are hidden here?
• What evidence would change your conclusion?
• How would you explain this to a client who knows nothing about accounting?
• Can you take us through an example that illustrates your conclusion?

Because ultimately, judgment is not built by typing numbers into spreadsheets. Judgment is built by repeatedly making, defending, challenging, and refining decisions. Redesigning apprenticeship solves only half the challenge. Firms also have to redesign the daily employee experience, because AI changes not just how people learn and what they will do, but how they feel about the work itself and even themselves.

About the author

Trisha Daho, Founder, Fractional Chief People Officer, Empowered Leadership Cultivation

Trisha Daho and Empowered Leadership Cultivation provide fractional chief people and culture officer services to mid-market accounting and law firms, including strategic implementation of AI integrated people structures, strategies, and cultures.