A naive impression of delegation is that it’s about the work. Suppose you’re hiring people to landscape your front yard. You might tell them plant a maple here, spread mulch there, build a wall around the oak, remove the hydrangea, and so forth. Then the crew digs, scrapes, plants, pulls, etc. according to your directions, while you keep your hands clean and your brow unsweated.

This is not how it goes in knowledge work. In knowledge work, what is being delegated is thinking. If someone is putting together a proposal, creating a financial model, constructing a product roadmap, drawing a wireframe, or building a new feature, the work is not the typing or the drawing. The work is the thinking. The work is taking an abstract idea and turning it into something detailed that is the best expression of that idea. If you’re frequently asking for guidance, then you’re not accomplishing the goal the delegator had when they gave you the task. The hard part is the thinking! If they still have to do a lot of the thinking, then the delegation failed. What the delegator wants is to never have to think deeply about this task again. That includes worrying about whether it’s getting done.

To be a successful delegate, you have to discover the questions and answer most of them yourself. For the ones that remain, you have to ask for guidance briefly and in a way that minimizes the cognitive load while also extracting the maximum information both for those questions and any future ones. And then you have to regularly show that you are making the expected level of progress, but with no more information than is needed. I want to be able to live in a world where 99.9% of the time this project does not exist. When I delegate something, the ideal outcome is I hear about it for about one minute every few weeks, and all that I need to say is an acknowledgment that I’ve heard and perhaps an affirmation of the delegate’s effort and talent. More than that and it’s not delegation as much as it is partnership or (ugh) supervision. I want to live with the benefits of this project and none of the costs except one, which I’ll happily pay: employing the delegate.