Delegation Is Not Taking Work Away

The one management class that stuck — situational leadership, the four boxes, and what it might mean for working with agents.

After I became a manager I sat through a lot of training. If you asked me to pick the one that stuck, I wouldn’t hesitate: delegation — or, more precisely, situational leadership. I’d filed it under “obvious” until I was actually leading a team and watched it line up, piece by piece. Here’s what I remember from the class, and a few things I re-confirmed long after.

A class called delegation

Delegation. Handing work off. The idea that a company would build a whole class to teach a manager how to give work away — and yet I remember the first line of the lecture running something like this: “As a leader or a manager, your resources are extremely valuable.” Because your resource is precious, hand the part you can to people you trust, and spend the time you save on higher-impact work. Grow your reach. The team member’s growth, the lecture said, is a bonus. The goal of delegation was, in the end, to get a report into a state you could hand off to — and then to actually hand off.

The frame for sorting those states was situational leadership: a four-box grid where the manager’s response changes depending on where the report stands.

Depending on the textbook, the axes were drawn as commitment vs. competence or as directive vs. supportive behavior. Commitment is the will to get the work done; competence is the skill to do it. Read it either way — the prescriptions come out the same:

• S1 — high will, low skill. Prescription: Directing. “Leader decides.”
• S2 — low will, low skill. Prescription: Coaching. “Let’s talk, leader decides.”
• S3 — high skill, low will. Prescription: Supporting. “Let’s talk, you decide.”
• S4 — high will, high skill. Prescription: Delegating. “You decide.”

That’s the textbook. Real life, of course, is a good deal more dynamic.

What the textbook didn’t say

At Google especially, a hard-won external hire usually lands at S1. The will is there; they just don’t know the lay of the land yet. The textbook does not claim one round of directing takes them to S4. Usually it’s S1 through S2 to S3, a long stay at S3, and then up to S4. Somewhere in there, some people stall or leave. The ones who make it through harden, and trust grows out of that hardness.

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Nagging doesn’t raise everyone’s skill on cue. Directing takes time; so does coaching. People move at different speeds, and the problems they’re handed differ in difficulty. The textbook doesn’t run on schedule — and a manager’s impatience never pulled a growth curve forward.

Higher skill doesn’t automatically mean ready to delegate, either. Someone loses steam at S3, or the org’s priorities shift, or the person wants a different topic. The manager’s “okay, they’re ready” can be the report’s “why now?” It’s one more reason nobody arrives at the delegate-able state all at once.

So what a manager actually needs is the ability to do the directing and the coaching themselves. To get someone to the point where you can hand off — S4 — you have to be able to stand beside them at S1 and S2. When my own technical skill fell short, I could delegate that part to a TL — a tech lead — on the team. Delegation doesn’t only run one direction, toward your reports; that, too, I learned in the same class. Which is as good a reason as any not to get lazy about learning.

What it means to hand work off

The thing that struck me most was the course repeating, over and over, that delegation is not taking work away. In Korean, even the everyday words for handing off and _entrusting_carry different weight. Work that’s handed off well creates the report’s visibility. The work becomes visible inside the org, and the person’s name gets spoken alongside it — a stage that simply wouldn’t exist if the manager had kept holding it.

There are environments where this frame doesn’t read cleanly. In a small company there’s often no separate manager at all, and directing and delegating swing back and forth inside one person. In Korean companies, delegation can read as offloading the work you didn’t want to do. A manager setting their own work down can look like slacking, or the person receiving it hears “why me?” In an org where this language is foreign, the word _visibility_can sound less like a stage and more like surveillance.

The steady read in one-on-ones, the tidying-up in assessment, the adjustment in calibration — the other facets of managing all move across this same four-box grid. Read the state, choose the prescription, build the stage. It’s not much of an exaggeration to say a manager’s day is nothing more than that.

These days the AI era is bringing a time of working alongside agents. Does an agent have an S1 through S4? I don’t know the answer yet. But the frame we’ve used to grow people seems like it could be useful for deciding how to use an agent — and when to entrust one. It had better be.

Part of Lessons from the Company — first-person notes from inside engineering organizations, from my years at Google and after. See the full series →

Adapted from my Korean essay on Brunch: brunch.co.kr/@chaesang/172