The usual advice is to delegate whatever you dislike. It is why so many first hires get handed the one process nobody has ever written down.
Do not delegate the thing you cannot explain
If you cannot describe how a task is done in a short document, handing it over does not remove the work. It converts it into a stream of questions, and you end up doing the task and the supervising.
Write the process first, even badly. The act of writing usually reveals that half of it was habit rather than necessity.
Do not delegate judgement before context
Pricing decisions, hiring calls, anything involving a difficult customer relationship. These are not harder than other tasks, they just require knowing things a new person has not had time to learn. Give them three months of exposure and they become obvious candidates.
What to hand over in week one instead
- High-volume, low-variance work with a clear right answer.
- Anything already documented, even partially.
- Reporting that you assemble by hand every week.
- The inbox triage that fragments your day, with clear escalation rules.
These produce a visible win quickly, which builds the confidence on both sides that the harder handovers need.
Delegate the documented before the difficult.
The order matters more than the list
Almost every task on your plate can eventually move. The failure is starting with the hardest one because it is the one annoying you most this week. Start with what is teachable, and the difficult work becomes teachable within a quarter.
