Delegate effectively

A large part of what worked early on in my career was my ability to take on a lot of initiatives at the same time. Brute force works until it doesn't, and over time it stopped being feasible.

Time and time again, my main development point was to delegate more. This felt difficult to do well because:

Unlike most skills, you can't learn it by watching others (e.g. you can learn how to write a great document by reading "great" documents and trying to do this yourself)
The feedback loop is slow and fuzzy. It's hard to know what specifically you could have done better

The main thing holding me back was trust - the more you trust someone, the easier it is to delegate. I never had a problem with delegating to someone I knew could do the job. The issue was always delegating to someone I wasn't sure could.

The answer wasn't to hand it over and hope. It was to build trust, or replace it with something else.

Pointers:

You can replace the trust element by having frequent catch-ups (the less you trust the person the more frequent the catch-ups)
You can also replace the trust element by checking what you can verify (instead of trusting the person's judgement, look at the raw output)
Don't expect the quality to be on the same level as the work you would do, and expect to have to get involved at certain points, but it still saves you a lot of time
Coach the person to help improve the work they produce. Sit with them to create a plan, or do part of the work required. If it still doesn't work the next time, raise it with their manager, especially if this work sits well within their domain and their role expectation